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10 Easy Weekend Getaways from Chicago—No Flights Required

Escape chicago for a few days with one of these 10, drivable weekend getaways and short road trips starting in chicago..

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Door County, Wisconsin, is one of the many easy-to-reach day trip destinations from Chicago.

Door County, Wisconsin, is one of the many easy-to-reach day trip destinations from Chicago.

Photo by Bailey Berg

Despite cries about that winter weather, Chicago is inarguably blessed with a little something we like to call location, location, location : With prime real estate on Lake Michigan, the Midwest city is about as far by car from Minneapolis (six hours) as it is Toronto (eight hours) and Nashville (seven hours). In this sense, it’s an ideal jumping-off point for a drivable trip. There are several weekend getaways from Chicago, whether you want to put some serious miles on your car or be somewhere new by the time your kids are done watching Cars. Read on for ten easy weekend getaway ideas from Chicago.

What cities are under three hours from Chicago by car?

  • Milwaukee, Wisconsin (1 hour, 30 minutes)
  • Madison, Wisconsin (2 hours, 25 minutes)
  • Grand Rapids, Michigan (2 hours, 47 minutes)
  • Peoria, Illinois (2 hours, 41 minutes)
  • South Bend, Indiana (1 hour, 39 minutes)
  • Indianapolis, Indiana (2 hours, 56 minutes)

The Dane County Farmers’ Market in Madison is one of the largest in the U.S.

The Dane County Farmers’ Market in Madison is one of the largest in the U.S.

Photo by MarynaG/Shutterstock

Geneva, Illinois

  • Distance: An hour by car
  • Best for: Singular art and great shopping

OK, OK. Geneva is technically a suburb of Chicago, but it feels worlds away, thanks to its small-town charm. Drop your bags at the boutique Herrington Inn & Spa , located on the Fox River, and set out to explore the city’s walkable downtown on foot. Public art abounds here, as do independent shops and restaurants (all told, there are more than 150 of them in the historic district).

Michigan City is a breath of fresh air not far away.

Michigan City is a breath of fresh air not far away.

Photo by Andy Konieczny / Shutterstock

Michigan City, Indiana

  • Distance: An hour and a quarter by car
  • Best for: Hiking (and swimming for the brave)

On a clear day from Michigan City, you can see Chicago’s skyline across the water. Enjoy towering sand dunes, the cool waters of Lake Michigan, and nearly 50 miles of trails at Indiana Dunes National Park ; in Michigan City proper, attractions include the 19th-century Barker Mansion —listed on the National Register of Historic Places—and family-friendly Washington Park Zoo .

A lighthouse in New Buffalo, Michigan

A lighthouse in New Buffalo, Michigan

Photo by Suzanne Tucker/Shutterstock

Harbor Country, Michigan

  • Best for: A beach and wine combo trip

Comprising the eight towns of Michiana, Grand Beach, New Buffalo, Three Oaks, Union Pier, Lakeside, Harbert, and Sawyer, Harbor Country is a favored weekend escape from the Windy City, thanks to its beach and country offerings. There are also a number of world-class wineries and breweries in the area, including the popular Lehman’s Farmhouse and Dablon Vineyards and Winery , in nearby Baroda.

Milwaukee is home to one of the largest German populations in the U.S.

Milwaukee is home to one of the largest German populations in the U.S.

Photo by Jayne Lipkovich / Shutterstock

Milwaukee, Wisconsin

  • Distance: An hour and a half by car
  • Best for: Brats and brews

Milwaukee has a rich German heritage, which means the city is full of places to get a good beer and brat (and more beer, if that’s your thing). Both Pabst Blue Ribbon and Miller are based here, but don’t sleep on the smaller guys, including Milwaukee Brewing and Lakefront .

Mary stands atop the Golden Dome of the University of Notre Dame Main Administration Building.

Mary stands atop the Golden Dome of the University of Notre Dame Main Administration Building.

Photo by Jonathan Weiss/Shutterstock

South Bend, Indiana

  • Distance: An hour and forty minutes by car
  • Best for: Whitewater rafting

There’s more to South Bend than Fighting Irish football, though we absolutely cosign the idea of a walk around Notre Dame’s scenic campus. Hit the rapids on East Race Waterway , North America’s first artificial white-water course, which cuts through the city, or visit the historic Robinson’s department store to throw your own pottery at the Pigeon and the Hen . Play arcade games—for free!—at the Garage Arcade and Bar , which has all the classics, Galaga and Ms. Pac-Man included.

The Fredrick Meijer Gardens spans 158 acres and features a host of outdoor art exhibits.

The Fredrick Meijer Gardens spans 158 acres and features a host of outdoor art exhibits.

Photo by SNEHIT PHOTO / Shutterstock

Grand Rapids, Michigan

  • Distance: Around three hours by car
  • Best for: Beer, of course, but also outdoor sculptures

Voted “Beer City USA” in several national polls, Grand Rapids is known for its suds: Check out the Beer City Ale Trail , a map showcasing all of the options in the city. For food, we’re partial to strolling Downtown Market , which counts more than 20 vendors in the hall south of Heartside Park (a perfect picnic location, if you ask us). For an outdoor experience that requires a bit more activity, head to the 158-acre Frederik Meijer Gardens & Sculpture Park : here, you’ll find art by Auguste Rodin as well as a hall dedicated solely to carnivorous plants.

A dinosaur breaks out of the Children’s Museum in Indianapolis.

A dinosaur breaks out of the Children’s Museum in Indianapolis.

Photo by James Kirkikis/Shutterstock

Indianapolis, Indiana

  • Distance: Three hours by car
  • Best for: Museums, both traditional and quirky

Indianapolis is an incredible museum city. Although two of its most popular attractions are the Children’s Museum and the sprawling indoor-outdoor Indianapolis Museum of Art , don’t miss some of the city’s quirkier options: the Indiana Medical History Museum (not for the faint of heart) and the Kurt Vonnegut Museum and Library . Visit Indy’s famed City Market to sample more than 25 locally owned eateries; when you’ve had your fill, descend underground on a public catacombs tour, which takes place on the select Saturdays, May through October, between 10 a.m. and 3.15 p.m. (Private tours can be booked with Indiana Landmarks .)

Ann Arbor university

Ann Arbor is known for its university, but a host of delights awaits all visitors.

Photo by Dark Vader / Shutterstock

Ann Arbor, Michigan

  • Distance: Around three hours and 45 minutes by car
  • Best for: Adventures on the river

Activities for all seasons abound in Ann Arbor, best known as the home of the University of Michigan. Tube, kayak, SUP, or canoe down the peaceful stretch of the Huron River—accessed from the 69-acre Gallup Park—or stroll U of M’s famed Matthaei Botanical Gardens and Nichols Arboretum . Be sure to make time for the city’s Kerrytown Market and Shops , a picturesque neighborhood full of independent boutiques and restaurants. ( Zingerman’s Deli , one of the best spots in Ann Arbor for a sandwich, is here.)

An aerial view of Door County, Wisconsin

An aerial view of Door County, Wisconsin

Photo by Matt Sampson Photography/Shutterstock

Door County, Wisconsin

  • Distance: Four and a half hours by car
  • Best for: Exploring rugged coastline

A 70-mile-long peninsula, Door County is often called the “ Cape Cod of the Midwest” —and rightfully so. Just 50 miles northeast of Green Bay, Door County has stunning coves, cherry orchards, harbors, lighthouses, wineries, and some 300 miles of coastline. Newport State Park is an International Dark Sky Reserve , and the 900-acre Rock Island State Park has no cars; for a dose of small-town charm, stop by Ephraim, a Scandinavian-style village .

Fall colors in Traverse City

Traverse City might be a bit further away, but it’s worth the drive—especially in the fall.

Photo by Gary R Ennis Photos / Shutterstock

Traverse City, Michigan

  • Distance: Five hours by car
  • Best for: Exploring shops and galleries in a justifiably popular small town

No wonder Traverse City was named one of the sweetest small towns to visit in summer : a lakeshore beauty with art deco architecture, the city is beloved by many Chicagoans (including Oprah herself). One of Traverse City proper’s most popular attractions is the Village at Grand Traverse Commons: a hospital complex from the 19th century, the historic venue has since been reborn into a mixed-use space, with shops, restaurants, footpaths, and art galleries. Northwest of Traverse City is Leelanau Peninsula, which is home to the striking Sleeping Bear Dunes National Lakeshore .

Where can I go by train from Chicago?

No car? No problem. You can get virtually anywhere from Chicago by train: Memphis is 10 hours by rail; Seattle is 46. But for a weekend getaway, we’re partial to these picks:

  • Indiana Dunes National Park (the South Shore Line from Chicago’s Millennium Station stops at four stations in the park )
  • Milwaukee, Wisconsin (about 90 minutes by Amtrak from Chicago’s Union Station)
  • Kalamazoo, Michigan (about two hours by Amtrak from Chicago’s Union Station)
  • Grand Rapids, Michigan (about four hours by Amtrak from Chicago’s Union Station)

Of course, there’s plenty to do in Chicago itself before you head off; it was ranked number 2 in the best cities in the U.S. for 2023 , after all, thanks to its top restaurants , world-class museums, and abundant hotel options. On the other hand, if you’re feeling really adventurous, you could always take the ultimate epic road trip: 2,448 miles all the way to Santa Monica , California.

Happy weekending.

This article originally appeared online in 2020; it was most recently updated on August 31, 2023, to include current information.

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24 Top Weekend Getaways From Chicago

From beaches to ballparks and trails to rails, explore top breaks from the Windy City.

A weathered wooden walkway on the Empire Bluffs Trail in Sleeping Bear Dunes.

(Getty Images)

Hike along Michigan's Sleeping Bear Dunes National Seashore on your next weekend getaway from Chicago.

Known as the birthplace of the skyscraper, Chicago is home to award-winning restaurants , top sports teams and prized cultural treasures. But when you need a break from the excitement of the nation's third largest city, there are countless getaways within easy driving distance. You can explore rural Illinois or enjoy neighboring Indiana, Wisconsin, Iowa or Michigan all within a weekend. Whether you're planning a romantic getaway to a small-town bed-and-breakfast or a family-friendly trip to a water park resort, these nearby Midwest destinations will relieve the stress of big city life.

(Note: Some of the following activities, attractions and locations may be affected by the COVID-19 pandemic. New policies may be in place, including capacity restrictions, reservation requirements or mask mandates. Check with the Centers for Disease Control and Prevention, the U.S. Department of State and local tourism boards before traveling.)

Best Weekend Getaways from Chicago:

About two hours or less:, fox river valley, illinois, harbor country, michigan, st. joseph, michigan, milwaukee, wisconsin, south haven, michigan, starved rock state park, illinois, gurnee, illinois, wilmot mountain, wisconsin, lake geneva, wisconsin, grand geneva resort & spa, wisconsin, about three hours or less:, turkey run state park, indiana, the american club resort hotel, kohler, wisconsin, whistling straits golf course, sheboygan, wisconsin, saugatuck, michigan, wisconsin dells, wisconsin, about four hours or less:, parke county, indiana, galena, illinois, dubuque, iowa, and the field of dreams, ann arbor, michigan, madison, wisconsin, about five hours or less:, traverse city, michigan, louisville, kentucky, st. louis, missouri, a quick flight:, minneapolis – st. paul, minnesota.

Fox River on a sunny day in Illinois.

Located along the picturesque Fox River on the western outskirts of Chicago lie the small towns that make up Illinois' Fox River Valley. Stretching from the village of Antioch in the north to Ottawa – the gateway to Starved Rock State Park – in the south, this area is an ideal daytrip from the Windy City. Go biking, hiking and cross-country skiing along the 32-mile Fox River Trail or rent a kayak for paddling on the Fox River. In addition to outdoor pursuits, unique cultural attractions abound, including Broadway productions and musical events in Aurora's historic and beautifully restored Paramount Theatre. Visitors rave about its exquisite decor and top-notch performances, applauding the Paramount for offering Broadway-caliber performances at Main Street prices. If you choose to overnight in the Fox River Valley, the Herrington Inn & Spa , which overlooks the Fox River in the small town of Geneva, would make for a romantic getaway.

New York has the Hamptons; Boston has Cape Cod . The summer playground for Chicagoans consists of eight glistening lakeshore towns dotting the coastline of southwest Michigan, collectively known as Harbor Country. Here you'll find beaches, orchards and plenty of outdoor activities. At the southern end of Harbor Country, just over the Michigan-Indiana state line and about 70 miles from Chicago's downtown loop, New Buffalo lures Chicagoans with its casual beach vibe and proximity. Families line up for burgers at The Stray Dog, but only adults can head up to the rooftop bar and patio. Patrons praise The Neighborhood Hotel Grand Beach for its modern design combined with cozy common areas, fire pits, ping pong tables and board games; they also appreciate the short walk to the beach and the heated pool.

[Read: The Top Things to Do in Michigan .]

Families will want to make the scenic 25-mile drive from New Buffalo north through the Harbor Country towns of Union Pier and Lakeside, past grand lakefront estates and bucolic farms, to St. Joseph, commonly called St. Joe's. The family-friendly Silver Beach Pizza is housed in St. Joe's former train depot, with diners saying it's well worth what can be a half hour wait for the amazing pizza. Across the street is the restored 1910 Silver Beach Carousel, a great option for passing the time while waiting for your table if you've got kids along. St. Joe's offers visitors the chance to step back in time with a beach, pedestrian-friendly downtown, boutiques and old-fashioned chocolate shops. One of St. Joe's more unique shops is Third Coast Surf, where you can rent a surfboard and sign up for surfing or sandboarding lessons. Not expecting a surf shop in the Midwest? Visitors are often surprised when they first see Lake Michigan, known to Midwesterners as the Third Coast: It resembles an ocean more than a lake.

Downtown Milwaukee skyline at sunset with Lake Michigan shore.

Located about 80 miles north of Chicago on Lake Michigan is the Brew City of Milwaukee , which boasts more than 200 breweries, museums, festivals and the Harley-Davidson Museum . As this city is home of the Milwaukee Brewers baseball team, no trip is complete without getting a taste for Milwaukee's beer heritage. Visitors give Lakefront Brewery tours high marks for entertaining guides, extensive selection, riverfront views and its popular Beer Hall restaurant with live music on Fridays. Families will enjoy the lakefront museum campus, which includes the Discovery World science museum and Betty Brinn Children's Museum, while culture lovers can visit the architecturally stunning Milwaukee Art Museum when the building's "wings" open and close several times a day. Motorcycle enthusiasts will be in hog heaven at the modern steel-and-glass Harley Davidson Museum, which celebrates the machine invented in Milwaukee that's come to symbolize the freedom of America and the open road.

Winters are harsh, so summer is one endless celebration, with a multitude of neighborhood festivals, outdoor concerts and ethnic celebrations – check out German Fest at the end of July, honoring the city's largest immigrant group. Summer excitement reaches a crescendo at the end of June with Summerfest, the world's largest music festival. After a day of sightseeing or revelry, a top lodging choice is Milwaukee's stately grand dame, the historic Pfister Hotel , offering Gilded Age elegance alongside 21st-century amenities like a pool with panoramic city views and a popular top-floor cocktail bar.

[See more of Milwaukee:  Things to Do  | Hotels  |  Photos ]

South Haven is a fun-loving beach town with a population that swells in the summer – especially in August for the National Blueberry Festival, since this Michigan destination claims to be the blueberry capital of the U.S. About 110 miles from Chicago, you'll hear a lot of Jimmy Buffett playing in the bars and restaurants of this laid-back boating town where the harbors take center stage. Kick off your visit by learning about the area's rich Great Lakes boating history at the Michigan Maritime Museum.

Along with its seven public beaches – some of the best beaches in Michigan – and iconic red lighthouse, South Haven also has a pedestrian-friendly downtown filled with unique shops and restaurants. Climb aboard the stationary Idler Riverboat, where casual dining combines with world-class waterfront views. Clementine's is another local favorite, as is Captain Lou's, which serves fresh perch and live music on the weekends. For a romantic getaway, consider Inn at the Park, a bed-and-breakfast one block from Lake Michigan: Guests praise the beautiful decor and sumptuous breakfasts, using locally grown blueberries. Travelers also love Yelton Manor Boutique Hotel for its manicured gardens, spectacular sunset views of Lake Michigan and proximity to town.

Cascade after the morning summer rain in St. Louis Canyon at Starved Rock State Park, Illinois.

Looking for an active adventure? Only about 100 miles southwest of Chicago, this wilderness known for its deep sandstone canyons and waterfalls is perfect for daytrips – though with 18 canyons to hike, there's plenty to keep you busy for a whole weekend. Walking along bluffs that lead to scenic lookouts over the Illinois River makes visitors feel immediately transported out of the flat Midwest heartland. Starved Rock State Park can be a weekend escape any time of year, but spectacular fall foliage makes it a favorite getaway for autumn in particular.

Starved Rock State Park has its own historic lodge with top-notch cabins , but kids may prefer going across the street to the family-friendly Grizzly Jack's Grand Bear Resort, with its massive water park, mini-golf, indoor arcade and Northwoods decor. Camp Aramoni is a great choice for a romantic getaway, with luxury glamping in safari tents outfitted with hardwood floors, air conditioning and heating, and full bathrooms with showers. Nightly stays include chef-prepared farm-to-table dinner and breakfast using produce grown in on-site gardens that guests are welcome to visit. End your day at Camp Aramoni's repurposed Airstream trailer that's been turned into a bar.

Looking for high-adrenaline family fun? About 35 miles north of Chicago, just south of the Wisconsin border, lies the village of Gurnee, home to the Six Flags Great America amusement park . Thrill-seekers will love the 17 heart-stopping roller coasters, but dozens of other rides mean you'll also find plenty for younger kids. Reluctant riders who want to steer away from high-speed coasters and intense drop rides can also enjoy the park's shows and other entertainment. On a hot day, plunge down steep waterslides or splash around the wave pool at Six Flags' 20-acre Hurricane Harbor water park. When it gets cold, a favorite local pastime is a stroll around Gurnee Mills, an outlet mall housing more than 170 stores.

Continue your Gurnee adventure with a stay at the Northwoods-themed Great Wolf Lodge, the most family-friendly hotel option in this destination. Guests say this water park resort makes even adults feel like kids again and rave about the endless family-friendly amenities, which include bowling, mini-golf, a ropes course and arcade – and, of course, the massive water park.

Since 1938 Wilmot Mountain has drawn visitors seeking wintertime leisure in the Midwest. About 25 miles northwest of Gurnee, just over Wisconsin's state line, Wilmot Mountain Ski Resort makes for a great cold-weather attraction when Six Flags is closed. The big-name Vail Resorts purchased Wisconsin's little ski hill in 2016 and rolled out plenty of upgrades, from improving terrain parks and snowmaking to adding chairlifts and elevating the dining experience. Enjoy winter sports over a variety of terrain at this alpine destination, whether you're looking to ski, snowboard or snow tube. There's no on-site lodging, but Gurnee's Great Wolf Lodge is still a relatively short drive away.

[Read: The Top Things to Do in Wisconsin .]

A stunning summer sunset in Lake Geneva, Wisconsin.

This Wisconsin resort city makes for an idyllic weekend or daytrip. About 70 miles northwest of Chicago, Lake Geneva is described as the " Newport of the Midwest" because of its opulent lakefront mansions. You can come surprisingly close to these impressive residences by ambling along the Geneva Lakeshore Path, a rustic 25-mile walkway that encircles the lake, cutting right through the backyards of magnificent mansions and second homes. Amazingly, there aren't any "No Trespassing" signs to scare away walkers; just beware the path is not intended for strollers, roller blades or bikes, since you'll have to maneuver past steps and other obstructions. When you've finished your stroll, a lakefront cruise is another fun way to enjoy this city. Visitors give Lake Geneva Cruise Line excellent reviews for being informative and entertaining. A variety of daily cruises are offered, but one of the most unique is the mail delivery cruise. As Lake Geneva is one of the few remaining places in the U.S. where mail is still delivered by boat, about 75 lakefront homes receive their U.S. mail service via boat – and passengers are invited to come along for the ride.

Consider a stay at the Abbey Resort, the only full-service resort directly on the shores of Lake Geneva, during a summer visit. This lodging option offers complimentary adult and kids bikes, ideal for use on the Lake Geneva Bike Path, which connects many of the resort town's amenities. The trail has five unique, color-coded segments, making it easy to find your way around. Things quiet down a bit in the fall, when the vibrant autumn colors set a serene scene.

[Read: The Best Midwest Vacations for Families .]

Tourists descend on Lake Geneva's charming downtown shops and restaurants in the summer, but the town has plenty to do year-round. One of the best winter attractions in this city is the Grand Geneva Resort & Spa , whose modest ski hill has three chair lifts, 20 runs and a terrain park. Grand Geneva Resort also has access to 5 miles of wooded trails for cross-country skiing and offers a limited number of ski rentals. Kids will love overnighting at Grand Geneva's family-friendly Timber Ridge Lodge and Waterpark for indoor aquatic fun while adults relax at the spa. Time your winter visit to coincide with Lake Geneva's Winterfest so you can observe one of the country's biggest snow sculpting competitions.

Turkey Run State Park is the crown jewel of Parke County and one of the Hoosier State's oldest and most popular state parks. Eleven trails ranging from a half-mile to 2 miles wind through rugged ravines surrounded by the park's signature sandstone cliffs – providing Midwest hiking at its best. Turkey Run Inn, a popular lodging option situated within the park, is appreciated by guests for its friendly staff and cozy atmosphere. There's an indoor pool and plenty of public sitting areas with fireplaces, whether you want to play a board game or read a book. Choose from rooms within the historic lodge or the adjacent cabins. Even if you don't stay at Turkey Run Inn, you can still enjoy its restaurant, The Narrows, which diners recommend for the catfish dinners as well as the fried biscuits and hot apple butter.

Most have never heard of this tiny town 140 miles north of Chicago, but Kohler is home to Wisconsin's only hotel to receive AAA's highest five diamond rating. The American Club Resort Hotel – part of the Destination Kohler Resort – is still owned by the family who built it: The Kohlers are best known for high-end plumbing and bathroom fixtures. The American Club's luxurious Kohler Waters Spa specializes in hydrotherapy, giving guests a chance to experience all the legendary bath and shower products Kohler is known for. Should you want to recreate that luxury spa experience in your own bathroom at home, a few steps away from the spa is the sleek, multistory Kohler Design Center, filled with model bathrooms and design ideas sure to give most of us bathroom envy. Amid your self-care ventures in Kohler, enjoy plenty of outdoor activities. Fall brings a boisterous bounty of color to this rural area, while winter experiences at The American Club include ice skating, curling, snowshoeing and cross-country skiing across miles of trails that wind through woodlands and meadows.

Ten miles from American Club Resort Hotel sits the Kohler-owned Whistling Straits Golf Course, which some golfers describe as reminiscent of the legendary Pebble Beach . Whistling Straits ranks among the top public courses in the country and has hosted 2021's Ryder Cup and three PGA championships. The two Pete Dye-designed courses at Whistling Straits offer stunning views of Lake Michigan or rolling green hills. Golfers will feel transported to Ireland's tranquil grassland or its rugged coastline as this course winds its way along the bluffs and dunes overlooking Lake Michigan.

Nautical scene with fall leaf colors in Saugatuck, Michigan.

It's easy to see why Saugatuck is one of the best places to visit in Michigan . Nicknamed the Art Coast of Michigan, this hip resort town about 130 miles from Chicago is stocked with galleries, boutiques, excellent dining and beaches. Perhaps surprisingly for a town of less than a thousand people, Saugatuck is also known for its lively nightlife and for being an LGBTQ-friendly destination. Take a seat at the counter of the century-old Saugatuck Drug Store and you'll get a taste of the town's more traditional side, served up via a classic malt or ice cream soda. Visitors are in for another nostalgia trip when you board the chain ferry: Operating since 1838, it claims to be the only remaining chain-driven ferry in the U.S., transporting passengers across the Kalamazoo River between downtown and Oval Beach. After disembarking on Oval Beach, active beachgoers love climbing the 302 steps to the top of Mount Baldhead – known as Mt. Baldy – and getting a bird's eye view of the area. Overlooking Lake Michigan, Saugatuck's Lake Shore Resort is applauded by patrons for its breathtaking views and many complimentary amenities, including bikes, kayaks, yoga and a heated pool.

About 190 miles northwest of Chicago is the ultimate Midwest family getaway: the "Waterpark Capital of the World." If traveling with kids to Wisconsin Dells, stay at one of the immensely popular water park resorts , such as the flagship property of Great Wolf Lodge. Guests appreciate the original Great Wolf Lodge for its signature Northwoods decor, endless amenities and the feeling of being in a tropical paradise year-round.

Beyond its myriad indoor and outdoor water parks, Wisconsin Dells boasts a wide variety of kid-friendly entertainment options, from zip lines to animal parks. Catch a performance at the Palace Theater, which offers everything from concerts to comedy shows to children's plays and Broadway-style productions; some theatergoers swear there isn't a bad seat in the house. More fun for the whole family can be found at the Rick Wilcox Magic Theater shows, which wow audiences with both humor and illusions that keep you guessing. Want to escape the indoor attractions for a natural one? Head over to Mirror Lake State Park for a scenic hike along a tranquil, no-wake lake set among sandstone bluffs. Pontoon boats, kayaks and stand-up paddleboards are available to rent here.

[Read: The Top Things to Do in Wisconsin Dells .]

Billing itself as the covered bridge capital of the world, Parke County, Indiana – about 160 miles south of Chicago – maintains 31 of these Instagram-worthy symbols of a bygone era. Visitors descend on the area every October for the Parke County Covered Bridges Festival, Indiana's largest annual festival. The popular biker bar Thirty Six Saloon is a family-friendly roadhouse in Rockville, the town where the popular fall festival is headquartered. Kids may be mesmerized by Thirty Six Saloon's vast collection of taxidermy, with animals from the region mounted throughout the restaurant. Diners compliment everything from the burgers and ribs to the fish sandwiches and unique decor. Another popular culinary option is the tenderloin sandwich at the Mecca Tavern in Mecca. Parke County's oldest tavern overlooks Mecca's historic schoolhouse and covered bridge. Locals and visitors alike say stopping by Wheelhouse Donuts is another must: This adorable bakery lets you design your own doughnut.

About 150 miles west of Chicago, in the northwest corner of Illinois, the charming Mississippi River town of Galena regularly makes national lists of best small towns . Its elegant dining, historic sites, quaint shops and bounty of bed-and-breakfasts make Galena an excellent choice for a romantic getaway. Because the glaciers that flattened most of the Midwest didn't reach here, the pastoral farmland is hillier, perfect for a Sunday drive. The 19th-century buildings in this old mining town have been painstakingly preserved, with 85% on the National Register of Historic Places – including the Ulysses S. Grant Home State Historic Site, a residence gifted to the nation's soon-to-be 18th president in 1865 by Galena citizens.

