fun tours in chicagoland area

THE 10 BEST Chicago Tours & Excursions

Chicago tours.

• Sightseeing Tours
• Cultural Tours
• Historical & Heritage Tours
• Up to 1 hour
• 1 to 4 hours
• 4 hours to 1 day
• 5.0 of 5 bubbles
• 4.0 of 5 bubbles & up
• 3.0 of 5 bubbles & up
• 2.0 of 5 bubbles & up
• Chinese (Traditional)
• Likely to Sell Out
• Special Offers
• The ranking of tours, activities, and experiences available on Tripadvisor is determined by several factors including the revenue generated by Tripadvisor from these bookings, the frequency of user clicks, and the volume and quality of customer reviews. Occasionally, newly listed offerings may be prioritized and appear higher in the list. The specific placement of these new listings may vary.

1. Chicago Architecture River Cruise

2. Chicago River 90-Minute History and Architecture Tour

3. Chicago River 45-Minute Architecture Tour from Magnificent Mile

4. Chicago Architecture Center River Cruise aboard Chicago's First Lady

5. Chicago: Gangsters and Ghosts Walking Tour

6. Lake Michigan Sunset Cruise in Chicago

7. Skydeck Chicago Admission Ticket

8. Experience Whim Chicago All-Access Passes

9. Chicago Favorites Ultimate Food and Walking Tour

10. Chicago River Boat Architecture Tour

11. Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour by Open-top Bus

12. Flyover in Chicago

13. Chicago Crime and Mob Bus Tour

14. 360 CHICAGO Observation Deck Admission

15. Chicago in a Day: Food, History and Architecture Walking Tour

16. Chicago Lake and River Architecture Tour

17. Chicago CityPASS®

18. Chicago's Secret Interiors Architectural Tour

19. Chicago Craft Brewery Barrel Bus Tour

20. Chicago River Cocktail Cruise

21. Chicago River Architecture Boat Tour

22. Chicago Gangster and Food Walking Tour

23. Chicago Buffet Lunch Cruise on Lake Michigan

24. Chicago Walking Food Tour With Secret Food Tours

25. Chicago City Minibus Tour

26. Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

27. 2-Hour Guided Segway Tour of Chicago

28. Lake Michigan Skyline Cruise in Chicago

29. Chicago's Chinatown Food and Walking Tour

30. Field Museum of Natural History Admission Tickets

What travelers are saying.

• Maksim M 1 contribution 0 5.0 of 5 bubbles River trip Very nice. Gives good idea about the architectural development in Chicago. Nice explanation, excellent views. Worth to come Read more Review of: Chicago Architecture River Cruise Written April 30, 2024 This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

• Chicago Architecture River Cruise
• Chicago River 90-Minute Architecture Tour
• Chicago River 45-Minute Architecture Tour from Magnificent Mile
• Gangsters and Ghosts Tour in Chicago
• Chicago Architecture Center River Cruise aboard Chicago's First Lady
• Inside Chicago Walking Tours
• Chicago Greeter
• Bobby's Bike Hike Chicago
• Tours With Mike
• Babylon Tours Chicago
• Pizza City USA
• Chicago Private Tours
• Free Chicago Walking Tours
• Chicago's Finest Tours
• Walk Chicago Tours
• Absolutely Chicago Segway Tours
• Chicago Elevated
• 3rd Coast Charters
• Steve's Segway Tours
• Urban Kayaks
• City Cruises Chicago
• Windy City Sailing

Chicago   Travel Guide

Courtesy of jaskoomerovic | Getty Images

28 Fun Things to Do in Chicago

Chicago shines for its world-class museums, various shopping districts, vibrant neighborhoods and lively nightlife venues. Explore the city's innovative roots at the Museum of Science and Industry, where you can walk inside the U-505 submarine.

• All Things To Do
• 1-Day Itinerary
• 2-Day Itinerary
• 3-Day Itinerary

Millennium Park and Cloud Gate Millennium Park and Cloud Gate free

U.S. News Insider Tip: Construction around the Cloud Gate sculpture will limit the public's access to this top tourist attraction until spring 2024. While you might not be able to snag a selfie with "The Bean," many other attractions are available within the park. – Cortney Fries

A first-time visit to Chicago isn't complete without a stop at Millennium Park. Situated in the Loop just north of the Art Institute of Chicago , this 25-acre space is used to showcase cutting-edge art, architecture and landscaping; it also acts as a backdrop for concerts and festivals. Most visitors come to Millennium Park to see the Crown Fountain and Cloud Gate, better known as "The Bean." Designed by Spanish artist Jaume Plensa, the Crown Fountain features two 50-foot towers that face each other at opposite ends of a shallow reflecting pool. The towers' LED screens project the faces of 1,000 different Chicago residents, which are perfectly aligned with spouts so that it appears they are spitting water on passersby. The water flows mid-spring through mid-fall, while the faces are projected year-round. Cloud Gate – created by British-Indian artist Anish Kapoor – is a 110-ton bean-shaped sculpture forged from stainless steel. The Bean's elliptical shape reflects the Chicago skyline. A quintessential Chicago souvenir is a photo of your reflection in The Bean.

Grant Park and Buckingham Fountain Grant Park and Buckingham Fountain free

U.S. News Insider Tip: If you're visiting Chicago Sept. 8 through 10, head to Grant Park early – around 11 a.m. to avoid the lines – for the Taste of Chicago. Enjoy the park and eat the best cuisine the city has to offer. Admission is free. – Sarah Estime

Often referred to as "Chicago's front yard," Grant Park is an approximately 313-acre swath of green space that starts at the eastern edge of the Loop and stretches down to the northern fringes of the Near South Side. First-time visitors should plan on spending a fair amount of time in Grant Park: This is where you'll find several of Chicago's most popular things to do, including The Field Museum , the Art Institute of Chicago and Shedd Aquarium . ( Millennium Park also rubs elbows with the northwest corner of Grant Park.) Baseball diamonds, flower gardens, walking paths and wide-open grassy terrain are available as well.

Art Institute of Chicago Art Institute of Chicago

Home to one of the country's most impressive collections of impressionist and post-impressionist art (plus works from numerous other genres), the expansive Art Institute of Chicago features nearly 300,000 works from all over the world in its permanent collection. You'll find pieces created in the Byzantine era, as well as paintings completed just a few decades ago. Highlights include Jacob Lawrence's "The Wedding," Georgia O'Keeffe's "Sky above Clouds IV" and Grant Wood's "American Gothic." The Art Institute's exhibits also include all sorts of intriguing artifacts, from European armor to the Thorne Miniature Rooms, which showcase interior design and furnishings in Europe and America from the late 13th to early 20th centuries. In addition to the permanent collection, the Art Institute hosts traveling exhibitions covering a variety of subjects and showcasing a diverse array of artists and genres.

The Art Institute of Chicago earns high praise from recent visitors, thanks in part to its impressive collection. Art enthusiasts particularly commend the museum's impressionist collection, which features pieces from famous artists like van Gogh, Monet and Renoir.

Popular Tours

Chicago Architecture River Cruise

(12360 reviews)

from $ 53.70

Chicago River 90-Minute History and Architecture Tour

(5152 reviews)

from $ 44.00

Chicago River 45-Minute Architecture Tour from Magnificent Mile

(987 reviews)

from $ 28.00

The Magnificent Mile The Magnificent Mile free

U.S. News Insider Tip: The Magnificent Mile, known for its world-class shopping, also has plenty to offer architecture buffs. Book a walking tour with the Chicago Architecture Center and hear the untold stories of North Michigan Avenue's architectural icons. Tours start at $30. – Sarah Estime

For shopping at more than 450 retailers within walking distance in downtown Chicago, make your way to The Magnificent Mile. This portion of Michigan Avenue – which stretches between Lake Shore Drive and the Chicago River – beckons to shopaholics with department stores and luxury retailers like Bloomingdale's, Marcus, Macy's, Tory Burch and Nordstrom. Additionally, The Magnificent Mile is home to several top-notch eateries and luxury hotels, including The Drake , the Sofitel Chicago Magnificent Mile and the InterContinental Chicago Magnificent Mile .

Navy Pier Navy Pier free

Extending out onto Lake Michigan, Navy Pier offers plenty in the way of family-friendly entertainment. The first thing you'll spot once you set foot on the pier is the towering Ferris wheel (which stands 196 feet tall); you'll also find a drop tower and a carousel. Once the kids have had their fill of thrill rides, you can spend some time cruising the Chicago River on a sightseeing or speedboat tour or spend a few hours exploring the Chicago Children's Museum , with hands-on exhibits ranging from treehouses to fire trucks.

But you don't have to be a kid to enjoy a visit to Navy Pier. Grown-ups can catch a show at the Chicago Shakespeare Theater, flex some credit card muscle at a variety of shops or grab a drink at the Navy Pier Beer Garden. And be sure to check Navy Pier's website for a list of events: Concerts are often held here, and from Memorial Day to Labor Day (as well as New Year's Eve), impressive fireworks displays light up the skies on Wednesday and Saturday nights. Many of the city's top Segway tours offer special summer evening tours to the pier to catch the semiweekly fireworks show.

Lincoln Park Zoo Lincoln Park Zoo free

U.S. News Insider Tip: North Avenue Beach is a short walk over the North Avenue Bridge when you park at the southern end of the Lincoln Park Zoo lot. Explore the zoo, then stroll over to the beach for an afternoon in the sand. – Cortney Fries

Located 2 miles north of the Loop in the North Side neighborhood of Lincoln Park, the Lincoln Park Zoo is home to nearly 200 species, such as zebras, sloths and hippos. Visitors can view the zoo's furry (or scaly) friends in their natural habitats: Check out the gorillas in the sprawling, award-winning Regenstein Center for African Apes, or head to the Kovler Seal Pool to get up close and personal with harbor seals. Seal training and feeding occurs daily at 11:30 a.m. and 2 p.m.

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360 CHICAGO Observation Deck 360 CHICAGO Observation Deck

One of Chicago's most notable attractions is its skyline, and one of the best places to experience it is at the 360 CHICAGO Observation Deck. Formerly known as the John Hancock Observatory, 360 CHICAGO towers 1,000 feet over The Magnificent Mile from its location on the 94th floor of the John Hancock Center (or 875 North Michigan Avenue as its more formally known). Encased by floor-to-ceiling windows, 360 CHICAGO boasts expansive views of the city; on a clear day, you can see four states. Meanwhile, the interactive screens will help you identify different landmarks that appear in your panorama.

For a different point of view (and an adrenaline rush), test out 360 CHICAGO's TILT. In this mechanized room, visitors hold on to handlebars as the top of the room's windows extend outward, tilting you toward bustling North Michigan Avenue down below. For another memorable way to immerse yourself in the views, try ClouldWalk, a 3D art experience introduced in 2022. Mural artist Nate Baranowski created an optical illusion on the observation deck that makes visitors feel as though they are standing on a crane platform in the clouds.  Should you prefer to experience the view without feeling your heart skip a beat, grab a cup of coffee, a glass of wine or a snack at the cafe and bar, or look for souvenirs in the gift shop.

The Field Museum The Field Museum

U.S. News Insider Tip: After hours of museum hopping, grab a kid-approved lunch at Kim & Carlo's Hot Dog Cart. The no-frills stand offers everything from vegan dogs to the traditional Chicago hotdog. Enjoy your lunch on the water. – Sarah Estime

This extensive natural history museum occupies half an acre of Grant Park 's Museum Campus and houses exhibits that showcase artifacts from multiple eras and destinations, making it a must-see for kids (as well as any fans of the "Indiana Jones" movies). Some of the most popular parts of the museum include the "Inside Ancient Egypt" exhibit, which features a reconstruction of a three-story replica of an Egyptian tomb, one of the largest collections of mummies in the United States and interactive representations of life on the Nile. There's also the Restoring Earth area in the Abbott Hall of Conservation, where visitors can learn more about sustainability through hands-on activities. But no visit to The Field Museum would be complete without some quality time with SUE, the facility's T. rex who just happens to be the largest, most complete T. rex ever discovered. SUE is 40 feet long from nose to tail and boasts 55 terrifying teeth.

Lake Michigan Sunset Cruise in Chicago

(866 reviews)

360 CHICAGO Observation Deck Admission

(726 reviews)

from $ 30.00

Chicago: Gangsters and Ghosts Walking Tour

(5588 reviews)

from $ 35.00

Chicago Architecture River Cruise Chicago Architecture River Cruise

A visit to 360 CHICAGO or Skydeck Chicago will give you a good overview of the city's layout. But if you want to learn more about Chicago's sky-high buildings, tag along on an architecture river cruise. During a river cruise, you'll gain great views and historical insight about well-known structures like the Wrigley Building, the Leo Burnett Building and the Fulton House.

Though several companies, including Wendella Sightseeing Co. and Chicago Line Cruises, offer architecture river cruises, most travelers recommend climbing aboard a Chicago's First Lady Cruises boat with a Chicago Architecture Center docent. You'll learn tons of information about the area's architecture, plus catch superb skyline photo-ops.

Maggie Daley Park Maggie Daley Park free

U.S. News Insider Tip: There are many restaurant options around the park, but Wildberry Pancakes & Café is a satisfying brunch spot. Choose from creative pancake options, a variety of omelets, crepes, sandwiches and salads. Go hungry and leave happy. – Cortney Fries

Opened in 2014, Maggie Daley Park is an expansive property located just east of Millennium Park in downtown Chicago. The 20-acre green space offers numerous activities for both kids and adults alike, including a climbing wall, a mini-golf course, a 3-acre playground, a public garden, an ice-skating skating "ribbon" during the winter and scooter and rollerblade rentals in the summer, not to mention a tennis facility. Whatever you choose to do, you'll get to enjoy fantastic views of the Chicago skyline. Recent visitors loved that the park is free to access, and they noted that the attraction is excellent for family fun.

Museum of Science and Industry Museum of Science and Industry

U.S. News Insider Tip: Mid-November through the first week of January, experience the annual "Christmas Around the World" and "Holidays of Light" exhibits. Volunteers decorate more than 50 trees in celebration of holiday traditions from around the globe. – Cortney Fries

Chicago's extensive Museum of Science and Industry is the Western Hemisphere's largest science museum, showcasing more than 35,000 artifacts and a variety of hands-on exhibits meant to inspire creativity. The museum resides in the 14-acre former Palace of Fine Arts, which hosted the famous World's Columbian Exposition in 1893. The fair brought together some of the world's greatest scientific minds, including Thomas Edison and Nikola Tesla, who at the time were competing to prove which type of electricity – direct current or alternating current – was more effective. 

Wrigley Field Wrigley Field

U.S. News Insider Tip: If you're visiting during the holiday season, don't miss Winterland at Gallagher Way for family-friendly rides and games inside and around the ballpark. Christkindlmarket Wrigleyville is free to enter. Enjoy festive shopping and international food and beverage selections. – Cortney Fries

Chicagoans take their love of sports very seriously. So, for a real taste of Chicago culture, head north of the Loop to Wrigley Field to watch the Chicago Cubs play ball at the Friendly Confines. History buffs will also appreciate this sports treasure, which first opened in 1914 and holds the honor of being the second-oldest Major League Baseball stadium in the country (after Fenway Park in Boston ).

Shedd Aquarium Shedd Aquarium

U.S. News Insider Tip: If you're visiting in the summer (June through August), check out Jazzin' at the Shedd. You can enjoy jazz music and drinks with incredible views from the terrace. Plus, the lights dim in the aquarium for a unique experience. – Elizabeth Von Tersch, Senior Editor

Shedd Aquarium is one of the world's largest indoor aquariums, housing around 32,000 creatures. While you're here, you can feel stingrays float beneath your fingers, listen to sea lions bark and learn all about a variety of turtles. A visit to Shedd Aquarium will lead you through a cornucopia of habitats, where you'll find additional animals like penguins, piranhas, sharks and beluga whales. Or, for an additional fee, you can participate in specialty experiences like animal encounters, feeding experiences and virtual reality.

Chicago River Boat Architecture Tour

(667 reviews)

from $ 49.00

Chicago Lake and River Architecture Tour

(1659 reviews)

Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour by Open-top Bus

(1686 reviews)

from $ 49.50

The Chicago Riverwalk The Chicago Riverwalk free

U.S. News Insider Tip: During the summer, there is nothing better than watching the boats go by as you relax at City Winery Riverwalk Wine Garden. Rent a retro boat from Chicago Electric Boat Company and cruise the river yourself. – Cortney Fries

When the weather warms up in Chicago, there are few better places to enjoy the outdoors than the Chicago Riverwalk. The 1.25-mile pedestrian walkway on the south bank of the Chicago River is the perfect place to take a stroll and observe the city skyline. Plus, there are numerous activity options to enjoy directly on the water, such as a boat or kayak tour . If you prefer to explore on your own two feet, visit the public gardens and art displays, or grab a meal at a popular restaurant or bar overlooking the Chicago River. And if you want to learn more about the river's unique history, check out the McCormick Bridgehouse & Chicago River Museum, which celebrates the city's famous movable bridges. What's more, Art on theMART – a massive digital art projection on the facade of theMART (formerly The Merchandise Mart) – is best viewed from the Riverwalk.

Skydeck Chicago at the Willis Tower Skydeck Chicago at the Willis Tower

More than 1.7 million people make their way to Willis Tower's Skydeck Chicago each year, and it's easy to see why. Occupying the 103rd floor – that's nine floors higher than 360 CHICAGO – of the 110-story Willis Tower (the third-tallest building in North America after One World Trade Center and Central Park Tower), Skydeck Chicago boasts breathtaking views of the city. Visit on a sunny day and you may be able to see far beyond Chicago's borders to Indiana, Michigan, Wisconsin and other parts of Illinois.

The highlight for most visitors is the Ledge. Extending 4.3 feet beyond the building's exterior, this platform is made entirely of glass – even the floor. Travelers also liked the video screens that show what it would be like to stand 103 floors above other Chicago attractions, including Wrigley Field and Millennium Park . However, long lines quickly form for Skydeck Chicago, so plan on arriving early or purchasing a Chicago CityPASS, which covers expedited admission into the attraction. Or, simply pay extra for expedited entry, which features an express line to the elevators. For the best views, it's advised that you visit just after opening or after sunset. If you'd like to enjoy the sunset from the tower, plan on arriving 30 to 45 minutes before sunset to ensure you have enough time to get through the elevator line and up to the top.

North Avenue Beach North Avenue Beach free

Located in Lincoln Park directly on Lake Michigan, North Avenue Beach is one of the most popular swimming spots in Chicago. The sandy beach has volleyball courts, plenty of space for visitors to stretch out and multiple things to do near nearby. Plus, it offers spectacular views of the city skyline. Beachgoers can also find restaurants, sports rental companies, restrooms and more inside a 22,000-square-foot beach house adjacent to the shore.

Recent visitors said the beach is a nice spot that is perfect for relaxing, biking and running, but they warned that it can get busy on warm summer days.

The Second City The Second City

If you've seen a sketch comedy show or hilarious movie in the last 40 years, it's likely that someone from The Second City appeared in it. The Second City is one of the world's most iconic improvisational comedy theaters, and it has helped launch the careers of numerous famous comedians, including Bill Murray, Tina Fey, Keegan-Michael Key, Steve Carell and Stephen Colbert. If you're in the mood for a laugh, check out a live show on any night of the week at any number of The Second City's seven stages (which are all housed in its facility at the northwest corner of North Avenue and Wells Street in Old Town). 

Recent reviewers said that everyone in their group could not stop laughing during the shows, which typically last 90 minutes to two hours. Ticket prices vary by the show and date, but run anywhere from $30 to $100.

The Chicago Theatre The Chicago Theatre

Aside from Cloud Gate and Buckingham Fountain , The Chicago Theatre's red and yellow marquee is perhaps one of the city's most recognizable landmarks. Illuminating North State Street at the northern edge of the Loop, The Chicago Theatre first opened its doors in 1921 as an extravagant movie theater and performance venue. Throughout its history, the theater has hosted such big names as Duke Ellington, Diana Ross and Prince, in addition to screening blockbuster flicks. Though the theater fell into disuse in the 1970s, new management and a full renovation in the 1980s helped return the venue to its former glory. Today, the theater is still used for a variety of comedic, theatrical and musical performances.

According to past patrons, the theater's historic appearance enhances the overall experience of catching an event here. Just remember, cameras and video cameras, including those on cell phones, cannot be used during tours or performances. If you're not in town for a show, consider signing up for one of the venue's guided tours. Tour tickets cost $20 for adults and $15 for kids ages 12 and younger. Tours are available Monday and Tuesday at noon and 2 p.m. and last about an hour.

Chicago Crime and Mob Bus Tour

(2315 reviews)

from $ 46.00

Skydeck Chicago Admission Ticket

(1327 reviews)

Chicago Architecture Center River Cruise aboard Chicago's First Lady

(1848 reviews)

from $ 54.00

Chicago Children's Museum Chicago Children's Museum

Located at Navy Pier , the Chicago Children's Museum offers temporary and permanent play-based exhibits for babies, toddlers and kids ages 4 and older. Founded in 1982 by the Junior League of Chicago as a response to cuts in arts programming, the museum was originally housed in two hallways of what is now called the Chicago Cultural Center . Today, children can dig for "teeth" and "bones" in "Dinosaur Expedition," climb through tunnels of "Cloud Buster," test their STEAM (Science, Technology, Engineering, Art and Math) skills in the Tinkering Lab and paint, draw or sew in the art studio.

Recent visitors appreciated the interactive, hands-on exhibits, which they recommend for young children.

American Writers Museum American Writers Museum

U.S. News Insider Tip: Across the street from the museum, you will find the first Nutella Café, where you can savor French and Italian dishes featuring the heavenly hazelnut spread. The gelato is roll-your-eyes-to-the-back-of-your-head good. – Cortney Fries

The first museum in the United States dedicated to celebrating the diverse voices and influence of American authors, the American Writers Museum is an interactive journey through more than five centuries of written and spoken word. This relatively small museum, which opened in 2017, features thoughtful and reflective exhibits that you can touch, smell, hear and see. 

DuSable Black History Museum and Education Center DuSable Black History Museum and Education Center

U.S. News Insider Tip: If driving in Chicago isn’t your thing, consider taking the No. 55 bus to the museum. The bus drops you off within just a five-minute walk of the museum. – Sarah Estime

The DuSable Black History Museum and Education Center, named for Jean Baptiste Pointe DuSable, the entrepreneur who is credited with founding Chicago, is a must-visit for anyone looking to learn more about African American history in the city of Chicago and America. It celebrates its 62nd anniversary in 2023, and is full of thought-provoking exhibits, including those that showcase fine art created by influential African American artists and historical materials. Note that visitors hoping to enjoy “The March” exhibit, an immersive experience depicting the historic March on Washington and Martin Luther King Jr.'s "I Have A Dream" speech, can go in groups of no more than four at a time.

Adler Planetarium Adler Planetarium

The first planetarium in the Western Hemisphere, the Adler offers unrivaled insights into our solar system. Indeed, "Our Solar System" is one of its permanent exhibits, along with "Mission Moon," "The Universe: A Walk Through Space and Time," "Telescopes: Through the Looking Glass" and "Astronomy in Culture," among others. Its facilities include the Doane Observatory, which has the largest telescope available to the public in the Chicago area, through which visitors can glimpse celestial objects trillions of miles away. The Adler also has three full-size theaters – the 3D Universe Theater, the Definiti Space Theater and the Grainger Sky Theater – in which it screens programs like "Destination Solar System," "Planet Nine" and "One World, One Sky: Big Bird's Adventure."

Space enthusiasts invariably find the Adler's presentations both informative and entertaining, if somewhat pricey. Most visitors suggest setting aside a few hours to explore the various exhibits and shows. Travelers recommend maximizing your parking expenses by also visiting the Shedd Aquarium or The Field Museum , which also sit on the Museum Campus. Reviewers also appreciated the Lake Michigan and skyline views as seen from the planetarium.

Offbeat Street Art Tour Offbeat Street Art Tour

U.S. News Insider Tip: If you’re looking for unique souvenirs from your Chicago trip, consider The Goddess & Grocer for its gift baskets. – Sarah Estime

In Chicago, you can find eye-catching street art nearly everywhere. As you sightsee, you’ll be greeted with unique, thought-provoking art on the sides of buildings and underneath bridges. If you’re looking for an experience that walks you through the history and cultural significance of Chicago's street art scene, look no further than the Offbeat Street Art Tour. On this two-hour tour, you’ll discover new artists and learn the inspiration behind their colorful works, along with some interesting neighborhood history. You’ll also be able to take great photos along the way.

Lake Michigan Skyline Cruise in Chicago

(669 reviews)

from $ 37.58

Chicago Favorites Ultimate Food and Walking Tour

(1068 reviews)

from $ 79.99

Chicago CityPASS®

(457 reviews)

from $ 139.00

The Green Mill The Green Mill

U.S. News Insider Tip: For visitors looking for a bite to eat after a night of jazz music, head across the street to Damera for an authentic Ethiopian meal, or down the block to the Fat Cat for a burger. – Sarah Estime

Best known for serving gangsters during its speakeasy days, the Green Mill invites travelers to step back in time. The long bar that runs along the club's left side sits in front of smokey mirrors and is peppered with decor reminiscent of the Prohibition era. The entire place is cast in a warm reddish glow while old-time jazz plays from the jukebox. The bar – one of Al Capone’s favorites – has no set menu; order whatever cocktails you like (though the chocolate martinis are delicious). There is also a selection of beer and wine.

Garfield Park Conservatory Garfield Park Conservatory free

One of the biggest botanical conservatories in the United States, the Garfield Park Conservatory houses thousands of plant species in eight indoor gardens, as well as 10 acres of outdoor gardens.

Each indoor space has a distinct focus. The Aroid House features varieties of its namesake, which are among the most popular houseplants; it also features sculptures by the world-renowned glass artist Dale Chihuly made specifically for the Aroid House. As its name suggests, the Desert House boasts cacti and succulents, while the Fern Room arranges ferns around an indoor lagoon. The Palm House, the conservatory's largest structure, recreates a tropical landscape complete with more than 70 palm trees. Meanwhile, the Elizabeth Morse Genius Children's Garden aims to educate little ones about plants. Horticulture Hall displays a range of flowers and plants and also has tables where visitors can take a seat and have a rest.

The Richard H. Driehaus Museum The Richard H. Driehaus Museum

Occupying a restored mansion built in 1883, the Richard H. Driehaus Museum presents exhibitions relating to architecture, art and design from the 19th century to the present day.

The Nickerson Mansion containing the museum boasts an entrance hall made with so much marble that the building was nicknamed "the Marble Palace." (The museum takes its current name from the philanthropist who founded it in 2003.) Its reception room features intricate woodwork as well as items from the museum's permanent collection, such as a Tiffany Studios lamp that dates back to the early 1900s. Meanwhile, the front parlor displays Renaissance Revival furniture original to the Nickerson Mansion. The dining room, fitted with elaborately carved oak, houses a silver punch bowl first exhibited at the 1893 World's Columbian Exposition. Other highlights from the permanent collection include a gem-encrusted inkstand, a ceramic clock, multiple chandeliers, paintings, sculptures and an array of decorative items.

Chicago Cultural Center Chicago Cultural Center free

The "People’s Palace," a popular destination occupying a full city block in the downtown Loop neighborhood, is a stunning architectural marvel as well as a venue for a great deal of cultural programming, including art exhibits and concerts. Among its features are one of the largest Tiffany stained-glass domes in the world (made with around 30,000 individual pieces of glass) and a marble lobby adorned with mosaics made of gold, glass and precious stones.

Visitors invariably rave about the impressive structure and its elaborate decorations, saying it’s worth it to pop in for free to see the ornate ceiling.

University of Chicago University of Chicago free

Founded in 1890 by John D. Rockefeller, the University of Chicago is an urban research university in the city's Hyde Park neighborhood close to Lake Michigan. Currently, it has more than 7,000 undergraduate students and more than 10,000 graduate, professional or other students as well as nearly 2,400 full-time faculty members.

Impressive as those statistics may be, they aren't reasons to visit. But the university's 217-acre campus, which was designated a botanic garden in 1997, and its mixture of English Gothic and modern architecture are. Some of the newer structures were designed by celebrated architects like Ludwig Mies van der Rohe and Eero Saarinen, while some of the older ones are adorned with gargoyles that date back to the 1893 World Columbian Exposition. The university welcomes visitors to explore its campus, and provides information about its architecture on its website. Those who've visited before routinely call the buildings diverse and beautiful, and many recommend stopping by in the spring when flowers bloom across campus, or fall when amber leaves transform the grounds.

Chicago in a Day: Food, History and Architecture Walking Tour

(735 reviews)

from $ 131.54

Chicago Gourmet Dinner Cruise on Lake Michigan

(279 reviews)

from $ 131.94

Chicago Craft Brewery Barrel Bus Tour

(220 reviews)

from $ 99.60

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The Top 23 Excursions and Tours in Chicago

If you’re planning some sightseeing in the Windy City, there are so many excursions to choose from. Try these top tours in Chicago!

Chicago, Illinois is famous for its amazing deep-dish pizza, beautiful architecture,  gorgeous waterfront, and unique history. It’s also one of the top tourist destinations in the Midwest and it’s no surprise why!  The city has a ton to offer visitors whether you’re interested in culture, sports, outdoor activities, or nightlife.  

We know that it can be a bit confusing to know where to even start when you’re planning a visit to a city with so many options so to help you get started, we have created this list of the top tours and activities to do in the Windy City.

So Many Ways to See Chicago

If you’re planning a trip to the Windy City, you can’t go wrong with scavenger hunt tours by Let’s Roam ! These walking tours in Chicago are app-guided , and there are options to suit any traveler. From family-friendly sightseeing experiences to adult-oriented pub crawls , there’s no shortage of fun!

The Best Excursions and Tours in Chicago

Below you’ll find a list of the best tours and excursions to do in Chicago.  This is based on the experience of our own in-house travel experts as well as TripAdvisor and Google Map reviews.  Some of them are walking tours while others rely on buses to get around. There are also a few that are adults-only so you may want to skip on those if you’re traveling with the kiddos!

Disclosure: All of the tour departure times and locations were correct at the time of writing however, it’s important to double-check the information before heading out for the tour as these may change, especially if COVID restrictions are put back in place.

