road trip to tennessee from chicago

Road Trip From Chicago To Nashville

A drive to Music City through a chain of incredible landmarks should be on everybody's to-do list - the road trip from Chicago to Nashville will take you past some of the fanciest cities, deepest caverns, and greenest forests in the Midwest and Upper South.

The 470-mile road trip from Chicago to Nashville takes 7 hours 10 minutes on the road. Sights en route include St. Louis and Fort Knox, Housier and Shawnee National Forests, stops at Mammoth Cave and Horse Cave, and the amazing Louisville Mega Cavern.

There's a lot of ground to cover during the trip, so continue reading until the end to make sure you don't miss a thing along this epic journey.

How far is Nashville from Chicago and how long will the road trip take?

The quicker route will have you following Interstate 65 through Indiana and Nashville. It covers 470 miles and takes around 7 hours 10 minutes to drive, and it'll take you all the way through Indiana and a decent chunk of Kentucky.

Another option is to add 10 miles to the drive by taking Interstates 57 and 24 through Illinois and a chunk of Kentucky. In terms of landmarks, this route is comparable to the first one, only instead of driving through Louisville, you can detour to St. Louis in Missouri.

Both drives can be done in a single day, but for the best experience possible, be sure to split the trip up into at least 3 days to explore as much as you can on the way.

Whether you're flying into Chicago or you simply don't have a vehicle in the city, renting a car for your road trip is something you'll want to take care of ASAP.

For an easy-to-compare view of rental options for your road trip from Chicago to Nashville, take a look at our partner site, RentalCars.com .

Best road trip route from Chicago to Nashville

There genuinely isn't a definitive road trip route from Chicago to Nashville. The route you choose should depend on which specific landmarks you want to check out, although your best bet is to take one on the way to Nashville and the other on the return trip.

The Indiana Route (via Interstate 65)

Leave Chicago via Interstate 90, following it to Gary - from there, continue south along Interstate 65, passing through Lafayette and Indianapolis.

Check out Yellowwood State Forest and Brown County State Park, then take a day or two to explore Louisville. Further south is Bernheim Arboretum and Research, followed by the action-packed Horse Cave and Mammoth Cave.

Further south, make an optional (but much-recommended) detour to Bowling Green before entering Tennessee. Take the time to explore Moss-Wright Park and Rockland Recreation Area in Goodlettsville, then continue south to Nashville.

The Illinois Route (via Interstates 57 and 24)

Take Interstates 90 and 94 south to Roseland, and from there, hop onto Interstate 57 and follow it out of Chicago, past Kankakee River State Park. From Champaign, do a detour to Allerton Park & Retreat Center, or continue along the interstate through Mattoon and Effingham.

If you feel so inclined, you can take Interstate 70 from Effingham to do a detour to St. Louis, which is sprawling with attractions like City Museum LLC and Gateway Arch.

Back on the main route, once you're past Marion, get onto Interstate 24 and follow it through Shawnee National Forest before crossing the Ohio River into Kentucky. Once there, pass Land Between the Lakes National Recreation Area, and stop in Clarksville before reaching Nashville.

Best places to stop between Chicago and Nashville

The great thing about the road trip from Chicago to Nashville is that there are heaps of luxurious stopover options. Here are some of your best accommodation options:

Enjoy the meal of a lifetime in Louisville

The City of KFC is renowned nationwide for its spectacular cuisine, and since you'll be passing directly through, there's virtually no excuse not to stop here and relax at a fancy hotel. With its legendary interior design, the swankiest resort in town would have to be The Brown Hotel .

The communal sitting area is almost cathedral-like in terms of presentation, and the bright, airy rooms are bound to leave a lasting impression. There's even a world-class "concert hall" with a grand piano and some of the most elegant decor you've ever seen.

To commemorate your stay with some regional artwork, be sure to stop by The Brown Gift Shop and Gallery for a souvenir, and follow it up with a meal at The Lobby Bar or one of the two on-site restaurants.

This historic hotel is definitely expensive, but when you consider all it has to offer, it has every reason to be. On top of that, the place gets bonus points for being so close to many major landmarks in the city, as it's only a mile from the center.

Take in the music in Nashville

The only thing that can make the sound of classic all-American tunes sweeter is a stay at a luxurious resort. Although Nashville has them in spades, the biggest standout is definitely The Hermitage Hotel .

From its luxurious lobby to the top-of-the-line rooms, the attention to detail at this hotel is second to none. A definite highlight would have to be The Deluxe King rooms, which look world-class yet have that unmistakable feeling of home.

Whether you're eating at the restaurant or enjoying a drink at the bar, every evening at this hotel feels like a business meeting in the best possible way.

If exploring Nashville doesn't tire you out, a workout session at the on-site fitness area definitely will. Once you're good and tired, take advantage of the concierge service and enjoy an in-room meal while enjoying the city view.

It should go without saying that this hotel isn't for a budget traveler, but if you can afford it, a stay at The Hermitage Hotel is one of the greatest Nashville experiences you could hope for.

READ MORE - Click here for great hotel options

Things to see on a road trip from Chicago to Nashville

The number of things there are to see on the road trip from Chicago to Nashville is quite staggering, and a lot of the attractions are located in or near major cities, so you don't have to do much offroading. It would be impossible to list everything there is to see, but be sure to check out the following places:

• Lake Michigan - The first part of your journey will take you around the southern point of Lake Michigan, the second largest of the Great Lakes and the only one located entirely in the United States
• Lafayette - Site of the Battle Of Tippecanoe during the American-Indian Wars; many museums and historic sites remain to tell its story
• Indianapolis - The capital and most populous city in the state of Indiana
• Louisville - The most populous city in the state of Kentucky
• Louisville Mega Cavern - A gargantuan cave system with an underground zipline system
• Hoosier National Forest - A premier hiking and fishing spot near Louisville
• Jim Beam American Stillhouse - Take a tour around the legendary factory of one of America's most famous whiskey producers
• Bernheim Arboretum And Research Forest - A 35-square-mile forest and nature reserve that plays home to numerous species of animals, plants, and trees. Miles of hiking trails and streams make this a perfect spot to get lost in nature for a while
• Fort Knox - The area was first used as a fort in 1861 during the civil war, before the legendary army base and gold depository was constructed in 1936
• Mammoth Cave - The largest known cave system in the world
• Horse Cave - A city known for the Kentucky Down Under Adventure Zoo and an array of intricate cave systems
• Bowling Green - Home to the Kentucky Museum and Library, as well as the National Corvette Museum and Historic Railpark and Train Museum.
• St. Louis - A major city in Missouri housing the tallest monument in the States, the Gateway Arch.
• Shawnee National Forest - Filled to the brim with sweeping hilltop views, this is one of the area's most popular forests for a reason.

Best time to go on a road trip from Chicago to Nashville

You can do the road trip from Chicago to Nashville almost any time of year and find something to enjoy, although Nashville's peak season is unique in that it lasts over 6 months.

Nashville is generally bustling and active while the weather is pleasant - mid-spring to mid-fall is when many of the local music festivals take place, attracting major crowds.

Be warned that mid-summer temperatures can reach the 90s, not to mention that the city can go from blazingly hot to massive rainstorms at the drop of a hat this time of year.

Although there's not as much to check out, visiting in late fall might also be a decent option if you're just looking to roam the city. Temperatures in November hover around 60 degrees, and hotel rooms come really cheap too.

Another viable alternative could also be winter, assuming you don't mind the constant 50-or-so degrees. If you're looking to keep your trip quiet, the city has relatively few visitors in February, and the weather gets noticeably warmer around early March.

You may also want to plan your trip around some of the stopover towns, as they all have their own seasonal highs and lows. For instance, Louisville summers tend to be on the rainy side, while St. Louis' hotel prices skyrocket around June.

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14 Stops that Should Be on Every Tennessee Road Trip

If you’re planning a trip to or through Tennessee via road travel, you definitely have to make several stops and explore the wonderful state. No matter how long you’ll be visiting Tennessee, here are 14 stops that you should definitely work into your itinerary.

As the second most visited home in the United States behind the White House, Graceland is a must see. Enjoy an interactive iPad tour hosted by actor John Stamos that features commentary by both Elvis and his daughter, Lisa Marie. Explore the mansion in full, from the living room to the famous Jungle Room, the kitchen and the Meditation Garden where Elvis was laid to rest. The only room off limits is the upstairs bathroom where Elvis was discovered on the day of his death.

Graceland, Elvis Presley Blvd, Memphis, TN, USA, +1 901 332 3322

Great Smoky Mountains National Park

With acres of forest and an abundance of plant and animal life, Great Smoky Mountains National Park is the most visited park in America. It straddles the border between North Carolina and Tennessee and is a great place to enjoy outdoor activities. Whether you spend a day hiking or camp out overnight, you can’t beat the views or the opportunities for adventure.

Great Smoky Mountains National Park, Tennessee, USA

Outdoor Knoxville

In an effort to increase Knoxville’s outdoor amenities and create better access to recreational areas, Legacy Parks Foundation runs Outdoor Knoxville . The adventure center offers visitors plenty of outdoor activities to enjoy, like renting paddleboards, bikes, or kayaks and fly fishing on the Tennessee River. The Billy Lush Board Shop, Neyland Greenway, and the Visit Knoxville Visitor Outpost are also located at the center.

Outdoor Knoxville, 900 Volunteer Landing Ln, Knoxville, TN, USA, +1 865 525 2585

Knoxville Sunsphere

Built in 1981, the Knoxville Sunsphere was designed as the theme structure for the 1982 World’s Fair and is one of only two remaining structures from the event. It stands 266 feet high and has a 24-karat gold, glass paneled ball that is 75 feet in diameter. On the fourth floor is an observation deck that features a gallery of Knoxville images and a 360-degree view of the city. It is free and open to the public daily.