One memorable overnight option would be a stay at the former county jailhouse – now the luxurious Jail Hill Inn. For a more romantic atmosphere, the Goldmoor Inn is beloved by guests for its stunning views of the Mississippi River, in-room fireplaces and two-person hot tubs. Galena is gorgeous any time of year, with plenty of travelers drawn here during harvest time for apple and pumpkin picking amid the abundance of fall colors. Winter brings its own charm with shops along Main Street resembling something out of a Norman Rockwell painting. The small town also houses a popular old-school ski resort: Guests say Chestnut Mountain Resort's decor and amenities are a bit dated, but its 19 ski runs provide scenic views of the river below.

Long exposure image of downtown Dubuque, Iowa, taken from the top of the Fourth Street Elevator.

Head 170 hundred miles west of Chicago, cross the Mississippi River, and you'll be in Dubuque, Iowa. Get a feel for how important the river is here by visiting the National Mississippi River Museum and Aquarium, or take a ride on a riverboat for another scenic way to experience the Mississippi. Visitors give the Celebration Belle river cruise high marks for being fun, informative and affordable. Another must-see attraction is Fenelon Place Elevator, a steep funicular railway providing fabulous views of the surrounding area. History lives on at the elegant Hotel Julien Dubuque, which guests compliment for its charm and friendly service. Baseball fans will want to make the additional 25-mile drive west to the town of Dyersville to explore the Field of Dreams, one of the best tourist attractions in the U.S. Play on the baseball diamond and tour the home where the movie "Field of Dreams" was filmed.

About 230 miles northeast of Chicago, Ann Arbor is a quintessential college town, filled with independent bookstores and great live music. University of Michigan alumni are a proud bunch – and not just on game days, when they march clad in blue and yellow to what's known as The Big House, the largest sports stadium in the country. Ann Arbor also scores an A when it comes to food and culture. The world-class University of Michigan Museum of Art displays works by Picasso, Monet and Warhol. A few blocks away on Liberty Street is the edgier public art canvas known as Graffiti Alley, just steps from the historic Michigan Theater and State Theatre, which delight visitors with film screenings, festivals and live music throughout the year (as long as you follow the theaters' COVID-19 regulations ). A pastrami sandwich at Zingerman's Deli is a 40-year tradition, but if you're hungry for a more budget-friendly option head to Frita Batidos and take a seat at one of the communal tables for Cuban-inspired street food. Hit the books at Literati, a beloved independent bookstore. A fun hotel choice is Graduate Ann Arbor with its University of Michigan-themed decor.

[See more of Ann Arbor: Things to Do | Hotels | When to Visit | Photos ]

About 140 miles northwest of Chicago, Madison is more than just a cool college town: It's also the capital of Wisconsin. No trip here is complete without visiting the beautiful, white-domed Wisconsin state Capitol building; free tours are given throughout the day. Madison's isthmus location on a narrow strip of land between two lakes means waterfront biking and hiking trails abound. Foodies will also get their fill at Fromagination, a cheese lover's paradise popular with Wisconsin cheeseheads as well as out-of-town visitors. Located across from the Capitol, this delightful cheese shop features dozens of one-of-a-kind artisanal Wisconsin varieties. If visiting Madison between April and November, head to Capitol Square on Saturday morning for the Dane County Farmers' Market, the country's largest producer-only farmers market. The 72-room, collegiate-themed Graduate Madison hotel is an easy walk to campus, dining, shopping and nightlife. Decorated in the University of Wisconsin colors of red and white, the hotel gets high marks from guests for its nostalgic decor and artwork, including collages of political buttons, a nod to the town's legacy of social activism.

[See more of Madison: Things to Do | Hotels | When to Visit | Photos ]

Cars parked watching the sunrise over the coast of Lake Michigan in downtown Traverse City, Michigan.

Those who have more time could leave the bright lights of Chicago for the serenity of Michigan's Traverse City to visit Sleeping Bear Dunes National Lakeshore and its 64 miles of pristine coastline and mountains of sand dunes. Traverse City is about 300 miles from Chicago, but you'll be rewarded with breathtaking beaches, peaceful hikes, top-notch cuisine and the added perk of what's considered the " Napa Valley of the Midwest": the 24 wineries of the Leelanau Peninsula Wine Trail. When the temperatures drop and the snow arrives, a great winter weekend getaway involves cross-country skiing in Pere Marquette State Forest or the Leelanau Trail, which runs from Traverse City to Suttons Bay. Traverse City and northern Michigan are also filled with summer lake resorts: Top options include Lake Leelanau's Fountain Point Resort, the upscale Homestead Resort and the all-inclusive White Birch Lodge in nearby Elk Rapids. With White Birch known for its water sports program, teens and tweens will love water-skiing, tubing and ending the day swapping adventures with new friends around a beach bonfire.

[See more of Traverse City: Things to Do | Hotels | Tours | When to Visit | Photos ]

Best known as the location of the Kentucky Derby, Louisville sits 300 miles south of Chicago and has a whole lot more going on than just horse racing. About 95 percent of the world's bourbon is made in Kentucky ; for a taste of the state's signature liquor, head to downtown Louisville's historic Whiskey Row. Here you'll find distilleries, unique restaurants and live music. Topping any sports lover's itinerary should be a visit to the Louisville Slugger Museum and the Muhammad Ali Center , which visitors applaud for honoring the boxer's life, faith and humanitarian service. Art lovers would enjoy staying at the 21C Museum Hotel Louisville , which houses its own contemporary art museum.

[See more of Louisville: Things to Do | Hotels | Photos ]

About 300 miles southwest of Chicago, just over the Illinois border along the Mississippi River, sits this Missouri city. St. Louis is well worth a weekend trip for its plethora of restaurants, breweries and cultural treasures. Nicknamed the Gateway City for its iconic Gateway Arch , St. Louis gives travelers the chance to take a tram ride to the top of this engineering marvel. After getting a bird's-eye view of the surrounding area, head over to the nearly 1,300-acre Forest Park , site of the 1904 World's Fair, now home to the Saint Louis Zoo and several museums. Music lovers can't miss the National Blues Museum, which sings the praises of that melancholy American music form. If you find yourself in need of more music lessons, make your way to the Scott Joplin House State Historic Site, where the king of Ragtime lived. After a busy day sightseeing, Drury Plaza Hotel St. Louis at the Arch makes a good place to rest. Guests rave about the unbeatable value of the hotel's free breakfast and happy hour with complimentary hot food and drinks.

[See more of St. Louis: Things to Do | Hotels | When to Visit | Photos ]

Minneapolis aerial with Downtown Minneapolis skyline in the background and Loring Park with Loring Pond in the foreground, during early autumn.

The Twin Cities of Minneapolis − St. Paul straddle the Mississippi River, about 450 miles northwest of Chicago, with Minneapolis as Minnesota's most populous city and St. Paul as the state capital. Minneapolis is known as a city of lakes, but visitors also like to walk along the riverfront, taking in the magnificent Mississippi. Groundbreaking pop musician Prince was born in Minneapolis; now his legacy lives on at Paisley Park, a sprawling complex in the nearby town of Chanhassen that was once the artist's studio and home. Millions more travel here to visit the largest mall in the Western hemisphere, Mall of America , located in the nearby suburb of Bloomington. As much an entertainment complex as a retail center, this mall houses the indoor amusement park Nickelodeon Universe, a highlight for kids. Guests give Minneapolis' Hewing Hotel stellar reviews for its character, charm and stunning views from the rooftop lounge.

[See more of Minneapolis − St. Paul: Things to Do | Hotels | When to Visit | Photos ]

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Tags: Travel , Midwest Vacations , US Vacations

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10 Best Weekend Road Trips From Chicago, Illinois

Posted by Brittany Varano June 01, 2021 Updated February 22, 2023

Sometimes you need a change of scenery, and these weekend road trips from Chicago make it easy to get away from the bustle of the Windy City.

Perfectly perched within reach to four different states, Chicago conveniently sits at the crossroads to destinations in Wisconsin, Michigan, Indiana, Iowa, as well as the rest of Illinois.

Its prime location means endless weekend road trips that range from city escapes to small-town excursions and outdoor getaways. And you’ll have your choice of several sandy beach towns lining the shores of neighboring Lake Michigan.

Below, you’ll find a diverse list of the best weekend road trips from Chicago to inspire your next adventure out of the city.

Related Read: The 10 Best Illinois Glamping Rentals

1. Milwaukee, Wisconsin

milwaukee road trip from chicago

Milwaukee is an easy weekend trip just north of Chicago over the Wisconsin border. Known for its craft breweries and local eats, there’s a lot to do and see in this smaller midwestern city. If you’re interested in learning about the local history, make time to visit Milwaukee’s beloved museums like the historic art museum or the Harley Davidson Museum to marvel at one of Elvis Presley’s classic motorcycles.

If you’re a sports fan, make time to catch a Milwaukee Bucks basketball game or tailgate outside of Miller Park before watching the Brewers play ball. The end of summer is also a fantastic time to visit Milwaukee as Summerfest is in full swing. Summerfest is a music festival held along the picturesque shores of Lake Michigan in downtown Milwaukee and brings notable acts each year.

Distance from Chicago: 93 miles (approx. 1 hour and 30 minutes)

Related Read: 11 Best Cabin Rentals in Illinois For an Outdoor Getaway

2. Starved Rock State Park

starved rock state park from chicago

If peace in nature is what you’re seeking, Illinois’ Starved Rock State Park is a beautiful outdoor getaway known for scenic sandstone canyons, numerous waterfalls, and miles of hiking trails. The park’s top sights include Lover’s Leap Overlook (a lookout point offering clear views of the Starved Rock Dam) as well as the Wildcat, French, and St. Louis canyons.

Summertime is the best time to visit, bringing sunshine and warm weather. Winter is also not a bad time to visit, when the canyon falls freeze over in a spectacular show of ice and snow. Many visitors opt to camp out in the state campground, where reservations can be made up to six months in advance. The park is on the Illinois River southwest of Chicago.

Distance from Chicago: 94 miles (approx. 1 hour and 30 minutes)

Related Read:   9 Fabulously Unique Places to Stay in Illinois

3. Indianapolis, Indiana

indianapolis 500

Indianapolis is an excellent weekend road trip from Chicago for city dwellers and racing fans. Home to the world-famous Indy 500 and the Indianapolis Motor Speedway Museum , car lovers can cheer on their favorite drivers and learn a bit about the sport’s history.

No visit to Indy is complete without sampling some local cuisine, including local specialities like pork tenderloin sandwiches and shrimp cocktail. The city was named as an ‘Underrated Food City in America’ by Condé Nast Traveler for its rich and diverse restaurants and dishes. Other popular things to do in Indianapolis include walking the eight-mile Indianapolis Cultural Trail that stretches through downtown or visiting the iconic Monument Circle.

Distance from Chicago: 184 miles (approx. 3 hours)

Related Read:   10 Romantic Getaways Near Chicago, Illinois

4. Galena, Illinois

galena roadtrip from chicago

For a taste of small-town living, look to Galena, Illinois . The city has consistently been ranked as one of America’s most livable cities and offers a lovely weekend trip from the big city. Galena is known for its quaint main street lined with historic brick buildings dating to the 1800s.

Visitors can tour the former home of Ulysses S. Grant and visit the beautiful grounds of the Dowling House, the oldest home in the city. Rolling hills and Native American effigy mounds surround Galena, such as the Horseshoe Mound, a nature preserve boasting views of three nearby states. The best way to experience Galena is to stay in a charming bed and breakfast or a local vacation rental.

Distance from Chicago: 164 miles (approx. 2 hours and 45 minutes)

5. Indiana Dunes National Park

Indiana Dunes National Park from Chicago

Boasting the shortest distance of all the road trips from Chicago, the Indiana Dunes National Park is a convenient road trip from Chicago to northwestern Indiana. The park protects over 15,000 acres of diverse landscapes that include sunny beaches, sand dunes, wetlands, and forests.

The park is a four-season destination offering wildflowers in the spring, water fun in the summer, fiery colors as the leave change in the fall (and sunsets are great), and cross-country skiing in the winter.

Most people opt to camp out in the national park campground or stay in nearby vacation rentals. Besides the outdoor adventures inside the park, make time to shop at the Saturday European Market in Chesterton, visit the Old Lighthouse Museum , and indulge in Indiana comfort food.

Distance from Chicago: 49 miles (approx. 56 minutes)

6. Grand Rapids, Michigan

Frederik Meijer Gardens Sculpture Park

Get a feel for Michigan city life with a weekend in Grand Rapids . About three hours north of Chicago, the city was once a hub for furniture manufacturing, securing the nickname “Furniture City.” Today, locals and visitors alike enjoy strolling the downtown riverwalk along the Grand River, eating out at hip restaurants like Divani and Stella’s Lounge,  and shopping at the Grand Rapids Downtown Market.

The Frederik Meijer Gardens & Sculpture Park is another must-see stop, with walking trails meandering through nearly 160 acres of colorful gardens and sculptures. In the evening, sip cocktails as the sun sets at the New Hotel Marten’s hip rooftop.

Distance from Chicago: 177 miles (approx. 3 hours)

7. Madison, Wisconsin

monona terrace madison wi

Home to the majestic Wisconsin state capitol building, Madison is a charming city best known for its location on an isthmus surrounded by four scenic lakes. The University of Wisconsin Madison campus sprawls through the downtown area, bringing with it a vibrant artistic atmosphere as well as hip bars and restaurants. Along the pedestrian friendly State Street, boutique shops and charming cafes lead the way to the capitol building.

One of the best things to do in Madison includes visiting the Saturday farmers market, where 150 vendors line the capital square selling locally sourced produce, flowers, and sweet treats. Grabbing a pitcher of beer at the Union Terrace along Lake Mendota and visiting the admission-free Henry Vilas Zoo are also popular things to do. That said, Madison is a very outdoorsy city, so you’ll find plenty of options for everything from paddling to hiking, biking, and outdoor movies and festivals.

Distance from Chicago: 147 miles (approx. 2 hours and 20 minutes)

8. Lake Geneva, Wisconsin

lake geneva road trip from chicago

Lake Geneva is a four-season resort destination in south-central Wisconsin. The city is named after the large 5400-acre Geneva Lake that attracts fishing and boating enthusiasts. The city’s Big Foot Beach State Park is one of the best places to go for swimming, sun tanning, and kayaking. If you enjoy casual walks, take a stroll along the Geneva Lake Shore Path that circles the lake for 21 miles.

While summer is an ideal time to make the most of the lake and surrounding beaches, winter also offers a unique weekend getaway. Every year, the Geneva National Resort and Club hosts the award-winning Ice Castles festival, where ice sculptures and structures amaze winter visitors. Prices and hotels cross into a variety of budget and lux options, but in general, it’s one of the cheaper towns for a summer getaway near Chicago.

Distance from Chicago: 83 miles (approx. 1 hour and 30 minutes)

Related Read:   13 Exciting Things to Do in Lake Geneva, Wisconsin

9. Saugatuck, Michigan

Saugatuck state park Michigan

Saugatuck, Michigan , is an artsy beach destination best enjoyed in the summer. This small town is on Lake Michigan and Kalamazoo Lake, offering fantastic water fun like fishing, swimming, and boating. The area is also famous for its idyllic grassy dunes, Mount Baldhead Park hiking, river cruises, and the Dutch windmills and gardens in nearby Holland, MI.

The city’s center features Butler Street, where visitors can enjoy up-and-coming gourmet restaurants and boutique shops. Don’t forget to pack your swimsuit for a trip to Oval Beach. For the best experience, opt for a cozy B&B along the water or in the downtown area, but be sure to plan ahead as lodging fills fast in the summer.

Distance from Chicago: 141 miles (approx. 2 hours and 15 minutes)

10. The Wisconsin Dells

Wisconsin Dells Road Trip from Chicago

Known as the waterpark capital of the world, the Wisconsin Dells is a resort town with 20 different indoor and outdoor water parks and resorts. It’s a perfect weekend road trio from Chicago for families looking for something fun but family-friendly – and the area offers more to do than just waterparks. Take a tour along the Wisconsin River and surrounding forests on a Wisconsin Duck, an amphibious truck that dates back to WWII.

Be sure to check out other popular activities such as local winery tours, the hiking trails through nearby Devil’s Lake State Park, and the vibrant nightlife of downtown. When visiting, there are plenty of cozy Wisconsin Dells cabins to stay at if resort living isn’t for you.

Distance from Chicago: 195 miles (approx. 3 hours)

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Seen in: Illinois , Midwest , Road Trips

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Posted by Brittany Varano

Brittany is a freelance travel writer and avid photographer with a love of hiking and nature. Originally from Wisconsin, she fell in love with travel blogging after living and teaching English in South Korea. She’s now location independent and enjoys slow travel to new and exciting places.

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Best Weekend Getaways From Chicago

By Nina Kokotas Hahn

One of the Kohler Lake Cabins

Chicagoans itching to travel right now should not underestimate the power of a great winter road trip, and not just because it may feel like the only safe option at the moment. In a break from the norm, we’ve found exciting places offering something fresh and surprising for the Midwest, making them well worth the drive. A fun, elegant cocktail experience, lakefront retreats that offer stunning views, snowy ski trips with plenty more to do off the slopes—it’s all available. Here are the best weekend getaways from Chicago .

(Editors note: Given the changing nature of the COVID-19 pandemic , the hours and accessibility of many venues are fluid and subject to change. Make sure to contact them before visiting.)

All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission.


Distance from Chicago 33 miles

Lake Forest Illinois Deer Path Inn

The Deer Path Inn

In less than 60 minutes by Metra or just over 30 minutes by car, find yourself feeling far from the city in this pretty Northshore town off of Lake Michigan. No doubt Lake Forest is fancy with its sprawling estates, Market Square, and upscale shops (check out the all-women-run Lake Forest Bookstore and Valentina boutique), and coveted waterfront views. Being here also puts you 20 minutes closer to the 385-acre Chicago Botanic Gardens , where the Japanese and dwarf confider gardens are especially sublime in winter.

Where to Stay

The main reason to go to Lake Forest now is a weekend away at the 57-room Deer Path Inn ( from $329 per night ), a fabulous, little-known gem that puts you in arm's reach of the shops and lake, and offers many experiences available only to guests. Opened in 1929 with the style of an authentic manor house, the elegant inn feels as storied and local as it does far-flung and English. Spacious, modern, and sophisticated rooms offer upscale amenities (think Frette linens and bathtubs that fill from the ceiling); recently, the inn began in-room delivery of its popular Afternoon Tea service, complete with a tower of tea sandwiches, petit fours, and tartelettes. Patio dining in the English Garden at Deer Path is scenic and doable in winter with heaters. Guests at the hotel can also reserve the inn’s hidden cellar for a new, private, and totally custom cocktail or wine tasting paired with dinner that's led by Deer Path’s fun and expert chief spirits officer, Jorge Centeno.


Distance from Chicago 49 miles

Indiana Dunes National Lakeshore

The dunes overlooking Lake Michigan at Indiana Dunes National Park

Drive just 60 minutes and find yourself surrounded by beauty in the 15,000-acre Indiana Dunes National Park , which packs in an astounding amount of botanical diversity thanks to its variety of lowlands, highlands, prairies, wetlands, forests, and Lake Michigan shoreline. Time your visit with cool winter conditions, when snow cloaks the park in white, and there’s a chance to see spectacular shelf ice formations on the water, not to mention you’ll get a far more secluded experience. Venture out on cross-country skis or snowshoes—the latter of which can be borrowed for free at the park’s Paul H. Douglas Center for Environmental Education. All of the park’s 50 miles of trails are available for winter activities, but opt for a one-mile loop or three-mile route on the Paul H. Douglas Trail, which takes you to the beach through a rolling black savannah, one of the rarest habitats in the country. Often confused with the national park, the two-acre Indiana Dunes State Park , immediately next door, is also open and admission is waived on weekdays in winter.

Nearby Chesterton offers a good location central to both parks, and interesting B&B’s are the way to go. Within walking distance to restaurants and shopping, Riley's Railhouse Bed & Breakfast ( from $140 a night ) is housed in a former New York Central style freight station and has rooms in real rail cars. The family-friendly DunesWalk Inn at the Furness Mansion ( from $125 a night—you can also rent the entire place out on Airbnb ) is another historic option that balances digs in an 1881 mansion with modern comfort, just a few minutes from the beach.


Distance from Chicago 75 miles

Harbor County MI

A view of Lake Michigan from the Water's Edge house

Didn’t score a Michigan beach house last summer? Winter isn’t hot, but it’s a gorgeous and secluded time to experience the dramatic Lake Michigan coast from the comfort of a luxury beach home, most of which can be had now at low season rates. Take your pick of towns on the state’s south coast like Union Pier, New Buffalo, and little-known Harbert. Sans summer crowds, this is the time to stop at the harborside Stray Dog Bar & Grill . Even better, book an igloo for outdoor dining at small-batch Beer Church Brewing , try alfresco wine tastings at Round Barn Estate , or get takeout from Red Arrow Roadhouse (try the buffalo cauliflower and nachos) and locally made whiskey from the Journeyman Distillery to bring back home. As everyone does, give into the pull of the lovely Lake Michigan coast, where dune walks and sledding at Warren Dunes State Park should be high on your list.

Bluefish Vacation Rentals (from $100 a night ) is your best option for a well-curated assortment of homes throughout Harbor Country, plus the bonus concierge-like guidance of the local husband-and-wife team who run it, Jason and Erika Milovich. In winter, most of their homes can be had at low season rates and don’t require summer’s usual full week stay. The scenery can’t be beat in Harbert at three-bedroom Water’s Edge , a splurge-worthy find tucked into a forested bluff overlooking a private stretch of Lake Michigan shoreline; spend $750 a night in winter verses the nearly double rate of $1,429 a night in summer. Walk the beach and watch glacier-like ice form with the waves, warm up in the hot tub, and light a bonfire under starry winter skies framed by trees. Other notable options include the three-bedroom Harbor Time , new five-bedroom Darby Cottage with its massive showroom-worthy open kitchen, and new four-bedroom Lake Life that puts spectacular lake views right in your lap.


Distance from Chicago 149 miles

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One of the Kohler Lake Cabins

One of the Kohler luxury Cabins

On a drive of just over two hours, cruise past Mars Cheese Castle in Kenosha (hit the brakes to load up on Wisconsin gold), and lakefront Milwaukee, on your way to Kohler. Popular in temperate months for its jaw-dropping golf courses, which regularly feature on the PGA Tour, Destination Kohler is a find in winter with fewer visitors, killer spa treatments at its Kohler Waters Spa, and invigorating outdoor adventures at its lesser-known River Wildlife preserve. Like Kohler’s golf courses, the 500-acre wilderness playground showcases the natural beauty of the landscape here. Try hikes and horseback rides through rolling trails, ice skating and curling at Winter Wonderland, guided trap shooting in a forest canyon, and brunch or hot toddies at River Wildlife Lodge, the preserve’s atmospheric log cabin outpost.

Options at the resort include classic hotel rooms at the 241-room American Club ( from $189 ), but four chic and splurge-worthy cabins (f rom $842 a night ) are the way to go, especially if you want privacy and space wrapped in some gorgeous nature. The two-bedroom Lake Cabin ( from $1009 a night )—one of two opened just last summer—positions you on a staggering bluff just above Lake Michigan. The beach is inaccessible from this rugged perch, but you won’t care with endless, ocean-like views from the back porch and firepit, and the sprawling evergreen forest at the front of the house that doubles as a wildlife crossing (watch for deer and wild turkeys). It’s all the more magical with a dusting of snow on the beach grass, a warm fire, and dinners inside your own beautiful kitchen—everything from tenderloin and ricotta gnocchi takeout from the new Taverne on Woodlake to whiskey pairings, curated Wisconsin cheese boards, and gourmet groceries delivered from Woodlake Market .

Distance from Chicago 164 miles

Historic town of Galena IL on the Mississippi River

Downtown Galena

With rolling forested landscapes, an historic downtown on the Mississippi River, and the best (one of the only!) ski mountain in Illinois, Galena is as charming as ever in winter. Even the two-hour-and-45-minute drive sets the mood as flat highways turn to one-lane roads that climb gentle hills and weave through farmlands and woods, eventually dropping you into this once-thriving river port town. Stroll the downtown’s Main Street for a superb array of local shops and studios; new options include Galena Book & Paper , the Galena Spoon Company for handcrafted spoons and carving classes, and Scent Workshop , where you can learn French perfuming techniques. There are loads of restaurants and boozy options here, too; go for especially good take-home dining and cocktail kits from French-meets-German Fritz and Frites , Miss Kitty’s Grape Escape , and the drive-thru Galena Brewing Co . Downhill skiers won’t want to miss Chestnut Mountain Resort, just 15 minutes from the downtown, with 19 runs that race to a halt at the bank of the Mississippi River.

It’s a-okay to vape in the new guest-only “potting shed” outside the pretty five-bedroom Aldrich House , Illinois’ only cannabis-friendly bed and breakfast ( from $145 a night ). For something upscale and romantic, it’s hard to do better than the luxury six-suite Jail Hill Inn , set in a former jailhouse at the end of Main Street and serving a three-course breakfast ( from $345 a night ). Families settle in nicely at the stylish, condo-like Ulysses Suites ( from $214 a night ), while south of downtown on 6,800 acres of Galena Territory, Eagle Ridge Resort & Spa offers a robust nordic activities program and everything from simple hotel rooms to full homes ( from $99 a night ).


Distance from Chicago 185 miles

The Bottleworks Hotel

The Bottleworks Hotel in Indianapolis' Bottleworks District

Every worthwhile weekend getaway from Chicago isn’t a charming small town or lakeside retreat. For those who want some city culture that isn’t their own, Indy’s Bottlework’s District is calling. Stop in Merrillville for proper road trip junk food—fresh Indiana-made gummy bears—at Alabanese Confectionery Group on the three-hour drive south to Indy. Once there, head to the new 12-acre, mixed-use neighborhood that spans the north side of Mass Ave in downtown Indianapolis and brims with local indie shops in historic industrial buildings. Explore the mix of offerings at Circle City Industrial Complex , a 500,000 square-foot warehouse opened in the old Schwitzer car manufacturing facility, where you should check out newly opened SoChatti dairy-free chocolate tasting room and a class at Indy Fused Glass. Other new places worth a visit are Good Neighbor for fresh duds and the Living Room movie theater. For dinner, head out of the district for romantic outdoor dining in the new fireside greenhouse huts at Public Greens , a modern, community-driven restaurant that shares its profits to feed nearly 2,000 of Indy’s less fortunate youth every week.

Opened in December in what was formerly the world’s largest Coca Cola bottling plant, the 139-room Bottleworks Hotel ( from $249 a night ) is the stylish new anchor for the Bottleworks District. The industrial, art-deco-inspired hotel occupies the top two floors of the historic building, showing off a white terra-cotta exterior and brass-patterned doors. High-style rooms have velvet couches, loft ceilings, and terrazzo-tiled floors. Adjacent to the hotel, find more dining options at Garage Food Hall , Indy’s first food hall opened this month in the factory’s former garages, with nearly two dozen vendors serving everything from lobster rolls and poke to Pakistani-Indian fare and Brazilian steak.