Chicago Walking Tours

With its grid-like streets and lovely Riverwalk, Chicago is a fabulous place for walking. Combine this with the show-stopping architecture and the engrossing history and you have all the ingredients that you need for days spent exploring the streets.  While it’s great to stroll along on your own, a sightseeing tour of the city will let you see a whole different side of a city and help you learn the finer details of what makes the city tick. It’s great to do one at the start of your visit as your tour guides can give you great insight into some of the best places to go for dinner or drinks after the tour and if you’re traveling on a budget, you may learn some great money-making tips!

1. Riverwalk & North Loop Tour

Run by Free Chicago Walking Tours , this two-hour walking tour gives an in-depth look into the history of Chicago going all the way back to the late 17th-century until today. The tour covers everything from the role that Chicago played in the Revolutionary War to the Roaring 20s and as you stroll through the Loop, you’ll see the Chicago River, Daley Plaza, the Chicago Cultural Center, and more.  The tour is on a pay-as-you-wish basis so you can be sure that the guides will work hard for their money! 

2. Let’s Roam Chicago Sightseeing Scavenger Hunts

Here at Let’s Roam, we think one of the best ways to get to know a city is through a destination scavenger hunt! On this intriguing   Chicago Loop hunt , you’ll be asked fun trivia questions about some of Chicago’s top attractions including The Bean, the Art Institute of Chicago, the Crown Fountain, and the world-famous Tiffany Dome. You’ll also have plenty of prompts to take great photos to remember your trip by! You’ll learn a lot about Chicago’s storied buildings and epic sculptures!

Once you have finished up with the Loop hunt, don’t forget to go back and do the Magnificent Mile Scavenger Hunt to see sites like Washington Square Park, the Tribune Tower, and the Wrigley Building.  Both tours take around an hour and can be conveniently done on your smartphone using the Let’s Roam app.

3. Chicago Gangsters and Ghosts Tour

After seeing Chicago’s famous attractions, it’s time to go into its underbelly and learn about the gangsters that used to rule this joint.  Chicago is infamous for its gangster past and during the 1920s and 1930s, mobsters were in control of much of the city.  100 years ago, murder and mayhem lurked in the shadows, and today, you can hear all about the men (and women!) that left their mark on Chicago.  

This fascinating (and occasionally bone-chilling Chicago Gangsters and Ghosts Tour is a two-hour-long affair that takes you through the Chicago Loop Vice District, stopping by the Congress Hotel, Death Alley, the Palmer House, and many other creepy places.  Rather than being a theatrical display, the guides tell the stories in a somber, delicate way that makes it easy to understand the impact that the mobs had on the psyche of the city.  Tours leave throughout the day with three daytime tours and one evening tour and you can book tickets online.

4. Dazzling Interiors of the Loop

Chicago is well known for its interesting blend of architectural styles and people around the world can easily identify its skyline. However, few people get a chance to see some of Chicago’s most striking Interiors and Inside Chicago’s Walking Tours wants to change this with their two-hour-long Dazzling Interiors Tour.  During the tour, you’ll get a chance to see the remarkable interiors hidden behind some of Chicago’s most famous facades.  Some of the highlights of the tour are art-deco lobbies, gilded ceilings, and early designs by master architect Frank Lloyd Wright. Tours cover just one and a half miles so they are suitable for people of all ages and this is the perfect way for art lovers to get an in-depth look at some of Chicago’s most distinctive buildings. 

5. Off the Grid Tour

Offered by Free Chicago Walking Tours , a pay-as-you-wish tour operator, the Off the Grid Tour veers off the standard tourist route and visits some of the city’s most Instagrammable spots including Death Alley, the Chicago Cultural Center, and the Pink Flamingo Wall at Flamingo Rum Club.  The tour starts at the ACME Hotel in the River North before leading you through the Loop where you can get photos in front of Chicago’s most recognizable landmarks before finishing up the world’s largest Tiffany Glass Dome.  

The Off the Grid tours are only held sporadically throughout the year so if you aren’t able to join one—don’t worry!  There are still plenty of other free walking tours to choose from including the Loop Interior Tour, the Crime & Gangster Tour, the Millenium Park Tour, and many more.  Take a look at their website for more information. 

Bike and Segway Tours

Walking is one of our favorite ways to explore a new destination but, sometimes, having your own set of wheels. Bike and segway sightseeing tours let you explore a city at a quick pace while staying having the time to soak up the atmosphere.  

6. Bikes, Bites & Brews Tour

What better combination can there be than biking, beer, and bite-sized treats.  During this four-hour tour led by Bobby’s Bike Hike Chicago , riders will cover a whopping 13 miles across Gold Coast, Lakeview, Lincoln Park, and Wrigleyville, making perfectly timed pit stops along the way where they can give their taste buds a workout with pizza, hot dogs, cupcakes, and, of course, beer.  

The wonderful guides and the long route make this the perfect introduction to the city and lets visitors cover an impressive amount of ground in a short period of time. The cost of the tour includes bike rental, food, and drinks and riders must be at least 21 years old.  If you would like to go on a family-friendly version of the tour, they also offer Bobby’s Bike Hike Chicago’s Family Food & Bike Tour. If you love biking, this is one tour of Chicago that you won’t want to miss!

7. Chicago Lakefront Segway Tour

With its relatively flat terrain and sweeping lakefront, Chicago is a fantastic city to explore by segway. Absolutely Chicago Segway Tours gives travelers the opportunity to zoom by some of the city’s most iconic attractions including Millennium Park, Monroe Harbor, and Museum Campus, home to the Shedd Aquarium, Soldier Field, the Field Museum, and much, much more on this eight-mile-long adventure.  Tours last roughly two to two and a half hours and the insightful and entertaining tour guides along with the thrill of riding a segway will make the time go by in a blink of an eye. Absolutely Chicago has a wide range of tours covering different areas of the city as well as themed tours like the Chicago Mob and Gangster Tour and a chilling ghost tour.

While we love the idea of going on walking tours, sometimes the weather (or our bodies!) just isn’t cooperating with us and it’s time to join one of Chicago’s many bus tours.  If you’re tight on time, bus tours are a great way to see many different areas of the city or if you have a bit more time to spare, they are a great way to discover the neighborhoods that you want to go back to!

8. Hop-On Hop-Off Bus Tour

It can be a bit challenging to plan a trip full of exciting sightseeing adventures (trust us, we know!) but Big Bus makes it easy to get a great overview of Chicago without even having to leave the comfort of your bus seat (but it’s much better if you do!).  These useful bus tours allow passengers to get on and off as often as they wish at one of the conveniently located stops.  This allows you to see the things that you want but skip the things that you aren’t interested in. Most tour packages are good for one day (roughly eight hours) and it’s possible to “upgrade” your ticket to include extra activities or even extra days.  Expert tip: Keep a close eye out for the bus signs or make a mental note of where you got off the bus as they can be really hard to see at a few of the attractions. 

9. See It All Minibus Tours 

If you love the idea of a bus tour but aren’t sure that the hop-on-hop-off buses are right for you, you may want to consider one of the See It All Minibus Tours .  During the tour, you’ll be whisked around downtown and the north side of the city in a climate-controlled minibus, passing by the Loop, Millennium Park, the Buckingham Fountain, the Wrigley Building, the Chicago River, Lincoln Park, and even the Original Playboy Mansion. 

There is an entertaining narration that plays throughout the journey telling you about the city’s long history and colorful characters and you can hop out and take photos at four designated photo stops along the way. 

If you want to keep the fun going after the tour, you can add on a Chicago River Architecture Boat Tour.

10. Family Secrets Bus Tour

If you want to get an inside look at a modern-day Soprano-like organized crime family, this unique tour can take you deep into the world of the mafia. The Family Secrets tou r is run by Frank Calabrese Jr. who once worked as a soldier in his dad’s Chinatown crew.  During the two-hour bus tour, he gives an unfiltered, firsthand account of life in the mob by telling stories of the drama and endless killings that he witnessed.  He takes you to actual crime scenes in the areas where the Chicago Mob once worked, lived, and played.   Private tours are available throughout the week and begin outside of the Chicago Chop House on West Ontario Street. 

11. Chicago Crime and Mob Bus Tour

Organized by Chicago Crime Tours and Experiences , this crime-themed two-hour-long bus tour gives visitors the chance to go deep into the world of Al Capone, John Dillinger, and The Untouchables, who ultimately brought them down through a series of stops at well-known crime sites, including the site of the infamous Valentine’s Day Massacre, and the courthouses where the city’s most prolific criminals had to stand trial for their crimes.  While their signature tour is offered during the day, there is also a two-and-a-half-hour-long nighttime tour that puts everything in an even darker light!

Food Tours and Bar Crawls

Here at Let’s Roam, two of our favorite pastimes include eating and touring so food tours are one of our must-do activities wherever we go. Food tours are an amazing way to not only try some hidden culinary gems but they are also perfect for learning more about some of the off the beaten track parts of a city. 

12. Gateway to the West Loop Food Tour

With a slew of mouth-watering delights hidden in eateries all across the city, it can be tough to know where to go for the best eats in the Windy City. Chicago Food Planet’ s three-hour-long Gateway to the West Loop Food Tour helps you get your hands on some of the best dishes that the city has to offer ranging from pizza to doughnuts.  Throughout the tour, you’ll learn insider information about the history of both Chicago and the West Loop and your guides will be more than happy to impart some local wisdom.  Make sure to come hungry as they give out some hefty portions during this tour. 

If you’re blown away by this tour, they also have a food tour of Chinatown.

13. Original Chicago Pizza Tour

If there is one food that you absolutely must try in Chicago, it has to be the deep dish pizza. On this tour led by Chicago Pizza Tours , you’ll get to visit some of the city’s most beloved, independently-owned pizzerias.  The tour includes six or more slices of pizza (wow!) and the guides are informative and fun and will teach you about a lot more than just pizza which makes it well worth the money.  They offer bus tours and walking tours so it’s perfect for people with mobility issues and if you want to make it a bit more festive, you can opt for the Chicago Pizza and Cocktail Tour. 

14. Taste of Chicago Food Tour

This is another food tour that’s sure to please even the pickiest of eaters. Run by Tastebud Tours , this appetite extravaganza takes you through Chicago’s downtown Loop stopping at many of the area’s most popular eateries to try the deep-dish pizza, sandwiches, and desserts. The tour guides will point out some of downtown’s most important attractions on the way and will impress you with this encyclopedic knowledge and endless enthusiasm.  

15. Historic Chicago Walking Bar Tour

History lovers who want to learn more about the Prohibition era can join this part-history tour, part-bar crawl offered by the team at Chicago Detours .  During the two-and-a-half-hour tour, you’ll visit some of Chicago’s most historic bars and pubs including a Jazz Age Hotel and the  Billy Goat Tavern, located inside a 19th-century mansion.  

If you’re looking for another off-beat tour, Chicago Detours also runs an 1893 World’s Fair Tour and a Chicago Neighborhoods Tour that takes you into the north, west, and south sides of the city and includes a stop in a neighborhood dive bar and the opportunity to dine at a home-style Polish restaurant. Yum!

16. Chicago Prohibition Bus Tour 

This bus tour is certainly unique!  The three-and-a-half-hour Chicago Prohibition Bus Tour visits four former speakeasies where you can learn about this eventful period in Chicago’s history including the types of drinks that people would have ordered when they strutted up to the bar.  All of the stops on the tour are very different so you don’t need to worry about things feeling repetitive and the smooth-talking guides help move the evening along nicely.  If you want to get some exercise, there is also a walking version that lasts two and a half hours.

17. Chi-town Bar Crawl Scavenger Hunt

If you want a unique take on the standard bar crawl, the Let’s Roam’s Chi-town Bar Crawl may be right up your alley! Here, you can battle your closest friends and drinking buddies to crazy challenges until one of you is the champion of Chi-town. The challenges go from easy-peasy to difficult and are perfectly designed to bring out your competitive side and you may even discover a new favorite hangout or rediscover your old stomping grounds. While the hunt normally takes around one and a half to two hours, you can make it as long or as slow as you want!

Between the enormous and sparkling Lake Michigan to the quaint and charming Chicago River, Chicago is a watery city so it probably comes as no surprise that one of the best ways to explore is by boat! Luckily, there is a huge array of sightseeing cruises to choose from and virtually all of them will give you great views.  Just keep in mind that Chicago has earned the nickname the Windy City for a reason and umbrellas may not be the best things to use as rain cover if you’re going on a boat tour. It is a good idea to pack a waterproof jacket or a poncho with you just in case!

18. Chicago Architecture Foundation River Cruise

This special architecture cruise takes visitors along the Chicago River while expert volunteer docents tell them the inside scoop on 50 of Chicago’s most notable buildings.  The Chicago Architecture Foundation’s River Cruise uses the fleet of Chicago’s First Lady Cruises for these 90-minute tours which means that you’re in the hands of professional staff and have access to full-service bars and open-air upper decks that are the perfect spot to get some great photos.  There are daytime and nighttime sailings and, for just about $5 more, you can also visit the Chicago Architecture Center.  

19. Chicago Sunset Cruise

This relaxing cruise run by Wendella Tours and Cruises is one of the best ways to finish off a long day of sightseeing.  During the 90-minute cruise on Lake Michigan, you’ll watch as the sun sets behind the city skyline and turns the sky into a swirl of pink, orange, and red.  The cruises have a full bar where you can purchase drinks and snacks and there is a climate-controlled lounge area that keeps you warm in the winter and cool in the summer.  The cruises leave from Michigan Avenue. The departure times vary throughout the year so make sure to check their website for the most up-to-date information and to book tickets.  

If you want something a bit shorter or only have time during the day, they also offer a 45-minute architecture tour on the Chicago River.  This tour will highlight some of the most famous Chicago landmarks and you can learn a lot during a short period thanks to the informative guides!

20. Historic Chicago Tour

Run by Urban Kayak Chicago Riverwalk , the Historic Chicago Tour gives you a “duck’s” view of the beautiful Riverwalk as you paddle down the Chicago River. Along the way, you’ll stop at key points to learn more about the area’s history and architecture. Although there is a bit of boat traffic along the river (OK, a lot of boat traffic), the guides know how to keep everyone safe and it’s appropriate for even beginner kayakers.  If you prefer to go it alone, Urban Kayak also rents kayaks and paddleboards and offers classes to help you up your paddling skills.

21. Skyline Lake Tours

With unparalleled views over Lake Michigan and the city skyline, Shoreline Sightseeing Skyline Lake Tours offers breathtaking, 40-minute cruises covering six miles of the shoreline.  Some of the highlights of the tour include the Willis Tower (home of the Skydeck Observation Deck and formerly known as the Sears Tower), the John Hancock Center, the Field Museum, and the Adler Planetarium.  There is a bar on board to buy drinks and a pre-recorded track of interesting information playing throughout the ride. While this is a more general tour, they offer an architecture tour, as well. 

Tours depart from Navy Pier on the half-hour, with extra cruises sometimes added in spring and fall. Excursions are dependent on weather, so be sure to check times and availability before you go. Generally, there are no tours during colder months of the year.

22. Chicago Skyline Sail

There is something truly special about sailing. From the wind rushing through to sails to the sound of the waves lapping against the boat, it’s a relaxing experience and a great way to explore Lake Michigan.   Tall Ship Windy (love the name by the way) offers a Skyline Sail onboard a 148-foot four-masted schooner.  You can get sweeping views of the Chicago skyline from the deck of the boat during the 75-minute ride and the soaring skyscrapers create a mesmerizing juxtaposition to the traditional sailboat.  If you’re traveling with kids, make sure to check their list to see if they have any of their pirate-themed outings or fireworks cruises while you’re in town!

23. Seadog Lakefront Speedboat Tour

While sailboats and cruises are a great way to get out on Lake Michigan if you’re in the need for speed look no further than the Seadog Lakefront Speedboat Tour operated by City Cruises by Hornblower. As you whiz across the lake during this 30-minute ride, you can absorb the skyline views while you listen to the guides give vivid and entertaining descriptions of what you’re seeing.  Keep in mind that the boat is open-air, so you might get wet, and it’s probably best to avoid it during rough weather.

If you want to zip across the lake even faster then you can opt for their extreme thrill ride. Conversely, for a more leisurely option, you can opt for a brunch, lunch, or dinner cruise or try one of their special holiday-themed boat rides.  There are plenty of options to choose from so it’s a good idea to check out their website before deciding on a tour.

Ready to roam?

We hope that this list of the top tours and excursions in Chicago has left you inspired to pack your bags and head to the Windy City for your next vacation.  If you need more expert advice, make sure to check our lists of the Best Things to Do in Chicago and the 25 Best Day Trips From Chicago , or download our app and try any of our Chicago scavenger hunts . 

As always, we would love to hear your feedback and please let us know if we have missed any hidden gems! 

Happy hunting!

Frequently Asked Questions

Some of the most popular walking tours in Chicago include options from Free Chicago Walking Tours, scavenger hunt tours from Let’s Roam , and the Chicago Gangsters and Ghosts Tour.

If you’re planning some sightseeing in Chicago , don’t miss out on the intriguing crime tours, and be sure to hop on a boat cruise. Lastly, try at least one of the app-guided scavenger hunt tours from Let’s Roam !

There are many great boat tours in Chicago , including the Chicago Architecture Foundation River Cruise, the relaxing sunset cruise from Wendella Tours and Cruises, and the Urban Kayaks’ Historic Chicago Tour.

The Windy City is full of amazing pubs and grub! If you’d like to tour Chicago pubs , try Let’s Roam’s Chi-town Bar Crawl , the Chicago Prohibition Bus Tour, or the Historic Chicago Walking Bar Tour.

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Best Things to Do in Chicago Today

This post has information on the most fun things to do in Chicago today, tonight, tomorrow, or anytime.

We include nighttime, free, as well as family-friendly events and activities. Let's get started!

• Nighttime Activities
• Free Things to Do
• Family-Friendly
• Top Attractions
• By Month/ Neighborhood
• Suggested Itineraries

TOP 10 EVENTS AND ACTIVITIES

Planning a visit to Chicago can be overwhelming with the sheer number of world-class attractions.

Our suggestions for the top fun things to do in Chicago are listed below.

For more ideas on top popular attractions, check out our comparison guide on tourist discount passes , which could help you save money on entry fees. 

1. Watch a Pro Sports Game

Chicago has multiple well-loved professional sports teams , which means that no matter when you come to the city there will most likely be a game happening somewhere. 

• Chicago White Sox | April - October
• Chicago Cubs | April - October
• Chicago Bears | September - January
• Chicago Blackhawks | October - April
• Chicago Bulls | October - April

Click here to see all the matches in Chicago .

Many of these teams will play evening games during their regular seasons, so this could be an excellent activity to enjoy after dark.

For more things to do in the evening, please read our nighttime activities section.

2. Learn about Chicago Architecture

One of the top things Chicago is known for is the diverse and impressive architecture you’ll find around the city.

Learn about the different styles and time periods on a guided Architecture Tour of Chicago.

Just as there are many diverse bridges, buildings, and structures, there are diverse ways of seeing it all and learning about the architects.

Architecture tours come in multiple forms like river tours , which give an interesting perspective, as well as free walking tours .

The biggest architecture enthusiasts will enjoy the Chicago Architecture Foundation’s over 3-hour bus tour . 

3. Attend a Concert

There is an abundance of great venues where you can find live music in Chicago .

The city has a wealth of local bands and also frequently attracts big-name artists.

If you’re interested in going to a concert, make sure to check and see what’s on at the following venues:

• Chicago Theatre
• Allstate Arena
• Hollywood Casino Amphitheatre
• Aragon Ballroom
• House of Blues Chicago
• Subterranean
• Concord Music Hall

Click here to find all the concerts in the city . No matter the genre you’re into, we’re sure you’ll find it!  

4. Take a Sightseeing Tour

The best introduction to Chicago is to take a tour.

Free Tours by Foot offers walking tours of Chicago of various neighborhoods, including the Loop, the Riverwalk, and specialty tours like an evening Chicago Ghost Tour.

If you’re looking for something a bit more exciting than walking, there are many ways to explore the city:

• Chicago Bus Tours
• Segway Tours

Foodies can get excited about Chicago’s culinary culture on food tours, as well.

You can sample your way through different neighborhoods with these self-guided food tours:

• Greektown Food Tour
• Little Italy Food Tour
• Andersonville Food Tour
• Mexican Pilsen Food Tour

5. Go to the Theater

Chicago’s theatre scene is a close second to New York’s Broadway (well, we think so!). Find all the theatrical performances in Chicago here . 

We also recommend taking a tour of the Chicago Theatre before or after catching a show.

The crowd-pleasing Blue Man Group has year-round shows in Chicago.

If you book soon enough, you could get seats in the Splash Zone and end up covered in colorful paint! 

Comedy fans will love seeing a performance at Second City or Annoyance Theater, which all offer extremely affordable tickets! 

The best way to see a show on a budget is during Chicago’s Theatre Week .

6. Visit Chicago’s Navy Pier

One of the most well-known attractions in Chicago is the Navy Pier.

It is a highlight of visitors’ visits to the Lake Michigan shore at any time of year, thanks to Winter Wonderland when it's cold out and fireworks in the summer. 

Here you’ll find boat tours (it’s an actual pier), the Chicago Children’s Museum, restaurants, and entertainment.

Find out more about how you can spend a few hours at the pier with our post about things to do at the Navy Pier .  

7. Find an Observation Deck

Chicago has an impressive skyline day or night.

You can see it all from a birds-eye view and marvel at the architecture from one of the city’s observation decks .

The main Observation Decks in Chicago are:

• Skydeck Chicago
• John Hancock 360 Observatory

Each is included for free on at least a few of the tourist attraction discount passes .

8. Enjoy a Dinner or Boat Cruise

From Chicago river cruises to the waters of Lake Michigan, there are multiple boat tours available to take . 

One of the most popular options is to have an enjoyable lunch or dinner on the water to relax and have fun with your travel buddies or family.

These lunch and dinner cruises usually last 2 to 3 hours. 

9. See the Most Popular Attractions in the City

From interesting architecture and museums to public art and sports stadiums, Chicago has plenty of popular attractions to see. 

Some of the Popular Attractions Include: 

• Wrigleyville and Stadium Tours
• Museums like The Field Museum
• Millennium Park
• Observation Decks

For a list of even more fun attractions take a look at the section below .

10. Save Money with a Tourist Discount Pass

Visitors can save up to 50% on retail admission prices with a Chicago tourist pass.

These services provide heavy discounts at some of the most popular attractions in the city.

Here are a few of the sites you can visit with various discount passes, which include great year-round activities such as:

• Shedd Aquarium
• Museum of Science and Industry
• 360 Chicago Observation Deck
• Adler Planetarium
• Art Institute of Chicago

If you plan to visit even a few of these attractions, you could easily save quite a few dollars as well as time, since select attractions on these cards have skip-the-line passes.

To find out which city pass will save you the most, read our full post . 

11. Honorable Mention: Take a Food Tour

If you want help finding the best dishes in Chicago, consider taking a Secret Food Tour .

This outing includes tastings at 6 different locations, giving you a good sense of the most popular meals in the city.

Guests can expect to enjoy samples of deep-dish pizza, Italian beef sandwiches, pierogis, multiple chocolates, and more.

In addition to all the great food, you can also get an upgraded drink package if you're interested in having a few good brews along the way.

For even more great options, check our post covering Chicago food tours .

THINGS TO DO AT NIGHT

Chicago has some exciting nightlife and entertainment to enjoy, from tours to live music and open-late attractions.

Most of these activities are fun things to do in Chicago for adults.

See our full post on things to do in Chicago at night for more ideas on what to do.

12. Try to Escape from The Escape Game

From an art heist to a prison break to special ops, you get an hour to go through this real-life puzzle.

The Escape Game Chicago has over 2300 5-star reviews - and don't worry if you don't make it, you'll get a discount to try again!

The Escape Game Chicago is fun for all ages.

13. Take a Chicago Ghost Tour

Discover the spooky history of Chicago and hear tales of the supernatural on a professionally guided ghost tour of the city.

In addition to learning about creepy myths and legends that were born in the area, you’ll also likely hear a lot about the more disturbing criminal history of Chi-town.

14. See a Live Performance in the Theatre District

No matter when you choose to visit Chicago, chances are you’ll have several opportunities to see a musical or other theatrical performance.

For more information about the best theatres in the windy city and excellent opportunities to save money on tickets, check our post covering the Chicago Theatre District .

15. Enjoy the City Lights From an Observation Deck

There are two really great observation decks in Chicago , and both of them are open after dark, giving you the opportunity to see the city as it lights up at night.

The Skydeck is open until 10 pm in the summer and 8 pm in the winter, while 360 Chicago is open until 11 pm on weekends.

16. Watch the Blue Man Group

This troupe has set up a semi-permanent residence in Chicago, which means that you can reasonably expect them to be performing whenever you choose to visit the windy city.

In addition to being an excellent nighttime activity, the Blue Man Group is also appropriate for kids and teens, which makes it a good choice for families as well.

17. Cheer on Your Favorite Team

As we mentioned in the top 10, there are a lot of great sports teams in Chi-town.

Many of them host games after dark, making this an excellent activity to enjoy at night.

Check this list of sporting events in Chicago to find a game that begins in the evening.

18. Go to a Chicago Symphony Orchestra Concert

This city tends to attract a lot of popular musicians throughout the year.

But, if you’re a fan of classical music, the Chicago Symphony Orchestra offers one of the best experiences in the area.

In addition to performing the works of beloved composers such as Mozart, Chopin, and more, this group also hosts movie concert events in which the music from the film is performed by the orchestra.

19. Go to a Museum After Dark

Some of the museums in Chicago offer fun activities in the evening.

The MCA has a summer jazz series called Tuesdays on the Terrace which typically starts at 5:30 pm and lasts about an hour.

It’s also worth noting that the Art Institute of Chicago is open until 8 pm on Thursday and Friday.

20. Savor a Chicago-Style Sausage

No jaunt to Chicago is complete without savoring a Chicago-style sausage and hot dog. These are no ordinary sausages—they're a culinary delight adorned with toppings like pickled cucumbers, tomato slices, and tangy mustard.

Roam the city and partake in a sausage journey, sampling offerings from various stands to find the best in town.

21. Enjoy a Chicago-Style Deep Dish Pizza

This is the only city in the world where you can order an authentic deep-dish pizza, so why not make this popular dish part of your dinner plans?

If you want some help finding the best slice in town, make sure to read our post covering where you can find some delicious Chicago-style deep-dish pizza .

22. See a Comedy Show at Second City

The Second City Theatre is one of the best comedy clubs in Chicago, and they host several great comedy shows throughout the year.

Many notable comedians like Chris Farley, Tina Fey, and Bill Murray have graced the stage here, making it a hallmark of Chicago's comedy scene.

Check this list of stand-up comedy shows to see who is performing in Chicago.

23. Take a Walk on the Chicago Riverwalk

If you’re looking for an affordable activity after dark, one of the best things to do is just down the Chicago Riverwalk .

This is a great location to enjoy watching the city light up as the sun goes down, and it’s also one of the best spots to either begin or end a romantic date.

24. Visit to the John Hancock Center

The John Hancock Monument stands as more than a lofty edifice—it's a beacon in Chicago's sky tapestry. As evening falls, this location gifts visitors with jaw-dropping panoramas of city glow and neighboring Lake Michigan.

The observatory remains open into the night, positioning it as a dreamlike venue for after-dark activities. Grab a signature cocktail from the on-site tavern and let yourself become enveloped in the vast urban vista for a memorable evening.

For thrill-seekers, don't miss the Tilt experience on the observatory floor, offering a unique and vertigo-inducing view of the Tribune Tower and beyond.

For more details, take a look at our full post on things to do in Chicago at night .

THINGS TO DO FOR FREE

There are plenty of things to see and do while visiting Chicago on a budget!

Read our full free things to do in Chicago post for more details. Listed in this section are our top 10 free activities in Chicago:

25. Take a Free Walking Tour

There are a lot of interesting things to see in this city, and many of them are included in free walking tours.

We have pay-what-you-wish services covering a variety of subjects such as the architecture of the city, the Chicago Riverwalk, the Magnificent Mile, Millennium Park, and even a Ghost tour!

Check this list of free Chicago walking tours to find one you’ll enjoy.

26. Go to a Free Concert or Festival

During the summer months, there are often several free festivals held at various public squares and parks throughout the windy city.

Many of these events will also include free concerts, allowing you to enjoy some live music without worrying about ticket prices!

Check our monthly TTD posts to see what’s on the schedule when you plan to visit Chicago.

27. Explore a Free Museum

There are several museums in Chicago that offer free admission on either a daily basis or at least once a week.

No matter what you’re interested in learning about, chances are there is a museum you’ll enjoy exploring.

Some of the most notable examples include the Chicago Design Museum, the Museum of Contemporary Photography, the National Museum of Puerto Rican Arts and Culture, and many more.

28. Spend Some Time in Wicker Park

This is one of the trendiest areas in Chicago, and it’s full of interesting shops, restaurants, and even street art.

We currently offer a self-guided walking tour of Wicker Park which includes several popular stops, including the public park itself and its statue of Charles Wicker.

29. Discover the Architecture of Chicago

The windy city is home to some of the most impressive architectural feats of modern times, including a variety of notable skyscrapers.

We currently offer a free architectural walking tour of Chicago , and there are also self-guided tours covering locations such as Navy Pier, Millennium Park and the Downtown Chicago Theatre District.

30. Visit a Public Park

There are several excellent public parks in Chicago where you can enjoy a nice walk, perhaps go on a picnic, or even take your kids to a playground.

If you’re looking for help picking the best park to visit, check our post covering 6 of the best Chicago parks .

31. Enjoy Beautiful and Interesting Street Art

You’ll find a lot of unique artwork sprinkled across this city, including both planned-out sculptures and original graffiti work from street artists.

Consider using our guide to public art in Chicago to find some of the most well-known and high-quality artwork which is entirely free to experience.

32. Get Free Entry to Popular Attractions

Depending on which service you choose and how you use it, you could easily use a Chicago tourist pass for enough different activities that eventually anything else you used it for would be entirely free.

33. Take a Free Brewery Tour

There are several great places to great beer in the windy city and even some breweries that offer entirely free tours.