Knoxville Sunsphere, Knoxville, TN, USA

Stonehaus Winery

The first licensed winery in Tennessee, Stonehaus Winery opened in 1991. It is the only winery in Tennessee with statewide distribution and offers complimentary wine tastings. When the winery first started, it offered five wines that were all sold on site. All of the wines were bottled by hand. After substantial growth, Stonehaus Winery wines can now be found in liquor stores and grocery stores across Tennessee as well as on site. After purchasing a new bottling line in 2006, the winery now bottles up to 3,000 bottles of wine per hour. Stonehaus Winery, 2444 Genesis Rd # 103, Crossville, TN, USA, +1 931 484 9463

Burgess Falls State Park

With four waterfalls that cascade down from over 250 feet, Burgess Fall State Park is known for its natural beauty and family-friendly activities. Visitors can take a 1.5-mile round-trip trail that leads to the edge of the waterfalls and into the gorge. Fishing is allowed below the dam and along the bank of the main waterfall. The Native Butterfly Garden offers native wildflower displays and is where the annual Butterfly Garden Celebration takes place, offering programs, hikes and creek studies. There is also a week-long Junior Ranger Camp available to youth during the summer.

Burgess Falls State Park, 4000 Burgess Falls Dr, Sparta, TN, USA, +1 931 432 5312

Jack Daniel’s Distillery

Established in 1866, Jack Daniel’s Distillery was the first registered distillery in the United States . Known for its signature Old. No. 7 whiskey, the brand has expanded its production and flavors over the years while still maintaining the not-so-secret to its success: the use of limestone spring water, which was Jack Daniel’s ingredient discovery. The distillery offers a variety of tours, some that include tastings and one that includes a meal at local Miss Mary Bobo’s Boarding House & Restaurant.

Jack Daniel’s Distillery, 133 Lynchburg Highway, Lynchburg, TN, USA , +1 931 759 6357

National Civil Rights Museum

Featuring information that spans five centuries, the National Civil Rights Museum offers artifacts, films, interactive media, and listening posts that cover the history of civil rights in the United States. Located at the Lorraine Motel where Dr. Martin Luther King Jr. was assassinated, the museum also explores the 1968 event in the Legacy Building, which begins with the American Civil Rights Movement Timeline. Exhibits feature information on the investigation of the assassination, as well as the American Civil Rights Movement’s impact on human rights across the globe.

National Civil Rights Museum, 450 Mulberry St, Memphis, TN, USA, +1 901 521 9699

Wildhorse Saloon

Each year, the 66,000 square foot Wildhorse Saloon welcomes more than 1.5 million visitors. The event space has three floors for guests to enjoy, acting as a restaurant, bar, dance floor, and concert venue. Bands large and small grace the stage to play live music, and the venue offers free line dancing lessons that are given by its trained staff. Enjoy hot chicken and fried pickles while dancing in your boots and listening to the sounds of rock and country music classics.

Wildhorse Saloon, 120 2nd Ave N, Nashville, TN, USA, +1 615 902 8200

2. Ryman Auditorium

Concert Hall, Music Venue

Tennessee Aquarium

Visitors to the Tennessee Aquarium have two different buildings to explore — River Journey and Ocean Journey. Both buildings feature exhibits that provide information about many types of aquatic and terrestrial wildlife as well as exotic plants. One exhibit, Stingray Bay, allows guest to touch different shark and stingray species. Alligator Bayou is where 13 American Alligators can be found. The aquarium is also home to the nation’s largest salamander, the hellbender, which breathes through its skin as tree frogs chirp around it.

Tennessee Aquarium, 1 Broad St, Chattanooga, TN, USA

One of Chattanooga’s most popular attractions is Ruby Falls , the largest and deepest waterfall open to the public in the United States. It’s located over 1,120 feet beneath the surface, inside Ruby Falls Cave, where hundreds of gallons of water rush over by the minute. Ruby Falls was formed sometime after Ruby Falls Cave, when a sinkhole developed and allowed large amounts of water to enter. This water hollowed out the dome area, and, by way of erosion, the waterfall was carved out. Ruby Falls, Chattanooga, TN, USA

Cherohala Skyway

Designated a National Scenic Byway, Cherohala Skyway was dedicated and opened in 1996. It crosses through Cherokee National Forest in Tennessee and Nantahala National Forest in North Carolina. At more than 40 miles long, the two-lane road has 15 scenic overlooks with elevations that range from 900 feet above sea level to over 5,400 feet above sea level. A trip across the entire skyway takes about two hours, and along the way you’ll find picnic sites and trail heads for enjoying short travel breaks.

Cherohala Skyway, USA

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.

Places to Stay

Where to stay in the great smoky mountains, usa.

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The best lakes to visit in tennessee.

The Best Places to See Fall Foliage in Tennessee

Where to Go Camping in Tennessee

The Best Hotels With a Water Park to Book in Tennessee

The Best Holiday Apartments in Tennessee

Must-Visit Tennessee Attractions

Where to Go Glamping in Tennessee

The Best Hotels to Book in Tennessee for Every Traveler

The Best Budget-Friendly Hotels to Book in Tennessee

The Best Cabins to Book in Tennessee, USA

The Best Glampsites and Cabins to Book in Tennessee

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Chicago to Nashville Road Trip: Skyscrapers and music on the open road

Whether you’re planning to enjoy a bite of deep dish pizza, go on a scenic hike or listen to a live musical performance, this Chicago to Nashville road trip has something that will appeal to your interests.

Known for its unique architecture, delicious local delicacies, and scenic lakefront, Chicago truly is one of a kind. Before you arrive in Nashville, which is known as the capital of country music, we have a few interesting towns and attractions for you to visit. Including a mixture of bustling cities and lush green spaces, our Chicago to Nashville road trip is great for any type of traveler, particularly if you enjoy good food and music.

1. Chicago 2. Indianapolis, IN 3. Brown County State Park 4. Louisville, KY 5. Bowling Green, KY 6. Nashville, TN

Info at a glance

• 5-7 day trip
• Type of route: City
• 6 stops along the route
• 512 miles of driving
• Visit some famous attractions in the Windy City.
• Attend a sporting event in Indianapolis.
• Go on a scenic hike in Brown County State Park.
• Explore the historic downtown of Bowling Green.
• Enjoy a live musical performance in Nashville.

Getting to the start

This road trip starts in Chicago, Illinois. If you’ll be arriving from a different part of the country or world for your Chicago to Nashville road trip, there are two airports that you can fly into: O’Hare International Airport and Midway International Airport. If you live in the region, there are several roads that can be used to enter Chicago, such as I-90 and I-294.

CAR RENTAL IN Chicago

When to Visit

A Chicago to Nashville road trip is fun not matter the time of year, but the months of May to October are typically ideal, as you can avoid snowy weather. It tends to be warm in the summer, so make sure to pack light clothes. If you travel during the winter, layers are best. Sunblock and sturdy walking shoes are a must, whether you will be sightseeing or decide to embark on a scenic hike.

Driving tips

This Chicago to Nashville road trip takes you through the states of Illinois, Indiana, Kentucky and Tennessee. You can expect to encounter some toll roads along the way. Each of these states has similar speed limits of about 65 miles per hour on interstate highways and 55 mph on highways.

What to know about the route

This Chicago to Nashville road trip spans about 470 miles, for a total driving time of around 7 hours and 45 minutes. The route lets you experience two unique cities, as well as a selection of charming stops in between. You will start in Chicago and then take I-65 S to the next destination of Indianapolis, Indiana. From there, you will continue to the town of Louisville, Kentucky. After Louisville, your next destination is Brown County State Park, which can also be reached via I-65 S. To go from Brown County State Park to Bowling Green, you can stay on I-65 S. If you continue on this interstate, you will reach the last stop on the road trip, which is Nashville. An SUV can be a convenient car rental for this trip, as it will provide you with plenty of space for any luggage and recreational equipment that you may want to bring along with you.

With its one-of-a-kind architecture, interesting museums and diverse culture, Chicago is a city unlike any other. To make sure that you have enough time to visit all of the different attractions and sights on your to-do list, it’s best to dedicate one or two days to visit this city.

Points of interest

For a unique experience, such as standing inside of a tornado or going deep into a coal mine, head to the Museum of Science and Industry. If you would like to learn more about this city’s rich history, pay a visit to the Chicago History Museum. Chicago is also home to the Ledge, an enclosed glass box on the Skydeck of the Willis Tower.

Where to eat, drink and sleep

Chicago is famous for its deep dish pizza, which you can order at many different restaurants, including Pequod’s Pizza and Bartoli’s Pizzeria. The city also has many unique cocktail bars, like the Violet Hour and Aviary. For lodging, you can choose from a variety of swanky hotels, including the 21c Museum Hotel Chicago and the Ambassador Chicago.

Sixt Insider Tip

Chicago has its own Broadway industry, so consider seeing a performance during your visit. There are several beautiful and unique theaters for you to choose from, including the James M. Nederlander Theatre and the Cadillac Palace Theatre. You can either buy your tickets in advance or try to purchase them from a ticket office the day of the performance.

From Chicago to Indianapolis (183 miles)

To head to your next destination, Indianapolis, you will take I-65 S. If you would like to stop along the way to fill up your tank, stretch your legs, or grab a bite to eat, you can do so in a few different cities, such as Lafayette, Indiana. With its vibrant community and beautiful green spaces, Lafayette is a charming place to explore.

Indianapolis, IN

A bustling city that has several sports teams and many interesting museums, Indianapolis is a great place to visit for a day or two during your trip. Many of the city’s attractions can be conveniently found downtown, making it a great area to explore and walk around for a few hours. 

If you’ll be visiting the area with your family, you can always head to The Children’s Museum of Indianapolis, which is famous for its interesting interactive exhibits. There is also The Indianapolis Museum of Art, which is home to more than 54,000 pieces of artwork from all over the world. 