Distance from Chicago 346 miles

Boyne Mountain Resort

A look down Boyne Mountain

Make your winter ski trip happen at Boyne Mountain Resort , one of the most exciting ski mountains within a reasonable drive of Chicago—five and a half hours, plus a one-hour time change. Rising up from the northern part of Michigan’s lower peninsula, the mountain offers 500 feet of vertical with 60 downhill trails for a range of skiers and riders, though the biggest perk of a visit here is the abundance of high-quality outdoor adventures that go beyond skiing. Rent a new sno-go ski bike and shred downhill runs, fat-tire bike on forest trails, zipline 50 feet in the air across the mountain, cross country ski or snowshoe on dedicated trails, ice skate or snow tube, and even dine outdoors in one of five igloos serving at Forty Acres Tavern. If you have a little extra time you can also tack on the 40-minute drive north to Boyne Highlands , the mountain’s sister resort, for even more challenging ski terrain plus the new “Enchanted Trail,” an illuminated two-mile trail for nighttime winter walks and snowshoeing. NOTE: Like other ski resorts around the country, both mountains are limiting capacity during the pandemic and booking lift tickets and gear rental in advance is recommended.

Spread out in one of the fully-equipped three- and four-bedroom Mountain Cabins that are part of the resort (f rom $607 per night ). Each is set in the woods with a hot tub on the deck, fully equipped for cooking your own meals, and offers ski-in/ski-out access. Some of the cozy one- and two-bedroom condos at the Village at Disciples Ridge also offer ski-in/ski-out access ( from $488 per night ). Pro tip: the best way to guarantee access to the slopes this season along with your accommodations is to book a “ Ski & Stay Package ,” which bundles lodging and lift together and lets you ski both resorts.


Trump International Hotel & Tower Chicago

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19 Awesome Road Trips from Chicago (with Timings)

Keeping your introduction to road trips from Chicago short and simple, let’s take a look at the summer, winter and weekend favourites!

The city of Chicago is awesome and all, but it’s also a great starting point for some great Chicago road trips. The city’s prime location acts as a portal to the Midwest – from historical cities to sprawling state parks and urban-stress-relieving beer. 

chicago road trip

Best Chicago Road Trips in Summer

If you’re looking for one of the longest Chicago road trips, how about driving from Chicago to New Orleans ? If you’re thinking a little shorter, then read on…

Do you need a rental car for your road trip? Check out the award-winning comparison site Discover Cars for the BEST DEALS the world over. Book early for the best price!

Distance: as far as you can go

No American road trip is complete without covering some part of classic Road 66 – of which, lucky for us, kicks off in Chicago!

road trips from Chicago

Snap a selfie at the official sign between East Adams and South Michigan Avenue then check-off stops such as the Gemini Giant, the Pontiac murals, Lincoln Presidential Library and more. If you can spare a month, make it all the way down to the Pacific Ocean.

best road trips USA

2. Illinois’ Great River Road

Distance: 3.5-hour drive

In a seemingly never-ending chain of historical sites and activities, the drive along Mississippi River to East Dubuque is one of the best road trips from Chicago.

Chicago road trips

Moline and Rock Island are two cool detours but you can head straight for East Dubuque for its Chicago Great Western Railway Depot Museum. John Deere Pavilion lets you hop from car to farm machines, while the city Nauvoo shows off many historic homes. 

3. Lake Michigan to South Haven

Distance: 2.5-hour drive

Escape the heat by packing your car with beach gear and setting off for a nice drive around Lake Michigan and towards South Haven.

Road adventures Lake Michigan

There are plenty of berry farms along the way so you can stain your hands with blueberries; or maybe you prefer to climb up a lighthouse?

To take your road trip even further, bring a bike! Cruise along the water front; take a dip or two. 

Do you have a favourite road trip quote? Click for the best long drive quotes to inspir e your next adventure!

4. Shawnee National Forest

Distance: 6-hour drive

One of the longest Chicago road trips on the list, it’s more than worth it to visit Shawnee National Forest. In fact, plan to camp amidst the spectacular range of landscapes for one of the best driving trips from Chicago!

Chicago days out

Local favourites include the Garden of the Gods – you’ll find super special rock formations like Anvil Rock. Little Grand Canyon and Bell Smith Springs feature moderate hikes; Inspiration Point offers panoramic views over the prairie, Mississippi River and the forest.

Not convinced? Shawnee Hills Wine Trail is a brilliant drive that links up vineyards and wineries in the area – a great stop on a road trip from Chicago.

How about driving from Chicago to Atlanta? Here’s my guide to the best stops on a Chicago to Atlanta road trip , just for you.

Best Chicago road trips in Winter

If you want the best road trips from Chicago when it’s colder and darker, then these are the best ones for you.

5. Grand Rapids

Distance: 3-hour drive

After just long enough of a drive, pull into Grand Rapids for a nice sweep of activities. The Beer City Ale Trail will keep you road-tripping on foot (or car, if you have a Designated Driver); or wander through Downtown Market for food adventures instead.

Chicago road trips

Warmed by booze, drop by the 158-acre Frederik Meijer Gardens & Sculpture Park where their installations are bright pops of colour against an all-white backdrop. 

6. Muskegon

Speaking of unusual winter activities, I’ve heard so much about Muskegon Winter Sports Complex. Just an hour from Grand Rapids, it’s a great next stop on your Chicago road trip.

Chicago road trip adventures

Their Olympian-designed ice-luge course is perfect for beginners, spanning 850 feet of forested speed racing. Muskegon is also home to USS Silversides Submarine Museum if you’re into marine vehicles, and there’s a great pier and lighthouse too.

7. Indianapolis

When temperatures are cold, cold, cold – you might opt for staying indoors. The city of Indianapolis is one of the best road trips from Chicago during winter because of its incredible indoor entertainment: museums.

Chicago road trip

From the Indianapolis Museum of Art to the Indianapolis Children’s Museum to quirky Indiana Medical History Museum, you can escape the cold all day!

Of course, drop by famous City Market for great eats and then maybe go on a catacombs tour underground too. This makes for one of the best road trips from Chicago.

8. Boyne Mountain Resort

Distance: 5-hour drive

Michigan winters are best captured with the ski resort of Boyne. Drive past snowy landscapes to reach 850 acres of skiing, snowmobiling, dogsledding and photography escapades.

Boyne Mountain Chicago

While the forested grounds offer romantic snow-covered views, don’t miss out on the epic zip lines that take you through the trees and slopes. 

If you like your road trips from Chicago with a bit of snow and ski thrown in, then this is a great option for you.

Your ESTA for the USA

Before you go to the USA make sure you have your ESTA organised. You can find help with this on this link: . It doesn’t take long and organising it beforehand will make things go that bit smoother at the airport.

9. Apostle Islands

Distance: 7-hour drive

Does driving over ice count as going off-road?

chicago road trip

It’s an unforgettable journey to Apostle Islands National Lakeshore as winter ice freezes thickly to transform water into road, ending with stunning ice caves!

Make sure to visit the only inhabited Madeline Island as well for a cool wind sled experience and hot tub stay. 

Day Road Trips from Chicago

10. lake geneva.

Distance: 1.5-hour drive

Chicago’s number one when it comes to day trips, Lake Geneva is one of the best lake town’s in the US.

Road trips from Chicago

Downtown boasts all the food and drinks you need for the inevitable food baby; you might even land a booze cruise.

Hot air balloon rides, Lake Shore Path, ziplines and even ski slopes make it a year-round place to visit. It’s a multi-visit destination for sure!

11. Harbor Country

Distance: 1-hour drive

Wind between the towns of Michiana, Grand Beach, Three Oaks, New Buffalo, Lakeside, Union Pier, Harbert and Sawyer. This Chicago road trip will have you hopping between wineries and breweries, not to mention the beach.

Road trips through chicago

It’s so close to the city, but the sand dunes and soft grasses make it a wholly different world. 

12. Starved Rock State Park

Distance: 2-hour drive

Families and romantics will love Starved Rock State Park for reasons that include: 13 miles of hiking, 18 canyons, free entry and nature-surround lodge.

It’s a great location to unplug for a day as you hunt down natural rock pools, waterfalls and incredible moss-strewn glades. You can even visit in the winter for cross-country skiing and cuddles in front of expansive mountain views. 

13. Saugatuck 

Making up Lake Michigan’s “art coast of Michigan”, Saugatuck and its neighbours (Fennville and Douglas) are house dozens of art galleries!

weekend trips from chicago by car

Unique and LGBTQ+-friendly shops feature alongside artsy hubs to make it a super welcoming town. Of course, famous Oval Beach appeals with soft dunes and paddleboat rides too. From craft booze tours to fruit picking and corn mazes, it’s one of Chicago’s best road trips.

14. Elkhart Lake

I won’t spoil it for you but this 292-acre lake and nearby Kettle Moraine State Forest is truly a place to unwind from the crowds.

Road trip in Chicago

You can hike the epic Ice Age National Scenic Trail or bike down Old Plank Road Trail. Pumpkin patches, race-tracking and fishing are all inclusive!

Want a charming hideaway? This is it.

Road Trips 4 hours from Chicago

Want your road trips from Chicago for a special weekend? Then these Chicago road trips are only 4 hours away.

15. Ann Arbor

If you’re looking for an all-season destination, Ann Arbor is the perfect road trip from Chicago.

driving from chicago

Huron River entertains with kayaking, paddle-boarding, tubing and swimming; Matthaei Botanical Gardens and Nichols Arboretum displaying beautiful foliage. Definitely spare some time for Kerrytown Market and Shops for all their indie offerings! 

16. Door Country

Also called ‘Cape Cod of the Midwest’, Door Country is a 70-miles-long basket of fun!

You’ll never get tired of exploring its orchards, coves, lighthouses and wineries. Away from the light pollution, Newport State Park offers stunning starlit skies while Ephraim is all the small-town charm you need. Just imagine – 300 miles of coastline.

You can reach Galena under 4 hours but I recommend taking your time. Pull up through scenic rolling hills to go back in time because the Galena Historic District is made up of cobblestone streets and over 1,000 buildings from the 19 th century.

Day trips from Chicago

For those non-history buffs, Chestnut Mountain opens as a ski resort in the winter; Stagecoach Trail and Apple River Canyon State Park are open year-round. 

18. Richland County

To really escape from people, Richland County is a rural road trip destination where you can bunk for the night. But away from the isolated and lush property of Candlewood Cabins are fields and hills that keep you outdoors all day.

The Ridge Road and Pine River Recreation Trail fulfils all your adventurous needs – where else would you find wildlife while biking over abandoned railroads?

You also have three rivers and five state parks within an hour’s distance, and the lovely 100-mile Lower Wisconsin River Scenic Byway for more driving way. 

19. Huron-Manistee National Forest

Michigan really surprises us again and again!

Huron-Manistee National Forest

Along the peninsula is the expansive Huron-Manistee National Forest, one of the best road trips from Chicago if you are a nature enthusiast. A single paved road takes you through dense forest (beautiful in the fall) to parking areas so you can hike your way through the serene space or canoe on the rivers. 

Road trips from Chicago

Of course there are loads of great things to do in Chicago but visiting Chicago really opens up a world of opportunities when it comes to road trips.

VickyFlipFlop up the Skydeck

Whether you’re taking the car out for an hour-long spin or you’re willing to buckle down for a few hours, you won’t be disappointed by the scenery along your journey or the fantastic destinations ahead. 

Related Posts:

  • 7 Ways to Make the Most of Your Road Trip Budget
  • 57 Coolest Things to Do in Chicago for 2023
  • Planning a Road Trip in the USA: 13 Best Routes!
  • Christmas Things to Do in Chicago in Winter: 21+…
  • 11 Unique Stops on the Drive from Chicago to Atlanta
  • 14 Awesome Stops on a Chicago to New Orleans Road Trip

Hi, I'm Vicky! I wrote this. I love a bit of adventure, will try anything once, and have a strong passion for the local food and drink, whatever it may be. I'm here to help inspire you to travel to places a little out of your comfort zone, or at least to explore the usual destinations in a different way. Stay, have a look around, and if you have any questions – let me know below.

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5 drives from Chicago every traveler will love

Bridge over Chicago River, Chicago, Illinois, United States

Editor's note: The team at The Points Guy loves to travel, but now is not the time for unnecessary trips. Health officials note that the fastest way to return to normalcy is to stop coming in contact with others. That includes ceasing travel. We are publishing travel guides because we should all use this time to think about and plan our next adventures. TPG doesn't advise booking trips for travel until the late spring or early summer -- and even then be mindful of cancellation policies.

Chicago, Illinois is one of the nation's most exciting cities, with a food scene that many say is the best in the country, an ideal location on Lake Michigan, an urban fabric that provides residents and visitors alike with a real big-city experience, rich traditions in sports and music, and much, much more.

One of Chicago's greatest assets is its geography: Much of the Midwest is accessible by car, and if you don't have a lot of time to spare, some of the region's most incredible places are within a couple hours' drive.

Adventure-seekers can fly down a 335-foot-long waterslide, careen through creeks on an ATV tour and soar with the birds on a hot air balloon ride. For people who travel to relax and rewind, there's a private cabin on 350 acres in northern Wisconsin. Active travelers will find plenty of cycling paths and hiking trails, including ones that navigate a series of sandstone canyons in an Illinois state park. History buffs can delight in seeing the former home of President Ulysses S. Grant, still decorated with its original furnishings, in small-town Illinois.

No matter what kind of traveler you consider yourself or where you go on a long weekend getaway from Chicago, you can find excellent food and drinks, be it the cheese curds in Wisconsin or taproom fare on a crawl of southwest Michigan's breweries, distilleries and wineries.

Best of all, this is all within 200 miles of the city; perfect for a long weekend or even a mid-week jaunt.

For more TPG news delivered each morning to your inbox, sign up for our daily newsletter .

Kohler, Wisconsin 

Kohler, Wisconsin. (Photo by gurineb/Getty Images)

Distance from Chicago: About 150 miles (~2.5-hour drive)

Please note that restaurants, bars and more are closed in Wisconsin until at least May 26, 2020, in accordance with the state's stay-at-home order due to the coronavirus pandemic .

The family behind the Kohler Kitchen + Bath company — the name you see on penthouse-worthy showers, soaking tubs and bathroom and kitchen faucets — runs a resort called Destination Kohler , where accommodations feature some of the most beautiful bathrooms you've ever seen. If you do muster up the willpower to leave your personal rain shower, a charming campus of indoor and outdoor activities awaits, highlighted by a quartet of championship golf courses and a spa offering hydrotherapy treatments.

What to do: Book a waterfall massage or acoustic bath at Kohler Waters Spa; hike and trap shoot at River Wildlife, a 500-acre wilderness preserve; and browse clothing stores and more at the Shops at Woodlake, an outdoor mall that's a short walk from the spa. Golf courses include Whistling Straits, home to the upcoming 2020 Ryder Cup in late September. Bold Cycle, which opened in May, is a 3,000-square-foot cycling studio with 35 sleek Stages bikes. Also new: the Journey package, which pairs you with a "wellness concierge" who will help you plan your itinerary around themes like unplugging from tech, mindfulness and meditation, or healthy diet and exercise. Of course, you can't miss out on exploring the Kohler Design Center , a showroom of model kitchens and bathrooms where showers change colors and bathtubs mimic infinity pools.

Where to stay: Rated a five-diamond property by AAA, The American Club — an ivy-clad brick building that feels more like a private mansion than a hotel — is the crown jewel of the property. There's also the Carriage House , which has the perk of being attached to the spa (head from your room to breakfast to your massage without taking off your robe and slippers), and the Inn on Woodlake , recently expanded to add more multi-bedroom suites for families and groups of friends.

What to eat and drink: The Horse & Plow, the casual restaurant and bar at The American Club, has some of the best food on property, including a strong contender for the best cheese curds in all of Wisconsin. Try braised elk at Blackwolf Run Restaurant, which has a wine list that has been honored by Wine Spectator every year since 2002 — and a terrace overlooking the 18th-hole greens of Blackwolf, a Pete Dye-designed golf course. For lunch, Craverie Chocolatier Cafe is the spot for salads, sandwiches and gleaming glass cases lined with chocolate truffles, terrapins and toffee bark, made on-property by a resident chocolatier.

Starved Rock State Park, Illinois 

Starved Rock State Park Illinois. (Photo by Matthew Crowley Photography/Getty Images)

Distance from Chicago: About 100 miles (~1.5-hour drive)

Please note that Starved Rock State Park is currently closed until at least May 30, 2020, in accordance with Illinois' stay-at-home order due to the coronavirus pandemic.

The tall bluffs at Starved Rock are a stunning sight in a relatively flat state and a destination for hikers looking for terrain to scale. The park's topography was formed thousands of years ago when melting glaciers eroded everything in the area except the resistant St. Peter sandstone. Today, steep sandstone walls create a series of 18 canyons that, after heavy rainfall, act as natural waterfalls.

What to do: Hike! There are 13 miles of trails to explore, appropriate for all skill levels, with 14 potential waterfall sites among the 18 canyons. Grab a map from the Starved Rock Visitor Center or take a free guided hike, departing from the Lodge lobby every Thursday at 9 a.m. A new riverboat, The Eagle 1 , offers tours down the Illinois River on Mondays, Wednesdays and Fridays for $45 per person. In the winter, hike in search of icefalls, created when the waterfalls freeze into ice formations along the canyon walls. Animal lovers can drive 15 minutes to Cedar Creek Ranch for guided horseback rides through nearby trails, a petting zoo and ATV tours.

Where to stay: Starved Rock Lodge , the only hotel in the park, has a main building with 69 rooms, but more fun is renting one of the lodge's five Pioneer Cabins, tucked in the woods (but still, for better or worse, a short walk to civilization). If you want the true outdoor experience, try pitching a tent in one of Starved Rock's 33 campsites , outfitted with electricity and near a bathhouse with toilets and showers. (Most sites have a 30-amp camper hookup; a limited number have a 50-amp travel-trailer hookup.)

What to eat and drink: Located at Starved Rock Lodge, Back Door Lounge has a patio known as the Veranda. Settle in with the gorgonzola nachos or a pepperoni flatbread, or make time for special Oktoberfest dinners in late October. In the nearby town of Ottawa, Hank's Farm Restaurant, open since 1941, is a converted dairy barn where fried chicken and baby back ribs share the menu with spaghetti, ravioli and chicken parmesan.

Southwest Michigan  

The Round Barn Winery Distillery and Brewery. (Photo by Jeffrey Greenberg/Universal Images Group/Getty Images)

Distance from Chicago: About 85 miles (~two-hour drive)

Please note that restaurants and bars are closed in Michigan until at least May 29, 2020, in accordance with the state's stay-at-home order due to the coronavirus pandemic.

Live in Chicago long enough and you will get invited to a bachelorette party planned around the pocket of wineries in the southwest corner of Michigan. Less talked about, but arguably better, are the area's breweries and distilleries. There are a handful of towns you can stay in to accomplish this tour de drink , some tucked flush against Lake Michigan and others slightly inward.

What to do: Make this a 21-and-up trip, and here's your holy trinity: Journeyman Distillery , purveyor of nine varieties of whiskey; Round Barn , which does wine, beer and spirits in a circular white barn built in 1912; and Tapistry Brewing , with a sunny beer garden and 20 taps pouring everything from a rye pale ale to limited-release double IPA Heart Full of Napalm. Of course, once there, you have to walk across the street to Transient Artisan Ales to some of its unique brews. (You'll need a designated driver, or you can rely on Uber .) Save one day for a bike adventure on a network of paved bike paths called Backroads Bikeways , which takes cyclists through up to 60 miles of gorgeous nature.

Where to stay: Neighboring resort Marina Grand in New Buffalo, Michigan is a 15-minute drive from Journeyman. The Inn at Harbor Shores in St. Joseph, Michigan is further north — a 20-minute drive from the breweries— but the spa, golf course, kayak rentals and sand volleyball make it a solid spot to spend a few nights. This is also an excellent area to find a vacation home rental .

What to eat and drink: Fuel up at any of your drink stops: Journeyman has a restaurant called Staymaker , home to dishes that incorporate its spirits (a charcuterie board with bourbon mustard, Detroit-style pizza with crust made from the whiskey grain mash bill used in the Last Feather Rye); Round Barn has Public House at its actual brewery, just three miles from the tasting barn; and Tapistry has a menu of sandwiches and apps, including smoked cheddar beer cheese served with pita bread.

Wisconsin Dells, Wisconsin

Hawk's Bill rock formation in Wisconsin Dells. (Photo by Rebecca Nelson/Getty Images)

Distance from Chicago: About 200 miles (~3.5-hour drive)

Please note that restaurants, bars and more are closed in Wisconsin until at least May 26, 2020, in accordance with the state's stay-at-home order due to the coronavirus pandemic.

The Dells is famous for Noah's Ark , a 70-acre waterpark that earns the title of largest in America, but the family-focused vacation town also offers a main drag filled with restaurants, shopping and mini-golf; with camping, ropes courses, spas and wineries within a 15-minute drive.

What to do: Still new among more than 50 rides and slides at Noah's Ark is a king cobra-shaped waterslide called Raja with a daunting 335 feet of track that takes you up to 32 miles per hour, ending in a 37-foot drop. Towel off and explore the rest of the Dells, including the year-old Bigfoot Ropes Course and new VR Universe, an arcade of virtual-reality games. Old standby attractions include the Haunted Mansion haunted house, Tommy Bartlett Show of boat and water-ski stunts and Capone's old-time portrait studio in Downtown Dells .

Where to stay: The adults-only Sundara Inn & Spa got a recent expansion that included a rooftop greenhouse, glass-walled meditation room and miles of hiking trails. For kids, Kalahari is a family favorite thanks to its two waterparks — one indoor, one outdoor — and indoor theme park boasting a Ferris wheel, carousel, climbing wall, go-karts, laser tag and mini-golf.

What to eat and drink: The sugar-sprinkled doughnuts and Friday fish fry at Paul Bunyan's Cook Shanty in Downtown Dells, a log-cabin restaurant guarded by a towering lumberjack statue, is a tradition for many families, but there's plenty of new food and drink to try in the Dells, too. Mid-April through October, head to the outdoor patio at Prairie Hawk Winery , a family-owned business that makes chardonnay, riesling and rosé with imported grapes, plus hard cider with local apples. Drinkers also won't want to miss Wollersheim Winery & Distillery. Boats can dock right at Summer House Grill & Bar , a restaurant on Lake Delton with a focus on local ingredients. And for a proper Wisconsin supper club experience, prime rib and brandy old-fashioned included, visit Ishnala Supper Club , which recently added a new bar and lounge area on its lower floor.

Galena, Illinois 

Downtown Galena, Illinois. (Photo by PickStock/Getty Images)

Distance from Chicago: About 165 miles (~three-hour drive)

Please note that bars, restaurants and more are currently closed in Illinois until at least May 30, 2020, in accordance with the state's stay-at-home order due to the coronavirus pandemic.

In the 1830s, Galena was the picture of small-town America, home to a vital trading post on the Fevre River and a thriving Main Street alive with carriages and foot traffic. Today, with its well-preserved 19th-century buildings, the town is a destination for history buffs and architecture fans — but with new restaurants, spas and B&Bs peppering the area, a trip here is definitely not just about the past.

What to do: Start at the Galena & U.S. Grant Museum, located in an 1858 mansion, to learn the history of the town, former home to 18th U.S. President Ulysses S. Grant. Grant's home, with its original furnishings, is also open to tour. Head from there to Dowling House, Galena's oldest home, built in 1826. The Haunted Galena Tour Company has an aptly named Spirits & Spirits Tour, a 90-minute, three-drink ghost tour which takes you through a haunted brewery, restaurant and hotel. Other attractions include Galena Jeep Rentals and, in nearby Stockton, the Valley of Eden Bird Sanctuary , which spans 409 acres with more than six miles of trails. Also nearby, pick apples from more than 5,500 dwarf trees at Terrapin Orchards, which opens for the season on Sept. 8.

Where to stay: The DeSoto House Hotel is Illinois' oldest operating hotel, with 55 Victorian-style guest rooms. At Aldrich Guest House , a popular bed and breakfast, innkeepers Robert and Douglas Mahan make next-level breakfast dishes, in addition to hors d'oeuvres for a daily wine hour. If you're looking to go all-out, Eagle Ridge Resort & Spa offers free-standing villas that offer privacy with access to all of the resort activities, including boating, fishing, ziplining, horseback riding and hot air ballooning.

What to eat and drink: Pudgy's on Main Street offers Chicago-style hot dogs and loaded cheese fries, while Galena classics include the steakhouse Log Cabin and Italian restaurant Vinny Vannuchi's , both also on Main Street. Drive 20 minutes to the shores of the Mississippi River to find the new Millennium Bar & Marina in East Dubuque, offering waterfront seafood boils, burgers and dangerous-looking rum buckets.

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  • Getaways From Chicago

10 Best Weekend Getaways From Chicago

Waterfalls, wildlife, and lots of small-town charm await.

Elizabeth Rhodes is a special projects editor at Travel + Leisure , covering everything from luxury hotels to theme parks to must-pack travel products. Originally from South Carolina, Elizabeth moved to New York City from London, where she started her career as a travel blogger and writer.

weekend trips from chicago by car

With fascinating architecture, great museums, and plenty of delicious local eateries (deep dish pizza, anyone?), Chicago has a lot to offer tourists and residents alike. That said, we could all use an escape from the hustle and bustle of the Windy City every so often, so we've rounded up the best weekend getaways from Chicago. Whether you're looking for beautiful landscapes or small-town charm, these quick trips are sure to please every type of traveler.

Here are our top 10 weekend getaways from Chicago.

Starved Rock State Park, Illinois

Wander through towering trees to find waterfalls and wildlife at Starved Rock State Park . This park, located on the Illinois River, is situated about an hour and a half from Chicago, making it the perfect choice when you want to trade skyscrapers for the great outdoors for the weekend. In the spring, the waterfalls are especially active, thanks to heavy rains, and in the fall, the leaves turn beautiful shades of orange, red, and yellow. Stay within the state park at the Starved Rock Lodge , or opt to spend the night in nearby Ottawa, a charming little town with restaurants, shops, and more.

Indianapolis, Indiana

Just a three-hour drive from Chicago, Indianapolis, affectionately referred to as "Indy" by locals, offers plenty to do. Kids will love the Children's Museum of Indianapolis and the Indianapolis Zoo , while sports fans will want to check out the iconic Indianapolis Motor Speedway . The Broad Ripple neighborhood has nightlife, dining, shopping, and more, and the Massachusetts Avenue Arts District offers theaters, galleries, and independent boutiques. History lovers should book a stay in one of the 1920s Pullman train car rooms at the Crowne Plaza Indianapolis Downtown-Union Station .

Saugatuck, Michigan

Summer is the perfect time to visit this lakeside town, located just under two and a half hours from Chicago. Lounge on the sandy shores of Oval Beach or Saugatuck Dunes State Park , rent a boat and explore the lake, browse the art galleries, or check out the local breweries. After a day enjoying Lake Michigan's most pristine beaches, rest your head at one of the adorable inns or bed-and-breakfasts in town.

Lake Geneva, Wisconsin

For another nearby waterfront escape, head to beautiful Lake Geneva , located just an hour and a half from Chicago. During the summer, you can get out on the lake, sunbathe on its beaches, or go zip lining, along with other outdoor activities. During the winter, check out the Ice Castles , an awe-inspiring display of icicles.