In addition to providing details about some of the best pubs and bars in the city, our guide to Chicago Craft Beer also includes information about local breweries and the (sometimes free) tours they offer.

34. Visit the Navy Pier

There are a lot of fun things to see and do at the Navy Pier, including a variety of notable sites like the Crystal Gardens, the Miller Lite Beer Garden, a Ferris Wheel, and more.

If you’re looking for help finding the best places to visit, check our self-guided tour of Navy Pier for guidance.

For more budget-friendly activities, check out our full free things to do in Chicago post.

35. Adventure to Cloud Gate (The Bean)

Misty Archway, informally dubbed "The Bean," is an essential city sculpture set in Millennium Park. The bonus—it's free of charge.

Its reflective surfaces create interesting opportunities for photography. The park itself is a frequent stage for no-cost artistic and communal events, serving as a core for creative spirits.

The park offers a unique view of the Chicago skyline, making it a contrast to the towering Willis Tower nearby.

36. Explore the Grant Park

Nicknamed "The People's Meadow," Grant Park delivers another complimentary experience. It showcases decorative floral arrangements, water art features, and relaxed pathways.

This is the optimal backdrop for casual strolls or alfresco dining with the family. In addition, the locale frequently serves as the setting for free community events such as musical fiestas and open-air films.

The park serves as a tranquil space for a stroll, offering a calming backdrop to the bustling Michigan Avenue.

37. Spend the Time at Lakeside Walkway (Lakefront Trail)

For those fond of walking or cycling, the Lakeside Walkway supplies miles of striking, free pathways.

Adjacent to Lake Michigan, this route presents captivating scenes and abundant options for outdoor fun. Beaches, gardens, and other natural highlights can be explored along this path without any financial commitment.

The trail offers vistas of Soldier Field and the 103rd floor of Willis Tower, adding another layer of interest to your outdoor experience.

THINGS TO DO WITH KIDS

Visiting Chicago with the kids?

Here are our top ten ideas for family-friendly Chicago activities that both children and their parents can enjoy.

Make sure you read our full post on things to do with kids in Chicago for more inspiration!

38. Take a Bike Tour of the City

With so many interesting things to see and do in Chicago, it can be difficult to get around and discover all the sites.

Thankfully, there are bike rental services that offer bicycles for both adults and children.

All bike rental companies provide helmets and other protective gear to keep everyone safe.

Kids love to ride bikes, so this is a fun way to explore the city and see some of the most notable landmarks as a family.

39. Visit the Chicago Children’s Museum

The Chicago Children’s Museum has a lot of fun, hands-on exhibits that are designed to help kids learn about the world around them.

If you’re looking for an activity that will engage the imaginations of your children, this is an excellent museum where they can go on a hunt for dinosaur bones, create art, play in a treehouse, and more.

Best of all, admission is free for children 15 and under on the first Sunday of every month, and they offer late hours every Thursday!

40. Cheer on a Chicago Sports Team

As we’ve mentioned before, Chicago is home to several great teams in multiple sports including baseball, basketball, hockey, and football.

No matter which sports your kids love, chances are you’ll have a chance to take them to a game during your trip to the windy city.

Check this list of sporting events in Chicago to find one that your children will enjoy.

41. Enjoy Family-Friendly Attractions For Less

There are a lot of popular kid-friendly activities and attractions that are included with Chicago tourist passes .

Depending on how you use these services, you could save anywhere from 20% - 50% off ticket prices.

If you plan to take your kids to locations such as Shedd Aquarium, 360 Chicago, Skydeck, LEGOLAND, Brookfield Zoo, Chicago Children’s Museum, or the Navy Pier, we recommend using a tourist pass to save money.

42) Explore the City Using Public Transportation

Chicago is well known for its public transportation system, which allows residents of the city to get around with ease.

Whether you want to hop on the train or take a bus, this is undoubtedly one of the most affordable ways to travel around Chi-town.

Check our post on the Chicago Public Transportation system for more information.

43. Spend Some Time on Lake Michigan

If you want a great view of the city skyline from the water, a cruise on Lake Michigan is an excellent and family-friendly activity.

There are several different Chicago cruises available, and there are also sailboat and kayak services you may want to consider.

44. Go to a Family-Friendly Comedy Show

Although most comedians tell jokes specifically for adult audiences, there are some comedy clubs and troupes that perform more family-friendly fare in Chicago.

CSZ offers excellent comedy shows aimed at all ages, and they also provide training for both adults and kids!

45. Take the Kids to Navy Pier

With its many family-friendly attractions and even amusement rides like a Ferris wheel and carousel, this is probably one of the most perfect locations in Chicago for children and their families.

In addition to all the traditional waterfront activities, there is also an IMAX Theatre, Funhouse Maze, the Chicago Children’s Museum, and more fun things to see and do at Navy Pier .

46. Winding Path at Maggie Daley Park

The Winding Path in Maggie Daley Park is a circuit designed explicitly for family amusement. During colder months, it transforms into a frozen skating loop, and in warm weather, it welcomes scooters and roller skates.

It offers an interactive and one-of-a-kind way for families to exercise in the great outdoors. This ribbon-like path is perfect for families, whether they prefer to ice skate in the winter or roller skate in the warmer months.

Mini-golfing located here has a certain whimsical charm, especially because the course is lined with miniature versions of well-known Chicago landmarks, such as the Picasso sculpture in Daley Plaza and the six-foot-tall Willis Tower.

47. Discover the Crown Fountain

Crown Fountain is more than just a water feature—it's an interactive marvel and a social gathering point. Nestled in Chicago's Millennium Park, this fountain stands out with its two glass-brick towers, each equipped with a large LED screen.

These screens project the faces of Chicago residents, making it a deeply communal and inclusive work of public art.

48. Discover the Tallest Buildings in Chicago

The windy city is home to some of the most historic skyscrapers in the world, and there are many different ways to see these landmarks.

Whether you’d rather save money with a self-guided tour, or you want to see these incredible buildings from the water on a cruise, there are several great Chicago architecture tours to choose from.

49. See a Live Magic Show

Give your kids the opportunity to be amazed at clever tricks and seemingly impossible feats performed by a live magician!

The Chicago Magic Lounge hosts a lot of great magic shows throughout the year, and these events are sure to be a hit with the family.

For more things to do with the kids, read our family-friendly activities in Chicago post.

CHICAGO’S TOP ATTRACTIONS

Below is a list of many of the best things to see and places to visit in Chicago.

For in-depth information on how to visit these Chicago attractions, simply click on the site’s name and you will find ticket prices, tips on getting discounts, and what you can see while there. 

Top Chicago Attractions:

• Lincoln Park Zoo | Lincoln Park Conservatory
• Chicago Theatre Marquee Tour
• Art Institute
• Chicago Field Museum
• Skydeck vs. Hancock 360*
• Lincoln Park Zoo | Lincoln Park Conservatory 
• Visit Graceland Cemetery
• The Navy Pier
• Free Museums and Art Galleries in Chicago
• Free Tourist Attractions

MONTHLY THINGS TO DO IN CHICAGO

We think any time is the best time to visit Chicago. See our monthly posts to see what's happening when you are in town.

• January   ( weather )
• February   ( weather )
• March   ( weather )
• April   ( weather )
• May   ( weather )
• June   ( weather )
• July   ( weather )
• August   ( weather )
• September   ( weather )
• October   ( weather )
• November   ( weather )
• December   ( weather )

Winter Season (Nov, Dec, Jan, Feb)

• Thanksgiving and Christmas Activities in Chicago
• Chicago Holiday Tours
• New Year's in Chicago
• Valentine's Day Ideas in Chicago
• Things to do in the Snow/Winter

Springtime (March, April, May)

• Things to do in the Rain 
• St. Patrick's Day in Chicago
• Easter in Chicago
• Cinco de Mayo

Summer in the City (June July, Aug)

• Top 10 FREE Things to Do in the Summer 
• Visit Chicago's Beautiful Parks
• Explore Chicago on a Bike! 
• Music Festivals
• Tall Ships Fest
• 4th of July in Chicago

Fall (Sept, Oct)

• Oktoberfest in Chicago
• Join our Pay-What-You-Like Haunting History Ghost Tour 
• Run or cheer for the Chicago Marathon!
• Halloween in Chicago
• Top 10 Things to do in Chicago in the Fall

Let Us do the Planning | Itineraries for Chicago

• Chicago in 24 hours | Budget Itinerary

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51 Best & Fun Things To Do In Chicago (Illinois)

By: Author Jerric Chong

Posted on Published: September 1, 2020  - Last updated: October 17, 2023

What comes to mind when you think about Chicago?

Is it the gleaming skyscrapers and metallic bridges and buildings?

Is it the museums, theaters, galleries and other places of high art?

Is it the deep-dish pizza with its sticky cheeses stretching between your fingers?

Chicago is all of these things and more.

It welcomes 57 million visitors per year, and they’re all looking for the best places to see within the city.

They don’t leave disappointed.

Here are just a few things to do in Chicago, Illinois.

They range from the fun to the fanciful, and they’re sure to give you great memories of the Windy City!

Table of Contents

1. Millennium Park

f11photo / Shutterstock

You can’t visit Chicago without visiting Millennium Park .

Not only is it one of the most famous places in the city, but its events, activities and festivities put it among the most-visited tourist attractions in America.

It’s anchored by “Cloud Gate,” the bean-shaped metal sculpture that has come to define Chicago.

Beyond the bean, you might recognize its ice rink from countless wintertime Christmas movies, or you might be familiar with its gigantic, video-playing water fountain that’s always a hot spot for selfies.

Other features of the park include a theater, botanical garden, art gallery and bike station.

An outdoor pavilion hosts concerts and carnivals.

A winding pedestrian bridge connects everything together.

If you’re looking for the best things to do in Chicago, it doesn’t get more iconic than Millennium Park.

It’s the Chicago equivalent of Times Square.

You’ll want to visit it at least once just to say that you’ve been there.

Address:  201 E Randolph St, Chicago, IL 60602, United States

2. Riverwalk

Page Light Studios / Shutterstock

The Riverwalk is exactly what it sounds like: a pedestrian trail that stretches alongside the Chicago River.

It’s 1.25 miles, so it doesn’t require a punishing amount of exercise, but it’s long enough to offer a wide range of events and activities for visitors of all types.

Are you feeling peckish?

Grab a bite to eat at one of the many cafes, bistros, bakeries and restaurants that line the water.

Do you want to shop ’til you drop?

Stock up on souvenirs everywhere from luxury boutiques to kitschy street stalls.

Culture lovers will enjoy the museums and theaters.

Outdoor enthusiasts can rent a bike, hop aboard a kayak or take a self-pedaling boat tour.

Couples can stroll under the stars; families can picnic in grassy fields or on top of stone steps that overlook the water.

The Riverwalk is a must see destination in Chicago.

There’s so much potential for fun that it’s almost like a mini-city in its own right.

You could spend your entire vacation exploring this 1.25 mile, and you still wouldn’t hit everything!

Address:  Chicago Riverwalk, Chicago, IL 60601, United States

3. Willis Tower

Atosan / Shutterstock

Formerly known as the Sears Tower, the Willis Tower is a staggering 1,729 feet at its tallest spire.

This used to be enough to claim the title of “tallest building in the world,” but the completion of other skyscrapers in Dubai and Tokyo has knocked it down the list.

Still, the Willis Tower is one of the crowning jewels of Chicago.

In addition to being a busy commercial space for television and radio, it also has several observation decks for tourists.

You’ll enjoy breathtaking aerial views of streets, sidewalks, lakes, bridges and clouds as you marvel at a horizon that stretches for miles.

The most well-known observation point is the Skydeck, a high-rising platform that has walls and floors made entirely of glass.

There’s also the Skydeck Ledge, a series of transparent boxes jutting out from the side of the building that will allow you to walk on air from dizzying heights.

It might not be the tallest skyscraper in the world anymore, but the Willis Tower is definitely the tallest in Chicago, and it might even be the tallest in Illinois.

It’s guaranteed to give you a swooping sensation in your stomach as you look out at the world from 110 stories high!

Address:  233 S Wacker Dr, Chicago, IL 60606, United States

4. North Avenue Beach

You might think of Chicago as a cold, windy place, and it’s true that it gets a lot of the snow that brews over Illinois every winter.

However, it isn’t winter all of the time.

A summer in Chicago can be one of the best that you ever have, especially when you hit the beaches!

North Avenue Beach isn’t the only place to get some sand and surf in Chicago, but it’s one of the best.

You can go swimming or boating; you can rent a bike, kayak, paddle board, jet ski or water tube; you can take a yoga class as the sun rises or play a volleyball game as the sun sets.

Indoor activities are also available at a massive beach house that’s designed like a blue-and-white ocean liner.

It covers more than 22,000 square feet, and when you’re not engaging in its many entertainments, it offers breathtaking views of the water.

Buy a hotdog on a stick and take a stroll down North Avenue Beach.

As one of Chicago’s best shorelines, it’ll always live up to the hype.

Address:  1600 N Lake Shore Dr, Chicago, IL 60613, United States

5. Taste of Chicago

hayden. h / Shutterstock

With more than three million visitors per year, the Taste of Chicago is the largest food festival in the world.

It’s an absolute smorgasbord of everything from sloppy street food to elegant, restaurant-quality dishes.

If you like getting your grub on, it should be at the top of your bucket list!

Admission is free, and the food is sold through a ticket system that allows for both sample- and full-sized purchases.

You can stuff your face with an entire pizza; you can explore different flavors of noodles, burgers, tacos, tamales, soups, pastries and ice cream bars.

One of the selling points of the Taste of Chicago is that it welcomes vendors from all around the globe, so you can enjoy everything from authentic egg rolls to crazy gelato cups on the same street.

There are other forms of entertainment, too.

While you’re munching your way through the stalls and trucks, you can also enjoy games, dances, outdoor concerts, live cooking demonstrations and bohemian art galleries.

One year even featured a silent disco!

Forget about the boundaries of Illinois or the United States.

The Taste of Chicago is a fun, multicultural food festival that will let your palate travel the world without actually leaving the city.

It’s a must do if you’ll be in Chicago over the summer.

Looking for more things to do in Illinois ? Why not check out some of the fun things to do in Springfield, IL ?

6. Lincoln Park Zoo

alisafarov / Shutterstock

The Lincoln Park Zoo is such a staple of Chicago that it’s sometimes called the “Chicago Zoo.”

The city doesn’t have its own, however, and it’s probably because the Lincoln Park Zoo is already doing such a great job.

For starters, it’s one of the oldest zoos on the continent.

It was built in 1868, and some of its original structures are still in use today.

There’s even an oak tree that predates the founding of Chicago itself!

It’s also home to one of the best animal menageries in the state.

You can watch lions prowling in the grass, rhinos snuffling in the mud, penguins waddling on the ice and monkeys lounging around hot springs.

If you’re adventurous enough, you can get close to the critters with special feeding and petting events overseen by the staff.

People from all over Illinois come to see the animals of Lincoln Park Zoo.

It’s a top 10 destination for the city of Chicago, so whether you’re interested in birds, bugs or bonobos, it should absolutely make your “must see” list.

Address:  2001 N Clark St, Chicago, IL 60614, United States

7. Art Institute of Chicago

MaxyM / Shutterstock

With a pair of heavy bronze lions flanking the front door, the Art Institute of Chicago is one of the most recognizable and culturally significant places to visit within the city.

It’s home to more than 300,000 paintings, portraits, sculptures, ceramics, fabrics, photos and textiles, and its artwork transverses the globe from Sao Paulo to Shanghai.

You’ll probably recognize a lot of the art hanging on the walls.

From Grant Wood’s American Gothic to Pablo Picasso’s The Old Guitarist, the museum has scored countless coups over the years.

They have works by Monet, Renoir, Pollock, Warhol, Matisse, van Gogh and many other classic names.

They also have exhibits and artifacts from cultures all over the world.

You can look at traditional, hand-stitched Japanese kimono from behind painted screens; you can marvel at the heavy metal weapons of European crusaders in 1000 AD.

You don’t have to be an art expert to enjoy the Art Institute of Chicago.

It offers so many things to see and do that you’re sure to find something that piques your interest within its fun-filled corridors.

Give it a visit if you’re looking for amazing vacation ideas in Chicago!

Address:  111 S Michigan Ave, Chicago, IL 60603, United States

8. Chicago History Museum

Mary at T-Comms / Shutterstock

If you’re interested in the trials and tribulations that forged Chicago, the Chicago History Museum is where you can learn everything that you need to know about the city.

Topics range from the Great Chicago Fire of 1871 to the building of Chicago’s first railroads in 1836.

Abraham Lincoln plays a prominent role in the political exhibits since he considered Chicago his headquarters for most of his life.

There are also displays dedicated to Prohibition, the Civil War, the Women’s Suffrage Movement and other major movements that touched Chicago.

The best thing about the museum is that it doesn’t just list names and dates on plaques.

It brings history to life with things like interactive videos, moving trains, simulated fires and children’s climbing structures that look like gigantic Chicago style hotdogs.

It’s fun, and that’s why it imparts its lessons so well.

The Chicago History Museum is a must visit while you’re in the city.

It’ll give you context for a lot of the museums and landmarks that you’ll see, and it’ll enrich your experience as you explore one of the most important destinations in Illinois.

Address:  1601 N Clark St, Chicago, IL 60614, United States

9. Bobby’s Bike Hike

Bobby’s Bike Hike

It’s hard to say whether Chicago is more famous for its pizzas or its hotdogs.

Fortunately, with Bobby’s Bike Hike , you don’t have to choose between them!

Bobby’s Bike Hike is a touring company that specializes in food-based travel.

Offering multiple routes throughout the city, they’ll allow you to sample some of the best eats that Chicago has to offer, and you can customize the way that you experience them.

Do you live for dessert?

The “Sweets and Spirits Dessert Walking Tour” is filled with truffles, cupcakes and candy-infused cocktails.

Do you want to burn some calories while you eat?

The “Bikes, Bites and Brews Tour” will put you on a nine-speed as you work your way through craft beers, sausage rolls, deep-dish pizzas and hotdogs with all of the fixings.

If you’re looking for touristy things to do in Chicago, a food tour is a great place to start.

Pick a route with Bobby’s Bike Hike and get to eating!

Address:  540 N Lake Shore Dr, Chicago, IL 60611, United States

10. Wabash Arts Corridor

wiredforlego / flickr

Created by students from Columbia College Chicago, the Wabash Arts Corridor was designed to take creativity out of the classroom and into the real world.

They had the freedom to create whatever they wanted, wherever they wanted, and the end result was an explosion of self-expression that transformed the neighborhood.

Art is everywhere in the Wabash Arts Corridor.

It’s painted on doors, walls, windows and archways; it’s built on brick and stone and marble; it climbs up staircases and sweeps down into the cracks and crevices of back alleys.

You can’t turn a corner without seeing a new mural or an old piece of graffiti.

It’s unlike anything else that you’ll witness in Chicago.

Another fun feature of the neighborhood is that its artwork is constantly changing.

People paint and re-paint all of the time.

Some of it’s deliberate sabotage from street taggers, but more often than not, it’s just artists finding new ways to express themselves on outdoor canvases.

The Wabash Arts Corridor is one of the most unique things to do in Chicago.

If you want to get off the beaten path and explore the hidden gems of the city, let your feet take you to this beautiful, transformative artwork that refuses to be covered for long.

Address:  635 S Wabash Ave, Chicago, IL 60605, United States

Exploring other areas of Illinois? Why not check out some of the things to do in Galena, IL ?

11. Wrigley Field

Susan Montgomery / Shutterstock

You can’t talk about Chicago attractions without talking about Wrigley Field .

It’s one of the oldest stadiums in Illinois, and it’s remained largely unchanged from its early days, so it still has things like old-fashioned floodlights and hand-turned scoreboards with peeling paint.

It’s also known for its ivy-covered outfield wall that has consumed many fly balls in its time!

Another cool feature of the field is that it’s located in the middle of a residential neighborhood.

Locals often sit on their roofs to watch games.

They also allow visitors to park in their driveways since there’s no parking lot connected to the stadium.

As for its events, Wrigley Field has hosted baseball, football, soccer and hockey games, and it’s also offered a number of concerts.

You should check the schedule to see what’s in store during your trip.

If you’re wondering where to visit in Chicago to really live and breathe its traditions, you’ll want to make time for Wrigley Field.

From the battered red marquee on the front entrance to the peanuts and hotdogs sold in the concession stands, it offers a classic baseball experience that’s hard to find anywhere else in the modern world.

Address:  1060 W Addison St, Chicago, IL 60613, United States

12. Shedd Aquarium

Marstar / Shutterstock

With more than 35,000 creatures, the Shedd Aquarium is one of the largest aquariums in Illinois.

Not only does it house all of the sharks and stingrays that you’d expect, but it also showcases birds, bugs, snakes, amphibians and other creatures related to the sea.

The exhibitions are mostly divided by theme.

For example, the “Wild Reef” recreates the colorful coral settings of the ocean, and “Amazon Rising” is a purposefully flooded walkthrough jungle that’s meant to evoke the topics.

Other notable features of the aquarium include a movie theater and an underwater virtual reality experience.

You can also register for tours, presentations, feeding events and animal encounters.

The coolest ones are always quick to sell out, so if you’re looking for fun things to do this weekend, make sure to book early!

Shedd Aquarium is easily one of the top sites in Chicago.

Even if you don’t consider yourself an animal person, it’ll make a convert out of you.

Address:  1200 S Lake Shore Dr, Chicago, IL 60605, United States

13. Chicago Lakefront Trail

Fotoluminate LLC / Shutterstock

Winding through the city for 18.5 miles, the Chicago Lakefront Trail is one of the best ways to check out the sights and sounds of a natural Illinois landscape.

You’ll pass through well-tended parks and overgrown marshes; you’ll see beaches, hills, groves, sidewalks and pedestrian bridges.

Your eyes will always have new scenery to roam.

Potential activities include everything from jogging to unicycling.

If you like being on wheels, there are several skate parks where you can practice your ollies and kickflips.

There are also ample places to stop and smell the roses if you enjoy picnicking.

As for places of interest, you can veer off the trail at any number of stops.

It’s located near piers, museums, clock towers, athletic stadiums and more.

Plan your trip around the Chicago Lakefront Trail.

Not only can it provide plenty of fun on its own, but since there are countless tourist attractions located on and near the paths, you can use it as a sort of natural compass for your trip.

You’ll never get lost when the trail is right there!

Address: 540 N Lake Shore Dr, Chicago, IL 60611, United States

14. Centennial Wheel

Scott K Baker / Shutterstock

The year was 1893.

The man was George Ferris Jr.

He wanted to build a gigantic metal wheel for the World’s Fair in Chicago, and despite skeptical reactions from everyone around him, he rolled up his sleeves and went to work.

Today, the Centennial Wheel is one of the most iconic tourist attractions in Chicago, and Ferris wheels are a standard feature everywhere from boardwalks to amusement parks.

It wouldn’t be an exaggeration to say that this little piece of Chicago forever changed the world.

You can still ride the Centennial Wheel.

It’s been renovated with modern safety features and all of the fun, high-class amenities that you could want, including a VIP gondola with plush seats and a glass-bottomed floor.

It’ll make for a great date night or family outing.

Ultimately, however, you don’t have to climb aboard the Centennial Wheel to appreciate the role that it plays in history or the importance that it has to Chicago, Illinois.

It’s a remarkable piece of architecture no matter what.

Address:  600 E Grand Ave, Chicago, IL 60611, United States

15. Untouchable Tour

Untouchable Tours – Chicago’s Original Gangster Tour

Illinois might not seem like a hotbed of mob activity, but Chicago is the exception.

It was famous during the Prohibition era as the central headquarters for Al Capone, Bugs Moran, Baby Face Nelson and many other mafia legends who made names for themselves with everything from bootlegging to gunrunning.

Not surprisingly, you’ll find lots of “mob tours” in the city that are designed to satisfy curiosity about these famous figures.

However, the Untouchable Tour is the original tour, and it’s also one of the best.

Its tour guides will actually dress up in suits and take on the personas of 1920s and 1930s gangsters as they show you around.

You’ll visit the places where dirty business took place, and you’ll get to see the murder sites for mobsters who killed each other or were gunned down by the FBI.

You’ll even get to see the site of the bloody St. Valentine’s Day Massacre of 1929.

The blood has been cleaned up, of course, but the legacy remains.

The Untouchable Tour is a must do for your vacation.

Not only does it offer a fascinating look into the dark history of the city, but it’ll also familiarize you with the streets and sidewalks of downtown Chicago, and that’ll come in handy for the rest of your trip!

Address:  600 N Clark St, Chicago, IL 60654, United States

16. Museum of Science and Industry

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Covering more than 400,000 square feet, the Museum of Science and Industry is the largest science center in the entire Western hemisphere.

It offers a staggering amount of things to see and do, so whether you’re into astronomy or zoology, its A-to-Z activity roster is sure to keep you entertained in Chicago.

Are you fascinated by natural phenomenon?

Stand inside of a simulated tornado or learn about the Earth’s forces with Wimshurst machines and Foucault pendulums.

Are you a geek for transportation?

Marvel at the airplanes dangling from the ceiling, and be sure to take a tour of the real-life trains, rockets and WWII submarines on display.

Other exhibits include everything from mirror mazes filled with optical illusions to 3D walkthrough models of the human heart.

If it’s a topic related to science, it’s probably featured here.

Between its events, activities and collections, the Museum of Science and Industry is a coveted jewel for Illinois.

It puts the state on the map in terms of scientific scholarship.

Even more importantly, it’s a lot of fun!

Swing by for a visit if you’re looking for the best and most educational places to go in Chicago.

Address:  5700 S Lake Shore Dr, Chicago, IL 60637, United States

17. Woolly Mammoth Antiques and Oddities

Woolly Mammoth Antiques and Oddities

The tables are covered in skulls.

The shelves are stacked with things like human dentures and lamps made out of alligator heads.

The bottles and jars are filled with eggs, skins, animal fetuses and other grotesque knickknacks.

Welcome to Woolly Mammoth Antiques and Oddities !

Created by a couple who wanted to “make (themselves) more comfortable with dying,” this bizarre shop has become one of the top stops in Chicago for the morbid.

It’s focused on death, but in a weird way, it’s also a celebration of life.

What can make you feel more alive than looking at a stuffed and mounted squirrel?

Drop by Woolly Mammoth Antiques and Oddities if you’re looking for unique tourist places in Chicago.

It isn’t something that you’ll find in a travel guide, but its utterly bizarre collection will definitely give you a story or two for when you return home.

Address:  1513 W Foster Ave, Chicago, IL 60640, United States

18. Chicago Theatre

You already know what the Chicago Theatre looks like.

Even if you’ve never stepped foot in the city, you’ve seen its vintage-style “CHICAGO” marquee in all kinds of films, shows and postcards.

It’s so widely recognized that it’s considered the unofficial emblem of Chicago.

There’s more to this theater than its signage, however.

Built in 1921, it’s a historical landmark that boasts amazing architecture and lavish, old-fashioned furnishings.

Walking into its front hall is like walking backwards through history to a time of high art and culture.

The balconies are plush.

The ceilings have chandeliers and gilded murals.

There’s even an authentic Wurlitzer pipe organ; it’s one of the last of its kind in the country.

The theater is operational, too.

It still hosts plays, musicals, orchestras, magic shows and more.

Its stage has welcomed everyone from comedians to motivational speakers.

If you’re looking for the best attractions in downtown Chicago, the Chicago Theatre is a must visit.

The marquee alone is worth a pilgrimage, but even beyond that, it’s a grand venue that’s designed to entertain and impress.

Address:  175 N State St, Chicago, IL 60601, United States

19. Navy Pier

If you’ve been making a to do list for Chicago, you’ve probably listed a few of Navy Pier ‘s attractions already.

It extends into Lake Michigan like a sort of overgrown boardwalk, and it’s absolutely packed with shops, restaurants, galleries, museums, movie theaters and other popular places for locals and tourists alike.

There are rides, too.

Navy Pier has a very festive atmosphere where you can always hear the jingling of carousel music and the whir of tower drops and wave swingers.

It’s also the home of the Centennial Wheel, the world’s first Ferris wheel.

Other attractions range from crazy funhouse mazes to elegant botanical gardens.

There are always things to see, and you don’t even have to visit the main attractions; you could have a fun, fulfilling afternoon just by wandering around, eating street food, listening to buskers and watching people cavort on the water.

For sheer entertainment value, Navy Pier is one of the top things to do in Chicago.

You’ll probably wind up visiting it even if you don’t plan on it.

It’s that ubiquitous to the social scene of Chicago.

20. Adler Planetarium

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Made with a dark, heavy granite, the Adler Planetarium is visually striking both indoors and outdoors.

The first thing that you’ll notice is the dome.

It measures a whopping 69 feet across, and it’s an architectural wonder.

When you sit down for a film or projection, the experience is so larger-than-life that you’ll feel like you’re careening through the stars on a real space shuttle!

Speaking of space shuttles, the planetarium has those, too.

Their exhibits include everything from meteorite chunks to old-fashioned metal space capsules from forgotten NASA projects.

If you’re a geek for astronomy, you might also like their special events for stargazing and celestial viewing.

Feel free to ask about their ongoing projects as well.

They’re an active research and observation station, and they host all kinds of educational programs for kids, couples, families, tourists and general visitors.

Are you looking for the best things to do in Chicago, Illinois?

Make time for the Adler Planetarium.

If you’ll forgive the pun, it’s out of this world.

Address:  1300 S Lake Shore Dr, Chicago, IL 60605, United States

21. Morton Arboretum

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There’s so much rugged natural beauty in Illinois that it’s almost a shame to stay in Chicago where the greenery has been replaced by skyscrapers and shopping malls.

Fortunately, there are still a few places in the city where you can get some fresh air, including the Morton Arboretum .

Like its name suggests, the arboretum is devoted to trees.

You’ll find many beautiful species here, including ones that are native to Illinois.

However, there are other things and places to see, so don’t limit yourself to a walk around the oak groves and conifer exhibits.

If you like flowers, you can check out the gardens and floral specimen collections.

If you’re traveling with kids, you can let them burn off some energy with a “troll hunt.”

There are also countless tours, trails and trams to let you explore every bit of the beautiful scenery that the landscape has to offer.