Indianapolis is a great place to eat some American comfort food, including items like fried pickles, tenderloin sandwiches and milkshakes, which you can grab from restaurants such as The Garage at Bottleworks. It also has many craft breweries, including Black Acre Brewing Co. For lodging, choose a charming hotel such as the Hotel Indy.

The city has more than 10 professional sports teams, like the Indianapolis Colts and the Indianapolis Racers. Make sure to check out the events calendar for the period that you will be staying in the city, as you may be able to head to a sporting event during your trip, depending on what season it is. 

From Indianapolis to Brown County State Park (57 miles)

You will hop on I-65 S to head to your next destination, Brown County State Park. Along the way, there are small cities to explore, like Columbus and Seymour. Both of these towns are fun to walk around for an hour or two, giving you a break from being cooped up in a car. 

Brown County State Park

One of the largest state parks in not just Indiana but also the United States, Brown County State Park spans across more than 15,000 acres. It’s a scenic green space that is the perfect location to go on a nice hike, do some bike riding or try to catch a glimpse of the local wildlife. 

If you enjoy horseback riding, keep in mind that you can do so within Brown County State Park. Guided trail rides are offered by professional riders, or you can always take a pony ride at the Saddle Barn. There are over 70 miles of trails that are accessible by horse, providing many scenic choices.

From Brown County State Park to Louisville (85 miles)

Louisville, Kentucky, is your next stop, and it can be reached by continuing on I-65 S. Before reaching this destination, there are a few different places that you can choose to stop, such as Seymour, where you can grab a bite to eat and take a break from driving. 

Louisville, KY

Louisville is a diverse city that is known for its unique and rich history, delicious southern food and impressive architecture. It’s a great spot to stretch your legs for a few hours and wander around downtown to visit some of the area’s most popular attractions before eating at a local restaurant. 

If you’re a baseball fan, you won’t want to miss out on visiting the Louisville Slugger Museum & Factory, which will teach you the history of the iconic baseball bat. Louisville is also home to Churchill Downs, which is one of the most famous horse racing tracks in the country. 

The city is famous for traditional Southern food, which you can taste at a few popular local restaurants, such as Doc Crow’s Southern Smokehouse & Raw Bar. It’s also a great area to try out craft beer, and Against the Grain is popular. For lodging, there are a few cozy hotels that you can choose from, including the Brown Hotel. 

You will find that there are many spas and salons in the city, making it a great place to treat yourself to some pampering. If you’re interested in having a massage, facial or another similar treatment, consider making an appointment at a spa such as Indulge The Spa, the Louisville Salt Cave or Xhale Salon & Spa.

From Louisville to Bowling Green (122 miles)

To reach your next destination of Bowling Green, you will hop back on I-65 S. Along the way, you may want to stop somewhere such as the Bernheim Arboretum or Mammoth Cave, a beautiful area that is popular amongst avid hikers. The Mammoth Cave Visitor Hangout Picnic Area is a great place to enjoy a snack. 

Bowling Green, KY

A fun city filled with historic neighborhoods and several national museums; Bowling Green is a must-visit during your road trip from Chicago to Nashville. Between its quirky attractions and thriving craft brewery scene, you’ll never run out of things to see or do while here, no matter what your interests are. 

Car enthusiasts will want to make sure that they dedicate a few hours to the National Corvette Museum, which focuses on this model that has been in production since the early 1950s. There is also the Lost River Cave, which is an interesting attraction that you can visit and take a boat ride through. 

Bowling Green specializes in traditional American food, so make sure to try some of this at one of the several popular restaurants, like 6.4.3 Sports Bar & Grill. It’s also a great place to enjoy a cold craft beer, like at Bowling Green Beer Works. There are many charming hotels and bed and breakfasts, including the Bryce Inn. 

The city often hosts fun annual events and festivals, so make sure to check out the official events calendar to see if anything will be taking place during your time in the area. Some examples of events that take place include football games and car shows, as well as art exhibits. 

From Bowling Green to Nashville (65 miles)

Your next stop, Nashville, is also the last stop on the road trip. While driving along I-65 S to this city, you can always choose to explore the quaint town of Whitehouse, which is almost exactly halfway between the two locations. If you need to refuel, grab some snacks, or just want to wander around. 

Nashville, TN

Famous for being the capital of country music, Nashville is a vibrant city that is filled with bustling saloons, charming music venues and interesting museums that will keep you entertained for hours. You will want to make sure that you have a day or two in order to fully explore this one-of-a-kind city. 

A trip to this city wouldn’t be complete without going to the Country Music Hall of Fame and Museum, which is known for being one of the largest museums in the world. You can also spend some time at the Grand Ole Opry, where you may be lucky enough to see a live performance. 

Nashville is best known for its Southern comfort food, and there are many popular restaurants for you to try out, like the Stillery and Etch. If you want to grab a cold beer, go to one of the city’s many breweries, such as Bearded Iris Brewing. For lodging, consider staying at a hotel such as the Hutton Hotel.

If you would like to see a live show during your stay in Nashville, you don’t necessarily need to purchase tickets to a concert. Many of the bars and saloons in the city will have music during the evenings, which is a great way to listen to local voices in a relaxing setting without having to break the bank. 

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Getting there can be as fun as the park itself. Enjoy these scenic drives and road trips to Great Smoky Mountains National Park and other spots in Tennessee and North Carolina.

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Nashville To Chicago Road Trip: The Ultimate Guide

Traveling from Nashville to Chicago is one of the best journeys you can experience in the USA . The 442 miles of road trip from Nashville to Chicago takes around 7 hours and 41 mins of driving without stops.

This article includes 17 top tips that turn your Chicago trip into an unforgettable journey. So if you’re looking for the best hotels, restaurants, and places to visit on the road trip from Nashville to Chicago, take your coffee and keep reading!

Table of Contents

6 Best Hotels On The Way From Nashville To Chicago

On the way from Nashville to Chicago, you may want to stay at some points on the way. Here are the top six hotels on the Nashville – Chicago route!

1. La Quinta Inn & Suites by Wyndham Bowling Green

La Quinta Inn & Suites by Wyndham Bowling Green is one of the best hotels you can stay on the road trip from Nashville to Chicago. Driving from Nashville to La Quinta Inn & Suites by Wyndham Bowling Green might take around 1 hour and 3 mins . This economy hotel is clean and comfortable and has good towels, beds, and hot water. It also has a hot breakfast with eggs, sausage, waffles, fruit, and other choices. The downside is that the breakfast ends at 9 am. Check the La Quinta Inn & Suites by Wyndham Bowling Green, one of the best hotels in Bowling Green, Kentucky, on TripAdvisor and Booking.com for recent reviews, prices, and availability.

2. Best Western Plus Nashville Airport Hotel

Another top hotel where you can choose the stay on the road trip to Chicago from Nashville is Best Western Plus Nashville Airport Hotel. Located in Nashville, Tennessee, the hotel is 9.4 miles away from Nashville, and it would take 15 mins to drive. This hotel was immaculate and conveniently located near the airport. There is also free breakfast in the mornings, which is perfect for travelers. If you want to learn more about the Best Western Plus Nashville Airport Hotel, you can check it on TripAdvisor or Booking.com .

3. La Quinta Inn & Suites by Wyndham Elizabethtown

Didn’t our first two hotel suggestions interest you? So we would like to introduce you to the La Quinta Inn & Suites by Wyndham Elizabethtown. La Quinta Inn & Suites by Wyndham Elizabethtown is located in Louisville, Kentucky, and it’s 134 miles away from Nashville. You can arrive there in 2 hours and 13 mins of non-stop driving. I was so happy to find a pet-friendly hotel on our travels. The staff was amiable, and check-in went quickly after traveling all day. The hotel was spotless and near plenty of food options. We also hit a nearby bookstore too! Check the TripAdvisor and Booking.com pages of La Quinta Inn & Suites by Wyndham Elizabethtown for more information.

4. Residence Inn Louisville East/Oxmoor

If you are taking the road trip from Nashville to Chicago, Elizabethtown, Kentucky, is must have a place you should visit. Plus, Residence Inn Louisville East/Oxmoor is one of the best hotels in town. It is Residence Inn Louisville East/Oxmoor, 178 miles from Nashville, and it would take 2 hours and 57 mins to drive. The hotel is clean, and the rooms are spacious. The breakfast is excellent, and the dinners are also delicious. However, the guest service that we received when we arrived was in a class above all others that we have experienced. If you need more info about the price and availability of Residence Inn Louisville East/Oxmoor, check the TripAdvisor and Booking.com pages.

5. Homewood Suites by Hilton Lafayette

Our next hotel is Homewood Suites by Hilton Lafayette, Lafayette, Indiana. It will take 5 hours, and 49 mins of car ride o reach this hotel from Nashville. The hotel is immaculate and well-equipped. There is also a small restaurant/bar in the hotel, which was nice not to have to leave the premises for anything. Check the Homewood Suites by Hilton Lafayette on TripAdvisor and Booking.com pages of Homewood Suites by Hilton Lafayette for reviews, prices, and availability.

6. Indianapolis Marriott East

Another hotel you can accommodate on the road trip from Nashville to Chicago is Indianapolis Marriott East. It’s possible to arrive at this hotel, located in Indianapolis, Indiana, within 4 hours and 46 mins drive from Nashville. We stayed at Purdue University when we toured the campus. The rooms were spotless, and towels were not the overly bleached kind. The whole breakfast area was also immaculate. It was in a great location to lots of restaurants. Before making the reservation, we suggest you read the latest reviews on TripAdvisor and Booking.com .

In this part, we explained six different hotels you can stay at on the road trip from Nashville to Chicago. You can pick one of them that suits your taste. Don’t forget to share your experience by writing a comment to this post. It will help people who will take the same Nashville to Chicago route.

Now, it’s time to discover the best restaurants from Nashville to Chicago. We have six restaurant recommendations worth your attention.