Milwaukee, Wisconsin

An hour and a half north of Chicago on Lake Michigan, you'll find Milwaukee, a city teeming with great museums and better beer. Milwaukee has played a major role in U.S. beer production, with Pabst Brewing Company and Miller Brewing Company calling this city home. Today, you can toast to the city's beer heritage by trying these classics or visiting one of the many local craft breweries. The Milwaukee Public Museum is a must-visit — it's home to fossils, a European village, a full-size display recreating the streets of Milwaukee in the late 19th and early 20th centuries, a butterfly garden, and more. Other sites worth visiting include the Milwaukee Art Museum , the Harley-Davidson Museum , and the Mitchell Park Horticultural Conservatory, also known as The Domes .

Indiana Dunes National Park, Indiana

Just under an hour from Chicago, Indiana Dunes National Park makes the perfect quick weekend getaway from Chicago. You can even squeeze it in for a day trip if you're short on time (it's accessible from the South Shore Line, so you don't even have to drive). This national park covers 15 miles of Lake Michigan's shoreline, making it ideal for a relaxing weekend away from the city. Go for a hike along the dunes, fly a kite on the beach, enjoy horseback riding, or check out the historic 1933 World's Fair Century of Progress Homes .

Madison, Wisconsin

Wisconsin's capital city is just over two and a half hours from Chicago, and it offers something for every type of traveler. Food-loving folks will want to visit the National Mustard Museum and try fresh ice cream at the Sassy Cow Creamery, located 20 miles from Madison. Meanwhile, outdoorsy types will love kayaking or taking a cruise around the lake during the summer and snowshoeing in the winter. Families will want to check out the Madison Children's Museum and the Children's Theater of Madison for kid-friendly entertainment.

Holland, Michigan

Holland, Michigan is a unique weekend getaway destination, located under three hours from Chicago. Taking its name from the region of the Netherlands, the city's Dutch heritage is evident in its famous attractions like the Windmill Island Gardens , De Klomp Wooden Shoe and Delft Factory , and Nelis' Dutch Village . The yearly Tulip Time Festival is another great reason to visit Holland — millions of tulips are planted across Holland, so visit in spring to see the beautiful flowers in bloom.

Wisconsin Dells, Wisconsin

For a family-friendly getaway, opt for a weekend trip to Wisconsin Dells , located about a three-hour drive from Chicago. This area, known as the "water park capital of the world," is packed with attractions kids will love, like Noah's Ark Water Park , the largest water park in the United States. To relax, take a scenic boat ride through the Dells or visit one of the local wineries and breweries.

Geneva, Illinois

Just an hour outside of Chicago, you'll find Geneva, Illinois , a destination perfect for people looking for a small-town getaway. Wander the city, check out the murals and outdoor sculptures, take a stroll through the Fabyan Forest Preserve , and browse local, independent shops selling coffee, tea, chocolate, gelato, ice cream, popcorn, baked goods, and more.

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  • Last Updated On
  • September 5, 2023

35 Best Weekend Getaways From Chicago — Quick Trips!

Cole Evans

There’s no better way to discover the heart of America than through Chicago.

It’s the third largest city in the country, where its skyline meets the shoreline.

And your best weekend getaways from Chicago start the moment you arrive.

Its modern architecture, museums, vibrant music scenes, clubs, and outdoor activities are just some of the many things you can see and do here.

But in a city this vast, you may think and ask what to do and where to stay.

It is a question relatable to many.

As a traveler with years of experience, I visited Chicago and explored its beauty.

I stayed in some of the best properties and toured the city.

And to help you out, I compiled and ranked those places based on different and practical criteria.

Are you keen on knowing more?

Then check out my review with tips below.

Best Weekend Getaways From Chicago Compared

For your best weekend getaway in Windy City, review my guide below.

Editor’s Choice

weekend trips from chicago by car

Four Seasons Chicago

Four Seasons Chicago is the best place where you can marvel at the beauty of the city’s skyline.

  • Room Variety: 5/5
  • Comfort and Cleanliness: 5/5 
  • Location: 5/5
  • Affordability: 3/5
  • Family-Friendliness: 4/5

#2nd Best Choice

weekend trips from chicago by car

Waldorf Astoria Chicago

If you want exclusivity in your stay in Chicago, choose Waldorf Astoria. It has 215 elegant guest rooms inclusive of oversize bathrooms with tubs.

  • Room Variety: 4.5/5
  • Comfort and Cleanliness: 5/5
  • Family-Friendliness: 

#3rd Best Choice

weekend trips from chicago by car

The Peninsula Chicago

It is a five-star hotel that will surely level up your stay in the city.

  • Affordability: 2.5/5
  • Family-Friendliness: 5/5

Here are the top 35 weekend getaways in Chicago.

1. Four Seasons Chicago (Editor’s Choice)

Four Seasons Chicago

120 E Delaware Chicago, IL 60611 (312) 280-8800 Visit Website Social Media Open in Google Maps

Ratings Criteria

  • Beautiful city view
  • Ideal for business or family trip
  • Not so spacious lobby area

Chicago is the home to some of the world’s earliest skyscrapers.

And it is still renowned for its inspiring architectural design.

But it doesn’t stop there.

A luxurious stay here is guaranteed with exceptional service, facilities, and amenities.

Its lobby and lounge are designed ideally for entertainment and socializing.

And its restaurant and bar offer nothing but the perfect taste of Chicago. 

What’s more notable is its perfect location where you can revel in food, drinks, art, and music in the city center.

2. Waldorf Astoria Chicago

Waldorf Astoria Chicago

11 E Walton St Chicago, IL 60611 (312) 646-1300 Visit Website Social Media Open in Google Maps

  • Complete amenities
  • Spacious rooms
  • Quite expensive

If you want exclusivity in your stay in Chicago, choose Waldorf Astoria.

It has 215 elegant guest rooms inclusive of oversize bathrooms with tubs.

Its suites are furnished with terraces where you’ll see the allure of the city’s skyscrapers right before your eyes.

Surrounded by the city’s highlights, you won’t miss a thing.

Go-to spots, shops, restaurants, and bars are just a breeze away.

And after a long day of being a tourist in Chicago, its spa and indoor lap pool is just waiting for you.

Or better yet, stay in your room or sit on the terrace and appreciate the glowing Chicago at night.

3. The Peninsula Chicago

The Peninsula Chicago

108 E Superior St Chicago, IL 60611 (312) 337-2888 Visit Website Social Media Open in Google Maps

  • Unsurpassed service
  • Nice location
  • Too expensive for what it offers

Whether it’s a weekday or weekend getaway you’re in, The Peninsula Chicago is just a step away.

Each part of it is designed for your perfect Chicago getaway.

Everything is incomparable, from its sophisticated rooms and suites to its fancy restaurant and rooftop spa.

Do you intend to stay longer?

Think about it as your third night is on them when you book at least three consecutive nights.

That’s a pretty reasonable offer, quite hard to resist.

Moreover, almost every must-visit spot is just a walk away from this property.

4. Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

7036 Grand Geneva Way Lake Geneva, WI 53147 (262) 248-8811 Visit Website Social Media Open in Google Maps

With its luxurious facilities, this 1,300 acres of AAA Four-Diamond resort is an excellent alternative to Waldorf Astoria Chicago and The Peninsula Chicago.

This resort encompasses 1,300 acres of countryside in Wisconsin.

It features two lodging options: The Grand Geneva and the Timber Ridge.

By car, Grand Geneva Resort & Spa is 1 hour and 27 minutes away from Chicago.

Enjoy an incredible getaway with the family in this popular resort.

The kids will enjoy the resort’s health and fitness facility, with its programs crafted especially for them.

They can participate in many kid-friendly activities in the adventure center, too.

If they prefer outdoor activities, they can go horseback riding or meet the animals in the zoo instead.

As for the adults, how does a spa treatment sound?

If you opt for physical activities, you can play water sports in Timber Ridge’s park or go wall climbing in the gym.

5. Milwaukee


Milwaukee, WI (414) 286-2489 Visit Website Social Media Open in Google Maps

This city in Wisconsin encompasses over 61,000 acres of land on Lake Michigan’s western shore.

It features breweries, museums, and event venues.

If you’re coming from Chicago, you can reach Milwaukee in 1 hour and 27 minutes.

Here’s one cool overnight trip you won’t forget.

Milwaukee has everything you need for the best weekend adventure.

Want some history?

Check out the Milwaukee Public Museum, with its beautiful recreation of the city at the turn of the 20th century.

If you’re more into nature, the Mitchell Park Horticultural Conservatory is the perfect destination.

It features three domes that each function as a greenhouse and botanical garden.

Enjoy the blushing peonies and firs for the complete nature experience.

Recommended Hotel: The Pfister Hotel

Related: Fun Day Trips From Milwaukee

Related: Hotels in Chicago

6. Indiana Dunes National Park

Indiana Dunes National Park

1215 North State Road 49 Porter, IN 46304 (219) 395-1882 Visit Website Social Media Open in Google Maps

This park stretches for 15,349 acres in northwestern Indiana.

It’s home to a visitor center, park trails, and historical structures.

The travel time from Chicago to Indiana Dunes National Park is 42 minutes.

Are you looking for short trips from Chicago for your weekend getaway with friends?

Head to the Indiana Dunes National Park.

Hike the Dunes Succession Trail, with its vast array of paths perfect for adventurers.

Wear comfortable shoes because you’ll have to walk sandy and wooden trails at the same time.

If you’re up for a challenge, climb 192 feet to the top of Mount Tom.

You’ll get rewarded with stunning views of the dunes and the lake.

Recommended Hotel: Spring House Inn


Madison, WI (608) 255-2537 Visit Website Social Media Open in Google Maps

Madison is the capital city of Wisconsin.

It’s on an isthmus surrounding Mendota, Monona, Waubesa, and Kegonsa lakes.

It’s also home to botanical gardens and architectural gems like the Wisconsin State Capitol.

You can reach Madison from Chicago in 2 hours and 18 minutes if you use a vehicle.

Madison is one of the best places near Chicago for vacation.

Visit any of the city’s nine national historical landmarks, including Jacobs I, a single-family home constructed in 1937.

Not much of a history buff?

Marvel at Jacobs I’s architecture instead.

The home built by architect Frank Lloyd Wright has been touted as the first Usonian home.

The Wisconsin State Capitol is a must-see, too, with its majestic dome and elegant gilded bronze statue on top.

Recommended Hotel: The Madison Concourse Hotel


Holland, MI (616) 355-1370 Visit Website Social Media Open in Google Maps

Spanning over 11,000 acres, Holland is the largest city in Ottawa and Allegan counties.

It’s a popular tourist destination for its rich Dutch heritage.

From Chicago, Holland is only 2 hours and 33 minutes away by car.

If you’re looking to have the perfect weekend getaway, Chicago and its nearby areas offer many options.

Chicago has beautiful parks and skyscrapers.

Meanwhile, Holland has deep Dutch roots evident in many of its landmarks.

In the Windmill Island Gardens, you’ll find the last working mill allowed to leave The Netherlands in 1964.

Check out Nelis’ Dutch Village, too.

The amusement park is home to a gorgeous reproduction of an 1800s Dutch village.

Recommended Hotel: CityFlatsHotel Holland, Tapestry Collection by Hilton

9. Wisconsin Dells

Wisconsin Dells

Wisconsin Dells, WI (608) 254-4636 Visit Website Social Media Open in Google Maps

Nestled on the Wisconsin River, this city stretches over 5,200 acres in Adams, Columbia, Juneau, and Sauk counties.

It features a wide array of water parks and nature spots.

You can reach Wisconsin Dells in 2 hours and 56 minutes if you’re driving a car from Chicago.

You and the kids will agree this is one of the best getaways in Chicago and nearby.

After all, who doesn’t like swimming in beautiful blue waters and going down long slides?

If you get tired of swimming in water parks, go on a duck boat tour instead.

Marvel at the beautiful creatures while floating on Lake Delton under the blue Wisconsin skies.

Recommended Hotel: Hilton Garden Inn Wisconsin Dells

Related: Restaurants in Wisconsin Dells, Wisconsin

Related: Weekend Vacations in Illinois


Geneva, IL (630) 232-7494 Visit Website Social Media Open in Google Maps

Geneva is in Kane County, located on the western side of Chicago.

It features an extensive bike trail system and historical sites, some dating back to the 1800s.

It’s a 49-minute drive from Chicago to Geneva.

Geneva is just the place to be if you want to bond with your significant other.

The city is one of the best romantic getaways from Chicago for its natural beauty.

Take a stroll in the beautiful Fabyan Forest Preserve.

Amid the lush greenery stands the majestic Fabyan Windmill, built between 1850 and 1860.

Check out the Fabyan Japanese Garden, too.

It’s a lovely oasis with a small pond and flora that stand out.

Recommended Hotel: Comfort Inn & Suites Geneva- West Chicago

11. Fox River Valley

Fox River Valley

Fox Valley Aurora, IL 60504 (630) 256-4636 Visit Website Social Media Open in Google Maps

Also known as the Fox Valley, this region extends from Antioch in northern Illinois to Ottawa in the south.

It’s home to the Fox River Trail, green spaces, and water bodies.

The travel time from Chicago to the Fox River Valley is 42 minutes.

This place will make any traveler’s list of inexpensive weekend getaways near Chicago.

The Fox River Valley, after all, is pure nature anyone can explore.

Bike a portion of the 32-mile Fox River trail for stunning views of Carpenters Dam and Tyler Creek.

You can rent a kayak if you prefer a water adventure.

Soak in the gorgeous nature views while gliding along the Fox River.

Recommended Hotel: Best Western Oswego Hotel

12. Harbor Country

Harbor Country

Three Oaks, MI (269) 469-5409 Visit Website Social Media Open in Google Maps

This region consists of eight towns in southwest Michigan: New Buffalo, Three Oaks, Lakeside, Harbert, Michiana, Grand Beach, Sawyer, and Union Pier.

It features gorgeous beaches and wineries.

You can get to Harbor Country from Chicago in 1 hour and 12 minutes.

Harbor Country differs from many Chicago weekend getaways.

Unlike your cheap Chicago vacations, this one entails a bit of shelling out money.

After all, Harbor Country is an upscale weekend getaway destination.

Think of it as the Hamptons of New York or the Cape Cod of Boston.

But even if you’d need to shell out a bit, it’s worth it.

You can enjoy the region’s beaches with delicious wine.

Then spend the night in a luxurious bed and breakfast with amenities.

Recommended Hotel: Fairfield Inn and Suites New Buffalo

13. St. Joseph

St. Joseph

St. Joseph, MI (269) 983-5541 Visit Website Open in Google Maps

This city stretches for over 3,000 acres on the shores of Lake Michigan.

It’s home to the sandy Silver Beach and parks.

You can get to St. Joseph in 1 hour and 35 minutes if you’re coming from Chicago.

If you prefer cheap vacations from Chicago, head to St. Joseph.

The city is a nature oasis you can enjoy anytime.

Have a picnic on the Silver Beach shore and enjoy the beautiful landscape.

If you prefer a more strenuous activity, go swimming in the gorgeous blue waters.

Are you a fitness enthusiast?

Go on a hike for your dose of exercise in Tiscornia Park.

Recommended Hotel: The Inn at Harbor Shores

14. South Haven

South Haven

South Haven, MI (269) 637-0700 Visit Website Social Media Open in Google Maps

This city encompasses 2,240 acres of land in Van Buren and Allegan counties.

It features a gorgeous harbor and beaches.

If you’re driving from Chicago, you can reach South Haven in 2 hours and 2 minutes.

Commune with nature in this popular tourist destination.

The city’s seven public beaches aren’t just the perfect spots for swimming.

They make for beautiful pictures, too, with their gorgeous sea waters and shores.

If you get tired of the beach, check out the beautiful South Haven harbor.

Enjoy the stunning water views, then walk downtown for the perfect meal.

Recommended Hotel: Hampton Inn South Haven


Gurnee, IL (847) 599-7500 Visit Website Social Media Open in Google Maps

This village borders Waukegan in the Chicago metropolitan area.

Located 35 miles from Chicago, it’s home to the Six Flags Great America amusement park.

If you drive a vehicle from Chicago, you can get to Gurnee in 50 minutes.

Enjoy pure family fun in Gurnee, with its amusement park known for its adrenaline-pumping rides.

Try all 17 of Six Flags’ heart-stopping roller coasters for the complete adventure.

But if you’re not a thrill-seeker, don’t worry.

You can enjoy the park’s entertaining shows instead.

Or just explore Gurnee Mills, a mall that features over 170 stores.

Recommended Hotel: Country Inn & Suites by Radisson, Gurnee, IL

16. South Bend – Indiana

South Bend - Indiana

South Bend Indiana, United States (574) 233-0311 Visit Website Social Media Open in Google Maps

An hour and 44-minute drive from Chicago lies South Bend, Indiana.

It’s a great day trip destination to explore more of what’s outside Chicago.

This city is home to the University of Notre Dame, a prestigious university known for its gold-domed main building.

And if you proceed to the city center, you’ll witness its thriving art scene.

There lies the Studebaker National Museum which has numerous displays of classic cars.

Morris Performing Arts Theater, a 2,564-seat concert hall, is a shouldn’t-miss part, too.

Surely you’ll see all the must-sees in the city within a day; a perfect place for your weekend getaway from Chicago.

Recommended Hotel: Antioch Inn & Suites Near Gurnee

17. Lake Geneva

Lake Geneva

Lake Geneva, WI (262) 248-3911 Visit Website Social Media Open in Google Maps

Located on Geneva Lake, this resort city features gorgeous beaches, parks, and Gilded Age mansions.

It is 65 miles northwest of Chicago.

If you use a car, you can get to Lake Geneva in 1 hour and 24 minutes.

Head to Lake Geneva, and you’ll see why it’s one of the best long weekend trips from Chicago.

Although small in size, the city has a lot to offer the traveler.

Explore Shore Path for stunning views of spectacular mansions, some dating back to the 1800s.

Check out the Stone Manor built by real estate magnate Otto Young in 1899.

Blackpoint, constructed in 1888 by Chicago beer baron Conrad Seipp, has 74 species of evergreen trees in front of his mansion.

If you’re not into architecture, you can immerse in nature instead.

Ride a boat on the 5000-acre Geneva Lake and soak in the beautiful views.

Recommended Hotel: Mill Creek Hotel

18. Turkey Run State Park

Turkey Run State Park

8121 Park Road Marshall, IN 47859 (765) 597-2635 Visit Website Open in Google Maps

This park, created in 1916, is Indiana’s second state park.

It stretches for 2,382 acres of land in Parke County.

It’s also home to historical sites, a pool, and public sitting areas.

If you use a vehicle, the travel time from Chicago to Turkey Run State Park is 3 hours.

You won’t run out of things to do in this park.

Experience nature at its finest while hiking a portion of the 14 miles of trails with varying degrees of difficulty.

Are you a history enthusiast?

The park has individual sites listed on the National Register of Historic Places.

Check out the Lusk Home and Mill Site, which date back to 1822 and 1826, respectively.

The Richard Lieber Log Cabin, built in 1848, is a must-see, too.

Recommended Hotel: Turkey Run Inn & Cabins

19. The American Club Resort Hotel

The American Club Resort Hotel

419 Highland Drive Kohler, WI 53044 (800) 344-2838 Visit Website Social Media Open in Google Maps

Built in 1918 as a male dormitory for Kohler employees, this lodging institution is now a five-star hotel that offers wellness and recreational opportunities.

By car, The American Club Resort Hotel is 2 hours and 22 minutes away from Chicago.

Who says you can’t have some incredible me-time in one place?

At The American Club Resort Hotel, you can.

Have the ultimate relaxing experience at the Kohler Waters Spa.

After your spa, enjoy your favorite book in the hotel’s reading area.

You can also check out the Kohler Design Center instead, with its stunning bathroom designs.

Enjoy an upscale meal in The Immigrant for the perfect bonding moment with yourself.

20. Whistling Straits

Whistling Straits

N8501 Lakeshore Road Sheboygan, WI 53083 (800) 444-2838 Visit Website Social Media Open in Google Maps

This luxury golf resort, owned by Kohler Company, is along the Wisconsin coastline.

The resort consists of two golf courses: the Straits and the Irish.

You can reach Whistling Straits in 2 hours and 28 minutes if you travel by car from Chicago.

If you love golf, Whistling Straits should be your go-to place.

Enjoy state-of-the-art 36-hole links-style golf courses set against a beautiful nature landscape.

Whistling Straits offers incredible views of Lake Michigan and rolling hills.

The Irish, meanwhile, will transport you to the gorgeous European country with its rugged coastline and smooth grassy terrain.

You won’t just get to play your favorite sport here.

Recommended Hotel: Harbor Winds Hotel

21. Parke County

Parke County

Parke County, IN (765) 569-3394 Social Media Open in Google Maps

This rural county stretches for over 284,000 acres of land along the Wabash River.

It lays claim to being the Covered Bridge Capital of the World.

If you’re coming from Chicago, Parke County is 3 hours and 26 minutes away by car.

Do you love architecture?

Go on a weekend getaway to Parke County, then.

You need more than enough time to visit the county’s 31 covered bridges, each with its unique architectural design.

The Portland Mills Covered Bridge is a must-see.

Built in 1856, it’s a single-span Burr Arch truss-covered bridge that’s also the second oldest in the county.

Check out the Jackson Covered Bridge, built on a base of hewn stone in Rockport.

Constructed in 1861, it’s the oldest standing bridge built by the acclaimed J.J. Daniels.


Galena, IL (815) 776-9200 Visit Website Social Media Open in Google Maps

This city in Illinois is the largest in Jo Daviess County.

Located in an unglaciated area in the northwest portion of the state, it’s famous for its rolling hills and 19th-century architecture.

Galena is a 3-hour drive from Chicago.

Although a city by classification, Galena exudes a small-town vibe, making it a popular destination.

Picture gorgeous red-brick structures lining the main road where traditional carriages occasionally ply.

Go kayaking along the river to experience stunning views of nature wherever you look.

You can walk through native prairies and interact with goats here, too.

Cap off your weekend with a challenging game of golf on any of the city’s 11 picturesque courses.

Recommended Hotel: Country Inn & Suites by Radisson, Galena, IL

23. Dubuque


Dubuque, IA (563) 589-4100 Visit Website Social Media Open in Google Maps

Nestled along the Mississippi River, Dubuque encompasses over 19,000 acres of land at the junction of Iowa and Wisconsin.

It’s a go-to place for its unique architecture and historical sites.

You can get to Dubuque from Chicago in 3 hours and 16 minutes by car.

Dubuque is heaven for architecture and history buffs.

Head downtown, and you’ll find the Dubuque County Courthouse.

It’s in the Beaux Arts architectural style, built from 1891 to 1893.

The Holy Ghost Catholic Church in the North End is a must-see, too.

Formed in 1896, the beautiful church’s Romanesque Revival style stands out.

In the South End, check out St. Raphael’s Cathedral.

The church traces its roots way back in 1833.

Enjoy its Gothic Revival Style amid Dubuque’s nature landscape.

Recommended Hotel: Hotel Julien Dubuque

24. Field of Dreams

Field of Dreams

28995 Lansing Road Dyersville, IA 52040 (563) 875-8404 Visit Website Social Media Open in Google Maps

Built in 1988 for the movie Field of Dreams, this baseball field now functions as a sports venue and pop culture destination.

It’s also home to a souvenir shop and a 2,600-square-foot barn that serves as an event center.

By car, Field of Dreams is 209 miles away from Chicago. So you can get to the iconic baseball field in approximately 4 hours.

This isn’t your ordinary baseball field.

It has pop culture significance as the filming site of the Academy Award-nominated movie Field of Dreams.

So when you get to the place, you can also tour the Kinsella family house as shown in the movie.

You can also purchase official Field of Dreams apparel from Baseballism, the movie’s on-site official retail store.

Spend a night in the newly remodeled three bed-room farmhouse for the complete movie experience.

Recommended Hotel: Super 8 by Wyndham Dyersville

25. Ann Arbor

Ann Arbor

Ann Harbor, MI (734) 794-6000 Visit Website Social Media Open in Google Maps

This city stretches for over 18,600 acres in the Midwestern state of Michigan.

It is home to the University of Michigan, museums, and parks.

The travel time from Chicago to Ann Arbor is 4 hours and 33 minutes by car.

Ann Arbor has everything you need for the perfect weekend getaway.

The University of Michigan Museum of Art will give you a one-of-a-kind artistic experience, with its collection spanning over 150 years.

If you’re more of a history buff, the Kelsey Museum of Archaeology is just the place for you.

It’s home to over 100,000 artifacts, including mummies.

Don’t worry if you’re not much of a museum-goer.

Ann Arbor has gorgeous parks you can explore, too.

Go paddle-boarding on the Huron River for fantastic views of the Michigan skies, flora, and fauna.

You can also hike the trails of Gallup Park and explore its 69 acres of open green spaces and water bodies.

Recommended Hotel: Graduate Ann Arbor

26. Traverse City

Traverse City

Traverse City, MI (231) 947-1120 Visit Website Social Media Open in Google Maps

This city stretches for over 5,500 acres in Grand Traverse and Leelanau counties.

It’s the largest city in the Northern Michigan region.

It’s home to beaches, at least 30 public parks, and historical sites.

By car, you can get to Traverse City in 5 hours and 8 minutes if you’re coming from Chicago.

The trip from Chicago to this city may take longer than your usual day trips outside.

However, it’s worth it.

Immerse in history with a tour of landmark sites, such as the City Opera House and Novotny’s Saloon.

Take the kids to Indian Woods Park, where they can also use playground equipment in a beautiful nature landscape.

If you want some physical activity, try hiking.

Just take your pick from the over 30 trails that meander through gorgeous woodlands and open green spaces in the city.

Recommended Hotel: Country Inn & Suites by Radisson, Traverse City, MI

27. Louisville


Louisville KY (502) 379-6109 Visit Website Social Media Open in Google Maps

Nestled on the Ohio River, Louisville is Kentucky’s largest city.

It features boxer Muhammad Ali’s home, some Fortune 500 companies, and a wide array of dining options.

If you’re driving from Chicago, you can reach Louisville in 4 hours and 47 minutes.

Experience the big city life in Louisville.

Marvel at the gorgeous skyscrapers that jut into the Kentucky skies.

The 400 West Market stretches 549 feet above the ground.

A close second is the National City Tower, with a height of 512 feet.

Then head to Mall St. Matthews for your shopping needs.

The mall features over 140 specialty retailers, which means you’re bound to find something to take home.

Recommended Hotel: The Brown Hotel

28. St. Louis

St. Louis

St. Louis, MO (314) 421-1023 Visit Website Social Media Open in Google Maps

This city is along the Mississippi River.

Commonly known as the Gateway to the West, the city has independent frontier-town roots and a vibrant blues music scene.

From Chicago, St. Louis is 4 hours and 35 minutes away by car.

If you love history, don’t miss out on St. Louis.

The city is home to majestic structures, some of them dating way before the Civil War.

Drop by the Basilica of St. Louis, built between 1831 and 1834.

The Christ Church Cathedral is a must-visit, too, with its Gothic Revival style completed in 1867.

Don’t forget to check out the arch that gave St. Louis its Gateway to the West moniker.