The Morton Arboretum is one of the most exquisite places to visit in Chicago, so if you’re keen to get away from the noise and traffic for awhile, treat it like a hideaway spot from the rest of the world.

The trees are just the beginning!

Address:  4100 IL-53, Lisle, IL 60532, United States

22. Superdawg Drive-In

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The lights are yellow and turquoise.

The hotdogs are served with fries, malts and milkshakes.

The carhops come right up to your vehicle after you’ve placed your order in the intercom.

Welcome to the Superdawg Drive-In , one of the last retro dining establishments in Chicago!

Founded in 1948, the Superdawg Drive-In hasn’t changed a thing about its operation since it first opened its doors during the days of poodle skirts and bouncy ponytails.

It’s still run by the same family, and they still serve the same salty, gooey and finger-licking goodness in paper hotdog trays.

Its authenticity is one of the reasons why it’s such a fun destination.

It isn’t pretending to be vintage; it really is!

If you’re looking for unusual things to do in Chicago, consider going back in time with the Superdawg Drive-In.

It’ll serve quick and delicious eats while hitting you with a blast of nostalgia that’s just as strong as the chill from your chocolate sundae.

Address:  6363 N Milwaukee Ave, Chicago, IL 60646, United States

23. Garden of the Phoenix

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Illinois might not be the first place that comes to mind when you think of cherry blossoms, but at the Garden of the Phoenix , they’re an annual event.

This beautiful, peaceful garden has been transported right out of a Japanese painting and into the heart of Chicago.

Curved bridges will lead you across ponds and streams.

Bonsai trees will provide shade from the sun.

Flower fields will offer amazingly fragrant mixes of camillas, chrysanthemums and morning glories, and birds will sing sweet songs over the sounds of babbling brooks and rustling tree leaves.

You’re probably impatient to hear about the cherry blossoms.

It’s okay.

Thousands of visitors flock to Chicago from all over Illinois just to see them every spring.

Their lives are brief, so make sure to time your trip when they’re actually in season, but seeing them in person is just as amazing as you think.

If you’re looking for attractions that you can’t find anywhere else in the state of Illinois, consider the Garden of the Phoenix.

Its cherry blossoms are a rare and exotic treat, but its real appeal lies in its beauty, serenity and tranquility.

Once you’re here, you’ll never want to leave.

Address:  6300 S Cornell Ave, Chicago, IL 60637, United States

24. Shoreline Sightseeing

Shoreline Sightseeing

Shoreline Sightseeing is a tour guide company that will put you on a boat and glide you through all of Chicago’s top attractions.

Rather than wandering around with your nose pressed into a map, you can grab a beer, kick your feet up and enjoy the sights from the sea.

There are several different tours to choose from, including an architecture tour that will showcase the city’s most famous landmarks and a lake tour that will give you incredible photo ops from the water.

In the summer, there’s also a fireworks tour to take advantage of Chicago’s weekly psychokinetic displays.

Amenities include drinks, snacks and restrooms.

Some tours come with free tickets for water taxi rides.

You can choose specific departure windows if you’d like to see a sunrise or sunset over the water.

If you’re pondering where to go during your Chicago vacation, consider a tour with Shoreline Sightseeing.

It will ensure that you don’t miss any of the major points of interest of the city, and since there are always tour times available, you could be sailing with them as early as this weekend!

25. Chicago Children’s Museum

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There are three stories to the Chicago Children’s Museum , and each one offers fun, dynamic experiences for families who want to combine learning and playing.

The Tinkering Lab has tools for builders and engineers.

The Dinosaur Expedition has hidden fossils that need to be dug up by pint-sized paleontologists.

The Cloud Buster has climbing structures for children who are more monkey than human, and Play It Safe has simulated emergencies in a firehouse to teach important lessons to tiny, helmet-wearing heroes.

As you can see, there’s a lot of stuff to do for kids.

But don’t worry if you’re a little tall for some of the rides!

Adults can find plenty of ways to entertain themselves as well, especially with after-hours events and programs.

Are you looking for Chicago attractions without age requirements?

Do you want something that offers more substance for your kids than shopping malls and amusement parks?

Spend an afternoon at the Chicago Children’s Museum.

The little ones will have fun, and if you’re lucky, they might just learn something as well.

Address:  700 E Grand Ave, Chicago, IL 60611, United States

26. Lincoln Park

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It’s an understatement to say that Lincoln Park is popular.

Not only is it the most-visited park in the state of Illinois, but it’s one of the most-visited in the entire United States.

It comes second only to New York ‘s Central Park in terms of annual visitors.

What draws people to the park?

For starters, it’s jam-packed with attractions.

There are zoos, gardens, conservatories, museums, movie theaters, cultural centers and more.

You can partake in the usual touristy things like dining and shopping, or you can try something new by visiting an archery range or going horseback riding in the hills.

Lincoln Park is also one of the most beautiful places in the city.

If you need a break from the skyscrapers for awhile, this is where you’ll find willow trees, lily ponds and tulip gardens.

Long story short, Lincoln Park offers the best of both worlds.

If you want excitement, visit the zoo or the beach; if you want peace and quiet, take a leisurely stroll on a nature trail.

Its versatility is probably one of the reasons why it’s such a crazy popular place in Chicago!

Address: 2045 N Lincoln Park W, Chicago, IL 60614, United States

27. Chicago Cultural Center

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With elaborate stained glass windows set in high-arching domes, the Chicago Cultural Center stands out even in a city already filled with amazing architecture.

It’s so impressive that it’s the meeting place of choice for presidents, princes, diplomats and other forms of royalty and celebrity.

They just can’t resist the grand staircases and mother-of-pearl mosaics!

If the architecture isn’t enough to tempt you into a visit, consider its activities.

You can find all sorts of interesting things to do here.

On any given day, for example, you might find lectures, concerts, film screenings, dance lessons, art lessons or theater performances.

Did we mention that it’s free?

Your wallet can stay in your pocket the entire time.

As a public outreach center, they won’t charge you for any tours or shows.

If you’re thinking about what to do in Chicago on a budget, consider the Chicago Cultural Center.

It’ll transport you into a high-class world filled with tea ceremonies and calligraphy classes, but amazingly, the trip won’t cost you a dime.

It’ll be an absolute steal for folks traveling through Illinois!

Address:  78 E Washington St, Chicago, IL 60602, United States

28. Petrillo Music Shell

Petrillo Music Shell

With a capacity of 35,000 people, the Petrillo Music Shell is one of the largest amphitheaters in both the city of Chicago and the state of Illinois as a whole.

As you might expect, it hosts a lot of concerts.

Its stages have welcomed everyone from indie folk bands to massive pop stars.

However, it’s also a venue that’s been used for rallies, sports events, food festivals and other forms of entertainment.

Here’s a small sample of the events that are held at the Petrillo Music Shell every year:

– Lollapalooza – Taste of Chicago – Chicago Blues Festival – Chicago Gospel Music Festival

It’s also hosted actors, athletes, comedians, popes, orchestras and even the Dalai Lama!

Long story short, the Petrillo Music Shell is more than just an amphitheater.

It’s a gathering place for the community.

If you’re keen on visiting the major points of interest in Chicago, you won’t want to miss this one.

Address:  235 S Columbus Dr, Chicago, IL 60601, United States

29. Merchandise Mart

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Designed to look like a warehouse, department store and skyscraper all rolled into one, Merchandise Mart boasts more than four million square feet of floor space.

It’s so large that it used to have its own zip code even though it was right in the middle of downtown Chicago!

It was mostly used for offices and businesses.

Today, Merchandise Mart is still a hub of commerce, but it’s also open to the public with shops, show rooms and services.

You can mail a letter; you can buy a bottle of wine; you can get your clothes dry cleaned.

This is a shopping center with all of the goodies that you could ever need, and a food court is available when you get hungry.

There’s a reason why the building is often called “a city within a city.”

Special events at the mart include art shows, trade fairs, book signings, fitness classes and more.

It’s another one of those tourist attractions where you’ll want to keep an eye on the itinerary since there’s always something new going on.

Merchandise Mart used to be the largest building in the world.

It’s lost that title in recent years, but it still dwarfs everything else in Chicago, Illinois.

It’s a site worth seeing!

Address:  222 W Merchandise Mart Plaza, Chicago, IL 60654, United States

30. Maggie Daley Park

Maggie Daley Park is one of the most fun things to do in Chicago.

It’s basically a gigantic, all-ages recreation area that resulted from the crazy visions of an architect who never said no to any idea.

As a result, the park offers a million different amenities in delightfully clashing ways.

There are lawns, gardens, harbors, playgrounds and picnic areas as far as the eye can see.

A winding “ribbon” is an ice skating path in the winter and a jogging and biking path in the summer.

There’s a place for rock climbing and a place for rollerblading.

You can play tennis on the tennis courts or golf on the golf courses.

Kids will love the sprawling playgrounds that include everything from multi-level towers and slides to jungle gyms with suspension bridges and tunnels.

Adults will enjoy the fun, unique attractions like the mirror maze or the upside-down forest.

Maggie Daley Park is one of the top destinations of Chicago, and since it’s open 365 days per year, there’s no reason not to check it out while you’re in town.

Just drop by whenever you’re ready.

Whether it’s next weekend or next year, the park will always be insane!

Address:  337 E Randolph St, Chicago, IL 60601, United States

31. Violet Hour

The Violet Hour

Open every night from 6 PM to 2 AM, the Violet Hour is one of the best destinations for barhoppers in Chicago.

It has a sleek, sophisticated air that makes it much nicer than some of the other dives of downtown, and with strict house rules that include proper attire and no cellphone use while on the premises, it will give you the thrill of exclusivity if you manage to make it inside.

The decor includes dim lights, heavy black curtains and smoothly-polished wood grain tables.

It’s vaguely inspired by the speakeasies of Prohibition-era Chicago, but don’t worry; there are no mobsters here.

The cocktails are both delicious and fanciful.

They have names like “Moonchild” and “Giving Life to Memory,” so they’re something to remember.

You can also order bite-sized plates from an award-winning chef.

Do you have plans tonight?

Do you want plans tonight?

Pencil in a trip to the Violet Hour.

It more than lives up to its name by providing after-hours fun for adults.

Address:  1520 N Damen Ave., Chicago, IL 60622, United States

32. Montrose Beach

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Montrose Beach is one of the hidden gems of Chicago.

It’s much less crowded than other, more centrally-located beaches, but if you’re willing to take a bit of a drive into northern Illinois, you’ll reap the rewards of a gorgeous landscape without a lot of tourists.

The water glitters in the sun. Sand dunes shift with the wind.

Several piers jut out over the lake if you want to soak your feet; otherwise, there are wading and swimming areas, or you can ride a bilk along the asphalt trail that follows the water.

There aren’t a lot of amenities, but that’s part of its charm.

It’s a quiet, serene destination where you can do your own thing without kids crying everywhere and vendors hawking sunglasses at you.

If you’re looking for undiscovered tourist spots in Chicago, you’ll definitely want to check out Montrose Beach.

It’s a chance to get away from the grind of the city and enjoy a sunrise over the water without worries, crowds or distractions.

Address: 4400 N. Lake Shore Dr, Chicago, IL 60613, United States

33. Four Lakes

Four Lakes Snowsports

Four Lakes is one of the most beautiful places in the US .

It’s a little outside of Chicago, but if you’re willing to take a short drive to Lisle, Illinois, you can enjoy the breathtaking sight of miles and miles of snow.

Popular activities include skiing, tubing and snowboarding.

It’s okay if you’re a complete beginner; they have staff members who will rent you the gear, teach you the basics and take you down the slopes.

If you’re confident enough to venture out on your own, you’re free to do your own thing.

The terrain ranges from gentle bunny hills to elaborate boxes and rails for jumps, flips and grinds, so you’ll have your pick of settings for wintertime fun.

Four Lakes is one of the best skiing destinations near Chicago.

The powder is always fresh; the air is always crisp and clean.

What are you waiting for?

Book some time on the slopes for this week!

Address:  5750 Lakeside Dr, Lisle, IL 60532, United States

34. Myopic Books

rafallg / flickr

Hailed as one of Chicago’s top destinations for bookworms and bibliophiles, Myopic Books isn’t like your usual Barnes and Noble.

For starters, it only sells used books.

Many of them are rare or obscure titles that you won’t find on mainstream shelves, and they range from vintage sci-fi and busty romance novels to historical textbooks and true crime thrillers.

It’s also quite cluttered.

The building has three stories, but since there are more than 80,000 books on site, it’s a place of crowded tables, crammed shelves and books spilling over from floor stacks.

Of course, this might sound like heaven to a book lover.

There’s something magical about getting lost in the cozy confines of a thrift shop bookstore.

The smell of old books alone can be enough to make you sigh dreamily!

Despite its shabby appearance, Myopic Books is a treasure trove for collectors and antiquarians.

It can also provide a fun way to kill some time if you’re just wandering around Chicago and wondering what to do with your afternoon.

Let yourself be transported into a Ghibli film by entering this picturesque little shop with its weird, wonderful books!

Address:  1564 N Milwaukee Ave, Chicago, IL 60622, United States

35. 900 North Michigan

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Shopping at 900 North Michigan is one of the coolest things to do in downtown Chicago.

Not only does it offer amazing views from its pillar-like towers, but since it’s all indoors, it’s perfect for a cold or rainy day.

Hundreds of retailers call it home.

Many of them are luxury shops or specialty boutiques that give the mall a classy, upscale vibe, but you can find plenty of discount stores as well.

A spa is located on one of the top floors.

Several restaurants take the place of traditional food courts.

There are also cafes, bookstores, fitness clubs and other recreational areas that can be a lot of fun.

Many people wonder what to do when it rains on their vacation.

Fortunately, there are places to go in Chicago where the weather isn’t an issue, and 900 North Michigan is one of them.

You’ll spend so much time exploring its shops, stalls and boutiques that the rain might even finish while you’re inside!

Address:  900 Michigan Ave, Chicago, IL 60611, United States

36. Soldier Field

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There’s nothing like the pounding of 66,000 feet to make the earth move during a football game or rock ‘n’ roll concert.

At Soldier Field , you can enjoy this energy to its fullest extent!

As Chicago’s biggest stadium, Soldier Field plays host to all of the city’s top events.

You can watch football, soccer, hockey or rugby; you can attend political rallies or monster truck shows; you can jam out to everyone from Bon Jovi to BTS.

There’s always something new on the schedule, and it’s always crazy.

If you like behind-the-scenes action, you can also arrange a tour of the stadium that includes a peek inside of the locker room, an envious trip around the VIP suite and an exploration of the main field and courtyard.

At Soldier Field, every football game is the Super Bowl.

Every concert is Woodstock.

You won’t find a better stadium experience anywhere, so if you’re looking for ear-ringing fun in Chicago, this is one of the best sites for it.

Address:  1410 Museum Campus Dr, Chicago, IL 60605, United States

37. Crystal Gardens

Growing beneath a glass atrium, the lush trees and flowers of the Crystal Gardens are like something out of a storybook.

They have deep, wild roots, but they’re neatly contained in symmetrical structures with natural light shining down on open, airy spaces.

The decor is mostly white, but the colors of the plants are vibrant pops in the palette.

They’re also dotted with sculptures, fairy lights, water fountains and other beautifully aesthetic decors.

It should come as no surprise to learn that many weddings are held at the Crystal Gardens.

It’s a popular rental space for fancy functions in Chicago.

You don’t have to get hitched to see the flowers, however.

The gardens are open to the public, and they’re conveniently located on Navy Pier if you’re visiting other tourist attractions in the area.

As a bonus, admission is free.

Visit the Crystal Gardens for a beautiful and breathtaking nature tour that just so happens to be indoors.

Rain or shine, you can enjoy their elegant floral displays.

You might even find yourself planning your future vows among the flowers!

38. Baha’i House of Worship

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You can be forgiven if you’ve never heard of Baha’i, an obscure but fascinating religion that came from the Middle East.

Despite its millions of practitioners, it only has a handful of temples and prayer houses around the globe.

The amazing thing is that Illinois has one.

In fact, Illinois has the oldest and largest one, and it’s the only of its kind in North America.

The architecture is magnificent.

A lace-patterned dome sits on top of nine pillars that come together to form its center.

Inside, there are painted murals and stained glass windows.

Outside, there are pools, gardens, fountains and other gentle and tranquil spaces.

The Baha’i House of Worship is one of the most unique Chicago attractions that you can put on your itinerary.

You don’t have to be religious to appreciate its beauty, history and serenity.

It’ll fill you with wonder whether you believe like the Baha’i or not, so it’s absolutely a place to visit while you’re in Illinois.

Address:  100 Linden Ave, Wilmette, IL 60091, United States

39. The Weiners Circle

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Its location might be small, but this bright yellow hotdog stand packs a major punch.

There’s a reason why it’s one of the best places to visit in Chicago!

The main draw of Wieners Circle is its funky late-night atmosphere.

It stays open until 5 AM on the weekends, so it’s a popular destination for bar hoppers and club goers who want to satisfy a drunken craving for cheese fries.

It also draws a lot of insomniacs who don’t care about traditional mealtimes and love digging into hearty, Chicago style hotdogs at any time of day.

Another fun thing about Wieners Circle is that its staff and customers are encouraged to yell at each other.

Mutual insults are an everyday thing.

It’s all part of the experience.

You won’t want to take your kids to Weiners Circle, but if you’re wondering what to visit in Chicago after the lights go off, this is a place where the fun never stops.

Even more importantly, it’s a place where you can get d*mn good hotdogs!

Address:  2622 N Clark St, Chicago, IL 60614, United States

40. Sky Rink

As you might expect from a place nicknamed “The Windy City,” Chicago’s weather can be pretty cold.

It helps if you lean into the chill rather than away from it, and to do that, you’ll need to visit a place like the Sky Rink.

Located at the top of Peninsula Chicago , a luxury hotel, the Sky Rink is a small and intimate ice skating destination where you can twirl under fairy lights while surrounded by bright, twinkling Christmas trees.

You’ll feel like the main character of a holiday movie as you enjoy the picturesque setting.

It’s quite romantic, especially if you’re traveling or honeymooning with a special someone.

When you’re done on the ice, a chalet service will be waiting to take your order.

You can warm up with everything from mulled ciders to powdered pastries that are fresh out of the oven.

With its chic decor and impressive amenities, a trip to the Sky Rink is one of the most fun things to do in Chicago.

You don’t have to be a guest at the hotel.

You can book a ticket anywhere and anytime, so it doesn’t matter if you’re arriving in the city today, tomorrow or this weekend.

Your dreamy date night is a go!

Address:  108 E Superior St, Chicago, IL 60611, United States

41. Welles Park

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If you’re looking for a quiet place to unwind, Welles Park can offer a respite from all of the lights, noises and crowds of Chicago.

It isn’t without amenities.

Its centerpiece is an ornate, wire-topped gazebo where bands can play outdoor concerts and community leaders can give rallying speeches.

Other features of the park include a swimming pool, fitness center, baseball field, football field and children’s playground.

The best thing about the park, however, is that you can ignore all of the attractions and simply enjoy it for the natural oasis that it is.

It’s a great place to escape the hustle and bustle of Chicago, so whether you’re looking for grassy fields for picnics or shaded tree groves for nature walks, you can find them here.

Don’t get us wrong. Chicago is amazing.

It’s just very, very busy, and there are times when you might need a breather.

Welles Park is where you can get it.

Many Chicago attractions are focused on glitz and glamor.

For a plainer, quieter sort of space, visit Welles Park.

It’ll soothe your frazzled nerves during a stressful vacation, and it’ll recharge your batteries for the rest of your time in the city.

Address:  2333 W Sunnyside Ave, Chicago, IL 60625, United States

42. Magnificent Mile

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Are you wondering what to do on a last-minute trip to Chicago?

Do you need attractions that are always open or ones that can be booked quickly and easily?

The Magnificent Mile is the answer to your prayers.

Framed by shops, restaurants, resorts, malls, landmarks and other places of interest, the Magnificent Mile runs through the heart of downtown Chicago, and it offers a wide variety of fun for both locals and tourists.

You could spend days just sightseeing with all of the towers and skyscrapers looming over you!

To truly experience Chicago, however, you’ll need to dive into its urban landscape.

The good news is that you’ll have plenty of options.

The Magnificent Mile is home to 460 stores, 275 restaurants and 51 hotels, and that’s just the traditional, commercial side of things.

There are even more spaces for things like gardens, museums, theaters, art galleries and historical statues.

The Magnificent Mile is one of the best things to do in Chicago, especially if you’re taking an unexpected trip without the benefits of pre-booked tickets and tours.

It has so many attractions that you can always find something that’s open.

Even if your trip is as early as this weekend, the “Mag Mile” won’t let you down!

Address: North Michigan Avenue, Chicago, IL 60611, United States

43. Medieval Times Dinner and Tournament

Medieval Times Dinner & Tournament

Located a few miles north of Chicago in Schaumburg, Illinois, this is an attraction that will require you to travel outside of the city limits, but it’s definitely worth it.

Where else can you enjoy stew in hollowed-out bread while you watch men in armor fight to the death atop white stallions?

Okay, they aren’t really fighting to the death.

They’re just fantastic actors.

But that’s the whole appeal of the Medieval Times Dinner and Tournament : It takes you right out of this world and into the pageantry and peasantry of 11th century Spain.

The knights will ride, joust, sword fight and perform amazing tests of courage and skill.

You’ll watch all of the action as you’re served a hearty four-course meal.

For authenticity’s sake, you won’t be given any utensils, so you might want to wear clothes that you don’t mind getting splattered with gravy or stained with ale.

If you’re looking for fun things to do in Chicago, consider the Medieval Times Dinner and Tournament.

You’ll need to take a bit of a drive to get there, but once you’re yelling yourself hoarse for knights engaging in hand-to-hand combat, you’ll be glad that you did.

Address:  2001 N Roselle Rd, Schaumburg, IL 60195, United States

44. Second City Chicago

The Second City

How long has it been since you’ve enjoyed a real, honest-to-God belly laugh?

If you can’t remember the last time that you cracked up, Second City Chicago can help.

It’s more than just a comedy club.

Second City has locations all across the country, and it’s launched so many careers that it’s basically a pipeline to Hollywood.

When you attend a show, you’re almost guaranteed a good time with up-and-coming talent.

To give you an idea of what might be in store for you, previous acts have included Bill Murray, Stephen Colbert, Tina Fey, Amy Poehler, Steve Carell and many, many more.

Second City Chicago is one of the most vibrant attractions of the downtown area.

If you’re wondering what to see in terms of shows, plays, musicals and comedy routines, this is a destination to put on your shortlist for sure.

Address:  1616 N Wells St, Chicago, IL 60614, United States

45. Chicago Pedway

EQRoy / Shutterstock

How do Chicago natives survive the harsh winter weather?

One of the reasons is the Pedway .

Officially known as a “pedestrian pathway system,” the Pedway is actually more of a sprawling underground network of halls, tunnels and corridors that connect different streets in Chicago.

You can enter and exit at various points to get back to the world above, but since lots of businesses have set up shop in the Pedway, it’s become a destination in its own right.

Stores are available for shopping.

Restaurants are available for dining.

Art exhibits are everywhere; one particular standout is a collection of elaborate stained glass windows.

There are above-ground locations for the Pedway, too.

They’re enclosed paths and footbridges that can lead you through the city without exposing you to the elements.

The Pedway is one of the coolest places to visit in Chicago.

It’s basically a subterranean city, so you can eat, drink, shop and explore in an entirely underground setting.

You don’t have to let Illinois weather define your vacation!

Address:  Chicago, IL 60606, United States

46. Poetry Foundation Library

Poetry Foundation Library

The Poetry Foundation Library is another attraction that you can’t find anywhere else in Illinois.

In fact, you’d be hard-pressed to find it anywhere else in the US.

There are only a handful of poetry libraries in the entire world, but the good news is that the Chicago version is one of the best.

More than 30,000 volumes have been collected over the years.

They contain everything from flowery sonnets to raunchy limericks, so they’re quite diverse.

They can be found in books, diaries, anthologies, newspapers, scholastic works and more.

You don’t have to spend all day hunched over a table, either.

In addition to their printed works, the library also offers listening booths for audio recordings.

Some poetry is recited by the very people who authored it!

One thing to note about the library is that it has limited hours.

It’s only open on weekdays from 11 AM to 4 PM, so it might not be an option for those with a strict itinerary in Chicago.

If you have the time, however, and if you can appreciate a beautiful haiku, you should check out the Poetry Foundation Library.

It’s a unique gem in Chicago, Illinois, so it’s worth a day trip.

Address:  61 W Superior St, Chicago, IL 60654, United States

47. Field Museum of Natural History

With millions of artifacts on display, the Field Museum is one of the largest natural history museums in the world, and it’s renowned for its research and public education efforts as well as its collections that are just plain cool.

Gigantic skeletons will show you the jaw-dropping sizes of dinosaurs and woolly mammoths.

The hall of gems will beckon you with wondrous colors and glittering edges.

Underground tours will show you the earth below; space films will take you out of your seat and into the sky.

Plants are displayed in glass houses. Meteorite pieces are tucked into slides.

Flowers are pressed and preserved; ancient texts are printed on scrolls and silk screens; cultural tokens date back thousands of years and then some.

Taxidermy animals include everything from extinct species to notable creatures like the man-eating lions of Tsavo.

If this sounds like a lot, you should know that it isn’t even a fraction of what the Field Museum has to offer.

It’s home to more than 24 million items in total!

There’s a reason why it always tops the list of Chicago attractions, so whether you’re into birds, bugs or black holes, this is the museum for you.

Address:  1400 S Lake Shore Dr, Chicago, IL 60605, United States

48. Six Flags Great America

Six Flags Great America

Thrill-seekers, this one is for you.

Six Flags Great America offers roller coasters, bungee jumps, water slides, tilt-a-whirls, plummets, racers, bumper cars and much, much more.

It’ll be the ultimate adrenaline rush for folks who are looking for high-octane fun in Chicago.

It should be noted that the amusement park isn’t quite within Chicago.

It’s located in Gurnee, Illinois, which is about an hour north of the city.

That said, you should definitely take advantage of being close to a Six Flags.

It’s one of the best places to travel for food, fun and festivities no matter where you are, so whether you’re looking to chomp on deep-fried candy bars or scream like a banshee on a ricochet ride, it’ll offer an amazing vacation experience.

Make time for a trip to Six Flags while you’re in Chicago.

Book early. Find a coupon for an all-day pass.

A little planning today can net you a big discount tomorrow!

Address:  1 Great America Parkway, Gurnee, IL 60031, United States

49. Chinatown

ben bryant / Shutterstock

Even if you’ve been to Chinatowns in other cities, you’ve never been to Chicago’s Chinatown .

It’s such a vibrant neighborhood that it puts others to shame.

For starters, it really is a neighborhood.

It has all of the shops and street food stalls that you’d expect from a Chinatown, but beyond the gimmicky, touristy areas, there are parks, schools, museums, libraries and other important touchstones for the local Chinese community.

It’s also quite large.

With a population of almost 100,000 throughout the greater Chicago region, it’s easily the biggest Chinatown in the state of Illinois.

As for its attractions, you can drink, dine and shop to your heart’s content.

The food is usually the biggest draw for tourists, but if you’re interested in things like plays, market events and gallery openings, you’ll find plenty of those as well.

A trip to Chinatown is one of the best experiences that you can have in Chicago.

Grab your chopsticks and get going!

A steaming platter of red bean buns is waiting for you!

Address: 318 W Cermak Rd, Chicago, IL 60616, United States

50. Chicago Mosaic School

Chicago Mosaic School

If you’re hoping to have unique experiences in Chicago, have you considered learning a new skill or hobby while you’re there?

The Chicago Mosaic School is the only one of its kind in Illinois.

Originally just a workshop offered by a local ceramicist, it’s grown into an award-winning institution that’s dedicated to the preservation of the trade and the celebration of fun, creative artwork.

You can sign up for a number of classes and programs at the school.

If you already know your way around tiles, you can also test your expertise with the only mosaic certification program in the US.

If you just want to take a tour, that can be arranged, too.

The school has lots of its handiwork displayed in galleries, exhibitions, studios and showrooms.

Try something a little different during your vacation with the Chicago Mosaic School.

Whether you’re interested in expressing your own artistic side or just marveling at the creativity and imagination of others, this school is a unique travel destination in Chicago.

Address:  1127 W Granville Ave, Chicago, IL 60660, United States

51. Grant Park

Tupungato / Shutterstock

Grant Park is such a famous destination in Chicago that you might be surprised to find it at the bottom of this list.

The reason is because it’s a massive, multipurpose space that branches off into a thousand different directions with a thousand different attractions, so if you missed any of Chicago’s greatest hits, you’ll have one last chance to visit them before your vacation is over.

Did you check out the metal bean at Millennium Park?

Did you take a selfie at Buckingham Fountain or stroll through the Lurie Garden?

Did you get a little culture at the Art Institute of Chicago, or did you rock with an outdoor concert at the Petrillo Music Shell?

All of these destinations are on or near Grant Park.

There are countless others as well.

Grant Park is known as “Chicago’s front yard,” and once you’re standing at the entrance and seeing the entire buffet of cool things to do, you’ll realize why it earned the nickname.

If it isn’t one of the first places that you visit, make it one of the last.

Start Planning Your Trip To Chicago

These are just a few of the best places to visit in Chicago, Illinois.

Whether you’re looking for refined art or bizarre street food, it’s a city that has a little bit of everything, so it’ll be an excellent destination for your travel bucket list!

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The 51 best things to do in Chicago right now

Discover the best things to do in Chicago, from iconic venues and views to cultural musts and late-night shenanigans.

April 2024 :  Spring is here and it's time to head outside!  Walk through a beautiful garden, take a hike on a trail or go on an architecture boat tour. Plus, baseball is back on the North and Side Sides. There are plenty of other options, too, so stay satisfied and busy with these fun activities in April.

No matter where your interests lie, you can always find something to get excited about in this no-nonsense Midwestern metropolis. The best things to do in Chicago run the gamut—from seriously fun to awesomely educational. Looking for culture? Spend a day exploring Chicago museums . Hungry? You've come to the right place, because Chicago is famous for its delicious cuisine. There are tons of amazing restaurants in Chicago that highlight the city's rich and diverse culinary landscape. (And plenty of uniquely Chicago bars that do the trick, too.) We've searched all across the city to assemble this list of the best things to do in Chicago. Follow it and never get bored here again.