6 Best Restaurants On The Way To Chicago From Nashville

If dining is a pleasure, some restaurants will please you on your Nashville to Chicago road trip. In this section, we list the six different restaurants to dine at on the road trip from Nashville to Chicago. Stay hungry and enjoy!

1. El Maguey Mexican Restaurant, Bowling Green

We would like to start our restaurant recommendation list on the road trip from Nashville to Chicago with El Maguey Mexican Restaurant, Bowling Green. El Maguey Mexican Restaurant, Bowling Green, is located in Bowling Green, Kentucky, and is 61.7 miles from Nashville. It would take 1 hour and 3 mins of driving. El Maguey was a great experience all around. Our drinks came out in carafes, and we were surprised to receive long straws instead of cups. The menu is extensive; lots of Mexican and Southwest dishes are available. We started with the shrimp cocktail, which was both ceviche-like and traditional shrimp cocktail in taste. The portion size was generous, as were the shrimp themselves. We also ordered tacos, arroz con pollo, and the spicy seafood fiesta dish – all of which were excellent! For more information about El Maguey Mexican Restaurant, Bowling Green, you can visit the TripAdvisor or Google Maps pages of El Maguey Mexican Restaurant, Bowling Green.

2. Monell’s Dining & Catering

Another top restaurant you can choose to eat at on the road trip to Chicago from Nashville is Monell’s Dining & Catering. Located in Nashville, Tennessee, Monell’s Dining & Catering is 1.4 miles from Nashville and would take 6 mins of driving. We decided to dine at Monell’s Manor based on the recommendation of a friend. This upscale restaurant features southern-style cooking that is reminiscent of grandma’s dishes. The historic building and gracious staff made our experience unforgettable. The food was fantastic, and the chicken was especially juicy and flavorful. We highly recommend this establishment! If you want to learn more about Monell’s Dining & Catering, you can check it on TripAdvisor or Google Maps .

3. J Graham’s Cafe

Another restaurant that can be preferred by those who are fond of food is J Graham’s Cafe. It will take 2 hours and 53 mins of car drive to take 175 miles from Nashville to J Graham’s Cafe, Louisville, Kentucky. My friend had chicken fried chicken, mashed potatoes, and green beans. All the food was homemade and looked like it was made just for them, and the waitress gave us some great suggestions for what to order next time we came. Everything on our plates looked delicious! You can check J Graham’s Cafe on TripAdvisor or Google Maps for more information.

4. Back Home Restaurant, Elizabethtown

Back Home Restaurant, Elizabethtown deserves to be on our list. It is one of the most recommended restaurants in Elizabethtown, Kentucky. We had a great time at brunch at this cafe. We were seated in a separate dining room adjacent to the main dining area, and the staff was always attentive to our needs. Back Home Restaurant, Elizabethtown, is 133 miles away from Nashville, and it would take 2 hours and 12 mins of non-stop car driving. If you want to learn more about Back Home Restaurant, Elizabethtown, you can check it on TripAdvisor or Google Maps .

5. Triple XXX Family Restaurant, Lafayette

If you enjoy dining, Triple XXX Family Restaurant, Lafayette, would be an excellent choice in Lafayette, Indiana. It’s 354 miles from Nashville and would take 5 hours and 59 mins of car driving. The waitress was very accommodating regarding allergies, and the service was great. The food arrived quickly and looked delicious. If you want to learn more about the Triple XXX Family Restaurant, Lafayette, you can check it on TripAdvisor or Google Maps .

6. High Velocity, Indianapolis

Another restaurant we recommend you to visit on the road trip from Nashville to Chicago is High Velocity, Indianapolis, Indianapolis, Indiana. It will take 4 hours and 43 mins of driving to reach High Velocity, Indianapolis, from Nashville. This diner is definitely worth a visit if you’re in the area. The food was amazing, and the service was top-notch. The atmosphere was great, too – I loved how it had a vintage feel, with outdoor seating available as well. For more information about High Velocity, Indianapolis, you can check TripAdvisor or Google Maps pages of the restaurant.

This section lists our six restaurant recommendations for you to eat on your road trip from Nashville to Chicago. We hope these suggestions will help you turn your 442 miles journey into a feast of taste. Of course, you can choose a suitable restaurant from the list according to your preference. Remember, like you, people planning a Chicago road trip need your opinion. Therefore, we kindly ask you to share your experience with us in the comment field at the end of the blog post.

In the next section, we list the destinations worth seeing along the route from Nashville to Chicago. Keep reading.

5 Places To Visit On The Way From Nashville To Chicago

A unique experience awaits you in Chicago. However, on your road trip, there are also some unique destinations like Bowling Green, Kentucky. We want to explain the top five destinations we recommend on the Chicago route.

1. Country Music Hall of Fame and Museum, Nashville

Country Music Hall of Fame and Museum, Nashville, will be the first destination we recommend you to stop by on your Nashville to Chicago road trip. Located in Nashville, Tennessee, the Country Music Hall of Fame and Museum, Nashville is 0.6 miles away from Nashville, and it would take 5 mins to drive.I enjoyed seeing all the memorabilia and the videos. It took about two and a half hours to see everything. If you enjoy Country Music, you should definitely visit the museum. If you want to learn more about the Country Music Hall of Fame and Museum, Nashville, you can check it on TripAdvisor or the official website .

2. Louisville Slugger Museum & Factory, Louisville

Louisville Slugger Museum & Factory, Louisville, Louisville, Kentucky is one of the destinations we recommend you to stop by on the Nashville to Chicago route. It’s 177 miles from Nashville, and it’ll take about 2 hours and 56 mins of driving. This car museum has a wide variety of cars on display. Each one is in great condition and looks like it just came out of the showroom. The place is spotless, and you can hear your shoes squeak on the floor because there’s never a spot of dirt or dust anywhere. The placards next to each car give detailed information about each one, including its story and how it ended up here. If you want to learn more about Louisville Slugger Museum & Factory, Louisville, you can check it on TripAdvisor or their website .

3. Swope’s Cars of Yesteryear Museum

One of the stops you should not neglect to stop by when you take the road trip from Nashville to Chicago is Elizabethtown, Kentucky. And if you visit Elizabethtown, Kentucky, we suggest you visit Swope’s Cars of Yesteryear Museum. You can arrive at Swope’s Cars of Yesteryear Museum after 2 hours and 14 mins of driving. A good place to watch a game in the middle of downtown is likely more interesting for kids than adults. Souvenir bats are available for purchase, making it a nice way to take home an extra memory from your visit. You can visit TripAdvisor and the official site of Swope’s Cars of Yesteryear Museum for more information.

4. Haan Museum of Indiana Art

Do you also like to travel and experience new things? Then, it would be best to visit the Haan Museum of Indiana Art, Lafayette, Indiana, on the road trip from Nashville to Chicago. Haan Museum of Indiana Art is 353 miles from Nashville, and you can arrive there after the 5 hours and 54 mins of drive. The Museum for Young Children is a great place to spend a day with your family. Parking was free, and the food was reasonably priced, although the portions were small and the quality wasn’t great. In addition, you should check TripAdvisor and the official website of the Haan Museum of Indiana Art before going there.

5. Children’s Museum of Indianapolis

Located in Indianapolis, Indiana, the Children’s Museum of Indianapolis ranks fifth in our list of tourist destinations on the Chicago road trip. You must take 4 hours and 51 mins of driving to arrive at the Children’s Museum of Indianapolis. The art and ceramics collection is excellent. We had a tour conducted by Mr. Haan himself, and it was fascinating to hear about the acquisition of each item and his personal love of Indiana art. If you want to learn more about the Children’s Museum of Indianapolis, you can check it on TripAdvisor or the official website .

FAQ of the Road Trip From Nashville to Chicago

Here we are answering the frequently asked questions about the Nashville to Chicago drive.

How Long Is The Road Trip From Nashville To Chicago?

• With ideal traffic and weather conditions, the road trip takes approximately 7 hours and 41 mins to drive. The distance between Nashville to Chicago is 442 miles.
• If you want to make the Nashville to Chicago road trip by bike , the time you spend on the road will be 1 day 14 hours .
• If you are crazy enough and plan to walk the Nashville-Chicago route, then you will have to walk for 6 days 4 hours .

Where Do You Stop On Driving From Nashville To Chicago?

There are many beautiful pit stops along the way to Chicago. Here we list five of them . For more information about the best places on the Nashville to Chicago journey, you can check the 5 Best Places To Visit On The Way From Nashville To Chicago part.

• Country Music Hall of Fame and Museum, Nashville: 0.6 miles / 5 mins to drive from Nashville | 441 miles / 7 hours and 42 mins of driving to Chicago.
• Louisville Slugger Museum & Factory, Lousville: 177 miles / 2 hours and 56 mins to drive from Nashville | 300 miles / 5 hours and 5 mins of driving to Chicago.
• Swope’s Cars of Yesteryear Museum: 135 miles / 2 hours and 14 mins to drive from Nashville | 345 miles / 5 hours and 55 mins of driving to Chicago.
• Haan Museum of Indiana Art: 353 miles / 5 hours and 54 mins to drive from Nashville | 123 miles / 2 hours and 15 mins of driving to Chicago.
• Children’s Museum of Indianapolis: 292 miles / 4 hours and 51 mins to drive from Nashville | 180 miles / 3 hours and 11 mins of driving to Chicago.

Where Should You Stay On The Road Trip From Nashville To Chicago?

There are many excellent hotels during your Nashville to Chicago road trip. We have selected six hotels for you. These hotels are listed below. Remember, you can find detailed information about these hotels in the 6 Best Hotels On The Way To Chicago From Nashville section.