Completed in 1965, the long arch is also an architectural beauty, standing 630 feet tall.

Recommended Hotel: Angad Arts Hotel

Related: Fun Day Trips From St Louis


Zion, IL (847) 746-4000 Visit Website Social Media Open in Google Maps

This city encompasses over 6,300 acres of land in Lake County at an elevation of 187 meters.

It boasts beautiful parks and historical structures.

You can get to Zion in 58 minutes if you’re coming from Chicago.

Have the ultimate nature experience in Zion, with its 24 parks offering incredible views of flora.

Go biking through Edina Park, with its serene pond and open spaces

Hermon Park is perfect for picnics, with its tall trees surrounding green grass.

If you still have energy for more workout activities, hike a portion of the trail that cuts through Carmel Park.

You’ll get stunning views of the clear Illinois skies and lush greenery.

Recommended Hotel: The Inn On Sheridan

30. Elkhart Lake

Elkhart Lake

Elkhart Lake, WI (920) 876-2231 Visit Website Social Media Open in Google Maps

This village in Sheboygan County runs along Elkhart Lake.

It’s famous for its natural beauty, museums, and road race events.

If you drive from Chicago, you can reach Elkhart Lake in 2 hours and 30 minutes.

You’ll enjoy your weekend getaway in Elkhart Lake with the tons of activities you can do here.

Hike the 3.35-mile segment of the Ice Age National Trail for beautiful views of rolling hills.

If you get tired of hiking, visit Road America, which stretches over 4 miles around the lake.

The track that has been around since the 1950s continues to host racing events.

Time your visit to the city based on the racing schedule so you can attend one.

Recommended Hotel: Baymont by Wyndham Plymouth

31. Richland County

Richland County

Richland County, WI (608) 647-8821 Visit Website Social Media Open in Google Maps

This county stretches for 376,960 acres in southwestern Wisconsin.

Richland County is home to Frank Lloyd Wright architecture, parks, and museums.

Richland County is 3 hours and 37 minutes away from Chicago by car.

Richland County has something to offer, whether you’re a history buff or a nature enthusiast.

Check out the Albert D. German Warehouse, designed by acclaimed architect Frank Lloyd Wright in 1915.

You can unwind at Alana Springs Campground, where you can set up your tent amid gorgeous nature.

The Pier County Park is a must-see, too, with its layered and blocked sandstone rising for about 60 feet.

Recommended Hotel: Ramada by Wyndham Richland Center

Related: Best Weekend Getaways From Minneapolis

32. Door County

Door County

Door County, WI (920) 743-5511 Visit Website Open in Google Maps

Situated on a peninsula between Green Bay and Lake Michigan, Door County is home to many beaches and parks.

Chicago is 244 miles away from Door County.

If you travel from Windy City by car, you can get to Door County in 3 hours and 48 minutes.

Door County has a little bit of everything for everyone.

For the nature buff, Cave Point County Park is a must-visit.

The park is home to gorgeous underwater caves and limestone cliffs you can explore.

For the history enthusiast, check out the Eagle Bluff Lighthouse, built in 1868.

The Door County Maritime Museum is a great destination, too, with its comprehensive exhibits on Great Lakes history.

Door County even has something for the wine lover.

Enjoy delightful wines made from California grapes in Stone’s Throw Winery.

Recommended Hotel: Gordon Lodge

33. Vilas County

Vilas County

Vilas County, WI (715) 479-3600 Visit Website Open in Google Maps

This county stretches for 548,480 acres in northern Wisconsin.

It’s home to nearly 90 scenic forest trails and over 1,300 lakes.

From Chicago, the drive to Vilas County will take you 5 hours and 44 minutes.

It’s quite a long journey from Chicago to Vilas County.

But when you get to the place, you’ll conclude the trip is worth all your time and effort.

After all, the place is a nature oasis.

Go boating on Eagle Lake and soak in the gorgeous lush greenery around you.

You can hike the 1.5-mile loop near Eagle River afterward.

Whatever you do, you’re in for a beautiful nature immersion.

Recommended Hotel: Hiawatha Lodge Inn

34. Shawnee National Forest

Shawnee National Forest

Herod, IL 629646 (618) 253-7114 Visit Website Social Media Open in Google Maps

Nestled in southern Illinois between the Ohio and Mississippi Rivers, this national forest stretches for 289,000 acres.

It’s home to forests, lush canyons, and ridges.

The travel time from Chicago to Shawnee National Forest is 5 hours and 25 minutes.

Travel to one of nature’s wonders for the perfect weekend trip.

Experience Cedar Lake a different way, on board a beautiful horse and under the gorgeous Illinois skies.

You can hike in the park if you prefer to walk.

How about exploring a portion of the 160-mile River Trail that will take you to gorgeous forest streams and greenery?

Recommended Hotel: Baymont by Wyndham Marion

35. Pictured Rock National Lakeshore

Pictured Rock National Lakeshore

N8391 Sand Point Road Munising, MI 49862 (906) 387-3700 Visit Website Social Media Open in Google Maps

This tourist destination encompasses the south shore of Lake Superior in Michigan.

It’s home to unusual sandstone formations and shipwrecks.

You can reach Pictured Rock National Lakeshore in 6 hours and 12 minutes by car.

This is one of the best weekend getaways from Chicago for a reason.

The place is a visual treat, with its magnificent cliffs.

The cliffs can go as high as 200 feet above sea level, with formations ranging from human profiles to castle turrets.

Bring your camera because you’ll want to take pictures of everything here.

Recommended Hotel: Comfort Inn & Suites Munising – Lakefront

Getaway Guide 

Comparing destinations: which one is right for you.

Knowing the pros and cons of each destination will help you decide which one is ideal for you.

And remember that your preference also plays a vital role in picking what’s best.

The Four Seasons Chicago lives up to what it promises guests: a luxurious and relaxing stay.

But for years in business, some parts need an update already.

Meanwhile, Waldorf Astoria Chicago is indeed a luxury hotel with unsurpassed facilities and amenities, but it also comes with a high cost.

On the other hand, The Peninsula Chicago has everything you need and expect from a five-star hotel.

But just like other luxury hotels, it’s also quite expensive.

Finally, Grand Geneva Resort & Spa has an array of activities for fun and relaxation for everyone.

But its customer service could be better. 

How I Picked The Destinations 

With years of experience as a blogger and traveler, I have learned much about picking the best destination and property to stay.

I thoroughly researched where to stay and what to do in Chicago.

My fellow travelers also gave reliable suggestions, and when I got there, I tried them myself.

My research and experience in the city strengthen my conclusion of what’s best.

Our Property Rating Method 

I rate these properties based on the following criteria:

  • Room Variety: I use this to rate the room options offered by every property. What room types are available? Can it accommodate different budgets, group sizes, and preferences? I ask myself these questions when evaluating the property’s room variety. 
  • Comfort and Cleanliness: This measures the overall cleanliness and comfort of the accommodations. Does it have comfortable beds? Are the rooms spotless and dust-free? These are important factors I consider when rating comfort and cleanliness. 
  • Location: This is used to evaluate how convenient and accessible the property is. How close is it to the attractions? Are there good public transportation options near the location? Is it easily accessible for families? These questions are important when I rate the location of every accommodation. 
  • Affordability: I use this to evaluate the property’s affordability. Are the room rates reasonable? Does the property have any additional fees? Does the property offer discounts or packages? I ask myself this in order to rate affordability. 
  • Family-Friendliness: This evaluates the family-friendliness of each property. Does it offer babysitting services and children’s activities? Does it have connecting rooms for families? I use these questions to rate the family-friendliness of the property. 

Frequently Asked Questions 

What are cities 3 hours from chicago.

Milwaukee, Rockford, and Michigan City are within a two-hour drive from Chicago.

How Far Is Lake Geneva From Chicago, And What Can I Do There?

Lake Geneva is about a 90-minute drive from Chicago. It offers a range of activities including boating, fishing, golfing, hiking, and skiing in the winter. The area is also home to several spas and wellness centers.

weekend trips from chicago by car

A stay in a property with a perfect location will give you nothing but only the best weekend getaways from Chicago. 

My Waldorf Astoria Chicago experience was beyond impressive.

I had a relaxing and with-a-view room.

The excellent location for shopping and restaurants was what I love most about The Peninsula Chicago.

And the variety of activities I did at Grand Geneva Resort & Spa was immense.

My favorite was the view of the calm lake

But the top pick of the bunch is the Four Seasons Chicago.

The welcoming staff, fancy and modern facilities, and countless amenities made me enjoy my stay. 

During my stay at the Four Seasons Chicago, I particularly enjoyed their renowned spa, indulging in a rejuvenating massage and a soothing swim in the indoor pool.

My family and I savored the diverse breakfast options, with my children relishing the fluffy pancakes. 

When exploring the surrounding areas, we appreciated the hotel’s proximity to the iconic Magnificent Mile, making it easy to shop and dine.

My kids had a blast at the nearby Navy Pier, where we enjoyed a fun-filled afternoon. 

Four Seasons Chicago offered the ideal blend of relaxation and adventure for our family getaway.

35 Best Weekend Getaways From Chicago — Quick Trips!

9 easy must-do weekend trips from Chicago

Weekend trips from Chicago

Chicago is blessed with world-class museums, an amazing food scene, some of the best breweries in the country, and everything else you’d ever want to do. But even the most passionate Chicagoans need to escape the city every now and then. Luckily, there are dozens of superb weekend getaway destinations, all within a few hours’ drive of the Windy City. 

There are miles upon miles of Lake Michigan coastline to explore, there are national and state parks with gorgeous nature, and there are charming cities and towns all over the Great Lakes region where you can find a little bit of quaint comfort. Planning will go a long way to ensure a successful weekend trip. So research where to go, find luggage storage in Chicago if you need to drop the bags off, book lodging, plan where to eat and what to do, and hit the road. 

Here are the best weekend getaways from Chicago: 

Weekend trip to Dubuque from Chicago

Dubuque, Iowa 

Located on the banks of the Mississippi River, Dubuque is the ideal weekend getaway for history buffs and older tourists. Baseball fans will want to visit the famous “ Field of Dreams ” ballpark, which is now the home of special events hosted by Major League Baseball. 

The town itself has been revitalized somewhat in recent years, with art galleries, breweries, murals, and restaurants opening in downtown Dubuque. Dubuque is heavy on the small-town charm and well worth a visit. 

Distance from Chicago 

It takes just under three hours to reach Dubuque from Chicago. Driving is the only option for transit. 

Our activity recommendations

This historic town is a delightful change from downtown Chicago, with a picturesque old-school Main street with many pre-Civil War buildings, like the Black Horse Inn. There’s also the Febekon Place Elevator, which is a scenic railway that overlooks the city and provides a spectacular aerial view. 

Best season to visit

Summer, fall, and spring are the best times of year to visit Dubuque. 

Holland, Michigan 

Western Michigan has a ton of delightful towns for weekend getaways, and Holland is one of the best family-friendly options. Located less than a mile from the stunning Lake Michigan coastline, Holland is famous for its large Dutch immigrant population and its furniture-making industry. 

Distance from Chicago

You’ll have to drive south and east for about two and a half hours to get to Holland. Driving really is the best way to get there, although Amtrak runs a train as well. 

Explore Holland’s (aptly-named) Dutch heritage by exploring delightfully kitschy attractions like Nelis’ Dutch Village, De Klomp Wooden Shoe, and the Windmill Island Gardens . 

In proper Dutch fashion, Holland (Michigan) celebrates the annual blooming of tulips every springtime. With millions of tulips planted across the area, it’s a gorgeous time of year to visit. Summer is also ideal, with the Lake Michigan shore and beaches only a mile away from town and gorgeous Lake Macatawa providing plenty of outdoor recreation. 

Chicago weekend trip to Grand Rapids, MI

Grand Rapids, Michigan 

While far from the largest city in the country, Grand Rapids has a massive beer scene. Since the industry’s boom in the past two decades, Grand Rapids has quickly become one of the craft beer meccas, drawing thousands of beer nerds to its taprooms and breweries. 

It’s a three-hour drive from Chicago to Grand Rapids, probably less if you miss Friday traffic. Amtrak also runs a service from Union Station directly into downtown Grand Rapids, the train ride is about four hours. 

Beer truly is the main draw for visitors, with companies like Founders, Brewery Vivant, Saugatuck Brewing, and Grand Rapids Brewing all operating popular taprooms. The food isn’t bad at all either, with local favorites Forty Acres Soul Kitchen and Terra GR being high-end dining options.

When you’re not drinking, renting kayaks or bikes to enjoy the riverfront are great ways to stay active. Lake Michigan is less than 30 minutes away by car too.

Summer and fall are perfect for enjoying some time outdoors, especially if you’re looking at kayaking and swimming along the river or Lake Michigan. Winter is also a great time to do a long weekend because you can hit the slopes at the nearby Cannonsburg Ski Resort. Also, the many Grand Rapids breweries are great for a cozy pint to warm up.

Indiana Dunes National Park, Indiana

The sandy dunes overlooking Lake Michigan have finally gotten their due and were made into a national park. Indiana Dunes National Park is the closest conservation and recreation area of its kind to Chicago and the perfect weekend getaway (or day trip) for outdoor enthusiasts.  

It’s only about 90 minutes by car (which is the most convenient way to get there) from downtown Chicago. Unless you want to explore the whole area and stay in a cabin, Indiana Dunes National Park is one of the best day trips from Chicago. The South Shore Line will also take you to the Indiana Dunes, but driving is easier and more flexible. 

There are over 15 miles of beautiful Lake Michigan shoreline to explore and enjoy. You can enjoy the beach, go for a swim, hike the trails along the dunes, and even go horseback riding. 

Summer and fall are the best times to go. Visiting during winter is absolutely inadvisable because of lake effect weather. Spring is better, but the weather brings frequent rain that impacts the hiking trails and terrain.

Weekend trips from Chicago to Lake Geneva

Kohler, Wisconsin 

Located north of Milwaukee along Lake Michigan, Kohler is famous for its resorts and golf courses. The American Club is a bucket-list course for golfers, and there are a number of spas and restaurants that make Kohler a relaxing destination. 

Kohler is a two-and-a-half-hour drive from Chicago. A great way to break up the trip is to stop in Milwaukee for lunch.

Our activity recommendations 

The upscale resorts and golf courses are the main draw at Kohler, which makes them frequent weekend getaway destinations for older travelers. The Kohler Waters Spa is the perfect place to unwind, and the American Club boasts one of the best golf courses in the country. 

For weekend getaways based around golf, summer and fall are the best times of year to head up to Kohler. Kohler is also a wonderful destination for spas and resorts during the winter. 

Lake Geneva, Wisconsin 

Of all the weekend getaways from Chicago, this one has to be the most popular. Lake Geneva is Chicago’s equivalent of The Hamptons. Basically, everyone knows someone with a house up there. This makes sense, given it’s only a 90-minute drive from Chicago, just over the Wisconsin border. There are plenty of hotels, like The Abbey and Grand Geneva Resort . Multiple golf courses surround the lake as well. But the main reason to head to Lake Geneva is to appreciate the natural beauty with friends and family. 

Lake Geneva is about as close to Illinois as you get, and it only takes about 90 minutes to get there from Chicago by car, which is the only real way to get there. 

All the best activities in Lake Geneva are based around the water. Renting a boat from one of the marinas is a great way to get the family out on the water. There are multiple public beaches as well. 

During the winter, there is a village of ice castles made by expert sculptors that’s worth checking out. Alpine Valley Ski resort is nearby, which also hosts concerts during the summer. 

Summer is the best time to take a weekend trip to Lake Geneva, but it does get busy during this time of year. During the fall, Lake Geneva gets a boost when the leaves change color, despite it being too cold for boating and swimming. 

Trip for the weekend from Chicago to Madison

Madison, Wisconsin 

Wisconsin’s capital city is one of the most popular weekend getaways from Chicago. All the best Wisconsin culture is represented in Madison, which mostly consists of beer, brats, and Badger Football. The University of Wisconsin’s gorgeous campus is located right in Madison, which gives the city energy when students are on campus. But there’s a nice variety of outdoor activities and culture in the city as well. 

Madison is a three-hour drive from Chicago. There are also bus routes between downtown and Madison that take about three hours and 30 minutes. 

For such a small city, there’s plenty to do in Madison. Snowshoeing in the winter, hiking in the summer, appreciating the leaves in the fall, and drinking all year long. 

Just outside of Madison is the Wisconsin Dells area, which has indoor and outdoor water parks and other outdoor activities. It’s a great excursion from Madison and less than an hour’s drive from the capital. 

Summer and fall are the best times to visit, especially when the leaves change and the University is in full swing.

Milwaukee weekend trips from Chicago

Milwaukee, Wisconsin

Chicago’s neighbor to the north is an obvious choice for weekend getaways. There is culture, there’s beer (and plenty of it), there are several pro sports teams, and there’s a lot of character. Milwaukee has all the amenities of a larger city, just without all the inconvenience of getting around a place like Chicago. 

If you’re driving up to Door County or Kohler, it’s well worth it to stop in Milwaukee for lunch. 

There is a train from Union Station that lands you right in downtown Milwaukee. This takes less than two hours and can save you some traffic headaches. The drive up to Beer City only takes about 90 minutes. 

There are a number of amazing museums to visit, including the Milwaukee Art Museum, which is a gorgeous modern building along the lakefront. There’s also the Harley Davidson museum which details the story of how Milwaukee became the largest builder of motorcycles in the world. 

Outside of that, there are world-class breweries, restaurants, and bars. Definitely make sure to try a famous Bloody Mary dressed up Wisconsin-style. 

The Milwaukee lakefront is incredible, and there are frequent festivals and events going on, so summer is an amazing time for a weekend trip. But there is enough culture that visiting Milwaukee is fun year-round. If you’re free during the first few weeks of July, hit up Milwaukee Summerfest , which is the largest music festival in the world. 

Starved Rock State Park, Illinois

As far as outdoor activities go, Chicago is hardly the best city in the world. But the area’s best hiking area is absolutely worth visiting. Starved Rock State Park, with waterfalls and topography (rare in a painfully flat state like Illinois), makes for a perfect weekend getaway for outdoorsy types.  

It’s only a two-hour drive from Chicago, but you’ll want to leave early to beat traffic and have a head start on the other hikers. Leaving yourself a full day to explore the nooks and crannies of this park is the best way to go. 

Essentially, there’s really only one thing to do at Starved Rock, and that’s hiking. With 13 miles of trails winding through glacier-carved canyons and terrain, it’s the best hiking Illinois has to offer. There are gorgeous waterfalls and winding streams to take a dip in if you’re hiking during the sweltering Illinois summer. 

Late spring, summer, and early fall are the best times of year to explore Starved Rock. Winter is basically out of the question. Early spring and late fall are entirely weather-dependent.

Easy weekend trips from Chicago

It’s hard for locals and transplants to find a place they love more than Chicago because there is a lot to love. But getting out of the city for a weekend getaway is a necessary way to recharge and reset. You’ll be more in tune with nature, you’ll feel a little more relaxed after taking a break from traffic, and you’ll have a new appreciation for the gorgeous region surrounding Chicago. If you’re short on time, you can always opt for a fun day trip from Chicago as well, and if you only have a limited time in the city itself, check out our guide on how to spend 3 days in Chicago to maximize your itinerary.

Planning one of the many fun weekend getaways from Chicago is a great way to find a new appreciation for not only the Midwest but also Chicago. Because you can only stay away from that deep dish for so long… 

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Weekend Getaways From Chicago

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Weekend Getaways From Chicago | Road Trips from Chicago

Here is the list of 27 weekend getaways from chicago, 1. indianapolis, indiana.

Indianapolis, Indiana

Located in Marion County in Michigan, Indianapolis is the most popular state in the U.S. The city is popularly known for its historic sites, sporting events, and several museums. With the largest collection of monuments dedicated to the soldiers/veterans of war casualties, parks, hiking and biking trails, Art and culture centres, etc. the city has a lot to offer. An abode to three Fortune 500 companies the city also hosts the world’s largest single-day sporting event called the Indianapolis 500. Other recreational activities include kayaking, bicycling, cross-country skiing, sightseeing, etc. Distance From Chicago: 185.4 miles from Chicago Best Time to Visit: May-September Popular Attractions: Indianapolis Zoo, The Children’s Museum of Indianapolis, Indiana State Museum, White River State Park, and More.

2. Woodstock, Illinois

Woodstock, Illinois

Located 51 miles northwest of Chicago Woodstock Illinois is a suburb that was named the nation’s Distinctive Destinations in 2007. The city includes a historic town square, which is anchored by Woodstock opera house and Old McHenry County Country House. Woodstock was formerly known as Canterville because of its location at the geographic centre of McHenry County. The historic town square in Woodstock offers many shops and retail establishments that are designed in the late 19th-century Victorian style. From handcrafted jewellery stores to antiques and restaurants the town square includes all. Every year Woodstock hosts several Arts and Entertainment events, festivals, and fairs, which attract a lot of visitors. Some of the events hosted here are the Fair Didley Art Fair, Summer Band Concerts, Farmers Market, Victorian Christmas celebrations, and many more. Distance From Chicago: 61.5 Miles from Chicago Best Time to Visit: May to September Popular Attractions: Woodstock water Works, Emricson Park, Boone Creek Conservation Area, Illinois Railway Museum

3. Midewin National Tallgrass Prairie

Midewin National Tallgrass Prairie

Situated in Northern Illinois, the Midewin National Tallgrass Prairie is the largest conservational site Chicago Wilderness region. Located at the former site of Joilet Army Ammunition Plant, it was the first national tallgrass prairie ever designated in the U.S. Visitors can enjoy Hiking trails, Bird-watching, native seed-gardens, and biking along with the Midewin’s trail system. The prairie spreads across 9100 acres of land with 16 miles of hike trails, biking trails, which also facilitates horseback riding. More than a hundred bird species are present in the prairie, with a large number of Upland Sandpipers and Loggerhead Shrikes. Open throughout the year the prairie also hosts guided tours for its visitors. Distance From Chicago: 50.6 Miles from Chicago Best Time to Visit: March-June Popular Attractions: McKinley woods, Lake ChaminWood Preserve, Des Plaines State Fish and Wildlife Area, Foxford Park.

4. Beloit Wisconsin

Beloit Wisconsin

Beloit is a small city located in south Wisconsin, which was originally named New Albany by its founder Caleb Blodgett. The city is a host to festivals including, the Beloit International Film Festival, Winterfest, Beliots Farmers’ Market, etc., which attracts a lot of visitors every year. Hikers and art lovers can also visit the art centres, savannah trails in the Beckman Hill park. Distance From Chicago: 96.8 Miles from Chicago Best Time to Visit: Mid June to Early September Popular Attractions: Wright Museum of Art, Logan Museum of Anthropology, Tefler Park, Beloit Art centre.

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5. Apple River Canyon State Park

Apple River Canyon State Park

Located in Jo Daviess County, the Apple River Canyon State Park is situated near the Wisconsin Border. Stretched across a land of 1900-acres the park was built in the year 1932. The scenic canyon is a result of the Apple River switching its course. The river that once flowed eastward into the Pecatonica river started flowing southwest through an erosion gorge to the Mississippi. State Park offers hiking, fishing, hunting, campgrounds, etc. The six camping sites are available at the Canyon Ridge Campground and Walnut Youth Campground. Pine Ridge, Tower Rock, River Route, Sunset, and Primrose trails are the trails that are available within the Park. The fishing, however, is allowed only during the spring season. Distance From Chicago: 144.6 Miles from Chicago Best Time to Visit: Mid April- October End Popular Attractions : Stagecoach Trails Livery, Thriving Thistle Market, The Cove Bar/ Grill

6. Glencoe, Illinois

Glencoe, Illinois

Located on Chicago's North shore is the village of Glencoe that is surrounded by Lake Michigan, the Cook Country Forest Preserve, and Glencoe Golf Course. The village is nestled with residential homes that are designed using the architectural styles and designs from the 1800s. Many of the homes are designed by known architects which include Llyod wright, Robert Seyfarth, Keck, and Keck, etc. The various parks, beach facilities, golf courses, etc makes it one of the attractive places along the North Shore. Surrounded to the west of the village are the Skokie Lagoons in a forest preserve and the Greenbay Trail that offer bike trails to the visitors. Visitors can enjoy golfing at the public Glencoe Golf Club, Skokie Country Club, and the Lakeshore Country Club or spend their day at the Glencoe Beach. Distance From Chicago: 24.2 Miles from Chicago Best Time to Visit: Mid June- Mid September Popular Attractions: Chicago Botanic Gardens, Skokie Lagoons, Glencoe Beach

7. Lake Mills, Wisconsin

Lake Mills, Wisconsin

The city of Lake Mills is located in Jefferson County, Wisconsin, and occupies the east shore of Rock Lake. In 1866, the city was named Tyranena, but a year later, it was renamed, Lake Mills. Lake Mills is picturesquely surrounded, by several wineries, restaurants, and shops. Home to the Azatalan State park, which nestles the Rock Lake, also offers hiking and biking trails along the Park. Distance From Chicago: 141. Miles from Chicago Best Time to Visit: Mid June To early September Popular Attractions: Rock lake, Aztalan State Park, Sandy Beach, Bartel’s Beach, and More

8. Fox River Valley, Illinois

Fox River Valley, Illinois

Centred on the Fox River in Northern Illinois, the Fox River Valley is also commonly known as the Fox Valley. The city is a mixture of rural, suburban, and 19th-century downtowns developments. With its Fox River Trail System, Trolley Museum, Buffalo Rock State Park, Outdoor theatre, the city offers a lot to its visitors. The 32-miles fox river trail system is perfect for hiking, biking, and cross-country skiing trails. Original electric cars and trains that travel a three-mile route along the fox river, the Trolley Museum commemorates more than a century of electric trolleys. With the cheap ticket prices and the snacks, the outdoor drive-in theatre is another great place to hang out in the city. Distance From Chicago: 38.5 Miles from Chicago Best Time to Visit: Mid June To early September Popular Attractions: the Morton Arboretum, Cantigny Park, Cosley Zoo, Philips Park Zoo, and More

9. Rockford, Illinois

Rockford, Illinois

Located in Northern Illinois and on the banks of Rock river, Rockford is a city in Winnebago County. It is the third-largest city in Illinois. It is a cultural hub and a focal point of many monuments of historical significance. The notable outdoor recreations of the city include camping, hiking, fishing, boating, and hunting. Several golf courses can elevate the golfing experience for golfers. Distance From Chicago: 88.8 miles from Chicago Best Time to Visit: Mid June –Early September Popular Attractions: Anderson Japanese Gardens, Rock Cut State Park, Discovery Center Museum, Klehm Arboretum, and Botanic Garden, and More.

10. Cedarburg Wisconsin

Cedarburg Wisconsin

Incorporated in the year 1885 and located 20 miles from Milwaukee, Cedarburg is a city in Ozaukee County, Wisconsin. The city has many German cultural associations that culminate the Lutheran churches, European-style spa, and breweries. A host to several art galleries, tourism is at its peak in the city due to Winter Festival, Strawberry Festival, German-themed October fest, Wine and Harvest Festival, as well Christmas celebrations are commemorated every year. Distance From Chicago: 112.5 Miles from Chicago Best Time to Visit: May- September Popular Attractions: Cedar Creek Winery, Ozaukee Interurban Trail, Cedarburg Art Museum, Chiselled Grape Winery, and More.