You can also find out more about how Time Out selects the very best things to do all over the world , or take a look at our list of the  best things to do in the world right now .

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• Restaurants

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Best things to do in Chicago

1.  Root, root, root for the home team at Wrigley Field

• Sports and fitness
• Baseball & softball
• Wrigleyville
• price 1 of 4

What is it? Arguably the city’s most famous and beautiful place to see a ball game.  

Why go? Synonymous with the North Side for more than 100 years, the Friendly Confines has updated ever-so-slightly over the years. It eventually gave in and added lights in 1988; a jumbotron was erected in left field a few years back. But it’s the ivy that the lines the outfield walls, the manual scoreboard and general old-timey awesomeness that will keep the stands here filled whether the Cubbies are winning or losing. 

Don’t miss:  For a true Wrigley Field experience, grab cheap(ish) tickets to the general admission bleachers section.  

2.  Travel across an elevated trail on the 606

• Parks and gardens
• Humboldt Park

What is it?  A formerly abandoned stretch of elevated railway track named after the first three digits in every Chicago zip code.  

Why go? Looking for a convenient way to get between Logan Square, Humboldt Park, Wicker Park and Bucktown? This is it. The 2.7-mile path was spruced up by the city and turned into a functional attraction that delights locals and visitors.

Don’t miss:  Local artist Jeff Zimmermann's colorful Conagra Mural (Urbs in Horto) just across the Milwaukee Avenue bridge, which acknowledges Chicago's agricultural legacy.

3.  Walk through a beautiful garden

• Things to do

What is it? The city’s lush green spaces, from Chicago parks to sprawling botanical gardens.

Why go? Get away from the bustle of the city and reconnect with nature by visiting one of these (mostly) free gardens. You’ll find stunning Japanese gardens, serene lily ponds, rose gardens, conservatories filled with thousands of plants, and much more.

4.  Bike to the ’burbs on the North Branch Trail

What is it?  A 16-mile paved trail beginning in Gompers Park that takes riders all the way to the Chicago Botanic Garden.

Why go?  If you're craving a quick escape from the city on your bike, you can take the North Branch Trail to attractions throughout the northern suburbs. Have a beer at Hubbard's Cave, get a pie at the Pequod's in Morton Grove or relax in the Erickson Woods in Winnetka.

Don't miss:  The four-mile loop trail through the Skokie Lagoons (which can also be used to get to the Chicago Botanic Garden).

5.  Catch a foul ball at Guaranteed Rate Field

• Armour Square

What is it? Home of the Chicago White Sox, formerly (and, to some, currently) known as Comiskey Park.  

Why go? Okay, so the South Side team doesn't command the rabid following of its neighbors to the north (although the whole city went nuts when it clinched the World Series in 2005). But the stadium is much more spacious than Wrigley, and it's almost always possible to walk up and purchase tickets.

Don’t miss:  You can get a corned beef sandwich and an Impossible dog, or satisfy your sweet tooth with a campfire milkshake.

6.  See gorgeous seasonal blooms

• East Garfield Park

What is it? A spring flower show at the Garfield Park Conservatory.

Why go?  Spring is here and one of the city's best green spaces is ushering in warmer days with its annual flower show. Explore the history and science of botanical nomenclature at Garfield Park Conservatory and check out spring bulbs like Tulipa ‘Rococo’, Lilium ‘Josephine,’ Viola ‘Matrix Yellow’ and Anemone ‘Giant Blue Poppy.’

7.  Hit the trails for a hike

What is it?  Hiking trails around Chicagoland.

Why go? Now that it's starting to warm up, it's the perfect time to go hiking. Visit a state park or nature preserve for an adventurous escape from the city. These sprawling, winding paths will take you through historic sites, sand dunes, woodlands and much more.

8.  Show off your putt-putt skills at City Mini Golf

• Millennium Park

What is it? An 18-hole miniature golf course located in Maggie Daley Park.

Why go? There's a kitschy kind of charm to mini-golfing in the shadow of the Chicago skyline, especially since the course is decorated with replicas of famous Chicago attractions (like a six-foot-tall Willis Tower and a teeny version of the Picasso sculpture in Daley Plaza). 

Don’t miss:  Snapping a photo next to the mini Chicago landmark of your choice.

9.  Cruise around town on a Divvy e-bike

• Transport & Travel

What is it?  These jet-black e-bikes allow riders to go up to 15 miles per hour with the help of a small electric motor.

Why try it?  Let's face it: the original bright blue Divvy bikes are heavy and cumbersome. These newer e-bikes (which you'll find at stations throughout the city) make it easier to see more of the city atop a shared ride. The pedal-assist system adds some additional power everytime you move your legs, allowing you to get to your destination faster—and possibly without breaking a sweat.

Don't miss:  Divvy e-bikes come with an attached lock, meaning that you can end your ride by locking it to a bike rake or sign post, though you may incur an extra fee. You can also place them in any Divvy dock.

10.  Hop aboard Chicago’s First Lady for an architecture tour

What is it? The breeziest way to survey the city's famed architecture.

Why go? An architectural tour is a must for any visit to Chicago, and t he Chicago Architecture Foundation employs certified volunteer docents who narrate the history behind more than 50 downtown buildings for the duration of a 90-minute cruise along the Chicago River.

Don’t miss:  An evening version of the tour that allows you to take in the twinkling city lights from the river.

11.  Check out rare Disney memorabilia

What is it? Disney100: The Exhibition.

Why go? In celebration of Disney’s 100th anniversary, the company has launched a new exhibit in Chicago. Fans have the opportunity to see over 250 artifacts, props, costumes and more as well as 10 imaginatively themed galleries. Plus, there's plenty of exclusive merch to pick up from the gift shop.

12.  Cheer on the Bulls and Blackhawks at the United Center

• Event spaces
• United Center

What is it?  Home to pro basketball and hockey, as well as big-ticket pop acts. 

Why go? You can't see Michael Jordan play at the United Center anymore (though you can get a picture in front of his statue in the venue's public atrium), but this West Side arena still hosts plenty of stars. During basketball and hockey season, the venue serves as home turf for the Bulls and the Blackhawks—two of the city's biggest pro sports teams. It's also a destination for major pop and rock concerts, including acts like U2, Drake and Madonna.

Don’t miss:  The arena has partnered with local restaurants like Honey Butter Fried Chicken and Lillie’s Q to provide dishes and drinks that handily outclass typical stadium fare.   

13.  Go mini-golfing (and drinking) at Puttery

• price 2 of 4

What is it?  A mini-golf cocktail bar.

Why go? If the weather outside isn't suitable for hitting the links, do the next best thing and go mini golfing at this unique concept. Housed in a 23,000-square-foot space, Puttery offers two themed courses and state-of-the-art technology like digital scorecards and trackable balls.

Don't miss: Take a load off after you're done playing by hanging out in the swanky lounge area. There's a a full menu of craft cocktails and approachable bites.

14.  Hop aboard the Chicago Water Taxi

What is it?  For the first time since 2019, the Chicago Water Taxi is operating seven days a week.

Why go?  If you're looking to get out on the water for budget prices, you won’t find a better option than the bright yellow water taxi—a one-way ticket will set you back just $6, while 10-ride pass is $25.

15.  Visit animals (for free!) at Lincoln Park Zoo

• Lincoln Park

What is it?  One of the last free zoos in the country, this 35-acre attraction connects visitors with animals from all over the world.

Why go? More than 1,000 critters are waiting for you to visit them—free of charge—in Lincoln Park.  From mammals (beavers, lions, otters and bears) to birds (penguins, eagles and parrots) to reptiles (snakes, crocodiles and turtles), there's something for every animal lover.  

Don’t miss:   The expansive Regenstein Macaque Forest, where snow monkeys swing from branch to branch. 

16.  See public art in Millennium Park

What is it?  The crown jewel of Chicago's front yard.

Why go?  Home to iconic public art installations such as   Cloud Gate   (a.k.a. "The Bean"), t his 25-acre park is one of the most popular gathering spots in the city . Visitors can walk through the vegetation in the Lurie Garden—renowned for its beauty throughout all of Chicago's seasons—or grab a requisite selfie in front of the Bean's reflective surface. 

Don’t miss:  Crown Fountain , an interactive installation featuring two 50-foot-tall LED video structures. 

17.  See Yoko Ono’s installation in Jackson Park

• Literary events

What is it?  Designed by activist and artist Yoko Ono, Skylanding is composed of 12 large steel lotus petals jutting from the ground of the Garden of the Phoenix in Jackson Park.

Why go?  Calling all public-art fanatics. This gleaming installation from the famed artist has become a major draw in the 600-acre park. The photogenic sculpture was erected as a symbol of peace, taking up residence on the site of a pavilion built by the Japanese government for the 1893 World’s Columbian Exposition .  

Don’t miss:  The park is also home to a beautiful, traditional Japanese respite dubbed the Garden of the Phoenix. 

18.  See live music at the iconic Morton Salt building

What is it?  The Salt Shed, Chicago’s new(ish) music venue from the team behind Thalia Hall and the Empty Bottle.

Why go?   Located at the site of the historic Morton Salt building (you know, the one you've probably spotted alongside the Kennedy Expressway), Salt Shed is an indoor/outdoor venue that's backed by a stellar sound system and skyline views during summertime performances.

Don’t miss:  Genuinely good concessions from notable Chicago restaurants.

19.  Eye masterpieces at the Art Institute of Chicago

• Art and design

What is it?  Guarded by an iconic pair of bronze lions, the Art Institute of Chicago houses a permanent collection of more than 300,000 artworks. 

Why go?   The Art Institute of Chicago is filled with masterpieces from every era, from Georges Seurat’s iconic painting   A Sunday on La Grande Jatte   (notable for its appearance in   Ferris Bueller’s Day Off ) to Andy Warhol's print of actress Elizabeth Taylor. This month, see Radical Clay: Contemporary Women Artists from Japan, an exhibit celebrating 36 contemporary ceramic artists through 40 stunning pieces.

Don’t miss:  Tucked away in the lower level of the Art Institute, the Thorne Miniature Room contains 68 recreations of American, European and Asian architecture and furniture, represented at 1:12 scale. It’s like a hyper-detailed, ultra-realistic doll house that you wish you had when you were a kid.

20.  Find serenity at the Garfield Park Conservatory

What is it? A gorgeous glass structure home to more than 100,000 plants. 

Why go? When temps start to dip, there are few better places in Chicago to escape the cold than Garfield Park Conservatory, where you can wander through eight indoor display gardens full of greenery. Marvel at towering tropical plants in the 65-foot Palm House, admire cacti in the Desert House and imagine the primordial settings of Illinois millions of years ago among the lush Fern Room.   

Don't miss: Swing by Horticulture Hall from Friday through Sunday for a lavender oat milk cold brew made by Monday Coffee Co., the conservatory's resident coffee pop-up.

21.  Tap your toes to late-night jazz at the Green Mill

• Cocktail bars

What is it?  An Uptown institution that books smart bebop and free jazz with a discriminating ear. 

Why go?  In the ’20s, Chicago gangsters like Al Capone were known to frequent the Green Mill, but ever since Prohibition, the club has garnered a reputation for hosting live jazz every night. 

Don’t miss:  Taking a picture under the glittering marquee, which wasn't actually destroyed in Michael Mann's 1981 neo-noir film Thief . 

22.  See a blockbuster movie at Alamo Drafthouse

• Movie theaters

What is it?  A popular movie theater chain from Texas.

Why go?  In addition to showing the latest films, the venue offers expansive food and beverage menus and servers will bring meals to customers' seats during screenings.

Don't miss:  The theater's special events, which include rowdy sceenings where talking is encouraged and movie parties—immersive and interactive viewing experiences featuring fun props, themed drinks and more.

23.  Hang out with a mummy at the Field Museum

• Science and technology
• Museum Campus

What is it?  A massive natural history museum that was founded to house the biological and anthropological collections for the World’s Columbian Exposition of 1893. 

Why go?   With 350,000 square feet of permanent exhibitions to explore, deciding what to see at the Field Museum can be a daunting task. We recommend starting in the institution's popular "Inside Ancient Egypt" exhibit, where you'll descend into a recreation of the 5,000-year-old tomb of pharaoh’s son Unis-Ankh. From there, you'll walk through an extensive assemblage of Egyptian artifacts, including one of the largest collections of mummies in the U.S.

Don’t miss:  "Bloodsuckers: Legends to Leeches," an exhibit dedicated to bloodsucking species both real and fictional.

24.  Watch the Chicago Symphony Orchestra perform

• Classical and opera
• price 3 of 4

What is it?  A world-renowned orchestra.

Why go?:  Considered one of the leading and oldest orchestras in the United States, the CSO plays a variety of enthralling music and hosts touring soloists and small ensembles as well. You can also catch special performances set to the scores of popular films like Star Wars and Harry Potter. During fall to spring, Symphony Center is home to the CSO. 

Don't miss:  The 2023/2024 season includes the Chicago debut of Canadian pianist Bruce Liu on June 2.

25.  See a stellar play from the Steppenwolf Theatre

What is it?  What people think of when they hear "Chicago theater."

Why go?  Steppenwolf is known for its all-star collection of ensemble talent (folks like Laurie Metcalf, John Malkovich and Tracy Letts number among its ranks).

Don't miss:  " Purpose," an epic family drama directed by two-time Tony Award winner Phylicia Rashad.

26.  Explore the universe at the Adler Planetarium

What is it?:  A museum dedicated to astronomy and all things outer space.

Why go?:  You'll escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. The Doane Observatory is also home to the largest public telescope in the area, and gathers 7,000 times more light than the human eye.

Don't miss: Adler at Night, the planetarium's afterhours event that takes place from 4pm-10pm every Wednesday. Best of all, entry is free for Illinois residents.

27.  Make a pit stop at the Chicago Cultural Center

What is it? Located just around the corner from Millennium Park, this gorgeous specimen of a building is the country's first free municipal cultural center; inside, you'll find tons of programming, exhibitions, and stunning architectural flourishes to explore, as well as a gift shop stocked with goods from local artists.

Why go? Anyone spending time in the Loop should make a point to check out any ongoing programming happening at the Cultural Center, which can run the gamut from art exhibitions to massive architectural expos. And did we mention it's completely free?

Don't miss: Once you've toured the 38-foot Tiffany glass dome in Preston Bradley Hall, head to the Landmarks Gallery  on the first floor to see "The Great Chicago Fire in Focus,"  an exhibit of images detailing the destruction of the historic disaster.

28.  Get acquainted with Frank Lloyd Wright’s architecture at the Robie House

• Historic buildings and sites

What is it?   A historic house that Wright himself called "the cornerstone of modern architecture." 

Why go?   Nearby Oak Park may be a mecca for Frank Lloyd Wright enthusiasts, but you can see some of the architect's finest work without leaving the city. The Robie House in Hyde Park exemplifies Wright's signature Prairie School style, both in its external appearance and interior design. You can take a peek inside the historic home (and get some decorating ideas) by taking a tour led by the Frank Lloyd Wright Trust, offered five days a week.

Don’t miss:  The bevy of beautiful art-glass windows and the furniture (also designed by Wright). 

29.  Go back in time at the Historic Pullman Foundation Exhibit Hall

What is it?  This destination  houses exhibits about the South Side 'hood's growth and preservation. 

Why go? When businessman George Pullman started a railroad sleeping car factory on the South Side of Chicago, he built an entire town to house his employees. The industrial complex has since been designated a National Park and the Pullman Exhibit Hall is the best place to start exploring the area.

Don’t miss:  Set out on a self-guided tour of the district, which includes historic buildings featured in films like  Road to Perdition  and  The Fugitive.

30.  Get high at 360 CHICAGO

• Streeterville

What is it?  Set atop the building formerly known as the John Hancock Center, this observatory offers views of the city (and surrounding states) from 1,030 feet above the streets.

Why go?  The sights from the 94th floor can't be beat, whether you're a longtime Chicagoan or a visitor. Stick around to enjoy a cocktail at 360 CHICAGO's bar or explore some of the interactive exhibits detailing the city's history.

Don't miss:  360 CHICAGO's most terrifying attraction: TILT. Guests board a glass-enclosed platform that slowly tilts over the side of the building at a 30-degree angle. Thrill seekers will want to fork over the additional fee for a ticket. 

31.  Catch rising bands at the Empty Bottle

• Rock and indie
• Ukrainian Village

What is it?  The best damn rock club in the States.

Why go? For more than a quarter of a century, a gig at the Empty Bottle has served as a rite of passage for local and touring musicians. The nondescript club on the edge of Ukrainian Village is far from the biggest venue in town (capacity is around 300), but the folks who book it have a knack for landing rockers, electronic acts and experimental musicians on the rise. Grab an Old Style, find a spot on the stairs by the stage and take in a sure-to-be memorable show. 

Don’t miss:  A slice of pizza before (or after) the show at next door's Pizza Friendly Pizza.  

32.  Take a stroll through Chinatown

• Public spaces

What is it?   A neighborhood that serves as one of the primary hubs of Chicago's Chinese community, filled with restaurants, shops and incredible nods to East Asian architecture.

Why go?  Chinatown is a great place to mosey from shop to shop and spend some time outdoors, whether you're walking through Chinatown Square or admiring the sweeping skyline views from Ping Tom Memorial Park. 

Don't miss:   Dumplings from QYX, bubble tea from the walk-up window at Joy Yee, Peking duck from BBQ King House, cocktails at Nine Bar... the list goes on. Start at Chinatown Square and work your way south down Wentworth, passing under the street's famous gate and into its central commercial strip.

33.  Get down to house music at Smart Bar

What is it?  An ace place to lose it to house music, right in the city that invented the genre. 

Why go? In the ’80s, Chicago served as the epicenter of the creation of a new sound that still influences the work of modern hip-hop and electronic artists. If you want to experience house music, there's no more authentic environment than Smart Bar. Within the subterranean Wrigleyville club, skilled DJs, drag performers and sweaty revelers come together to the steady pulse of a house beat.

Don’t miss:   The crowded Queen dance party, which takes place nearly every Sunday night.

34.  Hear live blues at Kingston Mines

• Folk, country and blues
• Sheffield & DePaul

What is it? You have to listen to blues music when you’re in Chicago, and few places are as fun to see the blues as Kingston Mines.

Why go? The city’s largest and oldest continuously operating blues club features high-energy live blues bands performing on two stages until 4am Thursdays and Fridays and 5am on Saturdays. Whether you’re hanging with bleary-eyed tourists from Iowa or friends of the local blues guitarists on stage, it’s hard to have a bad time here.

Don’t miss: The cover grants you entry to both rooms and its two different stages.

35.  Sip suds at Half Acre Brewery Balmoral

• Lincoln Square

What is it? The far North Side warehouse where one of the city's largest breweries produces the majority of its beer.

Why go?  Half Acre Balmoral's expansive parking lot beer gaden offers room to sip signature brews like Daisy Cutter and Tome in the open air. Plus, a menu of bar foods is available for hungry drinkers. There's also an indoor taproom for the colder months. 

Don’t miss: There are beers on tap here that are exclusive to this location, so be on the lookout. 

36.  Walk through an outdoor art gallery at the 16th Street Murals

• Lower West Side

What is it? A collection of murals and street art on an old railroad embankment in Pilsen that stretches from the Chicago River to Western Avenue.

Why go?  Take a stroll across 16th Street and you'll spot murals by local artists like JC Rivera and Hebru Brantley as well as international talents like The Yok and Sheryo.

Don't miss:  An infamous painting of a severed possum by Belgian street artist ROA, located just west of 16th and Laflin Street.

37.  Tour the work of Ludwig Mies van der Rohe at the Illinois Institute of Technology

What is it?  The college's Bronzeville campus is studded with one of the country's largest collection of buildings designed by Ludwig Mies van der Rohe, the German-born steward of the Bauhaus architecture movement in Chicago. 

Why go?  Mies was a pioneering figure in American Modernism, and he completed some of his most significant work while serving as the director of the Department of Architecture at the Armour Institute of Technology. The sleek, column-free S.R. Crown Hall—which houses the present-day College of Architecture at IIT—is considered his masterpiece, and the college's entire campus has been inducted into the National Register of Historic Places. 

Don’t miss:  You can always take a self-guided tour, but the Chicago Architecture Center offers two-hour guided sessions that lead visitors through the evolution of the campus, from Mies' heyday in the mid-20th century to the more recent McCormick Tribune Campus Center designed by Pritzker Prize-winning Dutch architect Rem Koolhaas.

38.  Explore the gallery district on Chicago Avenue

• East Village

What is it?   A string of art galleries located on Chicago Avenue between Ashland Avenue and Wood Street. 

Why go?  A combination of favorable real estate, happenstance and collaborative spirit has drawn some of Chicago's finest galleries—including Matthew Rachman Gallery, DOCUMENT, Rhona Hoffman, Chicago Truborn and many others—to this multi-block stretch in West Town, creating a concentrated (and not to mention, free) tour of curated work. Plan an afternoon around the exhibitions that pique your interest, and don't forget to make a reservation at each gallery ahead of time. 

Don’t miss:  Looking to splurge on, say, a mid-century Danish sofa or a luxury cowhide rug? Make an appointment at Matthew Rachman Gallery to view the furniture collection available for sale, where you'll find items from iconic designers like Vladimir Kagan, Jens Risom and Eero Saarinen.  

39.  Watch fish swim by at Shedd Aquarium

• Zoo and aquariums

What is it?  Chicago's only aquarium, home to thousands of colorful fish and other aquatic creatures.

Why go?   Permanent exhibitions like "Wild Reef" and "Amazon" allow you to gaze at fish, stingrays, an anaconda and sharks. But the interactive experiences may be the biggest draw, allowing visitors to get up close and personal with some of the animals that live at the Shedd Aquarium and learn more about them.

Don't miss:  The internet-famous rockhopper penguins, known for exploring the Shedd (and other Chicago institutions) during lockdown in 2020. You can say hi to them in the Polar Play Zone exhibit.

40.  Take in the skyline from Promontory Point

What is it? One of the best places to sit on a rock and look at tall buildings from afar.

Why go? Just north of the Museum of Science and Industry, this man-made peninsula is a short jaunt from the Lakefront Trail. When the sun is out, it's a beloved spot for picnics, lounging and canoodling on the rock steps that line the perimeter of the point.

Don’t miss: The Promontory Point Field House, an extremely popular wedding venue that looks like a miniature castle.

41.  Have your mind blown at the Chicago Magic Lounge

What is it? A love letter to all things magic hidden behind what  appears to be a laundromat.

Why go? After three years of performances at Uptown Underground , the Chicago Magic Lounge’s brick-and-mortar manifestation opened in early 2018. The spot sports three performance spaces. There’s the front bar, where you can enjoy a drink and some sleight-of-hand. Then there’s the 120-seat Blackstone Cabaret mainstage, where ticketed shows take place, as well as a smaller back room, dubbed the 654 Club, offers up-close magic. Don’t miss: While enjoying your cocktail in the bar, check out the magician’s table built into the center of the bar itself. 

42.  Watch 30 plays in 60 minutes at the Neo-Futurarium

• Interactive

What is it? A theater where performance art is populist and fun AF. 

Why go?  You never know what you'll see when you attend the Neo-Futurists' signature show,  Infinite Wrench , but it's nearly always entertaining. The ensemble races against the clock to cram 30 miniature, two-minute plays into a 60-minute show that bristles with madcap energy. Over the course of the evening, you might witness a dramatic monologue, a funny song or simply stare at someone eating a sandwich. 

Don’t miss:  Grab a seat toward the front of the stage if you're game for interacting directly with the show's performers (their plays occasionally call for audience participation). 

43.  Double over laughing at the Second City

• Comedy clubs

What is it?  Where Bill Murray,  Tina Fey, Gilda Radner, Chris Farley and Steve Carell  cut their comedic teeth. 

Why go?   Before they joined the cast of   Saturday Night Live   or became big-screen stars, those folks above practiced their craft on the mainstage at the Second City. The venue's premiere revue features some of the institution's most talented performers in a series of loosely-connected, topical comedy sketches.

44.  Drink all the brews at the Beer Temple

• Liquor stores

What is it?  A place of worship for hops-heads.

Why go? You'll always find something new or unexpected on tap at this Avondale bar and bottle shop, which has gained a reputation for stocking the most sought-after releases from local and out-of-state brewers. 

Don’t miss:  Follow the Beer Temple on Instagram to stay on top of what's newly in-stock. If you want to get your hands on the latest brews from Hop Butcher and other hard-to-find releases, you'll need to order quickly.

45.  Take a ride on Navy Pier's Centennial Wheel

• Towers and viewpoints

What is it? : A nearly 200-foot-high Ferris wheel.

Why go?:  You won't find many sights that can rival the ones from Centennial Wheel. Riders are treated to 360-degree views of the skyline and Lake Michigan while sitting in enclosed, climate-controlled gondolas.

Don't miss:  After your ride, head to the Original Rainbow Cone at Navy Pier for a tasty sweet treat.

46.  Find something strange at Woolly Mammoth Antiques & Oddities

What is it?  A store that's not for the faint of heart and is one hell of a conversation starter.

Why go? You never know what you'll find at this popular Andersonville antique store, which prides itself on stocking items that are "resurrected from the past." Taxidermy, diving helmets, military supplies and other interesting knick-knacks typically line the shelves.

Don’t miss:  The anatomy items, medical stuff, skull bones (of all kinds) and skeletons.

47.  Add to your reading list at Pilsen Community Books

What is it?  A worker-owned bookstore, offering new and used books for in-store browsing and curbside pickup.

Why go?  You can support a local business while chipping away at your reading list by ordering something from this Pilsen shop. Submit an order online or call and talk to a human during business hours if you need a recommendation.

Don't miss:  Add a donation to the Liberation Library to your order to support the purchase of books for incarcerated youth.

48.  Explore cinematic history at Doc Films

• Independent

What is it? The University of Chicago's single-screen theater is the longest continuously running student film society in the country.

Why go? In the fall, winter and spring, this Hyde Park institution sheds light on some of the most obscure corners of film history, showcasing retrospectives of underappreciated directors, deep dives into highly specific movie genres and rarely-screened foreign films. Best of all, a ticket will only set you back $7.

Don't miss: Prefer to see something contemporary on the big screen? Stop by on Saturday nights, which are typically reserved for screenings of new and recent releases.

49.  Find some new records at Dusty Groove

• Music and entertainment

What is it?  A Wicker Park destination for discerning record nerds.

Why go? The "dusty grooves" of course refer to the wonderous global rhythms found in the smartly curated bins, sorted into Tropicalia, Afrobeat, reggae, vintage soul, French pop, blues, jazz and other genres. 

Don’t miss:  Obscure titles that you'll have a hard time finding elsewhere in the city.

50.  Watch a movie at the Music Box Theatre

What is it?  Chicago's premiere arthouse theater. 

Why go? Aside from being one of the 50 most beautiful cinemas in the world , the Music Box's screens one of the best assortments of arthouse films, documentaries and foreign language pictures in the city. And if you prefer to turn your living room into a theater,  Music Box Direct allows you to stream movies at home.

Don't miss:  Performances on the theatre organ, which is played during weekend intermissions, monthly silent film screenings and other special presentations. 

51.  Set a high score at Logan Arcade

• Logan Square

What is it? An expansive, bar-equipped arcade housed inside a former hardware store.

Why go? There are many arcade bars scattered throughout Chicago, but Logan Arcade boasts one of the largest (and best maintained) collection of games. You'll find classics like Ms. Pac-Man and Q*Bert alongside more modern machines like Mario Kart and a Jurassic Park shooter. Pinball wizards will flip over the selection of tables, including ones inspired by properties like Game of Thrones and Star Wars . Plus, you can sip a craft beer or cocktail between high-score attempts.

Don't miss: The Killer Queen cabinet, which allows two teams of five players to face off in a bee-themed battle that requires some intense cooperation to achieve victory.

52.  Have your mind blown at the Museum of Illusions

• Exhibitions

What is it?  The Chicago outpost of a chain of trippy "edutainment" destinations, packed with mind-bending photo-ops.

Why go?  You'll be able to take a ton of cool Instagram photos at the Museum of Illusions, but you'll also have a chance to learn a thing or two along the way. Staff is present to explain the psychology and science behind each of the mind-bending displays.

Don't miss:  The museum's infinity room, which surrounds guests with mirrors and shimmering lights.

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35 Fun & Unusual Things to Do in Downtown Chicago, Illinois

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Thousands of tourists make their way to Chicago every year, and for good reason. The “windy city” has plenty to offer in the form of great architecture and a stunning skyline filled with skyscrapers, world-class museums, a growing craft beer culture, and a shoreline that mixes modern waterfront areas with miles of beaches and iconic landmarks.

The list of places to visit in Chicago is long and exciting and covers everything from amazing food to an exciting cultural scene.

No matter why you’re visiting, though, there are plenty of fun things to do in Chicago – so many, in fact, that we are focusing our list on the best things to do in Downtown Chicago , a 35-block area famous for its vibrant urban atmosphere.

1 – Take a sightseeing river cruise

There’s no better way to admire the city’s great architecture than from the water – and the Chicago River offers the perfect opportunity to relax on board a cruise and enjoy Chicago’s iconic skyline.

Most cruises depart from Navy Pier and for 60-75 minutes (depending on which cruise you choose) will take you to see many of the city’s most famous landmarks, including the Tribune Tower, Marina City, and the John Hancock Center skyscraper.

You’ll sail under historical bridges, be able to listen to a live narration, and discover all three branches of the Chicago River as you learn about the buildings that helped shape the city.

Drinks are available for purchase and cruises depart several times a day, so you can choose the time more convenient for you.

• boat tours in Chicago

Read more about the best Chicago architecture boat tours

2 – Soak up some sun at Millennium Park

Covering almost 25 acres, Millenium Park is much more than just a green space in the heart of Chicago. Filled with interesting art and great attractions, the park has become a gathering point and the place to be for major annual events (like the lighting of the city’s Christmas tree every year).

Crown Fountain is perhaps the best-known spot in the park – a video tower sculpture that displays videos as it spouts waters into the reflecting pool next to it.