• La Quinta Inn & Suites by Wyndham Bowling Green: 61.8 miles / 1 hour 3 mins to drive from Nashville | 413 miles / 6 hours and 56 mins of driving to Chicago.
• Best Western Plus Nashville Airport Hotel: 9.4 miles / 15 mins to drive from Nashville | 446 miles / 7 hours and 46 mins of driving to Chicago.
• La Quinta Inn & Suites by Wyndham Elizabethtown: 134 miles / 2 hours and 13 mins to drive from Nashville | 341 miles / 5 hours and 48 mins of driving to Chicago.
• Residence Inn Louisville East/Oxmoor: 178 miles / 2 hours and 57 mins to drive from Nashville | 307 miles / 5 hours and 16 mins of driving to Chicago.
• Homewood Suites by Hilton Lafayette: 352 miles / 5 hours and 49 mins to drive from Nashville | 123 miles / 2 hours and 12 mins of driving to Chicago.
• Indianapolis Marriott East: 292 miles / 4 hours and 46 mins to drive from Nashville | 189 miles / 3 hours and 21 mins of driving to Chicago.

Where To Eat Between Nashville to Chicago?

If you are thinking of taking a break and having a nice meal on your Nashville to Chicago journey, you can consider the six restaurants we have chosen. In addition, you can read detailed information about the restaurants in the section titled 6 Best Restaurants On The Way From Nashville To Chicago .

• El Maguey Mexican Restaurant, Bowling Green: 61.7 miles / 1 hour 3 mins to drive from Nashville | 413 miles / 6 hours and 54 mins of driving to Chicago.
• Monell’s Dining & Catering: 1.4 miles / 6 mins to drive from Nashville | 440 miles / 7 hours and 39 mins of driving to Chicago.
• J Graham’s Cafe: 175 miles / 2 hours and 53 mins to drive from Nashville | 299 miles / 5 hours and 9 mins of driving to Chicago.
• Back Home Restaurant, Elizabethtown: 133 miles / 2 hours and 12 mins to drive from Nashville | 343 miles / 5 hours and 51 mins of driving to Chicago.
• Triple XXX Family Restaurant, Lafayette: 354 miles / 5 hours and 59 mins to drive from Nashville | 123 miles / 2 hours and 13 mins of driving to Chicago.
• High Velocity, Indianapolis: 289 miles / 4 hours and 43 mins to drive from Nashville | 183 miles / 3 hours and 17 mins of driving to Chicago.

So, there you have it- a complete guide to planning a road trip from Nashville to Chicago. We have listed six hotels, six restaurants, and five places to visit on the way. We have also given you detailed information about each place so that you can make an informed choice about where to stay, eat, and what to see. We hope this guide has helped make your road trip from Nashville to Chicago as enjoyable as possible.

Share Your Thoughts

Have you ever taken a road trip from Nashville to Chicago? So, it would be perfect if you shared your experience with other travelers who want the same experience. You can share your thoughts about the road trip from Nashville to Chicago and your recommendations about this route by using the comment field below.

Video: Chicago Road Trip: Top 10 Things to Do in Chicago

In this video, you can find 10 things to do in Chicago. If you’re planning to visit Chicago, you should check the video.

Other Road Trips Worth Your Attention

• Dallas To Chicago Road Trip: Top 21 Tips
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31 Best Stops Between Chicago and Memphis

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How long is the drive from Chicago to Memphis?

The direct drive from Chicago to Memphis is 534 mi (860 km) , and should have a drive time of 8 hrs 46 mins in normal traffic.

If you’re going on a road trip from Chicago to Memphis, we did the research for you and compiled some great stops along the way — with Paducah , as well as top places to visit like Lake Katherine Nature Center and Botanic Gardens and Albanese Candy Factory Outlet, or the ever-popular Gabis Arboretum at Purdue Northwest.

Top city between Chicago and Memphis

Best stops along chicago to memphis drive, gabis arboretum at purdue northwest.

Lake Katherine Nature Center and Botanic Gardens

Albanese Candy Factory Outlet

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Rialto square theatre, harrah's joliet, kankakee river state park, route 66 association of illinois, pontiac oakland auto museum, kennekuk county park, champaign public library, meadowbrook park, allerton park & retreat center.

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World's largest wind chime, jeremy "boo" rochman memorial park, paducah wall to wall, the national quilt museum, historic riverfront, century casino cape girardeau, sikeston factory outlet stores.

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New madrid historical museum, reelfoot lake state park, west tennessee delta heritage center / tina turner museum, meeman-shelby forest state park, top searches in memphis, other popular road trips from chicago, explore nearby places.

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Frequently Asked Questions

Can i drive from chicago to memphis.

Yes! You can drive from Chicago to Memphis.

How far is Memphis from Chicago by car?

The drive from Chicago to Memphis is 534 miles (860 km).

How long does it take to drive from Chicago to Memphis?

Driving from Chicago to Memphis should take you 8 hrs 46 mins in normal traffic.

How much would gas cost from Chicago to Memphis?

Gas from Chicago to Memphis would cost around $47 to $109 , depending on your vehicle's fuel efficiency.

Where should I stop on the way from Chicago to Memphis?

You could check out Lake Katherine Nature Center and Botanic Gardens and Albanese Candy Factory Outlet, or the always popular Gabis Arboretum at Purdue Northwest!

What are the best cities to visit between Chicago and Memphis?

People love visiting Paducah, among others.

What's the weather like in Chicago?

It depends on when you visit! We've compiled data from NASA for each month of the year: see the links below for more information.

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What are some other road trips from Chicago?

There are plenty! Below you'll find links to all the road trips we've assembled for Chicago.

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The driving time from Chicago, Illinois to Nashville, Tennessee is:

7 hours, 9 minutes.

Average driving speed: 66 mph Kilometers per hour: 106.2 km/h This is based on typical traffic conditions for this route.

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Driving time from Chicago, IL to Nashville, TN

How long is the drive from Chicago, IL to Nashville, TN? The total driving time is 7 hours, 9 minutes .

Your trip begins in Chicago, Illinois. It ends in Nashville, Tennessee.

If you're planning a road trip, you might be interested in seeing the total driving distance from Chicago, IL to Nashville, TN .

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Nashville is a family-friendly destination. The Cheekwood Botanical Garden and Museum of Art is an all-seasons place to visit. This 55-acre estate was built by the Maxwell House Coffee. The Museum of Art has a collection of sculptures, paintings and decorative arts. The Botanical Garden comes alive with over 100,000 tulips in spring and every summer (Thursday evening in June and July), families are treated to performances just for children. In winter, the garden becomes a winter wonderland filled with Christmas trees, trains, Santa, reindeers and holiday lights and decorations. Nashville Zoo offers up-close encounters with clouded leopards and red pandas. Elephants and giraffes are roaming on wide, open spaces and kids and parents can take a memorable photo standing next to a kangaroo. The Nashville Zoo has the largest playground in Nashville, a Wild Animal Carousel and a Wilderness Express train. Unique to Nashville Zoo is the Historic Grassmere Home and Farm, a home listed on the National Register of Historic Homes. This home was built in 1810. You can take a guided tour and find out why the zoo is located near the home and check out the 3-tier heirloom garden and the family cemetery. The Lorikeet Landing is another special place at the Nashville Zoo where you can walk into the habitat and feed one of the more than 50 Australian lorikeet parrots.

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Road Trip From Chicago To Nashville

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A few weeks ago, I got an invitation to participate in a road trip from Chicago to Nashville, Tennessee. This year is my last year of law school, so I figured it was time to see the country and chase my dreams. By the time I found out about the trip, I was already entering the final stages of preparing for the bar exam. This was a good opportunity to take a trip with a bunch of other law students from a few states away, and I didn’t want to miss it.

Let’s face it: in the United States, we don’t drive much. Most of us take the train, cram our bodies into a car, and then drive a car that is usually only too big for one person. But what if you’re traveling with a friend? Sure, you can fit both of your bags in the backseat, but that doesn’t leave much room for a third person. Or for a dog.

This past Friday I hit the road with my family for a nearby Chicago vacation. We decided to take a road trip to Nashville, our last stop before our big vacation in Canada. We began our trip at 6:30am with a short drive from Chicago out to Milwaukee, Wisconsin. We had big plans for that day, including a stop in Jackson, Wisconsin, for a hot dog at the Jackson Hole hot dog stand. We were all very excited.

The road journey from Chicago to Nashville will take you through some of the fanciest cities, deepest caves, and greenest woods in the Midwest and Upper South, and will take you past some of the most amazing monuments.

From Chicago to Nashville, the 470-mile journey takes 7 hours and 10 minutes. St. Louis and Fort Knox are among the sights along the way, as are the Housier and Shawnee National Forests, visits at Mammoth Cave and Horse Cave, and the incredible Louisville Mega Cavern.

There’s a lot of territory to cover on this trip, so make sure you read all the way to the conclusion to make sure you don’t miss anything.

What is the distance between Nashville and Chicago, and how long will the journey take?

During your road journey from Chicago to Nashville, you have a few options for routes that have little overlap. The best part is that both routes follow an interstate, making the journey extremely simple for first-time road trippers.

The quickest route will take you via Indiana and Nashville on Interstate 65. It’ll take you all the way through Indiana and a good part of Kentucky, and it’ll take you about 7 hours 10 minutes to travel.

Keep in mind that traffic between Indianapolis and Louisville (both from the north and south) may be heavy, so this route might take you an additional hour on a bad day.

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Another alternative is to add 30 miles to the journey by traveling via Illinois and Kentucky on Interstates 57 and 24. This route is similar to the first in terms of sights, but instead of traveling via Louisville, you may take a detour to St. Louis, Missouri.

This route has the benefit of avoiding traffic congestion since Champaign and Mt Vernon are not as congested as the cities on the other route. Even so, if you’re traveling over the holidays, try using an app to track traffic.

Both drives can be completed in a single day, but for the greatest experience, plan on taking at least three days to see as much as possible along the route.

The best route from Chicago to Nashville for a road trip

There isn’t a clear road trip route between Chicago and Nashville. The route you take should be determined by the particular sites you wish to see, but taking one on the way to Nashville and the other on the way back is the ideal option.