11. Mount Morris, Illinois

Mount Morris, Illinois

Mount Morris is a small village in Ogle County, Illinois. The village is built on the former site of Mount Morris College, Illinois first institute dedicated to higher learning. Dillehay Park, Maunder Park, and Zickuhr Park are some of the parks in the village that has a basketball court, playground equipment, and a skating rink. Distance From Chicago: 106 miles from Chicago Best Time to Visit: Mid-June To early September Popular Attractions: Dillehay Park, Maunder Park, Zickuhr Park, Bald Hill Prairie Preserve

12. Holland, Michigan

Holland, Michigan

Located on the shores of Lake Macatawa, Holland is a city in Michigan. Found by the Dutch Americans, the city is thus known for its rich Dutch heritage. Every year the city hosts the must-visit Tulip Time festival, which is the planting of tulips. The festival started in the year 1930, and currently, there are over five million tulips all over the city. Scattered along the shorelines of lake Macatawa are several public beaches and hiking trails of the tunnel park, Holland State Park for the visitors. With over 100 swarming galleries and shops, the city upscales the shopping experience for its visitors. Distance From Chicago: 150.9 miles from Chicago Best Time to Visit: Late April or Early May Popular Attractions: Windmill Island, Nelis’ Dutch Village, Holland State Park, Lake Macatawa, and More

13. Madison, Wisconsin

Madison, Wisconsin

Madison is the second-largest city in Wisconsin and the capital city of Wisconsin. Also known as the City of Four Lakes, Madison encircles four lakes Lake Waubesa, Lake Mendota, Lake Monona, and Lake Kegonsa. The city is a focal point of an extensive network of parks and hiking trails, museums, Several lakes, and zoos. Henry Vilas Zoo in Madison is a 28-acre zoo that has over 70000 visitors every year. Nestled in the zoo are different species of birds, fishes, mammals, reptiles from several continents. Madison Arboretum is four miles from the University of Wisconsin is a research facility that manages many conifer/deciduous forests and prairies. Hikers can also enjoy the 20 miles of hiking trails and over 3 miles of bike trails in the arboretum. Distance From Chicago: 147.3 Miles from Chicago Best Time to Visit: July, August Popular Attractions: Wisconsin State Capitol, Henry Vilas Zoo, Lake Mendota, Madison Children's Museum and More

14. Saugatuck, Michigan

Saugatuck, Michigan

Saugatuck is a city in the Allegan County of Michigan that was incorporated in the year 1868. It has a population of 960 according to the 2019 census. With the many art galleries, restaurants, paddle-wheel boats, historic churches, and other attractions, the city is sprawling with tourists during the summertime. A boon for the art and music lovers as it also hosts art and music festivals throughout the year. The Paddle-wheel boat ride is one of the best in the city, as the boat ride gives daily tours of the river Kalamazoo river and Lake Michigan. Saugatuck church is one of the oldest buildings in the city, which also contributes to a vibrant community. Distance From Chicago: 140.7 miles from Chicago Best Time to Visit: May- September Popular Attractions: Oval Beach, Saugatuck State Park, Saugatuck centre for arts, Mount Baldhead, and more.

15. Lake Geneva, Wisconsin

Lake Geneva, Wisconsin

Lake Geneva is a city located in Walworth County, Wisconsin. Located on the shores of Geneva Lake, the city attracts many visitors from Chicago, Milwaukee, Rockford, etc., throughout the year. Camping sites, beaches, waterparks, hiking, biking, golf courses, museums, sightseeing, etc., the city has a lot to offer for its visitors. Enjoy a relaxed day at the beach, camp out in the various camping sites, or indulge in the various adventure sports, a city is a perfect place for all age groups. Their adventure activities include Zip lining, hot-air balloon rides, safari rides, skydiving, etc. Geneva lake has many beaches the Rivera Beach, Williams Bay Beach, Fontana Beach for the visitors to enjoy the Lake's pristine waters. Distance From Chicago: 83.0 Miles from Chicago Best Time to Visit: July, August Popular Attractions: Grand Geneva Way, Geneva Lake Museum, Big Foot Beach State Park, Lake Geneva Ziplines, and adventures.

16. Grand Rapids, Michigan

Grand Rapids, Michigan

Located on the Grand River and east of Lake Michigan, Grand Rapids is the second-largest city in Michigan. Encompassed in the city are the Van Andel Museum Centre, the Heritage Hill, Frederik Meijer Gardens, and Sculpture Park, etc., which makes it a popular tourist attraction. Found in 1854, the Van Andel Museum Centre is one of the oldest museums in the city. The Heritage Hill, the largest urban historic district, is a home of more than 1300 homes that are designed in more than 60 architectural styles. Spread across 125 acres of land is also the Frederik Meijer Gardens and Sculpture Park, which nestles a world-class botanical garden artwork from American/French artists. Dedicated to the art lovers are also various music concert venues that organize concerts every year. Outdoor recreation activities include Skiing, snowboarding, Ice fishing, etc. Distance From Chicago: 177.6 miles from Chicago Best Time to Visit: April-October Popular Attractions: John Ball Zoo, Grand Rapids Museum, Millennium Park, Rosa Parks Circle, and More.

17. South Bend Indiana

South Bend Indiana

Situated on the long tributary of Lake Michigan, St Josephs River, the South Bend City is located in Indiana. The city is a cultural hub and the fourth largest city in Indiana. Not only is the city a centre of arts and culture but, also hosts several music festivals every year. The great outdoors, sports venues, museums are some of the attractions that the city offers to its visitors. Distance From Chicago: 95.7 miles from Chicago Best Time to Visit: April-September Popular Attractions: Studebaker National Museum, Potawatomi Zoo, Nore Dam Golden Dome, The History Museum, and More.

18. Shawnee National forest, Illinois

Shawnee National forest, Illinois

Located in Southern Illinois, the Shawnee National Forest is situated between the Ohio and Mississippi river. With a plethora of flora and fauna, the forest is the perfect place for outdoor recreation and sightseeing. Some of the available recreational activities are camping, fishing, Hiking, Hunting, Bicycling, water activities, and much more. The camping experiences range from primitive backpacking to partial hookups camping sites. Swimming, water skiing, boating, etc., are some of the water activities offered to visitors. Distance From Chicago: 338.6 miles from Chicago Best Time to Visit: March-June Popular Attractions: Giant City State Park, Garden of the Gods, Kinkaid Lake, Tunnel Hill State Trail, and More.

19. Traverse City, Michigan

Traverse City, Michigan

Traverse City is the largest city in the Northern Michigan region. With a large production of Tart Cherries in the city, it also hosts the National Cherry Festival every year. Some of its other attractions include freshwater beaches, forests, skiing areas, camping sites, arts and culture centres, etc. Campers can enjoy camping at the 250 camping sites, art lovers can visit the Dennos Museum, which hosts a collection of art by the Arctic people. Kayaking, Swimming, fishing, surrounding wineries are some other recreational activities that are presented at Lake Michigan. Distance From Chicago: 319.6 miles from Chicago Best Time to Visit: June- August Popular Attractions:  City Opera House, Clinch Park, East Front Street, Mari Vineyards, and More. "

20. Galena Illinois

Galena Illinois

Located in Jo Daviess County, Galena is a small town in Illinois known for its 19th-century architectural style buildings. From the many historic sites, local cuisine to a plethora of boutiques and shops, the city has a lot to offer. With a ride in the hot air balloons, hiking, golfing, biking, etc., the city hosts several outdoor adventures along the Mississippi River. Distance From Chicago:  163.7 miles from Chicago Best Time to Visit: May- October Popular Attractions: Galena Grant Park, Belvedere Mansion, Old Blacksmith Shop, and More

21. Elkhart Lake Wisconsin

Elkhart Lake Wisconsin

Elkhart Lake is a village in Sheboygan County in Wisconsin. Located within the Town Rhine the village was popularly known to host road races in the 1900s’. Located a few miles away from the village is a race track called Road America. The village has several historical figures like the Victorian Village theatre, which is a 100-year theatre where still cultural programs are performed. There are two parks called the Broughton Sheboygan Marsh Park and Fireman's Park, which offer campsites, picnicking, fishing, and trails for its visitors. The recreational activities in the village are hosted every Summer, Winter, and Spring Season. Distance From Chicago: 149.4 Miles from Chicago Best Time to Visit: June- August Popular Attractions: Road America, Two Fish Gallery, Crystal Lake, Wade House Historic Sites, and More.

22. Starved Rock State Park, Illinois

Starved Rock State Park, Illinois

The Starved Rock State Park on the Illinois River is a wilderness area in the state of Illinois that offers several recreational activities for the visitors. The park is spread across 2630 acres of land and has waterfalls, 18 sandstone canyons, 13 miles of wooded trails, and diverse wildlife. Established in the year 1911, it attracts a lot of visitors every year. Among other recreational activities, the park offers camping, fishing, boating, horseback riding trails, ice skating, scenic views from the Eagle Cliff Overlook and Beehive Overlook. Distance From Chicago: 98.9 miles from Chicago Best Time to Visit: September- December Popular Attractions: Ottawa Canyon, LaSalle Canyon, Grand Bear Falls Indoor Waterpark, French Canyon, and More

23. Milwaukee, Wisconsin

Milwaukee, Wisconsin

Located on the western shore of Lake Michigan, Milwaukee is the largest city in Wisconsin. The city is known for its breweries, summer fest, and cultural attraction. With Over 140 well-developed parks that facilitate picnic spots, golfing, ice skating, the parks are spread across 15000 acres. The 2 km Monarch Trail highlights the migration of the milkweed butterflies. Nearby local markets and farmers markets sell the produce of local business, which includes seafood, gourmet, plants, and vegetables. Distance From Chicago: 92.4 miles from Chicago Best Time to Visit: June - September Popular Attractions: Milwaukee Art Museum, Harley Davidson Museum, Discovery World, Milwaukee County Zoo, and More.

24. Mineral Point, Wisconsin

Mineral Point, Wisconsin

Mineral Point is a city in Iowa County and the third oldest city in Wisconsin. The city’s historical significance and lead/ Zinc mining centres makes it a popular tourist attraction. Mineral Point is the endpoint of the 76-km Cheese country Trail in Southern Wisconsin. A historic district with many cottages and businesses that were crafted by the Cornish settlers. The restaurants in Mineral Point serve Cornish Foods following the Cornish heritage of the city. Distance From Chicago: 167 Miles from Chicago Best Time to Visit: June, July, August Popular Attractions: The Walker House, Orchard Lawn, Merry Christmas Hill, Pendarvis

25. Lake Forest, Illinois

Lake Forest, Illinois

Founded in the 1900s, lake Forest is a city along the shores of Lake Michigan located in Lake County, Illinois. With the Citadel theatre, the Wildlife Discover Centre, and the Lake Forest Symphony, the city is a cultural hub for visitors. Distance From Chicago: 32.7 miles from Chicago Best Time to Visit : Mid-June to Mid-September Popular Attractions: Wildlife Discovery Centre, Fort Sheridan Forest Preserve, Chicago Botanic Garden, Sunrise Park, and More

26. Ann Arbor, Michigan

Ann Arbor, Michigan

Founded in 1824, Ann Arbour is a city in Michigan that is the focal point of art, natural history, and sciences. Home of the University of Michigan and a sprawling tech-hub, the city draws several companies due to the research programs by the university. The local cuisine, outdoor activities, unique shopping, renowned arts, and culture, etc., are some of the recreations that the city offers. Seasonal sports like kayaking, canoeing, paddleboarding on the River Huron, ice skating, skiing, and snowshoeing are offered during different months of the year. Hikers can enjoy the best biking trails in the nearby state parks. Art lovers can visit the University of Michigan Museum, which displays century-old arts from all over the world. Distance From Chicago: 241.4 miles from Chicago Best Time to Visit: March-September Popular Attractions: Ann-Arbor Hands-on Museum, Matthaei Botanical Gardens & Nichols, University of Michigan Nichols Arboretum, Gallup Park, and More

27. Indiana Dunes State Park, Indiana

Indiana Dunes State Park, Indiana

Established in the year 1925 and located in Porter County, Indiana, the Indiana Dunes State Park is a few miles away from Chicago. The park is spread across 1530 acres of land and is an abode to several hiking trails and dune landscape. With the several hiking trails, picnic shelters, hiking tours, etc., there are several activities in this state park that the visitors can indulge themselves in. Their hiking trails extend over 16 miles, a bird observation tower for bird watching, swimming in the small portion of Lake Michigan shoreline, around 140 campsites with 50 amp electric hook-ups, and picnicking are some of the recreational adventures that attract a lot of visitors. Distance From Chicago: 50.1 miles from Chicago Best Time to Visit: Any time of the year Popular Attractions: Taltree Arboretum and Gardens, Chapel of the Resurrection, Portage Lakefront and Riverwalk and More

We hope you enjoyed our list of Weekend Getaways from Chicago. Drop your feedback in the comments section below.

This post was published by Akshita Dhiman

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Nashville, Tennessee, USA downtown city skyline on the Cumberland River.

12 Best Spring Break Road Trips from Chicago

Chicago is known for its world-class museums, including the Field Museum and the Museum of Science and Industry, but after the cold Chicago winter, most people will have exhausted the city's many indoor attractions. That makes spring break the perfect time to take a trip.

Whether you have a day, a weekend, or longer, there's a fabulous choice of spring break trips from Chicago. Drive to Cincinnati, Traverse City, Cleveland or Columbus, follow Scenic Route 61, or chase the sun south the Nashville, Hot Springs or Atlanta.

There's something for everyone in reach of Chicago, with great spring break road trips to suit if you're travelling with children, teens or childfree. Keep reading to find out some of the best places you can get to from the Windy City this spring break.

Best spring break road trips from Chicago

Chicago makes a great place for a spring break staycation, and with its museums, parks and the attractions around Navy Pier to enjoy you might even be heading there as your main spring break destination. But if you're ready to explore a little further afield after the St Patrick's Day party, or looking for a day trip or two while you spend spring break in Chicago itself, you have some amazing destinations to choose from.

After the long winter, why not head out for an adventure when spring break rolls around again? We've listed some of our favorite spring break destinations, so keep on reading to decide what kind of trip awaits you this spring break.

If you're thinking of taking a road trip from Chicago in another season, check out our Best Road Trips from Chicago article for ideas and inspiration!

Day trips (about 3 hours each way)

Chicago sits proudly on the shore of Lake Michigan and is in easy reach of many other great midwestern cities. That means that even if you're not looking for an overnight stay, you can still take an unforgettable spring break trip and be back home by evening.

1. Indianapolis, Indiana

3 hours 10 minutes from Chicago (180 miles)

Why you should visit: This is the shortest trip on the list, but there's plenty to see in the city whether you're travelling as a family with young kids or taking a break from college.

The Children's Museum is sure to be a hit for younger travellers – it's the world's largest children's museum. With a visit here your spring break can take you to modern Europe, ancient Egypt, or even into space.

Baseball fans might like to time the trip to catch the home opener of the Indianapolis Indians, which usually takes place in early April.

Lafayette, Louisiana, USA, view across the river

How to get there: Head out of Chicago on I-90 E then pick up I-65 which you'll follow south past Remington and Lafayette. After around 130 miles on the interstate you'll cross the White River to arrive in downtown Indianapolis.

Our highlights: Indianapolis Children's Museum in Nashville, Tennessee will definitely appeal to families on spring break. This huge space has engaging interactive exhibitions covering space travel, history, pop culture, science and technology and dinosaurs.

Families and college athletes alike will also appreciate the NCAA Hall of Champions, which even has sports simulators where you can try your hand at new activities.

Elsewhere, Indianapolis Museum of Art blossoms in springtime when the thousands of bulbs planted at Newfields' gardens burst into life.

Indianapolis also has breweries, wineries and distilleries which you can visit with the Indy Craft Pass – something that might appeal if you want to party during spring break.

Bonus: You won't be able to see the famous Indy 500 automobile race during your spring break visit, as this usually takes place in May. If you decide to make a return trip to see the race you'll be in good company – more than half a million people watch from around the Speedway.

Our travel tips: Weather can be variable during spring break, from 32 degrees F right up to 65 degrees. April is one of the wettest months of the year too, so pack accordingly.

2. Springfield, Illinois

3 hours 30 mins from Chicago (200 miles)

Why you should visit: This is a really easy drive out from Chicago, and with its presidential history it's a fascinating contrast to the Windy City. It's also a great place to spend a weekend, especially if you fancy following the Capital City Bourbon Journey.

Springfield is a great family getaway, especially if your kids have started to learn about the country's history.

You can immerse yourself in stories of the country's 16th President, Abraham Lincoln, who lived in the city for many years – his legacy as the country's Civil War-era president is sure to inspire grade schoolers and older teenagers alike, especially when you can visit the places where he lived and worked for real.

Abraham Lincoln Springfield House

How to get there: This is a really simple trip to navigate – just pick up I-55 S from your departure point in Chicago, and follow it all the way to Springfield, Illinois.

Our highlights: You could easily spend the whole trip exploring Lincoln-related sites. There's the Lincoln Home National Historic Site, where he lived until becoming President in 1861, and the unique, interactive Abraham Lincoln Presidential Library and Museum. You can also tour both the old and new state capitol buildings.

Younger kids will enjoy Kidzeum, a colorful museum where they can learn about keeping themselves and the planet healthy. Many of the exhibits are play-based – a perfect pick-me-up if they're getting fidgety after all that history.

With its vintage fighter planes, the Air Combat Museum might also appeal. Check ahead for opening times.

Alternatively, if you need to run off some energy, head to Knights Action Park, where you'll find arcade games, rides and mini-golf.

Springfield isn't just for families though – older visitors might like to follow the Capital City Bourbon Journey, which takes you on a tour of some fabulous bars and restaurants to try locally-produced makes.

Bonus: Springfield didn't invent the corn dog, but it does claim to be the birthplace of the iconic cozy dog – that's a hotdog on a stick covered in tasty batter for out of towners. For one of the best in town, head to the Cozy Dog Drive In.

Our travel tips: Springfield will feel chilly if your spring break falls earlier in the season, with March temperatures rarely topping 50 degrees Fahrenheit. You might even see a little snow.

Click here to skip back to the top.

Weekend trips (about 5 hours each way)

If you're able to spend a little longer on the road, then some more great destinations are in reach where you spend time relaxing in nature or enjoying the big city buzz of Columbus.

3. Cincinnati, Ohio

5 hours from Chicago (290 miles)

Why you should visit: Cincinnati is a beautiful riverside city which is at the longer end of the one-day range – it's also a great place for an overnight trip. There's plenty going on so it will appeal to visitors of all ages.

If your spring break coincides with Opening Day, come and join the party in Cincinnati. With unbeatable baseball heritage, the first pitch of the season sees the Findlay Market Parade and other events to celebrate the Reds (who always play their opening game at home).

Colorful Cincinnati river front looking from Kentucky with steam boat and ferris wheel.

How to get there: Follow the interstate as far as Indianapolis. You can stop for a break here but if you'd rather head straight to then bypass the city on I-465 which takes you onto I-74. Follow this road all the way to Cincinatti.

Our highlights: Baseball fans should head straight to the Cincinnati Reds Hall of Fame & Museum, where you can also take a tour of the Great American Ballpark.

If you're not in town for Opening Day, there's still plenty to see and do. Cincinnati Zoo holds its popular free Tunes & Blooms sessions on Thursday evenings through April. Enjoy live music among the colorful spring blooms in a family-friendly atmosphere. You can also enjoy the blooms in daytime if you need to hit the road back to Chicago by the evening.

At Krohn Conservatory, the spring sees the arrival of thousands of butterflies which are fascinating to watch when you visit the tropical glasshouse.

With its Dinosaur Hall and interactive science exhibits, Cincinnati Museum Center is also a great family day out. Head to the Children's Museum for some play-based fun.

Bonus: For many years the baseball season was officially opened with a first pitch in Cincinatti, whose team, the Reds, were the first in the country to go fully professional.

Our travel tips: The city will be really busy if you do visit for Opening Day, so expect some queues and leave extra time to get parked (we'd suggest arriving early). Book early if you want to try to get tickets for the game.

4. Traverse City, Michigan

5 hours from Chicago (320 miles)

Why you should visit: This is the only destination on our list that lets you carry on exploring the shores of Lake Michigan.

After the long winter, the wildflowers start to blossom around Sleeping Bear Dunes National Lakeshore, making this a fabulous weekend destination for fans of the great outdoors.

A weathered wooden walkway on the Empire Bluffs Trail is the perfect overlook to see Lake Michigan, the Sleeping Bear Dunes, and the Manitou island

How to get there: The interstate runs parallel to the shore of Lake Michigan most of the way to Traverse City. You'll start out on I-90 E before switching on to I-94. Follow this past Benton Harbor then change onto I-196 where the interstate divides. When you reach Grand Rapids join US-131 and continue north until you reach your destination.

Our highlights: You could spend days exploring the fabulous lakeshore, but seeing as you're only here for the weekend we'd suggest starting at Sleeping Bear Dunes with a hike along the Old Indian Trail or spending some time exploring Old Mission State Park. You can also visit the historic lighthouses – six in all – to enjoy more atmospheric views out across the lake.

It's too early in the year to swim in the lake but kids of all ages will love the huge indoor water park at Great Wolf Lodge.

If you're here without the family, take the chance to visit a winery or two, or taste some of the wine produced along the Traverse Wine Coast at one of the city's tasting rooms or bars.

Bonus: Traverse City is known as the Cherry Capital of the World. Spring break is out of both the cherry blossom and picking seasons, but don't miss the chance to try a slice of cherry pie while you're in town.

Our travel tips: Temperatures often dip below freezing even in April, and this can be a wet time of year, so plan for some indoor activities if you're making a spring trip here.

5. Columbus, Ohio

5 hours 30 mins from Chicago (350 miles)

Why you should visit: Ohio's state capital and largest city is packed full of things to do during spring break. The length of the drive means you'll probably want to stay at least a night (or maybe longer) but there's so much to do when you arrive that you definitely won't be bored.

You'll find a whole host of family-friendly attractions in Columbus, including one of the best science museums in the country at the Centre of Science and Industry.

The Ohio Statehouse in Columbus, Ohio

How to get there: Follow I-65 away from Chicago then at Indianapolis change onto I-70 to head east into Ohio. As you approach Columbus, merge onto I-670 to make your way to the downtown area.

Our highlights: The Center of Science and Industry (COSI) – named "America's number one science museum" – is packed full of interactive and informative exhibits which are guaranteed to keep children entertained for hours.

The Spring Thaw at Ohio History Center is a week of natural history-focused events to mark the end of winter. In 2023 you'll catch the Spring Thaw in early April.

Another sure fire hit with children is LEGOLAND Discovery Center. It doesn't just appeal to kids though, as there's a 3D cinema featuring Lego characters, as well as the chance to build and explore interactive displays.

Just outside town, Columbus Zoo & Aquarium is another entertaining attraction, and if your spring break coincides with Easter there are extra egg-themed activities and attractions

If you're feeling active, head to Hockings Hill State Park where you can escape the busyness of the city and hike through a fascinating sandstone landscape.

Staying outside, you can also visit Franklin Park Conservatory & Botanical Gardens, where the spring flowers will be starting to burst into life. It's a relaxing place to escape the hustle and bustle, and if you're travelling as a family children love exploring the tropical conservatory too.

Finally, round off the afternoon or evening on one of the city's rooftop patios to celebrate the spring sunshine.

Our travel tips: Spring can be a good time to visit Columbus, before the summer's humidity sets in.

6. Cleveland, Ohio

Why you should visit: As well as spending time by another of the Great Lakes, this trip also lets you follow one of “America's most scenic drives” with a detour along Indiana's Heritage Trail that starts at Elkhart.

If your spring break falls over the Easter period, come and join in the Dyngus Day celebrations! Held on Easter Monday, this Polish festival includes polka dancing, accordion music and beer tents – a really unique way to spend the spring break whatever your age!

Another interesting event that coincides with spring break is Cleveland Thyagaraja Festival, a celebration of Indian classical music which brings international stars to the city.

How to get there: From the center of Chicago, join I-90 and keep going. You'll drive all the way across Indiana and then into Ohio, passing to the south of Toledo and Lake Erie before arriving in Cleveland.

If you're following the marked Heritage Trail, leave the interstate at Elkhart then head east on IN-120 to Bristol. Carry on to Middlebury and Shipshewana before looping back round to visit Goshen and Nappanee. Wakarusa is the final stop on the trail, which then passes through Elkhart again before you rejoin I-90 to continue east towards Cleveland.

Taking this detour along the Heritage Trail will add around 2 hours 30 minutes to your driving time, plus any time for stops in the towns you'll pass along the way.

Our highlights: On your way to Cleveland, take a break from the interstate to travel along Elkhart County's Heritage Trail. Taking you through small towns and beautiful landscapes, you can download a free audio guide which gives you some of the background to this peaceful part of Indiana.

Once you've arrived in the city, you should definitely try out Maple Sugaring if you're visiting in March. This takes place at a number of locations in and around Cleveland.

If you're travelling with children, check out the themed trips on Cuyahoga Valley Scenic Railroad, which run through April.

If the weather's good enough to spend more time outdoors, go for a longer hike through Cuyahoga Valley National Park where Brandywine Waterfall should be in full flow. You could also spend a peaceful half hours walking through the daffodils which carpet Lake View Cemetery.

Bonus: Cleveland Thyagaraja Indian classical music festival is the biggest festival of its kind that you'll find without visiting India.

Our travel tips: As with some of the other destinations listed so far, spring weather in Cleveland can be unpredictable, ranging from late snow to bright sunshine.

Long weekend trips (6-8 hours each way)

There are some fantastic 3-4 road trips that you can take from Chicago. Visit another of the Great Lakes or head south to explore Tennessee's vibrant cities and stunning hills and mountains.

7. Nashville, Tennessee

7 hours 15 mins from Chicago (480 miles)

Why you should visit: Nashville is the first of our road trip destinations where you're likely to be able to enjoy some warmer spring weather, and the first one outside the Midwest.

Nashville is a great place to party , and with live music and warm weather likely to feature, it's perfect for a short spring break road trip from Chicago. It's a straightforward interstate drive south for the weekend, and once you arrive you can immerse yourself in the party atmosphere until it's time to leave.

It's also a fun place to take children, especially if they're happy to soak in the atmosphere. Many of the live venues on Lower Broadway welcome families during the daytime.

Nashville, Tennessee, USA with colorful neon store signs hang along the bars restaurants and record stores along Broadway Street in downtown Nashville.

How to get there: Although it's a pretty long drive, this 475-mile route is really easy to navigate. Just hop onto I-65 as you exit Chicago to the south, and follow it all the way through Indiana and Kentucky. Just after you cross the Cumberland River, turn onto I-40 to make your way into Nashville's downtown where you'll complete your drive.

Our highlights: You can't visit Nashville without seeing a live show or two, so head to Music Row and take your pick before partying late into the night on Broadway. Some venues host special spring break parties, but if these don't match the kind of vibe you're after there are plenty of other venues to choose from.