The park’s Jay Pritzker Pavilion, a massive outdoor amphitheater, is home to the Grant Park Symphony Orchestra and Chorus and holds musical series, summer concerts, and performing arts events.

Another favorite in the park is Cloud Gate (aka The Bean), a massive 10 m× 13 m×20 m stainless steel sculpture that reflects a distorted Chicago on every inch of its surface.

Near the northwest end of the park, there’s Wrigley Square, best known for its Millenium Monument, a fun semi-circle of 12-meter-tall Roman-style columns popular for photo opportunities and events.

3 – Get your culture fix at one of the many art museums in Chicago

Chicago is home to some incredible museums, and your list of things to do in Downtown Chicago should certainly include some of them.

With a world-class collection of over 300,000 pieces, The Art Institute of Chicago is a good place to start. If you’re still hungry for more great art, try the Museum of Contemporary Art , where the collection focuses on post-WWII artists.

With a massive collection of work by Ansel Adams, portraitist Julia Margaret Cameron, and street-photography pioneer Julia Margaret Cameron among many other famous names, the Museum of Contemporary Photography  is a great place to spend a couple of hours discovering the great American photographers of the past century.

Housed in a former private mansion, the Richard H. Driehaus Museum is an homage to the stunning decorative arts of the past two centuries. In addition to original art nouveau items, the home features lots of Tiffany glass and artworks and marble sculptures.

For a unique experience, it’s hard to beat the WNDR Museum , an immersive experience that features exhibits like an Infinity Mirror Room, audio-visual installations, and optical illusions.

Read more about the best museums in Chicago

4 – Enjoy the waterfront views at Navy Pier

The 1,000-meter-long pier has become one of Chicago’s most recognizable and popular destinations. Sitting right on Lake Michigan and home to a number of attractions, shops, and restaurants, the pier is a busy place no matter the season.

Outdoor attractions include everything from remote control boats to a drop tower, an old carousel, and a state-of-the-art Centennial Ferris Wheel that will take you over 60 meters up into the air for breathtaking 360-degree views over Chicago and Lake Michigan.

Other attractions include a 370-square-meter maze, a one-acre botanical garden, and the Chicago Children’s Museum. On rainy days, an IMAX theater and the Chicago Shakespeare Theater offer great indoor options as well.

Even if you don’t visit any of the attractions, the pier itself is a great place for a walk and often features outdoor art installations and live music in summer. The 45-meter Schooner Windy tall ship departs from Navy Pier and offers not only great views of the shoreline but also a choice of a Pirates-inspired sail or a sunset sail.

• Navy Pier Centennial Wheel tickets

5 – Say hi to marine creatures big and small at the Shedd Aquarium

Home to over 30,000 animals, the Shedd Aquarium is divided into major zones like Caribbean Reef, Amazon Rising, Polar Play Zone, and Waters of the World.

Learn about the animals inhabiting Chicago’s local waters, say hello to rescued green sea turtles, meet red-bellied piranhas and green anacondas, and pet giant rays. Or head to the underwater viewing area to come face to face with beluga whales, dolphins, and penguins.

A 4D theater inside the aquarium shows water-inspired films like Sea Monsters and Ice Age. There are also special temporary exhibits focused on beautiful marine creatures, the unique Australian Lungfish, sharks, and American alligators.

6 – Discover Chicago’s past with a gangsters and crime tour

The Windy City is historically known for being home to notorious mobsters during the 1920s Prohibition Era. Al Capone once called Chicago home and ran an underground gambling and bootlegging “industry” that was worth millions of dollars.

Today, plenty of tours will take you to the hot spots of Prohibition-era mobster activity, showing you the criminal underworld of Chicago and giving you a glimpse of how big names like Capone, the Untouchables, and John Dillinger forever changed the city.

Both walking and bus tours are available, and both come with a history-savvy guide who will take you to the most important location of Chicago’s criminal past. Visit the place where the St Valentine’s Day Massacre took place, stop by an old gangster headquarters, see where Al Capone used to carry out business and also where he went for fun, and stop by Harry Caray’s Italian Steakhouse to visit the secret vault once used by Frank Nitti.

Gangsters and Ghosts tours are also available, where you’ll get a peak into Chicago’s most haunted places, including the Palmer House and Death Alley.

• gangsters and crime tours

7 – Take the kids to the Chicago Children’s Museum

At the top of things to do in Downtown Chigaco if you have kids is this interactive museum located at the popular Navy Pier. At almost 8,000 square meters, it’s one of the largest children’s museums in the country.

Four floors of hands-on exhibits are divided into three age groups, including babies and toddlers, ages 4-8, and ages 9 and up. This means everybody gets a chance to have fun learning for hours on end at the Chicago Children’s Museum .

Exhibits include everything from boats and climbing corners to an art studio, a kids’ town, a dinosaur area (complete with an excavation pit), and a tinkering lab where young scientists can explore technology, math, and engineering concepts.

8 – Catch breathtaking panoramic views from the 360 Chicago Observation Deck

There’s no better place to catch breathtaking 360-degree views of Chicago’s skyline than from the top of the 360 Chicago Observation Deck.

Set 94 stories up in the air, near the top of the John Hancock Center skyscraper, the observatory offers bird’s-eye views of many city landmarks as well as the lakefront shoreline and it’s definitely one of the best things to do in Downtown Chicago.

Just getting to the observatory is thrilling (you’ll be riding one of the fastest elevators in the country), but the real excitement here is TILT, a thrill ride in the form of a glass platform that tilts forward at a 30-degree angle so you can get the best downward-facing views from 1,000 meters up in the air.

The observatory is also home to the Architect’s Corner Café and Bar and an open-air SkyWalk.

• 360 Chicago Observation Deck tickets

9 – Discover local delicacies with a food tour

Chicago has its share of special local foods – perhaps the most famous ones being the Chicago deep-dish pizza or Chicago-style pizza and the iconic Italian beef sandwich – and the best way to experience them is through a food tour.

Stroll through the streets of Chicago with an expert guide and discover the best spots to taste a number of foods. Learn about the history of the city as you walk past famous landmarks like the Chicago River and Millennium Park and discover great architecture and street art.

Sink your teeth into some deep-dish pizza, sip a local beer, taste a Chicago-style hot dog, and enjoy original Italian pastries. You can even choose special food tours like a 2.5-hour Taste of Chinatown walking tour or a half-day tour exploring both the food and the architecture of Chicago. There’s even a donut tour for a mouth-watering sweet experience at some of the best donut shops in the city.

• food tours in Chicago

10 – See Chicago like never before from the Willis Tower Skydeck

The 108 stories tall Willis Tower is best known for its observatory. It’s not only the tallest Skydeck observatory in the country but also one of Chicago’s most popular attractions.

Here, visitors can step into retractable glass balconies – essentially glass boxes with a glass floor extending more than 1 meter out from the building.

Not only can you look 400 meters straight down over the streets below, but also get 360-degree views over Lake Michigan and spanning four states on clear, sunny days. Don’t miss out on this thrilling experience when in Chicago!

• Willis Tower Skydeck Chicago tickets

Hot tip: Cheap Skydeck Chicago Tickets – How to Save up to 20%

11 – See the city’s most famous buildings with an architecture tour

Chicago’s most iconic buildings sit near the river – and there’s no better way to enjoy them than with an architecture river cruise tour. Jump onboard and let your expert guide introduce you to landmark buildings as you cruise along all three branches of the Chicago River.

You’ll pass by the 36-floor neo-Gothic skyscraper Tribune Tower, the Rookery Building (Chicago’s oldest standing high-rise), and the Wrigley Building, a stunning 1920s skyscraper with a bright white facade. You’ll also see the Chicago Water Tower, listed on the National Register of Historic Places and once used to pump water from the lake.

Would you rather try an architectural walking tour of Chicago? For a shorter, self-guided architecture tour, head to the 2 km-long Chicago Riverwalk .

Otherwise, try The Loop route, which takes you through the best of Downtown Chicago art-deco buildings, where you’ll step inside the dazzling lobby of the Rookery Building, see the vibrant facade of the Chicago Board of Trade, and marvel at the beauty of buildings right out of the roaring 1920s.

Some of these walking tours will also take you to the Chicago Cultural Center (famous for its Tiffany glass dome) and the Chicago Architecture Center , where you’ll have a chance to learn more about the city’s architectural history.

• architecture tours in Chicago

12 – Visit the stunning Holy Name Cathedral

This breathtaking Gothic Revival cathedral was built after the Great Chicago Fire of 1871 destroyed two of the main churches in the city.

The result is an architectural marvel that mixes dark wood with lots of stained glass and details like massive bronze doors, 21-meter-tall ceilings, and a number of sculptures and castings depicting the apostles and Old Testament scenes.

The church is home to two pipe organs often used during mass and an overall design that focuses on the “Tree of Life” theme of Biblical salvation.

The Holy Name Cathedral is open to visitors during the day if you just want to admire its beauty and take some photos.

13 – Walk the historical Michigan Avenue

Running from the shore of Lake Michigan all the way through the city, Michigan Avenue was once primarily residential. Over the years, the road has been extended north of the Chicago River and now crosses over the Michigan Avenue Bridge (officially named the DuSable Bridge), connecting Chicago’s south side and north side.

Today, a walk down Michigan Avenue is one of the must-do things in Downtown Chicago. Home to some of the city’s most important attractions – including Millennium Park and The Art Institute of Chicago – Michigan Avenue has become an attraction in itself. Part of the reason for that is the stretch of the avenue known as the Magnificent Mile .

Flanked by skyscrapers and similar to Fifth Avenue in New York, the Magnificent Mile is filled with luxury shops, restaurants and 5-star hotels, and a number of Chicago landmarks. During the Christmas season, over a million lights are used to decorate the trees lining up the avenue.

• walking tours in Chicago

14 – See the world’s largest dinosaur at the Field Museum of Natural History

With a collection of over 24 million objects, the Field Museum of Natural History (FMNH) is one of Chicago’s most impressive museums. The collection covers everything from fossils and meteorites to ancient civilizations, creepy creatures, gemstones, and biodiversity.

The main attractions here are, without a doubt, the dinosaurs – which include SUE (the most complete T.rex ever found) and Titanosaur Máximo, the largest dinosaur that ever lived at 37 meters long and almost 9 meters tall.

There’s also a 3D theater, a kid-friendly PlayLab, and an exciting Egyptian exhibit complete with mummies, a 4,000-year-old boat, and an ancient burial chamber.

The FMNH is part of the Museum Campus, a 57-acre waterfront park that’s also home to a number of other attractions such as the Adler Planetarium, the multi-purpose Soldier Field stadium, the Shedd Aquarium, and America’s largest convention space at McCormick Place.

• Field Museum of Natural History tickets

15 – Catch a game at the United Center

This multi-purpose indoor arena is the permanent home of the National Basketball Association’s Chicago Bulls and the National Hockey League’s Chicago Blackhawks. Other sporting events, including NCAA basketball, professional wrestling, and mixed martial arts tournaments are sometimes held at United Center as well.

With a capacity of over 20,000, the arena has also become a popular venue for concerts – over the years, everybody from Paul McCartney to Lady Gaga to the Rolling Stones has performed here.

The arena features a number of statues representing some of the most famous house players, including Michael Jordan and Blackhawks legend Bobby Hull.

If you’re visiting Chicago during the pre-season (which starts in October), you should be able to get tickets last minute to cheer for the local team.

16 – Discover the city with a hop-on hop-off bus tour

Save time and money and see all the city’s top sights with a hop-on hop-off bus tour. You’ll avoid headaches and trying to figure out an itinerary – just jump on board and get off at the stop of your choice to explore and take some photos.

When you’re ready, just get back on the open-top, double-decker bus and continue on your journey as you listen to the audio commentary and learn more about Chicago’s history and culture.

The bus takes you on a two-hour loop that includes 11 stops, such as the Navy Pier, the 360 Skydeck, Museum Campus, and the Chicago Riverwalk.

If you want to see a different side of the city, grab a seat on the Big Bus Chicago Night Tour , a 75-minutes non-stop tour that takes you to see the most stunning landmarks as the city lights turn on.

• bus tours in Chicago

17 – Celebrate the world of sports at the Chicago Sports Museum

The 2100-square-foot Chicago Sports Museum not only houses a massive collection of sports memorabilia, but it’s also home to interactive experiences that will make you feel like your favorite sports stars are right there with you.

Learn about the evolution of baseballs, test your vertical jump against the giants of basketballs, see game memorabilia, and explore the history of Chicago baseball. You can jump into a racing car simulator and learn about the superstitions and legends of the sports world.

You can even see the original Sports Almanac prop from the movie “Back to the Future II,” which predicted the Chicago Cubs would win the World Series in 2015. The Cubs, which had not won a World Series since 1908, actually won the title in 2016 – just a year off from what the movie predicted.

18 – Trick your mind at the Museum of Illusions

Stop by this museum to discover a great collection of magic and trickery exhibits that will both confuse you and amuse you! Get ready for lots of interactive fun created with paint, holograms, and clever design.

Over 80 mind-bending illusions will keep both kids and adults busy for a couple of hours – Step into a spinning vortex tunnel, walk into rooms that defy the laws of physics and practice some anti-gravity moves, come face-to-face with a bottomless pit, and shrink yourself to tiny sizes.

You’ll find plenty of perfect selfie opportunities here; each exhibit even has a mark to show you where to stand for the best photos!

• Museum of Illusions tickets

19 – Take a Segway tour around Grant Park

Looking for things to do in Downtown Chicago when you only have a couple of hours to fill? You can discover Chicago’s beautiful lakefront on a fun Segway tour as you learn about the area’s history and famous landmarks.

Most tours start at the Buckingham Fountain in Grant Park and then bring you closer to popular attractions like Lake Michigan and the city skyline, Museum Campus, and Millennium Park.

Don’t worry if this is your first time riding a Segway! Your tour guide will guide you through the basics before you set off on your adventure. There is nothing like seeing the city on a Segway tour – you’ll be able to cover a lot more ground than you would walking and have lots of fun in the process!

• segway tours in Chicago

20 – Spend an afternoon discovering Lincoln Park

Chicago’s largest park has so much to offer, you’d need an entire day to truly explore it all. Over 1,200 acres of green space serve as home to nature reserves, recreational facilities including a golf course and a skate park, and a number of public beaches that offer great swimming and boating facilities. North Avenue Beach is particularly popular and offers plenty of space for lounging shoreside and water activities.

Perhaps the most famous attraction here is the Lincoln Park Zoo , a 35-acre space home to over 1,000 animals. The Conservatory is another big draw, home to displays of everything from giant palms to an orchid room. The Peggy Notebaert Nature Museum is a nice complement, with a butterfly house and exhibits about the ecosystem of the region.

If you’re up for learning more about Chicago and American history, the Chicago History Museum offers a great look into the growth of the city, chronicles Lincoln’s assassination, and provides a number of exhibits for kids.

21 – Enjoy the magic of Lake Michigan

The largest (by area) of the five Great Lakes, Lake Michigan attracts thousands of visitors every year, who mostly come here for water sports like sea kayaking, kitesurfing, and yachting.

A number of wide and busy beaches line up the shoreline, with Ohio Street Beach offering convenience (it’s very close to Navy Pier) and lots of open space to lounge. Winter visitors often stop by the fascinating phenomenon of ice volcanoes forming on the lake.

Boat tours are a great way to discover the beauty of the lake. You can choose between a relaxing skyline or a brunch cruise. Or end the day with a relaxing dinner cruise where you can indulge both your eyes and your taste buds with a great all-you-can-eat buffet and onboard entertainment with DJ music.

Adrenaline lovers can choose an exciting speedboat ride that takes you on an architecture tour along skyscrapers and old bridges and ends with a massive fireworks display. There are also ferries that take passengers to different nearby islands for sunbathing in a bit more privacy.

If you’d rather stay on land, the 29km-long Lakefront Trail is a great way to explore the shoreline – no matter if you’re biking or hiking.

• Lake Michigan tours

22 – Get inspired at the American Writers Museum

The only museum in the country completely dedicated to American writers and their work, this quirky but interesting space offers exhibits on the work of novelists, poets, journalists, and even humor writers. There’s even a special section dedicated to the work of local Chicago writers.

Interactive stations allow visitors to play videos and sounds and even to activate scents connected to important literary works.

See how American writers from the 1600s and 1700s started to develop their own style away from European influence, what readers were choosing to read for fun through the centuries, and the writing habits of famous authors.

The American Writers Museum also hosts temporary exhibits and organizes special “meet the writers” evenings.

23 – Check out Soldier Field Stadium

The multi-purpose Soldier Field Stadium is home to the NFL’s Chicago Bears and the Chicago Fire FC soccer team, but it has also hosted a number of other events, including games for the Special Olympics, rallies from famous figures like Martin Luther King Jr, and the occasional hockey game.

The stadium can sit over 61,000 people, making it perfect for large events and shows. Concerts held here have included everybody from Barbra Streisand and Paul McCartney to The Rolling Stones, Madonna, and Jay-Z.

The 1924 stadium lost its National Historic Landmark designation in 2006 after an extensive renovation that modernized the space and added environmentally sustainable details.

24 – Visit The Second City, Chicago’s best comedy club

If you’re looking for things to do in Downtown Chicago once the sun sets, this one is a must. Chicago’s oldest improv theater takes its name from one of the city’s old nicknames. Back in the early 20th century, Chicago earned the second-place slot in an ongoing rivalry between Chicago and NYC as the best metropolitan area.

While this might sound like a loss, Chicago has embraced its nickname in a fun way – and you can see just that when you visit The Second City premier comedy club.

The club served as the starting point for many famous comedians – including Alan Alda, Mike Myers, and Bill Murray – and a number of well-known performers still take to the stage here regularly. Stop by any night of the week for a laugh-out-loud good time with live shows starting at 7 pm.

25 – Spend the day at Maggie Daley Park

The 20-acre Maggie Daley Park , located near Lake Michigan, is best known for its many activities and features available.

The biggest attraction is the half km long ice skating ribbon, which runs along one side of the park and offers slight changes in elevation for some fun challenges. During the summer, the space is used as a rollerskating area.

Two rock-climbing structures with a maximum height of 12 meters welcome both beginners and experienced climbers and offer both bouldering and lead-harnessed climbing.

For family-friendly fun, there’s an 18-hole miniature golf course, tennis courts, and an Alice-in-Wonderland inspired “play garden” filled with lots of water features, climbing spaces, slides, and bridges for kids of all ages.

26 – Take a helicopter tour over the Chicago’s skyline

Want to see Chicago’s beautiful architecture and green spaces from up above? A helicopter tour is the best way to do just that! Soar over Downtown Chicago, past the Willis Tower and over famous sights like Wrigley Field, the Navy Pier, and the Chicago River.

The 15-minute ride will allow you to capture stunning photos of the city in a Bell 206, turbine-engine helicopter. You’ll feel the rush of the flight combined with the excitement of seeing iconic landmarks like never before.

Private 45-minute scenic flights are a great choice if you’re traveling with your own group and want some privacy and out-of-this-world views of Chicago.

• helicopter tours in Chicago

Read more about helicopter tours in Chicago – which one is the best?

27 – Attend a performance of the Chicago Symphony Orchestra at Orchestra Hall

The historical Orchestra Hall at the Symphony Center has been home to the Chicago Symphony Orchestra and the Chicago Symphony Chorus for many years.

While the building retains many original architectural details dating back to 1904, the Orchestra Hall was extensively renovated in the 20th century to improve acoustics, re-organize seating spaces to avoid blind spots, and add rehearsal spaces and features like a cafe and better lighting.

The hall’s concert series includes a mix of classical masterpieces and unique new shows, including piano concerts, kid-friendly programs, and acclaimed guest conductors. There are also unique movie experiences throughout the year where you get to enjoy classic films — from Amadeus to The Princess Bridge to Harry Potter — on giant screens as the orchestra performs the film’s score live.

28 – Grab a drink or two during a beer-tasting tour

Chicago has become a great destination for craft beer, and you can try several of them in one single evening when you book a special guided tour of some of the best breweries in town – you’ll get a chance to see the brewing process and enjoy plenty of beer samples along the way.

For a truly unique experience, grab a seat on the Chicago Craft Brewery Barrel bus tour. Visit a number of craft beer breweries onboard a bus shaped like a giant barrel reminiscent of those used during the 1920s Prohibition Era.

Want to explore on your own? There are plenty of breweries in Downtown Chicago that are worth a visit, including The Moody Tongue brewery with its barrel-aged brews, Motor Row Brewing and its unique beers (don’t miss their Blonde Belgian honey wheat brew), and Rock Bottom Restaurant & Brewery , one of the original breweries in Chicago.

Miller’s Pub , one of Chicago’s oldest late-night spots, offers great comfort food and an old-school vibe perfect for grabbing some drinks.

• beer tasting in Chicago

29 – Indulge your inner space explorer at the Adler Planetarium

Despite its name, the Adler Planetarium is also an astronomy and astrophysics museum. Built in the 1930s as the first planetarium in the country, the Adler has become synonymous with the quest for understanding the universe.

Visitors should stop at the planetarium’s Doane Observatory first, which is open on select Wednesdays nights, before heading into the main building to explore more. There, you can catch a show at the massive Grainger Sky Theater or the Samuel C. Johnson Family Star Theater, which specializes in 3D shows.

The museum includes a number of exhibits dedicated to the history of stargazing, the Chicago night sky, the missions to the moon (which includes the original Gemini 12 spacecraft), and our solar system.

Visitors can take photos with some of NASA’s rovers, learn through interactive stations, and take a look through a 17th-century telescope.

30 – Test your wits at The Escape Game Chicago

Do you have what it takes to find clues, solve puzzles and beat the clock? You have just 60 minutes to test your problem-solving skills and unlock the room – and you will require great teamwork and a sense of adventure to make it happen!

Rated the #1 Escape Room in the country with over 6,000 reviews on Google, The Escape Game Chicago offers five scenarios to choose from. Become a secret agent in a mission around a mysterious spice market, travel back in time to the Gold Rush era, fix your spaceship that just crash-landed on Mars, or find a stolen Monet painting.

Expert players can try their luck in the Prison Break room, considered one of the hardest escape rooms ever designed.

• escape rooms in Chicago

Hot tip: Challenge your problem-solving skills at an escape room, highlighted as one of the best indoor activities in Chicago for groups

31 – Catch some late-night tunes at Buddy Guy’s Legends

Considered one of the best blues club in the country, Buddy Guy’s Legends prides itself for bringing the best blue acts and some of the world’s most talented musicians under one roof. Buddy Guy himself – a blues guitarist and singer who’s won eight Grammy Awards – performs at the club every January to a sold-out space.

Live shows are available seven nights a week but you can also stop by just to admire the amazing collection of personal items that cover the walls. From rare photos and artwork to Keith Richards and Eric Clapton’s personal guitars, there’s plenty to discover here.

32 – Grab a seat to the most exciting shows at the Chicago Theatre

The Chicago Theatre started life as an opulent movie theater in 1921 and is now considered one of the last surviving “grand movie palaces” in the country. The theater had space for a large live orchestra to accompany silent films, and an opulent interior that included stunning murals painted on the walls.

After years the neglect in the 1970s and a major restoration in the late 1980s, the Chicago Theatre now serves as a stage for everything from music concerts to comedy shows to stage plays.

Part of the restoration included revitalizing the theater’s interior and bringing back to life the grand lobby and staircase, Tiffany stained glass windows, and grand Wurlitzer pipe organ, one of the oldest of its kind still around.

• Chicago Theatre tickets & tours

33 – Connect with history at the International Museum of Surgical Science

Chicago’s most unique museum is home to a collection of items and exhibits focusing on the history of Eastern and Western medicine. From very early drawings and medical equipment to photographs, skeletons, and artifacts chronicling the breakthroughs and failures of medicine through the centuries, this is a museum that will awe, inspire and shock.

Special exhibits are dedicated to the 19th-century apothecary, polio and the use of the iron lung, pathology, the science of sight, and the history of dentistry.

The International Museum of Surgical Science also organizes temporary exhibits that focus on specific areas of medicine and history, such as a look into the deadly medicine of the Nazis, the world without polio, how the world has changed after 35 years of HIV/AIDS, and would healing through the ages.

34 – Catch a concert at the Civic Opera House

The country’s second-largest opera house, Civic Opera House , opened in 1929 and although it was extensively renovated in 1993, it still retains its original beauty. Limestone sculptures, gilt paint, and an opulent Art Deco lobby are still the heart of the building, where the traditional and the contemporary mix perfectly.

During the renovation, structural improvements and a state-of-the-art new sound system were added. Major operas like Madam Butterfly and La Boheme, as well as more modern options like Fiddler on the Roof now play here year-round.

35 – Let your imagination fly at the Briar Street Theatre’s Blue Man Show

Once a horse stable for the 19th-century Marshall Field department store, the space was abandoned and then used for several purposes until it reopened as the Briar Street Theater in 1985. With just 635 seats and an intimate elegant setup, this is a great space to truly appreciate a performance in the heart of Chicago.

While the theater still holds other performances (including full-length plays and musical shows) from time to time, it has mostly become known as the home of the performing Blue Man Group, where three characters painted in blue lead a multi-sensory experience combining music, theatrics, and visual effects.

• Blue Man Show tickets

How to get to Chicago?

A number of European airports (including Amsterdam, London, and Frankfurt) offer direct flights to Chicago’s O’Hare International Airport. From there, you can reach the heart of the city using airport shuttles and regional buses in about 40 minutes.

If you’re carrying a lot of luggage or arriving late and would rather go directly to your hotel, you have the option of using local taxi drivers, but be aware that extra fees might apply during busy hours or if you’re carrying lots of bags.

To save time and hassle, you can book an airport transfer . You won’t have to worry about timetables and you’ll arrive directly at your hotel’s door quickly and efficiently so you can make the most of your time in the city.

Where to stay in Downtown Chicago?

Sitting in a prime location overlooking the Chicago River, the Swissotel Chicago knows how to do luxury well. Expect sleek accommodations, a fitness center with panoramic views, and an award-winning restaurant. Plus, you’ll be within walking distance of all major Downtown Chicago attractions and steps away from Lake Michigan.

Just steps from Millennium Park, the Hampton Inn Majestic is a more affordable option with a great location in the theater district. It offers colorful, spacious rooms, and a 24/7 fitness center, and it’s surrounded by great restaurants and cafes.

Right on the Magnificent Mile, the 4-star Millennium Knickerbocker Chicago offers innovative design, well-appointed rooms, a ballroom with a gold-gilded domed ceiling, great farm-to-table cuisine, and a 1920s-inspired cocktail bar.

• best hotels in Downtown Chicago

Visiting Chicago on a budget?

If you’re traveling on a budget but still want to see as many tourist attractions in Chicago as possible, the Chicago CityPass or the Go Chicago Explorer Pass might be for you.

Both offer discounts of 48% or more on up to 7 attractions chosen from a long list of 25 available attractions that include Skydeck Chicago, Adler Planetarium, the 360 CHICAGO Observation Deck, and the American Writers Museum.

The passes often include extras such as skip-the-line access and unique features and attractions like four-hour bike rentals, a panoramic night tour bus, and a shoreline architecture river cruise to choose from.

Some of the passes are valid for 60 days after activation, so if you’re visiting Chicago for a week you could easily do one attraction per day and save lots of money.

Final thoughts

We hope you’ve enjoyed our list of the best things to do in Downtown Chicago! With plenty of world-renowned cultural attractions, beautiful waterfronts with innovative architecture, and a past right out of a gangster movie, you won’t run out of exciting attractions here.

Have another favorite must-see attraction in Downtown Chicago to recommend? Let us know in the comments below.

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Home » Travel Guides » United States » Illinois (IL) » 50 Best Things to Do in Chicago (IL) in 2023 by a Local

50 Best Things to Do in Chicago (IL) in 2023 by a Local

The Windy City has awe-inspiring skyscrapers, hunger-stomping food and culture to match almost any city in the world. But what never ceases to amaze me is just how much you can do for free in Chicago. Donations by philanthropists have bestowed the city with superlative museums and more than 700 works of public art, by Picasso, Chagall, Miró – the list is huge. These have turned the skyscraper forest of the Loop and the Millennium Park into one big outdoor gallery.

There are free events too, like Taste of Chicago , the largest food festival in the world, and music festivals to honor the city’s enviable music heritage. Chicago is also great to get around on foot, along the Lakefront Trail or the new Riverwalk, or even underground in the sophisticated Pedway system.

I’m a Chicago local and an avid traveler of my home state Illinois. I’ll guide you through some of the finest attractions the city has to offer, and there’s a lot so I made sure I included something for everyone. Let’s have a look at my list of the best things to do in Chicago :

1. River and Lake Cruises

Out on Lake Michigan and along the Chicago River you can sit back and give Chicago’s cityscape the attention it deserves. There’s a selection of cruises , from gentle lake tours to exhilarating speedboat rides. I took The Classic Lake Tour which is a 40-minute sightseeing trip giving you plenty of time to soak up the sights, and with a recorded commentary for interesting titbits. For the architecture admirers, I’d recommend the guided architecture tour .

At the old Navy Training Center on Navy Pier you can jet off on a speedboat for a 75-Minute Architecture Cruise, starting on the lake and heading upriver as far as the Willis Tower. The Chicago River Architecture Cruise has a more sedate pace, and gives you a clear view of more than 40 listed landmarks, accompanied by live commentary from an expert guide. I’ve done several cruises and think it’s one of the best ways to admire city.

The 442-metre Willis Tower was the tallest building in the world for 25 years, and is is still among the top 25. In my experience the Chicago Skydeck Experience Ticket  is great value for money, you can waste no time, skipping the line and speeding up to the Skydeck 412.4 metres above the west side of the Loop.

On the meandering route to the elevator, there’s a movie detailing the 45-year history of the Willis Tower and Chicago’s other architectural wonders. After a swift ride you’ll be struck by a view extending over 50 miles and four states. The Ledge at the Skydeck will either give you a buzz or make your stomach flutter: This is a set of four all-glass boxes projecting over a sheer drop of more than 100 storeys. While this was an amazing experience I realized I didn’t like heights as much as I thought.