The Indiana Highway (via Interstate 65)

Continue south on Interstate 65, going via Lafayette and Indianapolis, after leaving Chicago via Interstate 90.

Take a day or two to explore Louisville after seeing Yellowwood State Forest and Brown County State Park. Bernheim Arboretum and Research is located farther south, followed by the thrilling Horse Cave and Mammoth Cave.

Before entering Tennessee, take an optional (but highly recommended) diversion to Bowling Green. In Goodlettsville, visit Moss-Wright Park and Rockland Recreation Area before continuing south to Nashville.

The Illinois Highway (via Interstates 57 and 24)

Take Interstates 90 and 94 south to Roseland, and from there, hop onto Interstate 57 and follow it out of Chicago, past Kankakee River State Park. From Champaign, do a detour to Allerton Park & Retreat Center, or continue along the interstate through Mattoon and Effingham.

If you want to take a diversion from Effingham, you may travel Interstate 70 to St. Louis, which is vast and home to attractions like the City Museum LLC and the Gateway Arch.

Once you’ve passed Marion, go back on the main road and take Interstate 24 through Shawnee National Forest before crossing the Ohio River into Kentucky. Before reaching Nashville, drive through the Land Between the Lakes National Recreation Area and make a pit break in Clarksville.

Between Chicago and Nashville, the Best Places to Stop

The wonderful thing about driving from Chicago to Nashville is that there are so many luxury places to stop along the way. Here are some of the finest places to stay in the area:

In Louisville, have a once-in-a-lifetime dinner.

The City of KFC is known across the country for its delectable food, and since you’ll be traveling through, there’s almost no reason not to stay and rest at a posh hotel. The Brown Hotel, with its renowned interior design, is the swankiest hotel in town.

In terms of presentation, the common sitting space is almost cathedral-like, and the bright, airy apartments are sure to make an impression. There’s even a world-class “concert hall” with a grand piano and some of the most opulent furnishings you’ve ever seen.

Shutterstock.com/Sean Pavone

Stop into The Brown Gift Shop and Gallery for a memento and follow it up with a lunch at The Lobby Bar or one of the two on-site restaurants to remember your visit with some area artwork.

This ancient hotel is unquestionably pricey, but with all it has to offer, it has every right to be. Furthermore, since it is just a mile from the city’s center, the location receives extra points for being so near to many of the city’s main sites.

Take in the sights and sounds of Nashville’s music scene.

The only thing that can make the sound of classic all-American tunes sweeter is a stay at a luxurious resort. Although Nashville has them in spades, the biggest standout is definitely The Hermitage Hotel.

The attention to detail at this hotel is second to none, from the magnificent lobby to the top-of-the-line rooms. The Deluxe King rooms, which appear world-class yet have that distinct sense of home, are a clear highlight.

Every evening at this hotel seems like a business meeting in the nicest conceivable manner, whether you’re dining at the restaurant or having a drink at the bar.

If walking about Nashville doesn’t exhaust you, a workout at the on-site fitness center will. Take use of the concierge service and have an in-room dinner while admiring the city view after you’re nice and sleepy.

This hotel is not for the budget traveler, but if you can afford it, a stay at The Hermitage Hotel is one of the most memorable Nashville experiences you can have.

On a road journey from Chicago to Nashville, there are many sights to view.

The amount of sites to visit on the road journey from Chicago to Nashville is astounding, and many of them are in or near large cities, so you won’t have to do any offroading. It’s difficult to include all there is to see, but make a point of visiting the following locations:

• Lake Michigan – The first leg of your trip will take you around Lake Michigan’s southern tip, the second biggest of the Great Lakes and the only one completely inside the United States.
• Lafayette was the location of the Battle of Tippecanoe during the American-Indian Wars, and numerous museums and historic places still exist to recount the tale.
• Indianapolis is the state capital and most populous city in Indiana.
• Louisville is the capital of Kentucky and the state’s most populated metropolis.
• The Mega Cavern in Louisville is a massive cave system featuring an underground zipline system.
• The Hoosier National Forest is a great place to go hiking and fishing near Louisville.
• Jim Beam American Stillhouse – Take a tour of one of America’s most renowned whiskey manufacturers’ iconic facility.
• Bernheim Arboretum And Research Forest – Bernheim Arboretum And Research Forest is a 35-square-mile forest and nature reserve that is home to a variety of animals, plants, and trees. This is a great place to get lost in nature for a bit, with miles of hiking paths and waterways.
• Fort Knox – The location was originally utilized as a fort during the Civil War in 1861, before being transformed into the famous army post and gold repository in 1936.
• Mammoth Cave is the world’s biggest known cave system.
• Horse Cave is a city in Kentucky renowned for its Kentucky Down Under Adventure Zoo and a series of complex cave systems.
• The Kentucky Museum and Library, as well as the National Corvette Museum and the Historic Railpark and Train Museum, are all located in Bowling Green.
• St. Louis is a large city in Missouri that is home to the Gateway Arch, the country’s highest landmark.
• Shawnee National Forest – With sweeping hilltop vistas, it’s no surprise that this is one of the area’s most popular woods.

Shutterstock.com/Zack Frank

When is the best time to travel from Chicago to Nashville?

The road journey from Chicago to Nashville may be done at nearly any time of year and still be enjoyable, but Nashville’s peak season is unusual in that it lasts over 6 months.

When the weather is nice, Nashville is busy and lively; many of the local music events take place from mid-spring to mid-fall, drawing large crowds.

Be aware that temperatures in the city may reach the 90s in the middle of the summer, and that the city can swing from scorching hot to huge rainstorms at any time of year.

f11photo/Shutterstock.com

Although there isn’t as much to see, coming in the late autumn may be a good choice if you simply want to wander about the city. In November, temperatures remain around 60 degrees, and hotel rooms are inexpensive.

Winter is also a feasible option, provided you don’t mind the continuous 50-degree temperatures. If you want to keep your vacation quiet, February is a good time to go since the city has few tourists, and the weather starts to warm up around early March.

You may wish to schedule your journey around some of the stopover places, since each has its own set of seasonal highs and lows. Summers in Louisville, for example, are often wet, while hotel rates in St. Louis spike around June.

John and I are going on a road trip from Chicago to Nashville to see our nephew, and we’re documenting it in our blog. We’re traveling for the first time, so we decided to accomplish a few things in our time away. This blog post is about our preparations for the trip, and how we plan to live the trip without being tied to our computers.. Read more about places to go between chicago and gatlinburg, tennessee and let us know what you think.

Frequently Asked Questions

Where do you stop on the way to nashville.

I stop at the next city.

What is halfway between Chicago and Nashville?

The halfway point between Chicago and Nashville is in the middle of the Mississippi River.

How far is Chicago to Nashville TN?

Chicago is located in Illinois and Nashville TN is located in Tennessee. The distance between the two cities is approximately 2,878 miles.

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The Breathtaking Scenic Drive Through Tennessee That Runs Along The Tennessee River

Chris Dodge

My name is Chris Dodge and I live right here in the great state of Tennessee. My family and I are full adventurers filled with passion to see the amazing things our state has to offer. We are avid hikers and have explored many different places in Tennessee and beyond but we are always thankful to be living in such a glorious state.

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Have you ever noticed how many of the backroads in Tennessee follow a river or stream? The Tennessee River Trail is no exception, and actually takes you on a scenic tour de force following the most gorgeous river in our state. If you are looking for a scenic weekend adventure, make your way to the Tennessee River and ride along for a classic road trip. 

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The Tennessee River Trail is a great option for a scenic drive in the Volunteer State. As you can see there is also plenty to see and do all along the way so you can easily make this a classic road trip. So gather your friends and family and make sure you have packed plenty of snacks for the trip and then enjoy the journey. To make sure you don’t get lost along the way have this handy atlas in the car with you on your trip. 

For another pretty drive in Tennessee, check out the Ocoee Scenic Byway .

OnlyInYourState may earn compensation through affiliate links in this article. As an Amazon Associate, we earn from qualifying purchases.

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A Packed Road Trip to Bristol, Tennessee

W elcome to Bristol, the surprisingly divided city in the foothills of the Appalachian Mountains! Situated between Virginia and Tennessee, Bristol offers a unique shared experience. As the birthplace of country music, you’ll find a darling downtown area filled with neon lights, charming eateries, and a delightful sense of nostalgia. Prepare for a fun-filled road trip to Bristol, Tennessee, as we share what to do in this cool dual state city.

Birthplace of Country Music

In Bristol, country music legends recorded their first songs, including Johnny Cash, Dolly Parton, and Elvis Presley. The  Birthplace of Country Music Museum , located in downtown Bristol is a must-visit attraction and Smithsonian Museum affiliate home to a vast collection of historic recordings, artifacts, and exhibits that celebrate the story of country music’s pioneers. 

You will be delighted to learn about how country music emerged in Bristol. Visiting this museum is a unique opportunity to enrich your knowledge of country music history.

Adult tickets are $13, and a small discount is available for students, seniors, and the military.

Make sure to see the murals honoring the “Bristol Sessions” a few blocks away with beautiful images of the legends that made this area famous—Jimmie Rodgers, Tennessee Ernie Ford, and the Carter Family. The 76 songs recorded in 1927 during these ten days, with 19 artists, are where and when country music was born.

Downtown Bristol

If you are a history buff or enjoy strolling down cobblestone streets, visiting downtown Bristol is a must. You will love the unique architecture, specialty shops, fun neon lights, and colorful murals. Enjoy an ice cream or slice of homemade fudge from  Southern Churn Ice Cream and Candy Shoppe .

Need help choosing a flavor? You can’t go wrong with penuche or dark chocolate sea salt. 

The historic art-deco 1931  Paramount Bristol , a performing arts center showing movies and hosting concerts, is a must-visit site. The restored theatre (circa the 1990s) has a vintage Mighty Wurlitzer organ. It is one of the few remaining in the country.