A great all-year-round attraction that's a must-see in Nashville is the Country Music Hall of Fame. If really you want to immerse yourself in the heritage of Music City, you can carry on to the Johnny Cash Museum, RCA Studios or the Grand Ole Opry House.

When you're ready to take a break from wall-to-wall music, head to the Cheekwood Estate where the springtime Cheekwood in Bloom event sees over 100,000 tulip bulbs filling the peaceful gardens with bursts of color.

Just outside the city, Treetop Adventure Park is great for couples, groups and families alike – test your nerves as you travel across bridges, ropes and ziplines high up in the canopy (children must be over 7 to take part, and an adult has to climb with them).

Bonus: Book a stay at the Gaylord Grand Ole Opry Resort to enjoy a host of springtime activities for families.

Elvis recorded dozens of songs in Nashville, and with so many live acts performing in the city you might one day be able to say you saw the next big music star before they were famous.

Our travel tips: This part of Tennessee is known for its spring tornadoes. It's unlikely that you'll see one but watch out for local advisories while you're in town.

Even this far south you'll need to pack warm clothes as the evenings will be cool and the weather can still sometimes be unsettled, especially in early spring.

8. Knoxville, Pigeon Forge and Gatlinburg

8 hours from Chicago (550 miles)

Why you should visit: With the mild Tennessee spring weather in your favour, you can leave your winter gear behind and enjoy time in the great outdoors on this trip.

The Great Smoky Mountains will be bursting with color in the spring, from the lush new leaves on the trees to the carpet of wildflowers.

In between the winter snow and sometimes humid summer heat, spring break is the perfect time to lace up your hiking boots and explore. If you need to keep teens or older kids entertained too, the fun attractions at Gatlinburg and Dollywood will be just the ticket.

Autumn Scenics in the Great Smoky Mountains National Park

How to get there: Follow the route toward Cincinnati along I-65 and I-74, then take I-275 to bypass the city itself. You'll cross the Ohio River to enter Kentucky, then follow the interstate south towards Lexington. Continue along I-75 and you'll reach Knoxville around an hour after crossing the state border into Tennessee.

To reach Pigeon Forge and Gatlinburg, take I-40 out of Knoxville then turn south on TN-66. From Sevierville, turn onto Parkway which takes you to both towns. This part of the trip will add just over an hour to your drive time.

Our highlights: While you're in Knoxville, enjoy the city's nightlife under the beautiful dogwood blossoms, and check out April's Chalk Walk which sees colorful art on sidewalks across downtown.

When you're ready to head out of town, make for Great Smoky Mountains National Park where trails and lookouts are abundant, or follow the Newfound Gap Road for a spectacularly scenic drive through the mountains.

Just outside nearby Pigeon Forge, Dolly Parton's Dollywood amusement park is a firm favourite with visitors of all ages.

Thrill seekers should definitely head to Gatlinburg's Mountain Coaster, which races rollercoaster-style down the side of the mountain, or Smoky Mountain Ziplines, where you can get a whole new view of this beautiful part of the world.

Bonus: Great Smoky Mountains National Park receives more visitors than any other national park in the United States – more than 11 million a year.

Our travel tips: Because of its popularity the roads into the national park can feel a little crowded at busy times, especially during spring break. Parking lots fill up and you might hit traffic delays. Visit early in the day or in the evening if you want to avoid the crowds – you're also more likely to see wildlife at these times.

Longer trips (Over 8 hours each way)

While a drive of this length probably won't suit spring breakers with young families, this is a great time to take an adventure with older children or to hit the road with a group of friends.

Whether you're heading south for the sunshine or taking in the views on a scenic drive through Minnesota, stop off to explore the towns and cities along the way to add to the fun.

9. Chattanooga, Tennessee

9 hours 20 mins from Chicago (610 miles)

Why you should visit: Built around the Tennessee River and overlooked by Lookout Mountain, Chattanooga is a city where you can easily combine active adventures with big city entertainment.

For a longer spring break trip, stop in Nashville as well to enjoy even more of Tennessee's southern charm and hospitality.

Attractions in Chattanooga put on special events as part of the Spring Break Safari, making the city the perfect family spring break destination. There are child-focused art, science and nature activities on the itinerary, as well as the chance to explore caves, ride the Tennessee Valley Railroad or visit the Tennessee Aquarium.

Seven States Stone at Rock City viewpoint atop of iconic Lookout Mountain, Georgia. The city of Chattanooga Tennessee is nearby.

How to get there: Follow I-65 all the way to Nashville, where you'll merge onto I-24 after a brief stretch on I-40 as you cross the city. I-24 then takes you all the way to Chattanooga, crossing the Tennessee River Bridge then dipping into Alabama for about a mile before you complete your journey in the far south of Tennessee.

Our highlights: As well as being one of the stops on the Spring Break Safari, Tennessee Aquarium is the world's biggest freshwater aquarium. Check out the penguins, otters and alligators as well as plenty of underwater favorites.

A firm favorite with younger children is the Creative Discovery Museum, which features fun, interactive science-based exhibitions to keep them entertained for hours.

Another must-see in Chattanooga is Ruby Falls, a waterfall and cave system which sits under Lookout Mountain. The mountain itself towers above the city and if you're feeling energetic you can hike right up to the top for amazing views across Chattanooga and into Georgia.

A great activity for families or groups of friends, you can take a small pedal-powered boat out to enjoy food and drinks on the Tennessee River.

Bonus: Miniature golf was invented in Chattanooga nearly a century ago, so why not play a round during your stay in the city?

Our travel tips: Chattanooga is notorious for its traffic so avoid travelling in the morning or evening rush hours if possible

10. Hot Springs, Arkansas

10 hours 40 mins from Chicago (700 miles)

Why you should visit: As well as being a great spring break destination, you can turn the drive to Hot Springs, AR, into a fabulous longer road trip with stops in Springfield and St Louis along the way.

People have been coming to Hot Springs in search of the healing powers of its naturally heated spring water for nearly 200 years, so if you're in need of some relaxation and downtime during spring break, this is the place to come.

St. Louis skyscraper at night with reflection in Mississippi River

How to get there: Follow I-55 southeast through Illinois, passing Springfield before you cross the Mississippi River at St Louis, Missouri. After following the interstate south out of the city, turn onto US-67 which winds its way through the gently rolling hills of Missouri and into Arkansas.

At the town of Corning, turn right to continue along US-67/US-62, sticking with US-67 when the highways divide at Pocahontas. At Bald Knob the road merges with US-167 which takes you to the state capital Little Rock. Follow I-30 W out of the city, then turn onto US-70 for the final stretch of your drive to Hot Springs.

Our highlights: Top on most people's list in Hot Springs is a visit to a spa or geothermal spring. There are plenty to choose from, depending on whether your want a traditional bathing experience or a full day of pampering and relaxation.

Bathhouse Row is a National Historic Landmark District where 8 historic bathhouses still stand. Most no longer operate as bathhouses, but at Buckstaff Bathhouse you can still experience the same hot spring bathing experience that the first visitors here in 1912 would have enjoyed.

If some of your group are less interested in spa time than others, Adventureworks Hot Springs is a more active alternative. Ride zip lines and tackle a treetop rope course.

Crystal Ridge Distillery offers informative tastings and free tours where you can find out about the history of the moonshine that's traditionally been produced in this part of the country.

Bonus: The mineral-rich water from the hot springs is said to have healing qualities, and there are fountains across the city where you can take a drink or fill a bottle.

If you happen to be in Hot Springs over St Patrick's Day you can watch “the world's shortest St Patrick's Day Parade”. The event travels less than 100 feet but features several lively Irish-themed entertainment acts.

Our travel tips: Although there are a few natural open air pools where the hot spring water travels down the mountain, bathing in them is not permitted. You can only soak in the geothermal water at Hot Springs at indoor bathhouses and spas.

11. Highway 61 Scenic Drive

11 hours from Chicago (710 miles)

Why you should visit: This trip takes you right up to Grand Portage on the Canadian border, which is the northernmost point on our list.

Spring is one of the best times of year to see the Northern Lights, which are visible along this route. It's an unforgettable spectacle which is definitely worth the long drive out from Chicago. With the weather still feeling wintery, book into a cozy cabin and enjoy quality time together over spring break.

A Band of Green Northern Lights behind Partly Cloudy Night Skies above Traffic Trails on Highway 61 in Northern Minnesota

How to get there: Follow I-90 W out of Chicago for around 100 miles until you reach Wisconsin, then continue for another 100 miles to merge with I-94. From here the road takes you through Eau Claire before arriving in the twin cities of St Paul and Minneapolis.

Exit the city via I-35 W for a couple of miles, before continuing on I-35 N in the direction of Duluth. The interstate ends here and you'll complete your road trip by following Highway 61 Scenic Drive, which follows the shore of Lake Superior all the way to Grand Portage at the Canadian border.

Our highlights: If there is still snow on the ground, that means you can take a scenic dog sledding trip to explore the wild landscapes of the scenic north shore.

The scenic drive along the North Shore is one of the main attractions of this road trip, so make sure you leave plenty of time to stop and enjoy the views along the way.

If the snow has melted, pack your hiking boots and set out to explore Tettegouche, Temperance River or Cascade River State Parks, which are all easily accessed from Scenic Route 61 along the lakeshore.

At Lutsen you can ski in colder months or, if spring has come early when you visit, head up to the peak via gondola to enjoy stunning views.

Bonus: You can't drive this route without stopping off in Grand Marais to visit World's Best Donuts, a local legend.

Our travel tips: As you might expect this far north, temperatures can be cold especially if your spring break falls early in March. Heavy snow is possible but not guaranteed during March and April, so stay flexible in your choice of activities if you take this trip.

This trip is probably best suited for travellers who can visit a little later in the season if you want to comfortably spend more time outdoors.

12. Atlanta, Georgia

11 hours from Chicago (730 miles)

Why you should visit: Atlanta is the southernmost destination on our list and is an amazing place to visit from Chicago during spring break .

You're almost certain to enjoy some much-needed spring sunshine here, without the large crowds that you'll find further south in Florida or on the coast.

Centennial Olympic Park in Atlanta during twilight hour after sunset

How to get there: Head south through Nashville to Chattanooga on I-65 and I-24. As you enter Georgia just south of Chattanooga, I-24 merges with I-75 which takes you as far as the suburbs of Atlanta.

Depending on your final destination in Atlanta, you'll probably join up with I-85 to complete your journey in city's downtown.

Our highlights: Families should head straight to Centennial Park, a huge outdoor space which covers the site of the 1996 Olympic Park. The Children's Museum of Atlanta is on the edge of the park too.

Zoo Atlanta is a must-see for visitors of all ages. It's one of the only places in the United States where you can see Giant Pandas, alongside many other endangered species.

There's also a wealth of sites dedicated to modern US history and the Civil Rights movement in Atlanta, including the National Center for Civil and Human Rights and Martin Luther King Junior National Historical Park.

If you're travelling with older spring breakers, Six Flags Over Georgia theme park is a great stop, and sports fans should definitely check out the College Football Hall of Fame.

Bonus: Coca-Cola originated in Atlanta in the 1880s, which is why you'll find the World of Coca-Cola in the city today.

Our travel tips: “Rush hour” in Atlanta lasts all day. Allow plenty of time for your journey if you're using your car to get around the city.

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weekend trips from chicago by car

BEST Weekend Getaways From Chicago in 2023 (From a Local)

The best weekend getaways from Chicago in 2023 whether you love nature, beaches, cities or small towns. From romantic getaways for couples to fun vacations for friends or families, there is something for everyone on this list.

Best Weekend Getaways From Chicago

Looking for the best weekend trip from Chicago? Fortunately there are many places in the United States (and even Canada) that are a short drive or flight away. You will love these weekend getaways from Chicago – from amazing places in the Midwest that you can easily drive to from Chicago to a few incredible cities that are only a short flight away.

(And make sure to check out my  essential road trip packing list (with free printable pdf) if you are driving or my carry on packing list  to make sure you have all your travel essentials before you go!) Disclaimer: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.

Lake Geneva, Wisconsin

Lake Geneva Wisconsin is one of the best weekend getaways from Chicago

Lake Geneva, a resort city on the shore of Geneva Lake is a popular vacation destination from Chicago. In fact, wealthy Chicagoans built their mansions here during the Gilded Age. Visitors can still get an up close view of these beautiful homes by walking the 20 mile Geneva Lake Shore Path around the lake.

If being in the water is more your thing, you can rent just about anything (speedboats, jetskis, kayaks, pontoons, etc) for an adventurous day. While Lake Geneva is a great place for some beach fun, visitors can also enjoy zip-lining, a waterpark, golf, a petting zoo, spas and more.

Lake Geneva is also a great destination for a winter weekend getaway as visitors can go skiing and snowboarding or visit the ice castles .

Read about the best things to do in Lake Geneva here .

Stay: Grand Geneva Resort & Spa

Getting There: By Car: Lake Geneva is only 83 miles from Chicago

Elkhart Lake, Wisconsin

Elkhart Lake is a less known weekend getaway from Chicago

Elkhart Lake is a quaint town where visitors can really experience an authentic summer lake getaway but also enjoy the year-round offerings. Take a dip in the crystal clear waters, experience the various watersports (paddleboarding, kayaking, jet skiing), go fishing or just lounge around on a pool float.

While the lake is a big draw, there is so much more to the area. From hiking the picturesque Kettles, The Ice Age Trail or along the shore of Lake Michigan, there is no shortage of beautiful hiking spots. Golf enthusiasts will appreciate the top golf destinations located less than 30 minutes away. Motorsports lovers and thrill seekers will want to check out Road America Racetrack , North America’s longest natural road racing facility.

The fun doesn’t end when summer is over. Dog sledding, snowshoeing, skiing and carriage rides are available for winter time fun.

Stay: The Osthoff Resort

Getting There: By Car: Elkhart Lake is 150 miles from Chicago (about 2.5 hour drive)

Galena, Illinois

Galena Illinois is one of the best weekend getaways from Chicago

Galena is short road trip from Chicago but it is a great place for a weekend getaway whether on a romantic trip or traveling with kids. Galena is a charming and historic small town. A large portion of the city is listed on the National Register of Historic Places and there are many historical sights to explore including the Ulysses S. Grant Home, the Elihu B. Washburne House, Dowling House and the Old Market House.

Some things to do in Galena including shopping downtown at the many boutiques and antique stores, eating at local restaurants and wine tasting at local vineyards or exploring the lush rivers and hiking trails dotted throughout the area. Galena is close to Apple River Canyon State Park , an Illinois state park, where you can go hiking, fishing and more.

Stay: Country Inn & Suites by Radisson

Getting There: By Car: 164 miles driving distance from Chicago

Cheap Car Rentals

Dubuque, Iowa

Dubuque, Iowa’s oldest town, is located across the Mississippi River about 20 minutes from Galena, Illinois. With its historic architecture and hilly landscape, Dubuque is worth visiting year round.

Some of the best things to do in Dubuque including visiting the 14-acre National Mississippi River Museum & Aquarium and enjoyng spectacular views of the river from Eagle Point Park .

From April though November, visitors can ride Fenelon Place Elevator Company (also known as the Fourth Street Elevator), a historic cable car. This funicular railway has been called “the world’s steepest, shortest scenic railway” and has great views of downtown Dubuque, the Mississippi River and 3 states.

Winter activities include skiing and snowboarding at Sundown Mountain Resort, cross country skiing, snowshoeing and hiking.

Stay: Hotel Julien Dubuque

Getting There: By Car: Dubuque is 178 miles from Chicago (just over a 3 hour drive)

Milwaukee, Wisconsin

Milwaukee is famous for its beer -it is nationally recognized with the nickname “Brew City” due to its nearly two centuries of brewing heritage from multiple past major brewers including Miller Brewing Company, Pabst Brewing Company, and Joseph Schlitz Brewing Company. One of the best things to do in Milwaukee is to tour one of its many breweries. Another interesting attraction is the Harley-Davidson Museum.

Stay: Brewhouse Inn and Suites (boutique hotel housed in what was once the main Pabst brewery building)

Getting There: By Car:   93 miles driving distance By Train: Amtrak Hiawatha train offers frequent daily service between Milwaukee and Chicago. By Air: It probably does not make sense to fly but there are daily nonstop flights from Chicago O’Hare to Milwaukee Mitchell International Airport (MKE)

New Buffalo, Michigan

New Buffalo, Michigan is a charming beach town on the shores of Lake Michigan. The beaches face west and have beautiful sunsets.

In addition to the beaches, a must see attraction is Galien River County Park , a beautiful park with boardwalk paths through the marsh.  For those that enjoy gambling, New Buffalo is home to the Four Winds Casino Resort .

Getting There: By Car: 70 miles driving distance By Train: New Buffalo has daily Amtrak service from Chicago on the Blue Water and Wolverine lines.

South Bend, Indiana

One of the best things to see in South Bend is the Studebaker National Museum , featuring a large collection of Studebaker automobiles drawn from the history of the company, beginning with horse-drawn carriages. They also have the carriage that Abraham Lincoln took to Ford’s Theater the night he was assassinated.

For those with a sweet tooth, visit the South Bend Chocolate Company, which is home to one of the largest collections of chocolate memorabilia in the world, including a 1,300-year-old Mayan chocolate pot among the hundreds of tins, containers and chocolate boxes of all shapes and sizes.  Visitors can take a factory tour for a history lesson of chocolate and its origins, as a guide leads guests through all of the factory processes, including panning, enrobing and more, including a test sample at the end. For an extra special treat, you’ll dip a chocolate spoon, walk through the Chocolate Museum and receive 10% off your purchase that day.

South Bend is famous for being home to the University of Notre Dame. There are many attractions on the beautiful, large campus including the Golden Dome, Notre Dame Stadium, the Basilica of the Sacred Heart and the Grotto of Our Lady of Lourdes, a replica of the famous shrine.

Stay: Aloft South Bend or Morris Inn at Notre Dame (if you want to stay on-campus)

Getting There: By Car:   96 miles driving distance By Train: South Shore Line commuter rail runs multiple daily trains between Millennium Station in downtown Chicago and South Bend Airport station. By Air: United Express has multiple daily flights from Chicago O’Hare and South Bend International Airport (SBN)

Madison, Wisconsin

In addition to being the capital of Wisconsin, Madison is a fun college town full of cafes, breweries, restaurants, bookstores and other attractions. For those that enjoy being outdoors, Madison is a good base for nature-filled activities in the area including hiking, biking, fishing and boating.

Getting There: By Car: 147 miles driving distance from Chicago

Holland, Michigan

Located on the shores of Lake Michigan, the city of Holland, Michigan, which was founded by Dutch Calvinists in the late 1840s, proudly flaunts its Dutch origins, and is home to canals and a 250-year-old authentic Dutch windmill.

Holland is especially pretty in the spring when you can see colorful tulips in local gardens, parks, attractions and lining the streets. You can see millions of tulips at Veldheer Tulip Gardens . One of the mont popular times to visit is during the Tulip Time Festival , the largest tulip festival in the United States which is held every year in May.

Stay: Courtyard by Marriott Holland Downtown

Getting There: By Car: 150 miles driving distance from Chicago

Door County, Wisconsin

Door County , located in the northeast corner of Wisconsin, is a hidden gem full of charming villages and towns, lighthouses, state parks, vineyards, and outdoor attractions and activities.

Sturgeon Bay is a convenient base for exploring the area. The city is a fisherman’s mecca, with some of the best bass fishing in the world. You can also tour a restored tug, visit the Door County Maritime Museum, learn the history of Door County, stroll down historic 3rd Avenue, or enjoy nature at Potawatomi State Park on the city’s edge.

Explore one or more of several little towns located along the east and northeast coastline of Door County which full of unique shops, galleries, restaurants and breweries.

Bring your car or bike on the 30 minute ferry to Washington island, located northeast of the tip of the Door Peninsula.

Stay: Sturgeon Bay, Egg Harbor, Fish Creek, Bailey’s Harbor or Sister Bay all have good options

Getting There: By Car: 244 miles driving distance to Sturgeon Bay

Shawnee National Forest

Nestled between the Mississippi and Ohio Rivers in southern Illinois, the Shawnee National Forest is full of natural beauty, making it ideal for outdoor recreation from hiking to climbing.

The stunning Shawnee National Forest landscape features woodlands, hills, lakes, creeks, rock formations, cliffs and bluffs. You can also see wildlife such as bad eagles.

Shawnee National Forest is the best place to go hiking in Illinois with spectacular views. Trails include the long River to River Trail and the Rim Rock National Recreational Trail. The must see attraction is the Garden of the Gods wilderness area featuring ancient sandstone cliffs and formations.  Climbers should not miss the Jackson Falls climb on 60 feet of sandstone cliffs and boulders that include numerous freestanding towers.

If you enjoy wine, The Shawnee Hills Wine Trail features 11 wineries located along a 35-mile scenic drive along highway 127 and highway 51 in the Shawnee National Forest.

Stay: Riverview Mansion Hotel (a unique boutique style mansion)

Getting There: By Car: 300 miles driving distance from Chicago

Do you prefer to fly rather than drive? Here are a few cities worth visiting for the weekend that are only a short flight away.

Toronto, Canada

Canadian bucket list places to visit in canada during the summer

Although Toronto is in a different country, it is only a short flight away. You can even drive there in one day but that is long drive unless you have a long weekend.

Toronto is very similar to Chicago in that it offers great theater, shopping and restaurants. The CN Tower, the tallest freestanding structure in the Western Hemisphere is a must see attraction. If you are feeling brave, try the EdgeWalk, a walk outside on the ledge encircling the top of the CN Tower. Other must see places are St. Lawrence Market and the Distillery District.

Looking for more things to do in Toronto? Here is a 3 days in Toronto itinerary written by a local.

Stay: Fairmont Royal York (located right by Union Station)

Getting There: By Air: Several airlines offer nonstop flights between Chicago O’Hare and Toronto Pearson International Airport (YYZ) which is approximately a 1.5-2 hour flight. By Car:   523 miles (about 8.5 hour drive)

Atlanta, Georgia

Atlanta, Georgia is another great city for a weekend getaway especially if you want to indulge in some southern food.  Some must see attractions (especially for families) include Piedmont Park, Georgia Aquarium, College Football Hall of Fame and the World of Coke. Here are the best things to do with 2 days in Atlanta .

Getting There:

By Air: There are numerous flight options between Chicago and Atlanta from both Chicago O’Hare and Chicago Midway. Flight time is approximately 2 hours.

New York City

New York City is an easy city to fly to for the weekend. Here are the best things to do with 2 days in NYC .

By Air: There are numerous flight options between Chicago and New York City from both Chicago O’Hare and Chicago Midway. Flight time is approximately 2 -2.5 hours.

What are your favorite weekend getaway from Chicago ?

Related Posts

30+ BEST Things to Do in Chicago in the Summer 2023 (From a Local)


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St. Joseph lighthouses

The best day trips from Chicago

Explore small-town breweries, bakeries and artisan shops when you embark on these easy day trips.

Jeffy Mai

You don’t have to go far or spend a lot of money to enjoy a nice escape from Chicago. A simple day trip offers a fun change in scenery and is cheap and easy. Luckily, there are many exciting destinations within driving distance or accessible by train that provide the perfect getaway. Spend an afternoon soaking up the rays on beaches along Lake Michigan, go hiking near Chicago in a state park or sample a variety of beers and cheeses up north in Wisconsin. The attractions are endless, ranging from amusement parks and Japanese gardens to museums and historic lighthouses. So whether you’re low on PTO or just trying to keep travel costs down, check out our guide to the best day trips from Chicago to explore everything the Midwest has to offer.

RECOMMENDED: The best weekend getaways from Chicago RECOMMENDED: The most unique day trips from Chicago RECOMMENDED: The best Chicago staycation ideas

An email you’ll actually love

Top day trips from Chicago

Milwaukee, WI

1.  Milwaukee, WI

Driving time from Chicago: One and half hours

Getting to the Cream City requires a painless drive, but if you plan to fully indulge, ditch the car and hop on the BYOB-friendly Amtrak, which will deposit you in the heart of the city in an hour and a half. Start your day with a stack of pancakes and a round of mimosas at Sweetdiner . Meander around the Historic Third Ward and hop into home decor shops like The Home Market  or fun specialty shops like MOD GEN . Seek refuge and treats at the Milwaukee Public Market , where you’ll find a hodgepodge of the city’s best vendors, including blends from The Spice House , seafood from St. Paul Fish Company , hand-dipped chocolate from Kehr’s Candies  and vino from Thief Wine Shop & Bar . Before catching a train home, walk off the day with a trek along to Lakeshore State Park , a unique 22-acre urban oasis that juts out from the shoreline.

2.  Fennville, MI

Driving time from Chicago:  Two hours and 20 minutes

Many Chicagoans wait until fall to venture up to western Michigan’s fruit belt. But there’s a compelling argument to be made for hitting the area a couple of months earlier, when the countryside is tranquil and stone fruits like peaches and cherries are ripe for picking. The petite town of Fennville is a great base for tasting the region’s sweet bounty in a host of iterations. Start off with a slice or two of the good stuff at local favorite Crane’s Pie Pantry , a bakery, restaurant and winery housed in a 150-year-old barn. From here, a five-minute drive will deliver you to Virtue Cider , founded by former Goose Island brewmaster Greg Hall. Reserve a spot for a guided trail tour that includes a glass of cider. Finally, make your way to Salt of the Earth for wood-fired pizza and seasonal dishes made from scratch with local and sustainable ingredients.

South Bend, IN

3.  South Bend, IN

Driving time from Chicago:  One hour and 45 minutes

There’s more to South Bend than Fighting Irish football. Check out the city’s cultured side with an afternoon visit to the History Museum , a stately Victorian mansion that was once home to the family of local industrialist and inventor James Oliver. From there, browse the local bounty at the South Bend Farmers' Market , where you can shop everything from artisan breads and doughnuts to farm-fresh fruits and veggies. When hunger strikes, head to  Café Navarre , an upscale dining spot housed in a repurposed '20s-era bank. 

Madison, WI

4.  Madison, WI

Driving time from Chicago:  Two and half hours

Located on an isthmus between two lakes, Madison is a city that’s filled with beautiful sights—in addition to all the cheese and beer you’ve heard so much about. Begin your visit with a scenic tour of the college town on two wheels. You can rent a bike from dozens of BCycle stations , allowing you to make 30-minute trips. The Capital City trail winds around Lake Monona (the smaller of the two lakes) and provides plenty of picturesque stops for an Instagram snapshot of the skyline. Now, onto that cheese and beer: To drink like a local, head for The Malt House , a “craft beer oasis” that dates back to the Civil War era and boasts taps from local brewers like New Glarus and Central Waters. Head for Capitol Square to visit Fromagination , where you’ll find artisanal Wisconsin cheeses and knowledgeable cheesemongers to help you make a decision. Take an evening to visit the Memorial Union   Terrace , a lakefront space on the University of Wisconsin campus where you can enjoy brats, beer and live music during the summer months.