3. Food Tours

If it’s big portions and bold flavors you’re after, Chicago is the town for you. Chicago may be America’s top food city, and you would be brave to disagree. The staples are deep-dish pizza, hot dogs piled with seven toppings, Italian beef sandwiches, brownies and beer. Lou Mitchell’s and Twin Anchors have nationwide fame, but if you want local spots that might escape the attention of out-of-towners, there are a range of tours for hungry visitors.

The Secret Food Tour lets you in on these undisclosed locations. You can also take a Tasting Tour of Chinatown on foot. A nice alternative is filling up up on Mexican tortas and Polish pierogis on a Bike Tour .

4. Art Institute of Chicago

Three of the most studied and celebrated paintings of the past 150 years await at an art museum to match the best in the world. These works are Nighthawks by Edward Hopper, American Gothic by Grant Wood and Seurat’s A Sunday Afternoon on the Island of La Grande Jatte. They are all obligatory, as is Picasso’s Old Guitarist, but are only a gateway to a whole feast of art.

The Art Institute of Chicago has the largest collection of Impressionist and Post-Impressionist painting outside Paris, with more than 30 paintings by Monet, as well as works by Cézanne, Renoir, van Gogh and Toulouse-Lautrec.

For modern art there’s Jackson Pollock, Warhol, Jasper Johns and Matisse, while the modern architecture and design collection has drawings and models by Frank Lloyd Wright, Le Corbusier and more.

You can also delight in ancient Greek, Egyptian, Etruscan and Roman artifacts, from mosaics, to pottery, glass, coins, bronze and jewelry. If you don’t want to stand in line for tickets I suggest booking a ticket online. I recommended planning to spend at least a few hours at the museum as there’s a lot to see.

Related article : You may also like my guide on the most beautiful places to visit in Illinois .

5. Grant Park

Affectionately known as “Chicago’s front yard”, Grant Park fronts the Loop on Lake Michigan and is the city’s prime open space. These 319 acres contain lots of Chicago’s top attractions like Millennium Park, the Museum Campus Chicago, the Art Institute of Chicago, Maggie Daley Park and the epic Soldier Field, home of the Chicago Bears NFL team.

You could write a whole article on Grant Park and the layers of things to do in its boundaries. But it’s also worth remembering that the park is a lively place for Chicagoans just to unwind and be active, with baseball diamonds, tennis courts and lush boulevards to wander down.

In July Grant Park hosts the Taste of Chicago Festival, the biggest food event anywhere, and in October is the start and finish line for the Chicago Marathon.

6. Millennium Park

Created to herald the new millennium, this award-winning space in Grant Park is the most popular visitor attraction in the Midwest. Free to enter, the Millennium Park has bold public art, spellbinding architecture and some forward-thinking initiatives.

For a taste, the 2.5-acre Lurie Garden is part of the world’s largest green roof, while the McDonald’s Cycle Center is a sleek indoor bike station offering rental, repair and an array of services for Chicago’s cyclists. I’ll bring up a few of the showpiece sights in Millennium Park later, but you can’t miss the Jay Pritzker Pavilion.

This 11,000-capacity band-shell was conceived by Frank Gehry, and from spring to autumn has a packed calendar of concerts by major recording artists and the likes of the Chicago Symphony Orchestra and the Lyric Opera of Chicago.

7. Riverwalk

Chicago is a city that knows how to treat pedestrians, as you’ll see along the main branch of the Chicago River as it cuts through the downtown . A feat of urban planning, the Riverwalk is 1.25 miles long, made up of six coves or “rooms” up to Wolf Point. The route will take you past photo opportunities like the Wrigley Building and a whole of host of head-turning works of public art.

These might be bright graffiti panels or large-scale installations like Ellen Lanyon’s Gateway, recording Chicago’s story through 28 ceramic tile murals. You can board a cruise boat or water taxi of course, or take matters into your own hands on an urban kayak or “cycleboat” tour. With dramatic urban scenery, terraces stepping down to the water and bars grills and cafes, it’s no shock that the Riverwalk has become a go-to on date night.

8. Navy Pier

Set where the Chicago Portage enters Lake Michigan, the Navy Pier is a multifaceted visitor attraction extending over the water for six city blocks. As one of the top days out in the Midwest, an attraction of this magnitude is hard to sum up in one paragraph. But in 50 acres you’ll come across the vast multisensory Funhouse Maze and, my personal favorite, the nearly 200 feet Centennial Wheel, footed by fairground rides and amusements.

There’s also weekly fireworks in summer, an IMAX Theatre, the Chicago Children’s Museum and the Crystal Gardens botanical garden with more than 80 palms. You can use the pier as the jumping off point for cruises on the lake or river, take in some live music at the Miller Lite Beer Garden and watch the drama unfold at the non-profit Chicago Shakespeare Theater.

9. Cloud Gate

The anchor for the AT&T Plaza in Millennium Park is an enchanting piece of public sculpture by Anish Kapoor. Installed in 2006 and affectionately dubbed “The Bean”, Cloud Gate is a rounded arch, clad with 168 highly reflective stainless steel plates. After a few teething problems due to its complicated design, Cloud Gate has quickly become an emblem for 21st-century Chicago.

The monument was designed to bring to mind a blob of liquid mercury, and its value lies in how interactive it is. You can take photos of your own reflection against the distorted Chicago skyline, and while passing under the 12 foot, look up into the “omphalos”, a concave chamber that twists and multiplies reflections. I’ve seen countless tourists take a selfie here, it’s quickly become one of the most iconic sculptures in Chicago. Fun fact: it’s nicknamed ‘The Bean’ because of its shape.

10. John Hancock Center

A mainstay of Chicago’s silhouette, 875 North Michigan Avenue (formerly the John Hancock Center) is a 1,500 feet skyscraper on the Magnificent Mile. Tapering as it rises, the tower was topped off in 1969 and appears in pretty much any movie that needs an establishing shot for Chicago. Up close you can watch its characteristic X-shaped bracing zigzag up the facades.

The view from 360 Chicago on the 94th floor has been rated as one of the best in the country, and the ride up there takes less than 40 seconds. There’s a cafe and bar up, as well as interactive displays labeling the landmarks on the horizon in each direction. If you have a steely disposition try “Tilt”, a glass capsule that tilts forward at 15°, 25° and 40° for a bird’s eye view of the city streets 1,500 feet below. Might seem obvious but I recommend visiting on a clear day so you have a great view of the city.

Also see :  Amazing Hidden Gems in Illinois

11. Chicago Cultural Center

Formerly the home of the Chicago Public Library, in 1991 this striking Neoclassical building in The Loop became the first free municipal cultural center in the United States. There are more than 1,000 exhibitions and  here every year and they’re as diverse as you’d expect from a city like Chicago.

All for free, you can catch theater, dance, music, lectures, film screenings and family-oriented events.

No matter what’s on, you have to take the opportunity to look inside this building from 1897. The nation’s top craftsmen were hired for the interiors, working with valuable materials like fine hardwood, rare imported marble, polished brass and mother-of-pearl.

The two domes are not to be missed: The south is the largest stained glass Tiffany dome in the world, while the larger Renaissance-style dome on the north side is 12 meters in diameter and has 50,000 glass panels. I recommend visiting their website for more info on exhibits and tours.

12. Wrigley Field

The Chicago Cubs play at the second-oldest ballpark in the Major League. Wrigley Field (1914), nicknamed “The Friendly Confines” by the legendary Ernie Banks, is noted for its ivy-clad outfield walls and has an iconic manual scoreboard.

The stadium may catch you off-guard, as it sits in the middle of a residential neighborhood and has no car park, now a rarity for US sports venues. The wind blowing towards or away from Lake Michigan (out or in) can turn potential home runs into outs, or send balls out of the stadium altogether.

Come to see the 2016 World Champions at one of 66 regular season games, checking out the famous red entrance marquee from 1934 and to treat yourself to a Chicago hot dog .

As parking can be a nightmare I suggest to either to take a cab or to take the Red Line to get there.

13. Maggie Daley Park

In Chicago with kids? Visit Maggie Daley Park! Named for a former first lady of the city who passed away in 2011, Maggie Daley Park is one of Grant Park’s newest treasures.

Laid out by landscape architect Michael Van Valkenburgh, the park opened in the northeast corner of Grant Park 2014 and shines for its recreation and family facilities.

The whimsical Play Garden, for kids up to 12, is a playground like you’ve never seen, with six different zones like the Watering Hole which has a giant breaching whale, and the Enchanted Forest where you’ll walk under upside down trees . There’s also an ice skating ribbon, a quarter of a mile in length, picnic groves, an 18-hole mini golf course and rock-climbing walls.

14. Richard H. Driehaus Museum

In the Driehaus Museum you’ll step back into America’s Gilded Age at the refined Nickerson House, built in 1883 for the banker Samuel M. Nickerson. Close to the Magnificent Mile, on the Near North Side, the house looks a little out of place, dwarfed by the city’s bold Neoclassical monuments and glass-clad skyscrapers.

In 2003 the Chicago fund manager and philanthropist turned the Nickerson house into a museum, blending the original furnishings with luxurious Art Nouveau glazed tiles, stained glass, onyx, carvings and marble all sourced from other places.

The museum is heaven if you like decorative arts. You’ll find some lovely pieces by Louis Comfort Tiffany, like a large fire screen, a set of vibrant stemware, a blown-glass humidor and a peculiar centerpiece lamp.

The ballroom has Edward Colonna furniture you can sit in, while some other exceptional pieces include Sèvres vases, a suite of George A. Schastey neo-Empire chairs, pre-Raphaelite paintings and a rare Chickering and Sons grand piano. In case you’re looking for a bite I had a great pizza at nearby Giordano’s.

15. Buckingham Fountain

At the center of Grant Park, between the ornamental North and South Rose Gardens is a sight that needs a double take. Hewn from Georgia pink marble, the Buckingham Fountain (1927) is one of the largest in the world, nearly 280 feet in diameter, with nearly 200 jets and a pool.

The Rococo design is borrowed from the Latona Fountain at Versailles, and is an allegory for Lake Michigan, with four pairs of sea horses representing the states of Illinois, Wisconsin, Michigan and Indiana.

At any one time there’s 1.5 million gallons of water in the Buckingham Fountain. Stop by for the 20-minute water display on the hour, shooting jets up to high into the air.

16. Lakefront Trail

Eighteen miles of Chicago’s shoreline can be accessed on a waterfront path, threading through all four of the city’s lakeside parks. The Lakefront Trail is shared by cyclists, joggers and families.

People use the trail to get to work, and to stroll next to Lake Michigan and savor Chicago’s skyline. You can use the path to get to a whole catalog of interesting places, from the South Shore Cultural Center to Navy Pier and the Shedd Aquarium.

In summer you can hop from beach to beach and to get a dose of greenery at Grant Park or Lincoln Park. There are bike rental companies all along the trail, or you could buy a day pass for Divvy, Chicago’s bike sharing system. This is actually one of my favorite places to go jogging with my dog.

17. Museum of Science and Industry

Limitless inspiration for kids, the Museum of Science and Industry has show-stopping exhibits on an amazing scale. The venue is the old Palace of Fine Arts, built in 1933 in Jackson Park for the World’s Columbian Exposition.

Some of the jaw-dropping sights here are a full-size German U-505 submarine captured during the Second World War, the Pioneer Zephyr, a glorious stainless steel diesel locomotive from 1934 and the first Boeing 727 to enter commercial service.

Young scientists can wrap their heads around big concepts at the Science Storms exhibit, which has a Tesla coil, Foucault pendulum and Wimshurst machine.

There are relics from the Apollo missions at the Henry Crown Space Center , while the central pavilion has a replica of a deep-shaft bituminous coal mine, in which you’ll take a mine train and see historic equipment from the 1930s.

18. Magnificent Mile

Squeezed into eight blocks on the arterial Michigan Avenue is a whole world of shopping, entertainment, dining, dazzling architecture and more things to do than you could manage in a whole holiday. Many of the sights or attractions on my list are on this street, or a stone’s throw from it.

There are 275 restaurants and more than 460 retailers here, from flagship stores for Zara, Disney and Nike to scores of boutiques and ritzy emporia for Rolex, Boss, Burberry and any other high end brand you can think of.

Soaring overhead are icons of the Chicago skyline like the Tribune Tower (1925) and the Wrigley Building (1924) in the south and 875 N Michigan (1969) towards the north end.

For a more unassuming sight, stop for a snap of the castle-like Chicago Water Tower, dating to 1869 and the second oldest surviving water tower in the United States.

19. Garfield Park Conservatory

Well west of the Chicago Loop, Garfield Park warrants the 15-minute cab ride into a slightly down-at-heel neighborhood. The trip is for the world’s third largest garden under glass, an astounding botanical conservatory with eight indoor display gardens. The conservatory was completed in 1908 and designed to resemble the haystacks of the Midwest. As it’s indoors I’d recommend this activity if there’s a rainy day forecast during your trip.

The moment you step inside you’ll be in the Palm House with more than 80 varieties of palm tree. Also see the incredible ferns and cycads against the waterfall in the Fen Room, and one of the nation’s most varied collections of cactuses and succulents in the Desert House.

Come by any day in summer and there will be something going on, like free yoga, gardening demonstrations and a chance for kids to get up close to animals like harmless snakes and goats.

20. Mob and Crime Bus Tour

Now their misdeeds are in the distant past, there’s no denying the fascination evoked by Chicago’s prohibition-era mobsters. Names like Al Capone, Bugs Moran and Dion Johnny Torrio remain household names.

The city has changed so much in the last century that you’d never guess that benign looking neighborhoods witnessed a bitter war that claimed scores of lives in the 1920s and 30s. So you have to turn to local historians, and I found that GetYourGuide.com offers a 90-minute Mob and Crime Bus Tour . A similar tour is available on Viator as well.

This uncovers the dark past of the Windy City, profiling notorious men like Capone and John Dillinger. You’ll visit the site of the Valentine’s Day Massacre and the Biograph Theatre, where Dillinger was gunned down by FBI agents.

21. Shedd Aquarium

Sharing the Museum Campus Chicago with the Field Museum and the Adler Planetarium, the Shedd Aquarium (1930) was for some time the largest indoor aquarium in the world. Donated by the philanthropist John G. Shedd, the attraction has an incredible 32,500 aquatic creatures from across the planet.

These are in immersive zones like Amazon Rising, which has caimans, anacondas, piranhas and freshwater stingrays in tanks among the roots of rain-forest trees. Also mandatory are the Caribbean Reef, housing a rescued green sea turtle, the Wild Reef with four varieties of sharks and the historic Waters of the World gallery home to colorful starfish and seahorses.

Stingray Touch lets you find out what a cownose ray or yellow spotted ray feels like, while marine mammals like sea lions, penguins and sea otters can be found in the Oceanarium.

22. Field Museum of Natural History

One of the best and largest natural history museums in the world, the Field Museum’s museum collection has swelled to more than 24 million objects since it opened in 1893. This a place to feed your fascination for the natural world, with grand Neoclassical halls housing fossils, priceless gemstones and animal and plant specimens.

There’s also compelling anthropology for the Ancient Americas and Ancient Egypt, as well as Tibet, China, Africa and cultures in the Pacific Islands. The Geology Halls meanwhile have an exquisite collection of Chinese jade, and a stained glass window by Louis Comfort Tiffany.

The star of the show is the 28 feet tall Titanosaur in the Stanley Field Hall. In 2018, this herbivore from Argentina replaced SUE, a T-Rex specimen, which will reappear at the Evolving Planet Gallery in 2019. It took me a few hours to explore the entire museum so great value for money.

23. United Center

There was a time in the 90s when a seat at the United Center was the hottest ticket in town.

The Chicago Bulls moved to this arena in 1994 when Michael Jordan was on his strange hiatus in Minor League Baseball, and he’d return to lead them to three straight titles between 1996 and 1998. Out on the east side of the building is a statue in his honor, named The Spirit and showing him mid-dunk.

Fair to say that the 2010s aren’t a golden age for the Chicago Bulls, but if you are a fan or want to make a pilgrimage to this hallowed ground you can watch a game in the regular season from October to April.

At roughly the same time of year, the Bulls share the United Center with the Chicago Blackhawks NHL team, which has had a much more successful decade, winning the Stanley Cup in 2010, 2013 and 2015.

24. Chicago History Museum

In Lincoln Park you can lift the lid on Chicago’s rich history, perusing fascinating thematic exhibitions. Facing Freedom goes into depth on the various struggles for freedom to beset Chicago from the 1850s to the 1970s, covering the Civil War, Women’s Suffrage, the formation of labor unions and Japanese internment.

At Crossroads of America you can step into a jazz club or climb aboard Chicago’s very first L train, while the Chicago dioramas tracks Chicago’s breakneck rise from a lonely frontier outpost to an immense metropolis.

Sensing Chicago lets kids jump into a gigantic Chicago-style hot dog, ride a vintage high wheel bike and hear the roar of the Great Chicago Fire.

25. Lincoln Park Zoo

In 37 acres and dating back to 1868, this zoo deserves extra credit as one of the last remaining free admission animal parks in the United States. There are more than 1,100 animals here, in habitats that are constantly being revamped.

The polar bear and African penguin enclosures for instance have just been reopened, while a recent arrival in 2014 is the Regenstein Macaque Forest where you can see Japanese macaques bathing in a hot spring as they do in the wild.

There’s a hint of the great age of the zoo at the Kovler Lion House, constructed in 1912, while some other family favorites to tick off are the Helen Brach Primate House (1927), seal pool, family petting zoo, the superb Regenstein Center for African Apes and the Regenstein African Journey. This has indoor and outdoor habitats for giraffes, pygmy hippos, ostriches, gazelles and many more.

Best of all might be that entrance is free. However parking costs can be quite expensive so I’d recommend going there by public transportation, or foot if you’re located close by.

26. Chicago Picasso

Pablo Picasso produced this monumental piece of public art for Chicago in the mid-1960s. Standing in Daley Plaza, the Chicago Picasso weighs almost 147 metric tons and stands over 50 feet tall.

Since it was unveiled in 1967, the work, rumored to depict French model Lydia Corbett who sat for a series of drawings for Picasso in the 1950s, is a landmark for the city and something for kids to clamber on.

Early on, in a city that previously only dedicated statues to historical figures, the Chicago Picasso was a source of controversy, but now inspires affection as a famous meeting point and backdrop to public events on Daley Plaza like the Christkindlmarkt at Christmas.

27. Holy Name Cathedral

Chicago’s Gothic Revival Catholic cathedral, by Chicago Station on the Red Line, was completed in 1875 after its predecessor burnt down in the Great Chicago Fire of 1871. Eagle-eyed visitors will be able to spot an overarching Tree of Life Theme in the building’s fittings.

On arrival you’ll be confronted by the cathedral’s immense bronze doors, each weighing more than 500 kilos and cast to resemble planks of wood.

Inside, a few of the fixtures worth closer inspection are the Stations of the Cross in red Rocco Alicante marble, bronze sculptures depicting the Evangelists and the cathedra (bishop’s throne) for the Chicago Diocese.

There’s also a slice of Chicago gangland history outside, where a cornerstone inscription is still chipped from the 1926 murder of mob boss and Al Capone rival Hymie Weiss.

28. North Avenue Beach

Another of the many things to love about Chicago is the way the city has been planned to grant access to the lakeshore. In hot weather this means you can slip off your shoes and set foot in Lake Michigan, or plan a whole day at the beach. Being slightly removed from the fabric of the city, Lincoln Park has what many people agree to be the best beach in the city.

North Avenue Beach runs for a few hundred yards up to Diversey Harbor, with piers at short intervals to stop the sand being washed away. There’s a bar on the beachfront, as well as companies offering rentals and tuition for kayaking and stand-up paddleboarding.

International competitions take place at the South Volleyball Courts here, while in August North Avenue Beach is the place to catch the Chicago Air & Water Show.

29. Crown Fountain

The wonders keep coming in the Millennium Park, because we haven’t even mentioned the Crown Fountain (2004) yet. Here the Catalan artist Jaume Plensa designed two glass brick towers, 15 meters in height. They face each other across a black granite reflecting pool.

Those glass bricks are installed with LEDs displaying changing photographic facial images of citizens’ faces, filling the towers. For a playful touch, water spouts from the a nozzle between their lips from May to October.

Like most of the works in the Millennium Park the Crown Fountain is interactive, and on hot summer days you’ll see children paddling in the reflecting pools and cooling off under the waterfalls that cascade down the sides of the towers.

30. Michigan Avenue Bridge

The Burnham Plan of 1909 helped shape Chicago’s cityscape, and brought about this trunnion bascule bridge conducting Michigan Avenue over the main branch of the Chicago River. An official Chicago Landmark, the bridge opened in 1920 and once completed helped spur the flurry of development that gave rise to the Magnificent Mile.

Be sure to go in for a closer look at the north and south pylons, which have bold reliefs depicting scenes from Chicago’s past, carved by Henry Hering and James Earle Frasier respectively. The south pylons depict Defence and Regeneration, while the north pylons show the Discovers and Pioneers.

The southwest bridgehouse holds the McCormick Bridgehouse & Chicago River Museum, chronicling the history of the bridge and the Chicago River. If you’re in for a burger I recommend the nearby Billy Goat Tavern which has a delicious cheeseburger.

31. Robie House

To look at this house on the University of Chicago campus and know nothing about its origins, you’d never guess that it was built in 1910. Residential architecture would never be the same after the great Frank Lloyd Wright designed this home for Frederick C. Robie, the assistant manager of a company on the South Side.

The Robie House is considered the pinnacle of the early-20th-century Prairie style, and you can go in for tours Thursday to Monday.

The Prairie style expresses the sense of space in the prairie landscape of the Midwest, and this is captured by the low profile, long cantilevered eaves, broad balconies and even the use of narrow red bricks.

The Robie House has marvelous art-glass throughout, personally designed by Wright, along with the house’s curtains, rugs, furniture, bathroom fittings, fireplaces and lighting.

32. Museum of Contemporary Art

Dedicated to art from 1945 to the present, the Museum of Contemporary art is endowed with a serious collection, spanning surrealism, conceptual art, pop art and minimalism. You’ll get to see works by Chuck Close, Andy Warhol, Jasper Johns, Francis Bacon, René Magritte, Alexander Calder, Ann Hamilton and Richard Serra.

From June to September, Tuesdays on the Terrace is a programme of summer performances by members of Chicago’s dynamic jazz community.

33. Symphony Center

As one of America’s “Big Five”, the Chicago Symphony Orchestra is among the most prestigious classical ensembles on the planet. You can see them at the Symphony Center, a National Historic Landmark on South Michigan Avenue.

This venue is a complex made up of the Grainger Ballroom, Buntrock Hall and the 2,522-seater Orchestra Hall. On the frieze above the facade’s arches windows you’ll read the names “Bach, Mozart, Beethoven, Schubert and Wagner”. By 2018 Riccardo Muti had been the conductor for eight years.

34. Second City Chicago

An absurd amount of comic talent has come out of Chicago over the last 60 years, and one of the reasons for that is Second City. This fabled comedy club and improv company on Wells Street counts Steve Carell, Billy Murray, Tina Fey, Amy Poehler, Stephen Colbert, Dan Aykroyd, John Belushi and John Candy among its alumni.

There are three stages at Second City, “Mainstage” and “e.t.c. Stage” for sketch comedy and improv acts, and the UP Comedy Club for stand-up. Chances are you’ll get see a future TV or film star honing their comedic powers here.

35. Chicago Theater

One of five Tony award-winning venues in Chicago, the Chicago Theater warrants a photo, even if you’re not planning to see a show. That’s partly because of the marquee and vertical sign, which often appear in movies set in the city.

The venue opened in 1921 as an opulent motion picture house, and if you step back across State Street you can get a good look at the facade. This has a beautiful central arch that mirrors the false-perspective effect of the Palazzo Barberini in Rome, and is glazed with Tiffany stained glass.

Now one of Chicago’s best spots for performing arts, the theater is owned by the Madison Square Garden Company and puts on a varied program of comedians, world-famous musicians, dance companies and lectures by renowned cultural figures. Madonna, Hamilton, Trevor Noah and more are all in store for this year. I recommend checking their event calendar.

36. Oriental Institute Museum

While you’re down at the Robie House, head to this awesome museum at the University of Chicago’s Oriental Institute. Opened with funding from John D. Rockefeller Jr., the ivy-clad museum is a treasure chest of ancient artifacts discovered during digs in Turkey, Israel, Egypt, Iran, Iraq and Syria.

A couple of the most remarkable exhibits are an imposing statue of King Tutankhamen and a giant human-headed winged bull from the Assyrian city of Khorsabad.

From around the same period there’s a set of ornate Luristan Bronzes produced in western Iran in the early Iron Age, and a stunning array of paper-thin ivories carved in the ancient city of Tel Megiddo, now northern Israel.

Like so many places on this list, I really like that the museum is free (it does encourage donations).

37. Tribune Tower

Built in the mid-1920s for the Chicago Tribune, this iconic Gothic Revival skyscraper on the Magnificent Mile is now being turned into condominiums. The Tribune Tower is clad with Indiana limestone, and came about after a design competition to mark the paper’s 75th anniversary.

At night you’ll get a clear view of the buttresses and tracery at the very top, while there are lots of details to discover on the lower storys. In the years before the tower went up, the Tribune’s publisher Robert R. McCormick had asked his correspondents to bring him fragments of famous monuments from around the world.

So, embedded in the stonework are pieces from the Hagia Sophia, Taj Mahal, the Butter Tower of Rouen Cathedral, the Alamo, the Great Pyramid and the Great Wall of China, to name a few.

38. Adler Planetarium

In Grant Park, the Adler Planetarium (1930) is both a respected institution at the Museum Campus and a noble landmark in its own right. The planetarium occupies a nub of land sticking out over the lake on Northerly Island. By the water to the north is the Adler Planetarium Skyline Walk, blessed with the ultimate view of Chicago’s skyline.

Inside, kids can interact with exhibits dealing with topics like the Solar System, the composition of planets and the Moon missions. You can also find more fact-heavy exhibitions about the history of telescopy and the origins of the universe.

Projected shows are the cornerstone of any planetarium, and the Adler has a big choice, showing the sky above Chicago with light pollution filtered out, and sparkling presentations about the mysterious Planet Nine and nebulae.

39. Chicago Children’s Museum

The Chicago Children’s Museum, which I first visited in my younger years on a school trip, promises a few hours of active, engaging fun for youngsters. On Navy Pier the museum has 15 interactive exhibits over three storys, each mixing play with learning.

In that spirit, the Tinkering Lab for instance features genuine tools and materials giving kids the freedom to create whatever comes to mind, while Skyline is a crash course in architectural engineering, letting children experiment with skyscraper designs.

Play It Safe is a fun indoor play zone in partnership with the city’s Fire Department, teaching little ones about fire safety as they escape from a room filled with pretend smoke and shoot down a fire station pole.

There’s a whole calendar of special activities and workshops, and something different happening on a every visit.

40. Chicago Shakespeare Theater (CST)

Based on Navy Pier, this adored non-profit theater company has done as much as anyone to help keep Chicago on the cultural map over the last 30 years.

In short order the theater has earned three Laurence Olivier Awards, as well as a regional Tony in 2008. Its main aim is to introduce people to the works of William Shakespeare, through school tours, summer plays in parks and productions at its own majestic venue, adding up to 600 performances a year.

The Chicago Shakespeare Theater has been at Navy Pier since 1999, in a complex with two auditoriums: The 510-seater Courtyard Theater and the more intimate Upstairs theater.

The program is crafted for everyone, and has meaty productions of Macbeth and Hamlet, and light family musicals like Peter Pan and Bedknobs and Broomsticks.

41. Alfred Caldwell Lily Pool

People go out of their way to visit a masterpiece of landscape architecture in Lincoln Park. This pond is named after its designer, Alfred Caldwell who worked on it in the second half of the 1930s.

In the same vein as the Robie House, the environment is laid out in the Prairie style. You’ll definitely sense the Prairie school’s love for low horizontal forms and the natural landscapes of the Midwest.

A National Historic Landmark since 2006, the pool is traced by winding stepping-stone paths, wide stratified slabs of limestone, circular benches, plants native to the Midwest, a waterfall and waterside pavilion.

42. Peggy Notebaert Nature Museum

This child-friendly museum in Lincoln Park presents the natural history of the Chicago region in smart and interactive ways.

As an institution the museum was founded back in 1857 and moved into a new home in the park in 1999. The old museum, now used by the zoo, was known for its detailed static dioramas, and while these are still here, they’re joined by spellbinding living environments like the astonishing Judy Istock Butterfly house, where 1,000 butterflies flutter in a 250-square-meter greenhouse.

During the “Critter Connection” every day at 11:30 kids can get an up close look at more than a dozen different amphibian species at the Animal House.

There’s also a bird walk, leading to a platform over Lincoln Park’s North Pond, as well as hands-on stations where kids can learn about rivers, solve nature-inspired puzzles and explore a beaver lodge.

43. Chicago Pedway

Under the city streets and spanning more than 40 blocks north to south, Chicago has a vast network of pedestrian tunnels, as an answer the vicious winter weather and to provide easy links between “L” stations.

The oldest sections, between State and Dearborn streets date back to before the Second World War. The rest of the network was begun in the 1950s and expanded in the 60s and 70s. Not all of the Pedway is subterranean, as there are enclosed raised footbridges.

As ever, there are works of public art adorning the tunnels, along with restaurants and shops. In the Pedway by Macy’s check out the beautiful display of 22 stained glass panels, a holdover from the defunct Smith Museum of Stained Glass. There are free walking tours available but in my experience the free tours cost you just as much, because at the end of the tour they do ask to contribute whatever price you think the tour is worth and most people will feel obligated to pay a decent price.

44. Chinatown

Strolling along the Chicago River you’re sure to see the yellow Chicago Water Taxi zipping past. In this part of the city, these boats stop at Michigan Avenue and further west along the Riverwalk. One idea for a trip is to catch the taxi down to Chinatown.

The scenic journey through the Loop and South Loop will take about 40 minutes and there are services all day in summer, but especially around lunchtime. And that’s because one Chinatown is a Dim Sum paradise.

Head for Dolo Restaurant and Bar and MingHin Cuisine where there are so many options you won’t know where to start. But people come a long way for MingHin’s Macau pork belly at deep fried taro puffs. I started exploring from Chinatown Square which is a great place to start.