Henry Rollins, Joan Osborne, Kathy Mattea, and Oklahoma (the musical) are coming attractions. 

Original Burger Bar

One of my favorite places in downtown Bristol is the  Original Burger Bar , a retro stop you won’t want to miss. This nostalgic diner, circa 1942, is excellent for never-frozen burgers, hot dogs, shakes, and 1950s rock & roll.

It is also where singer Hank Williams, Sr., was last seen alive. 

I loved the “Your Cheating’ Heart” burger! This award-winning diner is closed Sundays and Mondays.

You’ll also find some amazing meals in nearby Johnson City, TN.

Bristol Motor Speedway

Are you a car racing enthusiast? Don’t miss the opportunity to visit the Bristol Motor Speedway , one of the most iconic race tracks in the world. It’s known as “The Last Great Colosseum” and “Thunder Valley,” and has a seating capacity of 162,000 people.

Bristol Motor Speedway was built in 1961 and is known for its unique pit stop and racing formats. You can tour the Speedway and visit the gift shop and museum to learn about racing history. Buy your tickets early, as these races are highly in demand.

Pal’s Sudden Service

Be sure to check out  Pal’s Sudden Service , a local fast-food chain that offers a unique take on classic Americana food. Pal’s Sudden Service has been a popular chain in the region since 1956. It has won many awards for its unique menus, high-quality service, and delicious food. 

Try their signature snack, “Frenchie Fries,” or the tasty hot dogs, shakes, and even breakfast items.

Shopping at The Falls and Pinnacle

Are you a shopping enthusiast? Consider visiting The Falls and  The Pinnacle , Bristol’s two largest shopping centers. You can explore over 70+ combined stores (Hibbett Sports, Belk, Bass Pro, etc.) to find the latest fashion trends, home décor items, and more. 

The Falls offer a beautiful outdoor area, while the Pinnacle offers open-air shopping. Whether you are looking for designer fashion or gifts for loved ones, you are sure to find everything you need here.

State Street Brewing

No trip to Bristol is complete without visiting  State Street Brewing , known for its delicious, handcrafted beers. You can sample some of State Street’s unique beer blends, including the Bristol Blonde, Euphoria, and Hopnotch. Keep in mind this is on the Virginia side of town.

State Street Brewing also serves light lunch options, like sandwiches, soups, and salads, making it the perfect spot for a casual meal. They are closed Mondays and Tuesdays.

Bonus Offerings

If you are a golfer, Clear Creek Golf Course is an 18-hole public course that is fun to play. History lovers should consider a short drive to Rocky Mount State Historic Site in Piney Flats. The property houses a living history museum where guests can step back into 1791 to look at frontier families. There is also a barn and adorable sheep. 

End your evening with a nostalgic experience, or one the kids may have yet to experience – a drive-in movie.  Twin City Drive-In Theatre  features two screens to watch new releases back to back. They also have a great concession stand with reasonable prices. 

The drive-in converts to a campground during Bristol race weekends. 

FYI : If your travels bring you to Bristol the second weekend of September, the Bristol Rhythm and Roots Reunion music festival will be going on, a three-day extravaganza with 150+ artists.

Blackbird Bakery

My very favorite thing in Bristol is Blackbird Bakery . I would put their tempting desserts and pastries up against any bakery around the country—that’s how delicious they are. Blackbird Bakery also has enjoyable coffee, bread, and ice cream.

Try an affogato, the best of both worlds: coffee and ice cream.

If you’re looking for a sweet treat to wrap up your visit to Bristol, stop by the Blackbird Bakery. This locally-owned bakery is known for its delicious variety of pastries, croissants, cakes, and macaroons. You can also try their artisanal coffee, brewed with premium local coffee beans.

Cootie Brown’s

For dinner, how about a classic eatery? Shoney’s is popular in this part of the state, as is Cootie Brown’s , an eclectic restaurant that is sure to please. Cootie Brown’s features tamales, pizza, and even a Sunday brunch.

My top pick is the Jamaican Jerk chicken with black beans & rice and roasted sweet potatoes. 

A Road Trip to Bristol: Experience the Appalachian Movement

Bristol, Tennessee, is a fantastic getaway destination to add to your must-visit list. This charming city has something for everyone. Whether you are road-tripping with friends or family, you’ll enjoy this city’s memorable experiences.

Come to Bristol, and you will discover a gem worth revisiting again and again.

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Tennessee Whiskey Trail: What to know when planning your custom trip

Of all the spirits, American whiskey has one of the biggest stories to tell. The story of Tennessee whiskey in particular seems to have only just begun, and the rest of the country is taking notice.

That's in part because of the whiskey's allure. Immortalized in song and championed by a growing number of smart, young distillers and consumers, Tennessee whiskey is having a momen t.

In 2022, the Tennessee Whiskey Trail, a collaborative effort put together by more than 30 Tennessee distillers, welcomed 7.8 million visitors into statewide distilleries. That's an increase of 1.3 million visitors over 2019. To say interest in Tennessee whiskey is on the rise is an understatement, said Whiskey Trail executive director Charity Toombs.

The Tennesee Whiskey Trail links together more than two dozen distilleries in a whiskey road that runs from the mountainous eastern border to the barbecue-steeped culture of Memphis in the west. It's as much a celebration of the state itself as it is of its whiskey.

"It's an adventure, and that's what we invite guests to do, is immerse themselves in these adventures and to partake in and enjoy the spirits and the distillers who call Tennessee home," Toombs said.

The iconic Jack Daniel Distillery and its scenic Lynchburg environs often serve as a starting point. But Toombs said that, as visitors fan out across the state, they're often charmed by the lesser-known distilleries. The state and its diverse topography from end to end is its own draw.

Among the smaller whiskey makers on the trail is Brushy Mountain Distillery, set in a historic former state penitentiary wedged in a narrow mountain valley. Woodbury's Short Mountain Distillery , set on a 300-acre working farm, boasts nearby falls and hiking trails. And Bootleggers Distillery, situated on the North Carolina-Tennessee border, has as a backdrop Smoky Mountain ridges, which blaze with color in the fall.

Experiential distillery tours providing far more than a snifter of booze appeal to younger consumers, Toombs said.

"We're seeing that even in the distillery experiences," she said. "It's not just going to the distillery for a tasting. These distilleries are truly trying to create immersive experiences."

Tennessee Whiskey Trail organizers have seized on that thirst for more, creating trail itineraries for music lovers, holiday shoppers and outdoor enthusiasts. One popular route takes visitors close to natural waterfalls and hiking trails.

Their guides help break the trail into manageable bites. With so much ground to cover, visiting all 28 stops takes real dedication.

"We had a guest that was from the U.K. who started the trail in 2017 and completed it in 2020," Toombs said. "He took three international trips to complete the trail."

For subscribers: Tennessee whiskey industry is old and giant — but also new and fledgling

Tips for taking the Tennessee Whiskey Trail trek

Plan your trip: Consider an itinerary. Find curated trips and trail routes at tnwhiskeytrail.com/trip-planner , including Waterfalls and Whiskey , Urban Getaway and Outdoor Adventurer . Or pick your trail visit based on region.

Get your passport: The official Tennessee Whiskey Trail Passport is your guide to getting around. Download your digital passport at tnwhiskeytrail.com/passport , then collect stamps digitally by “checking in” to distilleries along the trail. Or pick up a hard copy at a Tennessee distillery. Collect stamps at each distillery visit and redeem your completed passport for a commemorative gift. 

Download your trail map: There's a handy Google Maps version of the Tennessee Whiskey Trail. Download it at tnwhiskeytrail.com/maps-downloads and hit the highway.

Study up before you go: Check out a directory of the distilleries at tnwhiskeytrail.com/distilleries . Make sure to visit each website and see what kind of arrangements you need to make before hitting the road. If you need to book tours in advance, for example, you'll want to know before your show up at the distillery's doorstep.

See what Tennessee has to offer: Mix up your Whiskey Trail experience. Try starting the day with a distillery in a rural area, such as the Jack Daniel Distillery in Lynchburg. End your day at an urban distillery, such as Corsair and Nelson's Green Brier Distillery , both located just an hour and a half from Lynchburg in downtown Nashville's growing Marathon Village .

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The 12 Best Things to Do in Chicago

Famously known as “the Second City” (meaning second in population to New York), I feel like Chicago is often overlooked by travelers. It sees a fraction of the visitors LA and NYC receive, which is a shame, as it’s one of my favorite cities in the world .

Chicago is chock-full of world-class institutions, Michelin-starred restaurants, awe-inducing architecture, and verdant parks. There is a lot to do here and the city has a really rich history. I think more people should visit.

Sure, the winters are brutal. But, come spring, Chicago blossoms into a dynamic urban landscape of street life, outdoor cafés, and sunny parks when locals take over the outdoors to enjoy the few months of nice weather. (I don’t think you can really beat Chicago in the summer.)

To help you plan your visit, here’s my list of the best things to do in Chicago:

Table of Contents

1. Take a Walking Tour

2. relax in grant and millennium parks, 3. take in some art at the art institute of chicago, 4. admire amazing architecture on a river cruise, 5. stroll down the magnificent mile, 6. visit the shedd aquarium, 7. take in some natural history at the field museum, 8. get a stunning view at 360 chicago observation deck, 9. feast on deep-dish pizza, 10. stroll the chicago riverwalk, 11. eat your way through the mexican eateries in pilsen, 12. watch an improv show, 13. have fun at navy pier, 14. catch a game at wrigley field, 15. feast in chinatown, 16. experience st. patrick’s day, 17. explore oz park.

One of the first things I do when I arrive in a city is take a walking tour. They’re a great way to see the main sights, get the lay of the land, and connect with an expert local guide who can answer all my questions. Free Chicago Walking Tours hosts regular free tours that can introduce you to the city. You’ll get to see many of the coolest buildings in the city while also learning about the history of Chicago. The tour lasts a few hours. Be sure to tip the guide at the end!