5.  Gurnee, IL

Driving time from Chicago:  One hour

Located right off I-94, the village of Gurnee is a shopping and entertaining hub that draws 23 million visitors each year—including plenty of nearby Chicagoans. Start your day by fueling up with the brunch buffet at The Chocolate Sanctuary , where you can pile your plate with housemade bagels with lox, shrimp cocktail and chocolate-dipped strawberries. Spend some time digesting while you stroll around Gurnee Mills , which hosts more than 160 stores selling everything from sporting goods to home decor. Thrill seekers won’t want to miss Six Flags Great America , where you’ll find high-speed roller coasters and intense drop rides. On a hot day, you’ll want to plunge down the water slides and splash around the wave pool at Hurricane Harbor. If you can resist indulging in funnel cakes or turkey legs at the park, save your appetite for Primo Italian American Cuisine , where the dinner menu features black truffle ravioli and a tomahawk ribeye. Those visiting on a Friday can end the night with live music in The Parlor, Primo’s speakeasy-style lounge.

6.  Oglesby, IL

Driving time from Chicago:  Two hours

It may not be the mighty Colorado, but Oglesby’s Vermillion River offers the best rafting you’re liable to find within a quick jaunt from Chicago. A 9.5-mile run with Vermillion River Rafting will shoot you over 14 rapids, most of them class I and II. After you’ve handed over your paddle, hop in the car and head up the road to Starved Rock Lodge , where you can catch your breath and lunch on casual fare like burgers or a strawberry pecan salad at the Back Door Lounge. When you feel sufficiently refreshed, hit the hiking trails at adjacent Starved Rock State Park to spot dramatic waterfalls and explore cool glacial canyons. Unwind from your nature adventures by grabbing a nostalgic treat at The Rootbeer Stand   or check out "farm to foam" at The Lone Buffalo by Tangled Roots Brewing Company  in nearby Ottawa. 

St. Joseph, MI

7.  St. Joseph, MI

Golden, sandy beaches and a picturesque shoreline attract visitors to St. Joseph and its twin city Benton Harbor. You can spend an entire day out on the water with a rental from Blue Water Boat Rentals , or walk over to the St. Joseph Lighthouses — guided tours are available. If you’re hungry, you won’t have to wander far for good grub, as Silver Beach Pizza —located inside a century-old train depot—slings dependable tavern-style pies. Oenophiles, hit up a variety of vineyards and tasting rooms on the Lake Michigan Shore Wine Trail for some fine Midwestern pours.

8.  Harbor Country, MI

Driving time from Chicago:  One and a half hours

Just across the Indiana border, Michigan’s lakeside “Harbor Country” is only an hour and a half drive from downtown Chicago. Start at the north end, in Sawyer, where you can visit the original taproom of Greenbush Brewing Co.  Pair a pour of Star Chicken Shotgun IPA with some barbecue or Cajun fare. Up next, take the Red Arrow Highway down the lakeshore for great shopping, like hunting through the Harbert Antique Mall . Head back inland to the artsy community of Three Oaks to finish your day at Journeyman Distillery . A $13 tour and tasting nets you samples of 12 different spirits made in the converted corset factory. Plan to sit down for a meal at the distillery’s Staymaker restaurant afterward; you’ll need some food before getting back on the road to Chicago. 

Kenosha, WI

9.  Kenosha, WI

Driving time from Chicago:  One hour and 15 minutes

About an hour north of Chicago sits this Wisconsin town filled with a plethora of things to do. Within a mile radius of the downtown area are five museums—you can gaze at dinosaur fossils and learn about the link between the prehistoric reptiles and birds at the Dinosaur Discovery Museum , or explore how the Civil War affected people on the western front at the Civil War Museum . During spring to fall, visit the Southport Lighthouse and climb 72 steps to the top for unparalleled views of Kenosha and, on a clear day, the Chicago skyline. If it’s summertime, you must check out the Bristol Renaissance Faire , where you’ll find a recreated 16th century port city populated with fairgoers dressed as knights, maidens and much more. After you’ve worked up an appetite, head over to Frank’s Diner , an almost century-old restaurant set inside an old railway car. And don’t forget to grab some cheeses and New Glarus beers at the famed Mars Cheese Castle on the way home.

Rockford, IL

10.  Rockford, IL

Situated less than 100 miles northwest of Chicago, Rockford is a surprisingly plentiful road trip destination for families. If the kids are in tow, start the day with a visit to the Discovery Center Museum , which boasts more than 300 hands-on exhibits focused on everything from light and art to color and electricity. For a dose of fresh air and nature, wander through the Anderson Japanese Gardens , a breathtaking 12-acre oasis that's filled with winding pathways, koi-filled ponds, and colorful plants. Everyone in the car will find something to love at Prairie Street Brewing Company , where bar food is elevated through dishes like Korean street tacos, Cajun mac ‘n cheese and wild mushroom quesadillas. Pick up a few cans of Screw City Light—with notes of fresh-baked bread—to take home and extend your day trip. 

Cedarburg, WI

11.  Cedarburg, WI

Located just 20 miles north of Milwaukee, Cedarburg is an ideal place to wind down and take things slow. The charming small town is brimming with old-world architecture, friendly Midwesterners and culture galore. If you can, plan your trip around one of the town’s seasonal events, with options including the Wine & Harvest Festival and Oktoberfest —all of which offer ample opportunities to meet local vendors and sample their wares. When you’re not rubbing elbows with the close-knit community at a street fest, make time to walk around the Cedarburg Art Museum , which hosts exhibitions from Wisconsin artists inside a former home that was designed in 1898. If wine bars are more your scene, head to Cedar Creek Winery , where you can sip your way through a $10 wine fight or enjoy a seasonal wine and cheese tasting for $25. On your way out of town, make one last stop at Amy’s Candy Kitchen to grab a hand-crafted caramel apple for the road. 

Kankakee County, IL

12.  Kankakee County, IL

Driving time from Chicago:  One and half hours

The Kankakee River has been a treasured area for centuries, occupied by the Illini and Miami tribes in the 17th century. Kankakee River State Park surrounds the river for about 11 miles, totaling to 4,000 acres of protected land. It’s a popular spot for fishing, canoeing, hiking and bicycling. Frank Lloyd Wright fans can visit the B. Harley Bradley House , built in 1900 and billed as the architect’s first Prairie Style home. Bring the kids to Perry Farm Park , which features a children’s museum, nature trails, playground and picnic areas. 

Oak Park, IL

13.  Oak Park, IL

Drive time from Chicago:  Half an hour

You can't call yourself a Frank Lloyd Wright fanatic until you've spent the day in Oak Park, where you'll find the famed architect's home and studio as well as a smattering of other Prairie-style abodes he designed. If it's your first time, book a tour through the Frank Lloyd Wright Trust . Now that you've worked up an appetite, grab brunch or dinner at Maya del Sol , where margaritas flow like water and the ceviche is tops. Have time for one last stop? Grab a seat at Kinslahger Brewing Company , a small but mighty taproom pouring lagered brews. 

Grand Rapids, MI

14.  Grand Rapids, MI

Driving time from Chicago:  Three hours

Summer and fall are peak seasons to visit Grand Rapids, but you’d do best to plan ahead and book your visit during ArtPrize , an international art competition in September and October when art is displayed in museums, bars, public parks and hotels. Regardless of when you go, Grand Rapids has you covered on the beer front with dozens of breweries—so be sure to bring a designated driver. First stop: Brewery Vivant for poutine and a German- or Belgian-style beer. A quick 10-minute drive will put you in the middle of downtown, where you should find parking and hoof it a while. Stop at Madcap Coffee for a post-beer pick me up before heading to City Built Brewing for creole bites and a range of beers for every palate. Finally, grab your car and head to Butcher's Union  for a dinner complete with prime cuts of beef and pours of whiskey.

New Buffalo, MI

15.  New Buffalo, MI

Driving time from Chicago:  One hour and 15 minutes

A charming beach town in Harbor Country, New Buffalo is popular during the warmest months. Escape the crowded Chicago lakefront and head for the sandy shores of the Mitten State, where the water’s warmer and clearer. Soak up some rays and then stroll down Whittaker Street to peruse cute shops and art galleries. Book a spa treatment at The Harbor Grand Hotel for a re-energizing experience; adventurers can rent a kayak or paddleboard from Third Coast Paddling and go exploring on the Galien River. When you need to refuel, grab a seat on The Stray Dog Bar & Grill’s bustling patio or sink your teeth into a big, juicy burger from Redamak’s . But make sure to save room for unique ice cream flavors, like Mackinac Island Fudge and Jacked Up Tennessee Toffee, at Oink’s Dutch Treat .

Monroe, WI

16.  Monroe, WI

If your cheese preferences embrace the pungent, you’ll find yourself in good company in charming Monroe, Wisconsin, gateway to a region teeming with cheesemakers specializing in varieties like Swiss and nostril-tingling Limburger. For some context, begin your day at the National Historic Cheesemaking Center , where you’ll get a crash course in south central Wisconsin’s cheesy history. Next, head to the Alp and Dell cheese store to browse more than 100 varieties of cheese, mostly from local producers, and all the wine, beer and sausage you’d want to pair them with. When you’re ready for lunch, make your way to the unapologetically old-school Baumgartner’s Cheese Store & Tavern on Monroe’s pleasant courthouse square and order the infamous specialty: a slab of Limburger on rye crowned with mustard and sliced red onions. For a chaser, stroll around the block to Minhas brewery. 

Lemont, IL

17.  Lemont, IL

Driving time from Chicago: One hour

The Village of Lemont developed as part of the construction of the canal linking the Illinois River and Lake Michigan, which also led to the discovery and development of the limestone quarries used to supply materials for iconic Illinois buildings like the Chicago Water Tower. Today, you can hop on the Metra and visit the Heritage Quarries Recreation Area , where you can walk, bike or fish along the I&M Canal (just be sure to look out for the many water birds drawn to the area). If you’re hoping for a bit more excitement, visit The Forge: Lemont Quarries . The adventure park features laser tag, a zipline and ropes courses for all ages and skill levels. Afterwards, head to the village’s historic downtown area to visit Pollyanna Brewing Company and try The Full Lemonty, their signature golden ale. You can also find the brewery’s beer on tap at Wooden Paddle , where you can watch your wood-fired pizza and other small plates being prepared before they hit your table.

Holland, MI

18.  Holland, MI

Driving time from Chicago:  Two and a half hours

Once a stronghold of Calvinist separatists who arrived here from the Netherlands in the mid-19th century, the town of Holland continues to celebrate its Dutch heritage. To go Dutch for the day, start off with a breakfast of flaky, almond paste-filled bankets and house-roasted coffee at deBoer Bakkerij . Afterward, head across town to Veldheer Tulip Gardens , where five million of the eponymous flowers explode into bloom each spring. When hunger hits, make your way downtown for lunch and a beer at New Holland Brewing , one of the Midwest’s best-loved brewpubs. (Not sure what to sip on? Look for limited-release variations on brewery fave Dragon’s Milk, a bourbon barrel-aged stout, enriched with ingredients like cocoa nibs and peanut butter.) Wrap up your trip with a leisurely stroll around Windmill Island Gardens , a picturesque park centered around a 250-year-old Dutch windmill purchased by Holland residents in the 1960s. 

Long Grove, IL

19.  Long Grove, IL

Driving time from Chicago:  45 minutes

Located 35 miles northwest of Chicago, Long Grove was founded in the 1800s by German farmers, and many of the town’s original homes and buildings are still standing. Try to visit Long Grove during one of its many delicious festivals such as Apple Fest or Strawberry Fest , when local chefs and other vendors flock to the historic downtown area to offer numerous versions of the spotlighted food. Stop by  Buffalo Creek Brewing and have a beer in their Bavarian-style taproom or in the Biergarten, which hosts live music and food trucks during the summer. Before you hit the road, swing by Long Grove Confectionery to pick up some peanut brittle or their signature Giant Myrtle, made with roasted pecans or cashews topped with caramel and milk or dark chocolate.

Lake Geneva, WI

20.  Lake Geneva, WI

Lake Geneva has long been an accessible weekend destination for wealthy suburban Chicago families. But no matter your budget, a quick retreat to this idyllic vacation town is sure to be a blast. The town rests on Geneva Lake, an 8-square-mile body of water made for summertime fun. First things first: Get out on the water. Rent a kayak or paddleboard from Clear Water Outdoor , or take a wake surfing private lesson at Gage Marine . If you can’t get your sea legs, trek a portion of Lake Geneva’s 21-mile circumference on the Geneva Lake Shore Path and gawk at the century-old mansions that rest on the shore. When you’re hungry, Egg Harbor Café and Simple Cafe , both in the town center, offer delicious, no-fuss diner eats. If you’re feeling spendy, Baker House , a 19-century mansion-turned-hotel, offers a popular Champagne brunch with waterfront views. 

Evanston, IL

21.  Evanston, IL

Driving time from Chicago:  40 minutes

If you're short on time but craving a day away from the city, hop on the Purple Line and head to Evanston. The sweet college town is located just a few miles north of Chicago, which means you can explore the day away and still be home for dinner. Start the morning at the otherworldly Baha'i House of Worship , an architectural gem located a few miles north in Wilmette. Wander the pristine grounds before stepping inside the functioning temple, one of the oldest of its kind in the world. Up next: Fill up on colorful macarons, cakes and doughnuts at Bennison's Bakery before checking out the outdoor exhibition at the Block Museum of Art and taking a free art walk to see the 16 sculptures placed in public spaces on Northwestern University’s campus. Don't get back on the train without grabbing a brew from Temperance Beer Co. If you have the time, take a $10 brewery tour that includes samples and a souvenir pint glass. 

Michigan City, IN

22.  Michigan City, IN

If you’re car-less, this small city is a perfect option for a day trip from Chicago. Hop on the Amtrak at Union Station and you’ll be in Michigan City in just over an hour. Or, take the South Shore Line and you can hop off right at the Indiana Dunes National Park , 15 miles of gorgeous sand dunes on the southern shore of Lake Michigan. Michigan City proper, too, is filled with great things to do. Visit Washington Park where you can picnic on the beach or check out the lions, wolves and other animals from around the world at the Washington Park Zoo . Hungry? Walk over to Shoreline Brewery , a gem of a microbrewery with a rotating selection of beers on tap and tasty pub grub. You can also sample local flavors at Fiddlehead , which serves high-quality comfort food including fried lake perch and grass-fed beef burgers. 

Galena, IL

23.  Galena, IL

Driving time from Chicago:  Three hours

While this city on the Mississippi River might be best known for its resorts, you don’t need to stay the night to enjoy its mix of historical sites and outdoor activities. Start your day with brunch at Otto’s Place , where you can enjoy biscuits and gravy featuring housemade buttermilk biscuits and locally sourced sausage with a Bloody Mary or mimosa. Head across the Galena River to Nuts Outdoors and rent an electric bike to ride along the trails and into town. Take a tour of the city’s proudest attraction, the Ulysses S. Grant Home , which was gifted to the 18th president when he returned from fighting in the Civil War. If you want to learn more, you can visit the Galena & U.S. Grant Museum , which also features an offsite working blacksmith shop. That history is also on display at Galena Brewing Company , where you can sip Ult’s Dark oatmeal stout while listening to live music and feasting on a bison burger or a giant pretzel with beer cheese and house mustard.

Fairbury, IL

24.  Fairbury, IL

Observant Chicago foodies may have noticed a couple of names popping up over and over again in the menu sourcing notes that have become de rigueur in these locavore-obsessed times: Kilgus Farmstead (for dairy) and Slagel Family Farm (for a range of meats). Turns out, our favorite chefs’ favorite suppliers sit just a three-mile hop from each other in the central Illinois town of Fairbury. On an hour-long tour of Kilgus , you’ll get acquainted with the farm’s herd of sweet, doe-eyed Jersey cows, learn the ins and outs of milking, and sample freshly spun soft-serve. Bring a cooler and hit the on-site store for Kilgus dairy and meat as well as goods like eggs and honey from nearby producers. Slagel has teamed up with chefs from notable Chicago restaurants to put on a program of farm dinners throughout the summer and fall. After an interactive tour and a butchering demo, you’ll retire to a picturesque barn for the main event, a family-style, BYOB meal prepared by the guest chef. 

New Glarus, WI

25.  New Glarus, WI

Driving time from Chicago: Two and a half hours

Chances are you’ve already heard of New Glarus thanks the town’s eponymous brewery — which offers self-guided tours Monday through Friday and a lovely beer garden—but there are plenty of reasons to visit “America’s Little Switzerland” other than beer.  This charming, walkable town features a variety of tempting shops, hearty restaurants and themed events celebrating the town’s Swiss history and culture like the Heidi Folk Play Festival   in June . Be sure to grab a nut horn at the New Glarus Bakery , and get your fondue fix at the Chalet Landhaus restaurant. If you visit between May and October, don’t miss the seasonally-open Swissland mini golf course, featuring Alpine-themed obstacles and friendly goats.

26.  Spring Green, WI

Driving time from Chicago: Three and a half  hours

Despite boasting a population just shy of 1,700 people, this town west of Madison has a lot going on. Most visitors are here to visit one of two sprawling complexes: Taliesin , the estate and studio of legendary architect Frank Lloyd Wright, or the infinitely weirder House on the Rock , the brainchild of artist Alex Jordan where curious travelers can explore rooms on rooms of infinity mirrors, dollhouses, nostalgic cars, circus ephemera and the world’s largest indoor carousel. When you’ve had your fill of architecture or funky assorted collections,  get a taste of traditional Wisconsin hospitality at Arthur’s Supper Club . Theater buffs can take in a show at the American Players Theatre .

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Man suspected of killing 8 people in suburban Chicago was related to most of the victims, police say

Kathleen Foody And Ken Miller

Associated Press

CHICAGO – A man suspected of shooting and killing eight people in suburban Chicago this weekend was related to most of the victims, authorities said Tuesday, a day after the 23-year-old fatally shot himself during a confrontation with law enforcement in Texas.

The Illinois authorities provided a clearer timeline of the shootings on Tuesday, saying they believe all eight people killed and a ninth person wounded were shot Sunday and Romeo Nance fled the area by that evening. But they told reporters there is no evidence of a motive yet for the killings.

“We can’t get inside his head,” Joliet Police Chief Bill Evans told reporters. “We just don’t have any clue as to why he did what he did.”

Investigators believe Nance first shot seven people at two relatives’ homes in the city of Joliet on Sunday, then fired randomly at two men — one outside an apartment building and another on a residential street, Joliet and Will County officials said Tuesday.

Police said they had not yet determined the victims' exact relationships to Nance.

The Will County coroner on Tuesday identified the victims found at the Joliet homes: 38-year-old Christine Esters, 47-year-old Tamaeka Nance, 35-year-old William Esters II, 31-year-old Joshua Nance and 20-year-old Alexandria Nance. The names of two teenage girls, 14 and 16, were not released.

Authorities previously identified the man killed outside the apartment building as Toyosi Bakare, a 28-year-old man originally from Nigeria who had been living in the U.S. for about three years.

Nance fatally shot himself Monday evening after U.S. Marshals located him near Natalia, Texas, about 30 miles (48 kilometers) southwest of San Antonio and more than 1,000 miles (1,690 kilometers) from Joliet, authorities said. He had no known ties to Texas, Illinois authorities confirmed Tuesday.

Nance's death was announced hours after Illinois authorities used social media and a news conference to share initial details of the killings there.

Medina County, Texas, Sheriff Randy Brown said his office received a call Monday about a person suspected in the Chicago-area killings heading into the county on Interstate 35. Brown said he believes the suspect was trying to reach Mexico.

“It seems like they (criminal suspects) all head to Mexico,” which is about 120 miles (193 kilometers) south of Natalia along Interstate 35, Brown said Tuesday.

Officers from multiple agencies confronted Nance, Brown said.

The Texas Rangers are investigating Nance’s death and believe he shot himself, said Lt. Jason Reyes, a spokesperson for the Texas Department of Public Safety, of which the Rangers are part.

Reyes said he could not provide any other information about the circumstances of Nance’s death or his confrontation with law enforcement officers, saying his agency was only brought in to investigate after the fact. The Rangers routinely investigate deaths involving law enforcement in Texas.

The Illinois shootings represent the fourth mass killing in the U.S. this year, according to a database maintained by The Associated Press and USA Today in a partnership with Northeastern University. The third happened Sunday in another Chicago-area suburb, Tinley Park, where police have charged a man with killing his wife and three adult daughters.

The database defines a mass killing as an attack in which four or more people have died, not including the perpetrator, within a 24-hour period.

The victims were found Sunday and Monday at three separate homes, authorities told reporters at a news conference earlier Monday evening.

Police were first notified of a man found with an apparent gunshot wound Sunday outside of apartments in Will County and pronounced dead at a hospital, later identified as Bakare. Shortly after, they learned of a man shot in the leg outside a home nearby.

Curtis Ellis said he lives next door to the man wounded in that shooting and captured it on a surveillance camera aimed at their street.

The footage shows the driver of a red car speaking briefly to Ellis’ neighbor, driving to the end of the block before making a U-turn then stopping and firing nine times. Ellis said he was watching the Detroit Lions play the Tampa Bay Buccaneers in an NFL playoff game when he heard the shots, saw his hurt neighbor outside and called police.

“That could have been me or my wife in the front yard, which is scary,” Ellis, 56, said. “You haven’t done nothing to anybody, why would somebody just target to shoot you?”

Will County Chief Deputy Dan Jungles said deputies used video surveillance and license plate readers to identify the car of the suspected shooter late Sunday and to set up patrols near his known addresses. By Monday, the car hadn't been seen locally and deputies went to Nance's last known address around noon, the office said.

Jungles said no one answered at that home, they went to another home connected to Nance and his family across the street and saw blood on the door and bullet holes on the exterior of the house.

Police then forced their way into both addresses and found the bodies of the seven people killed, Jungles said. Authorities believed at one point that a three-year-old boy was missing, but the child was later found with a relative in another city, Evans told reporters Tuesday without providing more detail.

“I’ve been a policeman 29 years and this is probably the worst crime scene I’ve ever been associated with,” Evans said during a news conference outside the Joliet homes Monday evening.

Less than two hours later, a helicopter had identified Nance's car on I-35 in Texas and law enforcement there surrounded him at a gas station.

Miller reported from Edmond, Oklahoma. Associated Press writers Jake Bleiberg in Dallas, Todd Richmond in Madison, Wisconsin; Claire Savage in Chicago; and Lisa Baumann in Bellingham, Washington; contributed to this report.

Copyright 2024 The Associated Press. All rights reserved. This material may not be published, broadcast, rewritten or redistributed without permission.

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Chicago to extend migrant shelter stay limits over concerns about long-term housing, employment.

Sophia Tareen

Associated Press

CHICAGO – Chicago will again extend its 60-day limit on shelter stays for asylum seekers, Mayor Brandon Johnson announced, just days ahead of a deadline that could have evicted nearly 2,000 migrants.

Johnson said Monday the idea is to give people more time to resettle and find work. The policy change adds 30 to 60 more days for roughly 14,000 migrants already living in the city’s 28 shelters, which include warehouses and park district buildings.

Chicago has twice delayed enforcement due to weather .

“Our plan for temporary emergency shelter was never meant as a long-term housing solution, but we want to give every person and every single family that has come to our city enough time to process their work authorization, find housing, start a new life in our great city,” Johnson said at a City Hall news conference.

Chicago and other U.S. cities, including New York and Denver, have put shelter limits in place as they struggle to house and care for the growing population of migrants arriving by bus and plane. Mayors have also pleaded for more federal help .

Chicago has had a hard time finding space and has also relied on using police stations, airports , and city buses as short-term solutions.

Extensions will be based on migrants' original dates to exit the system and will be either 30 or 60 days, city officials said. The earliest notices to leave will now come in mid-March.

For example, nearly 2,000 people who were set to leave on Thursday will now get another 60 days. City officials said less than half had been able to apply for rental assistance to help them live independently.

Any migrants newly entering shelters will get the standard 60 days. There will be exceptions, including for people who are pregnant or ill. Once evicted, arrivals would have to re-apply to stay in shelters.

More than 35,000 migrants have been sent to Chicago since 2022, largely under the direction of Texas Gov. Greg Abbott . Roughly 11,500 have been resettled through a state program and about 4,100 have left the shelter system after connecting with friends and family.

The city's shelter limits have been criticized, most recently by a group of aldermen who wrote Johnson a letter last week asking him to scrap the limits out of concern over the health and safety of new arrivals, particularly in the winter. Conditions at some shelters have also been in the spotlight, including after the death of a young boy living at a shelter who suffered a medical emergency in December.

Copyright 2024 The Associated Press. All rights reserved. This material may not be published, broadcast, rewritten or redistributed without permission.

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A river flood warning in effect for Victoria County

Girlfriend of suspect in fatal shootings of 8 in chicago suburb charged with obstruction, police say, kyleigh cleveland-singleton accused of trying to prevent romeo nance’s apprehension before killing himself in natalia.

Associated Press

JOLIET, Ill. – The girlfriend of a man suspected of fatally shooting seven relatives and an eighth person last weekend in a Chicago suburb has been charged with obstruction for allegedly trying to prevent her boyfriend’s apprehension, police said.

Kyleigh Cleveland-Singleton, 21, of Joliet appeared Thursday morning in a Will County courtroom where she was ordered to be placed on home confinement with electronic monitoring.

She was being represented by a public defender. The Associated Press left a phone message Thursday seeking comment from the public defender's office.

Singleton's next court appearance has been scheduled for Feb. 8.

Cleveland-Singleton was charged after the Will County State’s Attorney Office reviewed information provided by detectives who interviewed her Monday, Joliet police said.

Joliet police said Cleveland-Singleton agreed to be questioned by police Monday after she was identified as the girlfriend and mother of the 3-year-old son of shooting suspect Romeo Nance, 23, who fatally shot himself Monday during a confrontation with law enforcement in Texas.

After police questioned Cleveland-Singleton, “detectives believed that she made statements in order to prevent the apprehension of the suspect and obstruct this investigation,” Joliet police said in a news release posted on Facebook. The news release did not include what statements she allegedly made.

Officers found Cleveland-Singleton at a home in Plainfield, about 14 miles (23 kilometers) northwest of Joliet, after detectives learned Nance's young son might be with his mother and grandmother at a home there, police said.

The eight people who police said Nance fatally shot over the weekend were found Sunday and Monday, according to authorities. No motive has yet been provided.

Seven of the victims were found Sunday in two homes in Joliet and were identified as Nance's mother, Tamaeka Nance, 47; his brother Joshua Nance, 31; sister Alexandria Nance, 20; two younger sisters, ages 16 and 14; aunt Christine Esters, 38; and uncle William Esters II, 35.

Another man, 28-year-old Toyosi Bakare, was fatally shot outside an apartment building. Police said Nance is believed to have randomly fired at him and also another man, who was wounded in the leg on a residential street, after killing his family members.

Nance fatally shot himself Monday evening after U.S. Marshals located him near Natalia, Texas, about 30 miles (48 kilometers) southwest of San Antonio and more than 1,000 miles (1,690 kilometers) from Joliet, police said.

Sheriff Randy Brown of Medina County, Texas, said he believes Nance was trying to reach Mexico, which is about 120 miles (200 kilometers) south of Natalia along Interstate 35.

Copyright 2024 The Associated Press. All rights reserved. This material may not be published, broadcast, rewritten or redistributed without permission.


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