45. Chagall’s Four Seasons

Under a glass canopy at the Chase Tower Plaza in the Loop is another exceptional piece of public art ready to enchant passers-by. This figurative mosaic is by Marc Chagall and was donated by the stockbroker Frederick H. Prince. The Four Seasons is big by any measure. I’ve walked by countless times and each time I take a sec to admire it.

It is made up tens of thousands of inland chips in more than 250 colors, and has hints of the Chicago skyline, suns, flowers, birds, fish , lovers and musicians. While we’re talking about Chagall – when the artist came to install the mosaic in the 70s he produced a set of stained glass windows for the Art Institute of Chicago to celebrate America’s Bicentennial.

They are among the most treasured works in the collection, and you may recognize them if you’ve seen Ferris Bueller’s Day Off!

46. Brookfield Zoo

A Metra train ride out to the suburb of Brookfield, this zoo is in 216 acres of green parkland and boasts more than 450 species. The Brookfield Zoo made waves when it opened in 1934 as it pioneered the use of moats and ditches instead of cages, and was also the first in America to have giant pandas. I loved wandering around and enjoyed spotting all the different animals.

One of the most recent additions is the Great Bear Wilderness, letting you get within inches of North Americas mightiest carnivores. Also new is Wild Encounters, where you can pet tame goats, walk through a wallaby enclosure and enter one of the largest free-flight parakeet aviaries in the world.

Naturally, kids’ favorites (and mine too) like big cats, rhinos, giraffes are all at Brookfield Zoo, while Humboldt penguins are the stars at the Living Coast habitat.

47. Live Music

In a city that gave its name to whole genres of blues and house music, you can bet that Chicago is a big live music town. To tap into the city’s jazz and blues heritage, look for a few spots that have achieved legendary status.

This an apt time to bring up Buddy Guy’s Legends, founded by the blues veteran on South Wabash in 1989, and where he still plays a series of shows every January.

Kingston Mines in Lincoln Park dates back to 1969 and has two live shows a night without fail, while the venerable Green Mill Cocktail Lounge (1907) was run by mobsters in the Prohibition era, and Al Capone’s favourite booth is still here.

On a wider scale, there are 225 live music venues in all, as well as some of the nation’s most exciting festivals, both free and ticketed, from the Chicago Jazz Festival to Lollapalooza and Pitchfork.

48. Taste of Chicago Festival

In mid-July Grant Park puts on the world’s largest food festival. The Taste of Chicago Festival drives home the full diversity of Chicago’s dining options.

Bring an appetite and you can take a culinary trip around the world, discover the creativity of Chicago’s contemporary restaurants or renew your love affair with Chicago classics like Italian beef, cheesecake, pizza and hot dogs.

There are pop-up restaurants, a whole armada of streetfood trucks and stands representing Chicago’s top eateries. You can go sample crazy, or see highly skilled chefs doing their thing at live demonstrations. And as the perfect accompaniment the festival organizes live music by famous acts and the best of Chicago’s music scene.

49. Chicago Jazz Festival

This totally free four-day music extravaganza takes place across the Labor Day weekend in Millennium Park. The event is now in its fifth decade, and dates back to 1974, when a festival was organised in Grant Park to honor Duke Ellington who had just passed away.

The list of performers who have taken the stage at the Chicago Jazz Festival is a who’s who of jazz, gilded with names like Dizzy Gillespie, Ella Fitzgerald, Miles Davis and Sun Ra. Each year there’s a helping of Jazz royalty sharing the bill with stars of contemporary jazz and some undiscovered talent.

Shows take place at the pavilions in Millennium Park (headliners play at the Jay Pritzker Pavilion), as well as Chicago Cultural Center.

50. Chicago Air & Water Show

To round the whole thing off, here’s another big event that the city lays on for free. The Chicago Air & Water Show goes back to 1959 and remains the city’s second favorite festival, as well as the largest free show of its kind in the United States.

Across a weekend in mid-August more than two million people line Lake Michigan, particularly the North Avenue Beach, for an exhibition of supersonic jets, formation flying, sky-diving and skywriting.

These are normally Army and Air Force groups, like the Golden Knights parachute team and the U.S. Air Force Thunderbirds.

Tip: There’s no better time to visit 360 Chicago, the Skydeck or take a cruise on the lake, while shore-side restaurants and bars put on viewing parties, though tickets will sell out months in advance.

I truly hope you enjoyed my picks for Chicago, if you have any comments or tips feel free to contact us !

50 Best Things to Do in Chicago (IL) in 2023 by a Local:

• River and Lake Cruises
• Art Institute of Chicago
• Millennium Park
• John Hancock Center
• Chicago Cultural Center
• Wrigley Field
• Maggie Daley Park
• Richard H. Driehaus Museum
• Buckingham Fountain
• Lakefront Trail
• Museum of Science and Industry
• Magnificent Mile
• Garfield Park Conservatory
• Mob and Crime Bus Tour
• Shedd Aquarium
• Field Museum of Natural History
• United Center
• Chicago History Museum
• Lincoln Park Zoo
• Chicago Picasso
• Holy Name Cathedral
• North Avenue Beach
• Crown Fountain
• Michigan Avenue Bridge
• Robie House
• Museum of Contemporary Art
• Symphony Center
• Second City Chicago
• Chicago Theater
• Oriental Institute Museum
• Tribune Tower
• Adler Planetarium
• Chicago Children's Museum
• Chicago Shakespeare Theater (CST)
• Alfred Caldwell Lily Pool
• Peggy Notebaert Nature Museum
• Chicago Pedway
• Chagall's Four Seasons
• Brookfield Zoo
• Taste of Chicago Festival
• Chicago Jazz Festival
• Chicago Air & Water Show

• Virtual Escape Rooms
• In-Store Team Building
• Virtual Team Building
• The Escape Game

The Best 30 Attractions In Chicago For Adults

Chicago is one of the best cities for adults to find countless fun and exciting things to do from top-notch museums to beautiful city parks. Here are 30 of the best things to do in Chicago for adults!

Feb 23, 2023 16 min read

Chicago is one of the best cities in America where adults will find countless fun and exciting things to do. Top-notch museums, beautiful city parks, and amazing cuisine make it a place to add to your list of must-see destinations.

To get you started on planning your trip, here are 30 of the best things to do in Chicago for adults, whether or not you are traveling with family!

1. Pose with the Bean in Millennium Park

Seeing The Bean in Millennium Park is a must-do! This iconic sculpture, whose real name is Cloud Gate, is massive and weighs 110 tons! It’s one of the largest sculptures of its kind in the world. The Bean is in Millennium Park which itself is a destination. Spending time here is one of the best things adults can do in Chicago. The Pritzker Pavilion has events, concerts, and movies. In the winter, there’s ice skating at the McCormick Tribune Plaza Ice Rink.

2. Step out on The Ledge at Skydeck

Another great thing to do in Chicago is to go to Skydeck for breathtaking views of Chicago’s skyline and Lake Michigan. Skydeck is on the 103rd floor of the Willis Tower and is the third tallest building in the Western Hemisphere. If you dare, step out onto one of the glass boxes that jut out from Skydeck and see Chicago’s streets 1,450 feet beneath you. If you are in town with family, this is one of the most popular things to do with teens in Chicago .

3. Find a way out of an escape room

The Escape Game Chicago is a perfect thing to do for adults who pictured themselves as a detective when they were younger! You’ll have 60 minutes to find the way out of a “locked” room by solving challenging clues and riddles. Rooms vary in amusing themes and difficulty levels. Rescue a stolen Monet painting from the hands of a maniacal art thief. Prevent a global catastrophe by hunting down evil conspirators hiding in a mysterious night market. Playing an escape room at The Escape Room Chicago brings out the inner sleuth in everyone!

4. See magnificent Impressionist artworks

At the Escape Game Chicago, you’ve got to hunt down a stolen Monet but at the Art Institute of Chicago , Monet paintings are right there! The Art Institute houses the largest collection of Impressionist art outside the Louvre. With over 300,000 pieces of art from around the globe spanning 5,000 years, the Art Institute will satisfy those who love all kinds of artworks. If you find yourself in Chicago on a rainy day , this museum, or any of the others in this article will keep you happy and dry!

5. Dig into a Chicago-style deep-dish pizza

Deep-dish pizza is perhaps Chicago’s most iconic food. Naturally, the competition is fierce over who makes the best deep-dish pizza. The top two spots are Lou Malnati’s and Giordano's . Lou Malnati’s is said to be the first family name in deep-dish pizza, serving pies since the 1970s. Giordano’s also opened in 1974, making its deep-dish pizza using a family recipe from the family’s ancestors in Torino, Italy. Whichever spot you choose, you’ll love this Chicago treat!

6. Catch the Chicago Cubs at Wrigley Field

Baseball fans will love seeing the Chicago Cubs at Wrigley Field , one of the oldest ballparks in America! This is an especially good thing to do if you are a group of adults looking for a fun time in Chicago, filled with pretzels, beer, and baseball history! Cubs fanatics will like the Chicago Sports Museum with its collection of exclusive items and gear used by some of the Cubs’ greatest players and the largest collection of memorabilia from the 2016 World Series.

7. Stroll along Riverwalk

Along the Chicago River is a picturesque 1.25-mile-long path called Riverwalk . A stroll along Riverwalk is a great way to see some of Chicago’s architecture, like the city’s recognizable Marina Towers, that's appeared in films and commercials. For adults looking for a relaxing thing to do in Chicago, Riverwalk is the place to go for a glass of wine at the water’s edge. Check out the nightly light show, Art on The Mart, where artwork is projected onto the massive Mart Building. It’s quite the sight! If you are looking for a perfect date night idea in Chicago , look no further than a stroll here.

8. Soak up the sun at North Avenue Beach

Chicago has 26 miles of shoreline along Lake Michigan, with more than 20 public beaches along Lake Michigan. One of the most popular Chicago beaches is North Avenue Beach where there are plenty of fun things to do for adults besides sunbathing. Join a volleyball game, take a yoga class, or rent a kayak and venture out onto lovely Lake Michigan. The beach is quite nice with spectacular views of the skyline and a 22,000-square-foot beach house, nearby restaurants, and beachfront bars. On a hot day in Chicago , gran a towel and head here!

9. Take a Lake Michigan Tour

The views from the beach are lovely but the views from a cruise on Lake Michigan are amazing! If you aren’t up for a kayak ride at North Avenue Beach, look into one of several cruises that get you out onto the water, enjoying a nice breeze, and taking in the skyline sights. Most tours showcase the key sights along the shore. Some offer educational information about the marine life of the lake. Combine your cruise with lunch or brunch or take a romantic nighttime cruise. Many cruises depart from Navy Pier, a fun destination in Chicago. Find out about cruise options here .

10. Head to Navy Pier

For an awesome night out in Chicago , head to Navy Pier . Walk along the boardwalk, dine at one of several restaurants, and do some light shopping. For amazing views of the city, ride the famous Centennial Wheel that takes you 200 feet up in the sky. If you are in Chicago in the summer months you can see fireworks every Wednesday and Saturday night.

11. Stop by Chicago’s most famous fountain

Before The Bean landed in Millennium Park, Buckingham Fountain was Chicago’s most-visited landmark. Located in the center of Grant Park, this 1927 fountain is one of the largest fountains in the world. Its Beaux-Arts-style design makes it one of America’s finest fountains. Its main appeal in the modern era is the nightly light show that uses 15,000 gallons of water per minute and lights of all colors accompanied by music. The show takes place every hour on the hour.

12. Say hello to Chicago’s animals

Located in Lincoln Park, the free Lincoln Park Zoo is an easy-to-reach zoo with over 1000 animals both big and small. See majestic gorillas, playful meerkats, red wolves, pygmy hippos and so many other of nature’s creatures. Just north of the zoo is the Lincoln Park Conservatory with manicured outdoor gardens and an elegant 1890 glass house with exotic flora and fauna. In town with children? A visit to the zoo is one of the top things to do with kids in Chicago !

13. See some comedy

An iconic spot of Chicago’s nightlife, the Second City offers adults a fun night out with excellent comedy shows. Second City is best known for launching the careers of dozens of Saturday Night Live alumni and movie stars including Dan Aykroyd, Martin Short, John Candy, and Catherine O'Hara. Planning a work party in Chicago ? A comedy show is just the thing to keep everyone having a great time!

14. Meet SUE, Chicago’s T. Rex

A top Chicago museum for both adults and kids is the Field Museum of Natural History , one of the largest natural history museums in the world. Dinosaur lovers will go crazy for SUE, the largest and most complete T.rex ever discovered. Pass through Evolving Planet which follows the evolution of life on Earth over 4 billion years, Inside Ancient Egypt where you can see mummies and artifacts of everyday life, and the Grainger Hall of Gems with a large collection of diamonds and gems.

15. Have a Chicago-Style Hot Dog

A Chicago Hot Dog is not just your average frankfurter. It’s all about how it’s served that makes it unique. A Chicago dog starts with an all-beef frank inside a poppy seed bun. It’s then covered with yellow mustard, sweet pickle relish, chopped white onions, tomato slices, pickled sport peppers, and a dash of celery salt topped off with a dill pickle spear. Whatever you do, do NOT ask for ketchup! Popular spots for a Chicago hot dog are the historic Portillo’s and Superdawg .

16. Take a bike ride

Chicago is quite bike-friendly and has 26 miles of lakefront trails you can bike along. Lakefront Bike Path is 18.5 miles long and is perfect for a leisurely ride with nice views. You can rent bikes from a private bike rental company like Bike and Roll or Chicago Bike Adventures or opt to use Chicago’s bike-share program, Divvy . Just rent a bike from one of Divvy’s self-service docking stations anywhere in the city and then return it to any dock.

17. Get to know Chicago’s history

The Windy City has a storied past and you can learn about it at the Chicago History Museum (CHM). A big part of the city’s past is the Chicago Fire of 1871, and the CHM covers it extensively in its permanent exhibit City on Fire. Another element of Chicago’s history is the 1893 Chicago World's Fair and the museum has a mammoth collection of related objects and artifacts. Its visiting exhibitions are also excellent.

18. Walk the 606

The 606 is a recreational walkway built on an old, elevated train line that runs through several neighborhoods in Chicago’s northwest. With multiple access points, visitors can enter or exit the 606 and visit any of the interesting attractions along the way. The 606 itself has interesting stops including permanent public artworks and Damen Arts Plaza featuring rotating art exhibits. Make a stop at Park No. 567 for interesting events like astronomy nights and live concerts.

19. See the Chicago Bulls

Basketball fans will love being able to see the Chicago Bulls, one of the most successful NBA teams ever. They play out of the United Center and though you won't be seeing legends like Michael Jordan, Scottie Pippen, and Dennis Rodman, you will have an exciting time watching a great team! When the Bulls aren't playing at home, the United Center hosts concerts of top performers as it is the biggest venue in Chicago.

20. Marvel at Modern Art

While so much attention falls on the Art Institute, Chicago’s Museum of Contemporary Art (MCA) is worth visiting for modern art lovers. With provocative artworks from 1945 and after, the museum is one of the world’s largest contemporary art museums. You can take a free tour to learn about the works on the walls. For a fun thing to do in Chicago, enjoy one of MCA’s after-hours events for adults, 21 and over that are scheduled throughout the year.

21. Go on a self-guided street art tour

No need to go inside to see captivating art! Chicago has a vibrant street art scene featuring large-scale murals found in many neighborhoods. Take this free, self-guided mural walk that takes you through alleys and off-the-beaten-track streets in three sections of The Loop in Chicago's downtown. If you prefer a guided tour, look into this free Wicker Park Culture & Chicago Street Art Tour .

22. See a show in the Theater District

The Chicago Theatre District is where to go to see a Broadway show or theatrical performance. The district includes iconic theaters like the Chicago Theatre, James M. Nederlander Theatre, and the Cadillac Palace. Shows to see include top Broadway hits, like Chicago, including Les Misérables, Cats, 1776, Annie, The Book of Mormon, A Soldier’s Play, Jagged Little Pill, Into The Woods, Disney’s Aladdin, MJ, Hamilton, A Wonderful World, and BOOP! The Musical. Check here to see what’s on when you are in town.

23. Explore Magnificent Mile

This eight-block stretch of Michigan Avenue offers so many things to do in Chicago that you may end up spending hours here! Magnificent Mile is lined with stunning architecture, from the 1920s like the double-decked steel DuSable Bridge, Wrigley Building, inspired by a Spanish Cathedral, and the Gothic Revival style Tribune Tower. Not only is Magnificent Mile dazzling, but it’s also jam-packed with 275 restaurants and more than 460 retailers! If you are in Chicago for a Girls' Weekend , Magnificent Mile is a must-visit!

25. Discover Aquatic Creatures

Located in Downtown Chicago , the Shedd Aquarium has more than 32,000 specimens of sea and ocean life from 1,500 species. The aquarium’s engaging exhibits contain different natural habitats that feature marine life and animals found in those habitats. There’s a coral reef with sharks, stingrays, and turtles, and a flooded rainforest with exotic frogs, birds, snakes, and more. The Abbott Oceanarium introduces guests to the colorful coastal ecosystem of the Pacific Northwest with dolphins, sea lions, sea otters, and beluga whales. The Shedd truly is a notch above other aquariums.

Chicago Tours Adults Will Love

Sometimes it's nice to have another adult do all the explaining, which is why city tours are such a popular thing to do in Chicago. Here is a list of tour options.

25. Walking Tours

Chicago is very walkable but it is also very big! Walking tours generally cover specific neighborhoods to condense your sightseeing into a compact amount of time. Plus, guides are usually very knowledgeable and entertaining. Take a look at tours by the Chicago Architecture Center, Inside Chicago Walking Tours, and Free Tours By Foot Chicago.

26. Chicago River Tours

These tours are a relaxing way to see Chicago’s beautiful buildings along the Chicago River and learn about the city. Companies with excellent offerings are Wendella Boats and Shoreline Sightseeing.

27. Bus Tours

Chicago has several bus tours that let you discover the city at whatever pace you like. Take a sightseeing bus for an overview of Chicago or a hop-on-hop-off bus tour to disembark at attractions of your own interest. The top companies are Big Bus Tours, Grayline, and CitySightseeing.

28. Bike Tours

Chicago’s flat terrain makes seeing the city on a bike a really fun thing to do! There are all kinds of bike tours in Chicago. Choose from classic sightseeing tours, food tours, night tours, and even ghost tours! Bobby’s Bike-Hike and Bike and Roll are great companies.

29. Food Tours

Taking a food tour helps you avoid the hit-or-miss process and guarantees you’ll try the best of the rest! Look into these highly rated companies: Sidewalk Food Tours of Chicago, Secret Food Tours, and Chicago Food Planet.

30. Segway Tours

Chicago’s a big city with a lot to see! Segway tours are a fantastic way to cover a lot of ground without getting on a bus. Some segway tour companies are Absolutely Segway Tours, City Segway Tours, and #1 Chicago Tours.

Find out about more things to do in Chicago here .

For suggestions on how to plan your time, check out our   2 day Chicago itinerary !

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30+ kid-friendly things to do in Chicago

It’s the inspiration kids find in all the things to do and see in Chicago that makes the city feel like home — if home was the ultimate playground. From toddlers to teens, there’s a family friendly activity or attraction to satisfy every interest and fuel all imaginations.

Free things to do in Chicago with kids

Outdoor things to do in chicago with kids, indoor things to do in chicago with kids, kid-friendly attractions & museums.

Lincoln Park Zoo Free to the public, this is one of the nation’s oldest zoos . Kids love the old-school carousel, locomotive rides, and the Pritzker Family Children’s Zoo, a kid-friendly home for North American animals. Just next door is the Farm-in-the-Zoo, which gives kids the chance to pet goats, cows, and ponies, and experience a little country life in the city.

Brookfield Zoo Brookfield Zoo is set within a 216-acre nature park. World-renowned, the zoo’s 2,000+ residents have captivated and educated visitors since 1934. Don’t forget to take in a dolphin show at Seven Seas, and sign up for seasonal giraffe feedings, penguin encounters, and education-focused animal kingdom experiences.

Millennium Park In Millennium Park each summer, kids splash around in Crown Fountain’s shallow pool and dash underneath the water spouting from the lips of video-projected Chicago locals. Springtime is perfect for a self-guided scavenger hunt through Lurie Garden. In winter, skate with the city skyline as your backdrop at the magical McCormick Tribune Ice Rink. And no matter the season, and make faces in the reflective surface of the stainless steel sculpture Cloud Gate, aka “The Bean.”

Navy Pier Iconic Navy Pier is the place for rides on a towering climate-controlled Ferris wheel, an old-fashioned Wave Swinger, and a whimsical 1920s-inspired musical carousel at Pier Park. And it’s the place to feel the excitement of summer fireworks, sightseeing cruises, Segway tours, an amazing maze, the Chicago Children’s Museum, fun stores, and the immersive FlyOver Chicago ride.

Shedd Aquarium Right next door to Adler Planetarium and Field Museum on the Museum Campus, Shedd Aquarium gives new meaning to “wow.” Not only can you explore underwater worlds from across the globe, but the Shedd offers unique, up-close-and-personal experiences, like museum sleepovers, behind-the-scenes tours, and extraordinary animal encounters, like joining in a shark feeding tour, being a trainer for a day, and interacting with stingrays.

Art Institute of Chicago Don’t think the kids will enjoy an art museum? Then you haven’t visited the Art Institute ‘s Thorne Miniature Rooms. These meticulously reproduced miniature rooms bring the world of art and architecture to a kid’s level. There’s also free admission to the Ryan Education Center, which hosts special events, interactive workshops, and family programming for kids 14 and under.

American Writers Museum Visit the Children’s Literature Gallery at the American Writers Museum to get the kids all fired up about reading. A fabulous mural created by celebrated illustrator and author Paul O. Belinsky adorns the gallery, depicting friendly squirrels reading classic kids’ books.

Bronzeville Children’s Museum The Bronzeville Children’s Museum is the first African American children’s museum in the country. It’s filled with exhibits for children aged 3 to 9, with a unique tour format that ensures kids get maximum educational value from each exhibit.

Chicago Children’s Museum Kids can stretch out, crawl, and use all five senses throughout interactive exhibits such as WaterWays, Dinosaur Expedition, and Treehouse Trails. Best of all, the Chicago Children’s Museum is located at Navy Pier — a goldmine of family-friendly things to do on Chicago’s scenic lakefront.

Chicago History Museum Climb aboard the very first ‘L’ train car, ride a high-wheel bicycle, hear the Great Chicago Fire, catch a fly ball at Comiskey Park, smell the Union Stock Yard, dive into a giant Chicago-style hot dog — all at the Chicago History Museum .

Sloomoo Institute Kids — and kids at heart — and invited to experience the Sloomoo Institute ‘s interactive slime museum. Visitors can explore a variety of hands-on exhibits featuring all sorts of textural, scented slimes. Come experience the joys of sensory play, soothing ASMR, and contemporary art.

Chicago Sports Museum The Chicago Sports Museum combines high-tech interactivity with unique sports memorabilia and an impressive collection of game-used treasures and other artifacts. Kids can test their skills against some of the all-time greats, use CSI-type technology to unravel some of Chicago’s most infamous sports mysteries, step into a replica broadcast booth and call a game just like Harry Caray, and so much more.

Field Museum Field Museum takes adventure to a whole new level with the likes of SUE the T. rex , man-eating tigers, and Máximo the Titanosaur, the largest dinosaur known to man. The Field sits on the lakeside Museum Campus, along with Adler Planetarium and Shedd Aquarium. Take a Shoreline Sightseeing boat from Navy Pier or Willis Tower and explore all three.

Museum of Science & Industry The Museum of Science & Industry  is the largest science museum in the Western Hemisphere, which means there’s plenty of room for spinning tornados, a real-life U-boat, trains, planes, and, well, just about everything else you could possibly imagine. Oh, and don’t miss screenings at the five-story, wraparound Giant Dome Theater.

Peggy Notebaert Nature Museum From native animals and nature-inspired art, to toddler-friendly play spaces and an exotic butterfly house, the exhibits at Peggy Notebaert Museum are sure to thrill young visitors (and grown-up ones, too). As a bonus, the museum sits within the grounds and gardens of Lincoln Park, where kids can run wild among shady trees, blossoming flowers, and chattering squirrels.

Adler Planetarium Part of the lakeside complex known as Museum Campus, Adler Planetarium is the oldest planetarium in the Western Hemisphere. It’s also a great museum. Future explorers and astronomers of tomorrow will marvel at interactive exhibits, immersive planetarium shows, and special programming designed to inspire the rocket scientists of tomorrow.

Kid-friendly outdoor activities

Maggie Daley Park Maggie Daley Park is a magical place where you’ll find a Skating Ribbon, a 3-acre Play Garden created in the spirit of Alice in Wonderland and Charlie and the Chocolate Factory, a mini golf course that takes you through Chicago-themed obstacles (like a mini Willis Tower), and a climbing wall right on the lakefront.

Bike tours Sign up for Bobby’s Bike Hike’s kiddie edition, Bobby’s Tike Hike, designed specifically for kids aged 10 and under. Both Bobby’s Bike Hike and Bike and Roll Chicago give you the option of buying infant/toddler tickets that include special equipment such as child seats, comfy trailer carriers, and tag-a-long attachments.

Grant Park Skate Park It’s not only skateboarders who love the skate park at Grant Park . You’ll see rollerbladers and BMX bike enthusiasts making the most of the park’s multi-skill-level concrete ramps and grinding rails — all with a lakefront view.

Kayaking Take the kids on a kayak tour of Chicago’s waterways from Monroe Harbor or the Chicago River. Sail along with Urban Kayaks and be guided through breathtaking city vistas. No experience is necessary, guided tours are provided.

Kid-friendly experiences

American Girl Place For little kids with big imaginations, a visit to Chicago would not be complete without a trip to American Girl Place, the first store of its kind in the United States. Consider making a reservation for the café at the downtown doll mecca, which serves brunch, lunch, afternoon tea, and dinner. American Girl is located in Water Tower Place on The Magnificent Mile .

Escape rooms Take the kids on the greatest adventure ever with a Chicago escape room. Make a prison break, escape an ‘L’ car, and even take a mission to Mars while testing kids’ problem-solving and team-building skills. Take your pick from Escape Artistry , The Escape Game Chicago , and Fox in a Box – Chicago , among others.

Indoor skydiving It’s like skydiving, without the sky — or the dive. iFLY is the ultimate indoor body-lift experience, and you don’t need any prior experience to give it a whirl. This is a sure win for teen and tween visitors in particular.

LEGOLAND Discovery Center Take a day trip to LEGOLAND Discovery Center , a giant indoor playground located in nearby suburban Schaumburg. Two rides, 10 LEGO build-and-play zones, and a 4D cinema are just a few of the great LEGO-themed experiences you’ll have here. Once back in the city, visit the colorful building-block wonderland that is The LEGO Store at Water Tower Place.

Skydeck Chicago Walk on air at Skydeck Chicago . Located in Willis Tower, one of the tallest buildings in the world, glass boxes extend approximately 4 feet from the skyscraper’s facade, more than 1,300 feet above ground level.

TILT at 360 CHICAGO Literally tilt outward over 1,000 feet above The Magnificent Mile and get 360-degree views of four states. Located at 875 N. Michigan Ave., TILT is housed in the former John Hancock Building, one of Chicago’s most iconic buildings.

Urban Adventure Quest Experience an adventurous city tour by competing in a family-friendly Urban Adventure Quest scavenger hunt. Incorporating elements of the Amazing Race, this competition involves solving clues and completing challenges, all while learning about local history.

Kid-friendly theatre

PlayMakers Laboratory PlayMakers Laboratory has been celebrating the power of children’s imaginations since 1997, with arts programs that focus on storytelling, theatre, and social-emotional skills. In fact, the professional actors perform material written by Chicago Public School students, providing a unique outlet for their creative works.

Blue Man Group Blue Man Group is the epitome of theatre fun — a multi-sensory, performance art experience that keeps kids wide-eyed from the moment the curtain goes up. And if you pick a seat in the “Splash Zone,” expect things to get pretty messy!

Chicago Children’s Theatre For two decades, Chicago Children’s Theatre has presented a year-round schedule of plays, classes, and camps designed to inspire curiosity in kids and families. 

ComedySportz ComedySportz ’s interactive 90-minute show has kids in stitches as two teams compete for laughs during improvised comedy scenes, songs, and games. Geared toward all ages, this is a great way to get kids in on the act, with audience suggestions as the actors’ inspiration.

Broadway in Chicago Broadway in Chicago brings hit musicals, world premieres, and more exciting productions to Chicago stages. Check the schedule for family-friendly programming like Peter Pan , The Lion King , Beauty and the Beast , and more.

See the best attractions in Chicago at up to 48% savings with CityPASS.

Explore the famous Shedd Aquarium, see scientific discoveries at the Field Museum, take in spectacular views from the Skydeck and more! With two options to choose from and up to 9 days to enjoy, you can't go wrong.

• Lincoln Park Zoo and Brookfield Zoo

Millennium Park

Maggie daley park.

• Garfield Park Conservatory
• Lincoln Park Conservatory
• Free museum days
• Chicago Cultural Center
• Hyde Park Art Center
• Bobby’s Bike Hike  and  Bike and Roll Chicago

Urban Kayaks

• Lake and river boat tours
• Chicago Children’s Museum

Shedd Aquarium

Art institute of chicago, american writers museum.

• Bronzeville Children’s Museum
• Chicago History Museum

Chicago Sports Museum

• Field Museum
• Museum of Science & Industry
• Peggy Notebaert Museum

Adler Planetarium

• American Girl Place
• Skydeck Chicago

Sloomoo Institute

• TILT at 360 CHICAGO
• PlayMakers Laboratory
• ComedySportz

Blue Man Group

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Special Event Venues

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Tours & Attractions

Lincoln park zoo.

Lincoln Park

Convention Centers / Conference Facilities

Streeterville

Bronzeville Children’s Museum

South Shore

The Magnificent Mile

Museum of Science and Industry

Peggy Notebaert Nature Museum

Fox in a Box – Chicago

The Escape Game Chicago

River North

360 CHICAGO Observation Deck

Urban Adventure Quest – Amazing Scavenger Hunt Adventure – Chicago

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Sports & Recreation

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Csz theater chicago.

Bobby’s Bike Hike Chicago – Bike, Walking, Food Tours & Rentals

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