For a more unique tour, try the Gangsters and Ghosts Tour . You’ll learn all about Chicago’s dark side and creepy past as you explore the Chicago Loop. The tour lasts two hours and really talks about one of the pivotal times in Chicago’s history. Even if you’re not a history buff like me, you’ll get a lot out of it.  

Located downtown, these gigantic parks provide a great place to hang out, have a picnic, or go for a run. People play chess here when the weather is nice and, during the summer, there are a lot of free concerts and events here. The larger Grant Park stretches along Chicago’s waterfront, while Millennium Park is the subsection where the famous “Chicago Bean” sculpture is located. This iconic work of public art is a must-see. And, starting at noon on the first and third Saturdays from April through November, the Chicago Cultural Center hosts walking tours focusing on the art of Millennium Park. It’s really interesting. I love strolling through the park or just chilling here with a good book on a nice day.  

To beat the crowds, skip a weekend visit as the place gets packed. Instead, go on a Monday or Thursday evening (they’re open late on Thursdays). You’ll have the place virtually to yourself.

111 S Michigan Ave, (312) 443-3600, artic.edu. Open Thursday-Monday 11am-5pm (8pm on Thursdays). Admission is $32 USD ( $40 USD for advance skip-the-line entry ). Daily tours (included in the price of your ticket) are offered at 1pm and 3pm.  

Chicago is an architecture lover’s dream. The very best way to take in its famed buildings is via a river cruise . This way, you can sit back and cruise down the canals while an expert guide provides context for what you’re looking at. The guides will give you a detailed history of the architecture. Some of the buildings you’ll see on the boat ride include the Tribune Tower, 333 West Wacker, Navy Pier, the Willis Tower, the Wrigley Building, and Marina City, among others. All in all, there are about 50 structures to see on this fascinating tour, and I promise, it’s much more interesting than it sounds!  

Often nicknamed “Mag Mile,” this stretch along Michigan Avenue from the Chicago River to Oak Street is known for its upscale designer boutiques. In fact, rent here is the third highest in the US (after Fifth Avenue in New York City and Rodeo Drive in Beverly Hills). Even if you don’t want to blow your budget shopping, it’s still an experience to stroll along the avenue and take in the sights and the people, and enjoy the view of the Chicago River. There are several landmarks and attractions along the way too, including the 360 Chicago Observation Deck for expansive views over the city (more on this below).  

If you’re visiting the city with kids (or you’re a kid at heart), head to the massive Shedd Aquarium. It’s the third-largest aquarium in the Western hemisphere and home to over 32,000 animals. They have turtles, penguins, sea otters, snakes, sharks, and more. They really emphasize education here so you’ll learn a ton while you roam the different exhibitions. You can even pay extra to do things like feed penguins and sharks, and they also host all kinds of fun evening events (such as live music after hours). I absolutely love coming here. Just make sure to book your ticket in advance as they do get busy and sell out!

To beat the crowds, skip the weekend and visit during the week instead. Also, try and visit right when it opens (especially Wednesday-Friday). It’s usually quieter then.

1200 S DuSable Lake Shore Dr, (312) 939-2438, sheddaquarium.org. Open 9am-5pm Monday-Friday (9pm on Tuesdays), 9am-6pm Saturday, and 11am-6pm on Sundays. Tickets start at $37 USD. Admission can also be included with the Chicago CityPASS .  

One of the biggest museums in the world, the Field houses extensive collections spanning anthropology, geology, botany, and zoology. Some important collections include the displays of taxidermied animals, a wing dedicated to astronomy, and fascinating artifacts from ancient Egypt. I recommend planning to spend at least 3-4 hours to really take it all in.

1400 S. Dusable Lake Shore Drive, (312) 922-9410, fieldmuseum.org. Open daily 9am-5pm (last admission is at 4pm). Basic admission is $30 USD . Special exhibitions are an additional charge (which varies), though you can get an all-access pass for $43 USD.  

Chicago is a skyscraper city, including a few rather iconic towers. Located atop what was formerly known as the John Hancock Building and now (uninspiringly) called 875 N. Michigan, the 360-degree viewing deck a thousand feet up and allows visitors to get the best view of the Windy City and Lake Michigan. You can even grab a pint at the Cloud Bar, which serves beer from Moody Tongue, a local brewery.

If you’re a thrill seeker and want more than just the view, sign up for Tilt. This part of the observation deck is where you can stand in front of a glass window, which then tilts forward, until it appears you’re looking directly down at the street, 94 floors below.

Just make sure to check the weather before you go so you will actually have a view to enjoy. Additionally, if you want to beat the crowds, come early (before 10am).

875 N Michigan Ave, (888) 875-8439, 360chicago.com. Open daily 9am-11pm (the last entry is at 10pm). Admission starts at $30 USD ( get your tickets in advance for skip-the-line access ).

If you really want to indulge, hop on a Chicago Pizza Tour , on which you’ll get to sample all the varieties on offer in town. Tours start at $49 USD.  

Stretching from Lake Michigan to Lake Street, the 1.25-mile Riverwalk along the Chicago River makes for a fun stroll. Along the way, you’ll not only get fantastic views of the river and city, but you’ll encounter a legion of waterfront restaurants, cafés, and bars. There’s a ton of public art and green space too (great for picnicking and people-watching). It’s the perfect place to slow down and enjoy the moment in this Midwestern metropolis, but if you prefer a more active experience, there are also lots of aquatic activities here too (such as kayaking or taking a river cruise).  

The neighborhood of Pilsen was founded in 1878 by Czech immigrants, who named the area after the fourth-largest city in the Czech Republic, where pilsner beer was born. The Czechs may be gone now, but today Pilsen is Chicago’s main Latino neighborhood, particularly Mexicans from the Michoacán region. Today you can wander the area, eating some of the best tacos while taking in the vibrant street art.  

The Second City is one of the most popular and well-known improv troupes in the country. It’s where greats like Bill Murray, John Candy, Catherine O’Hara, Steve Carell, Tina Fey, and Amy Poehler all cut their teeth. They put on regular performances and also host all kinds of special events. They even host workshops and classes if you want to give improv a try yourself. Just be sure to get your tickets in advance as the most popular shows sell out fast.

230 W North Ave, (312) 337-3992, secondcity.com. Performances are held daily so check the website for what’s on. Tickets start at $35 USD.  

600 E Grand Ave, (312) 595-7437, navypier.org. Open Sunday-Thursday 11am-8pm and Friday-Saturday 11am-9pm (individual attractions and restaurants may have separate hours). Admission to the pier is free, though attractions charge their own fees ( the Centennial wheel is $21.30 USD , for example).  

Home of the Cubs, Wrigley Field, on Chicago’s North Side, is smack in the middle of town. It also happens to be one of the oldest baseball stadiums in the United States (it opened in 1914). If you’re in Chicago during the baseball seasons (April to October) and the Cubs are in town, do yourself a favor and go to a game. It’s one of the most intimate and atmospheric baseball stadiums in the country. If the Cubs are not in town, you can also take a 90-minute behind-the-scenes tour of the stadium.

1060 W Addison St, (773) 404-2827, mlb.com/cubs/ballpark. Tour dates and times vary depending on the season (check the website for availability). Tour admission is $30 USD. Tickets to see a game vary greatly but start at just $10 USD (for better seats at a popular game, expect to spend closer to $80-125 USD).  

Bring your appetite to Chinatown, where you can feast on cheap dim dum, do karaoke, or relax at one of the many tea houses. One of the oldest Chinatown’s in the country, over a third of Chicago’s Chinese population lives in Chinatown, making it one of the largest concentrations of Chinese-Americans in the USA. Don’t miss Ping Tom Memorial Park, and keep an eye out for colorful murals around the neighborhood. Some of my favorite places here are Hing Kee, MCCB Chicago, and Phoenix. &nbsp

The tradition began in 1843, when Chicago’s first Irish parade was held, but it wasn’t until 1962 that the dyeing of the river started, at the suggestion of a plumber’s union, which is still responsible for the green river each year, though it won’t divulge its secrets about what’s used (it’s environmentally friendly, though). Take a river cruise on the emerald waters or snap a pic from the sidelines and enjoy. This is one of the biggest days of the year here!  

This whimsical little park, located in the Lincoln Park area, was created to honor L. Frank Baum, the author of The Wizard of Oz . He lived in the area at the end of the 19th century, and when the city wanted to renovate the park they decided to do so in a way that honored Baum’s popular book.

There’s a playground named after Dorothy, a green space called the “Emerald Gardens,” and numerous life-size statues of popular characters from the musical adaptation, including the Dorothy, Toto, the Tin Man, the Cowardly Lion, and the Scarecrow.

Open daily 6am-11pm. Admission to the park is free.

Chicago doesn’t get the attention it deserves. I think it’s fun and perfect for a weekend getaway. And you really can’t beat the summers here either. With lots of interesting museums, plenty of green space, and some great eats, Chicago should be on every traveler’s list!

Book Your Trip to Chicago: Logistical Tips and Tricks

Book Your Flight Use Skyscanner to find a cheap flight. They are my favorite search engine because they search websites and airlines around the globe so you always know no stone is left unturned.

Book Your Accommodation You can book your hostel with Hostelworld as they have the biggest inventory and best deals. If you want to stay somewhere other than a hostel, use Booking.com as they consistently return the cheapest rates for guesthouses and cheap hotels.

Don’t Forget Travel Insurance Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:

• Safety Wing (best for everyone)
• Insure My Trip (for those over 70)
• Medjet (for additional evacuation coverage)

Looking for the Best Companies to Save Money With? Check out my resource page for the best companies to use when you travel. I list all the ones I use to save money when I’m on the road. They will save you money when you travel too.

Want More Information on Chicago? Be sure to visit our robust destination guide on Chicago for even more planning tips!

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