Road Trips

What to See and Do on a Chicago to Nashville Road Trip

Posted by
Holly Riddle
February 13, 2023
Updated February 14, 2023

chicago to nashville road trip

Heading from Chicago to Nashville? Or simply looking for a unique road trip experience? This journey from the Midwest to the South showcases some of America’s most underrated gems, creating a trip you’ll never forget.

This underrated route will escort you down the entire length of Indiana, through the bluegrass hills and horse farms of Kentucky, and then right on down to the home of country music. To experience this route to the fullest, slow down and stay awhile.

See what cabin rentals await in Indiana, or which ones in Kentucky have fabulous hot tubs, perfect after a long car ride. Here are our top recommendations for what to see and do on a Chicago to Nashville road trip.

Chicago to Nashville Road Trip by Section

It takes about seven and a half hours, or just under 500 miles, to get from Chicago to Nashville if you travel down Interstate 65. But, there are several detours that are absolutely worth a stop along the way.

To spread this trip over several days, we’re splitting it into two segments: Chicago to Louisville, Kentucky, and Louisville to Nashville. Along the way, there’ll be a whole lot to see and ample opportunities for some little detours.

Segment 1: Chicago to Louisville

The trek between Chicago and Louisville is nearly five hours, but you won’t need to sit in the car that long because you’ll be stopping off and making some detours.

So, grab some deep-dish pizza for the road as you depart the Second City and begin your journey, first stopping in Indiana’s capital…

Segment 1 Highlight: Indianapolis

chicago to nashville road trip - indianapolis
Photo: James Kirkikis

Indianapolis is about a three-hour drive from the Windy City, so stock up on snacks and settle in for a bit of a jaunt. You might want to head out to Indianapolis in the morning, then plan to stay in the city at least overnight, if not for a day or two.

In Indianapolis, you’ll find lots to do, no matter what kind of traveler you are. Families will love the budget-friendly amenities and, of course, the world’s largest children’s museum, the Children’s Museum of Indianapolis. You can’t miss it. Just look for the giant dinosaur out front (and keep your eyes peeled for the giant dinosaurs inside as well!)

NASCAR fans will also love visiting the city, thanks to its famous racetrack, the Indianapolis Motor Speedway. Since Indianapolis is the world’s racing capital, you can find lots of racing-related events occurring here throughout the year – as well as the Union Jack Pub, an English-style pub that’s loaded with racing memorabilia.

Segment 1 Side Trip: Cincinnati

chicago to nashville road trip - cincinnati
Photo: Stephanie A. Sellers

Cincinnati, Ohio, is admittedly out of the way – but if you’ve never visited the Midwest city, which continuously receives acknowledgments and accolades for its status as a growing tourist destination, it’ll be well worth the extra effort.

But while you’re in Cincinnati, there’s so much to do and see, including quite a few free things to do in Cincinnati, like art museums, parks, and trails — there’s always something fun to do here, for every budget.

Cincy is also known for its zoo, which is consistently ranked as one of the best and biggest in the country, and if you’re a coaster fanatic, there’s a world-class theme park hiding in the woods just outside of town. King’s Island is home to award-winning coasters and thrill rides, all tucked into the Ohio woods, giving the park a distinctly forested feel (it also makes some of the rides way scarier at night!)

Before you leave, don’t forget to have a 3-way at Skyline Chili! And no, not that kind of 3-way… It’s their famous dish, which sees spaghetti noodles get topped with chili and cheese.

Related Read: 9 Beautiful Cabin Rentals Near Cincinnati, Ohio

Segment 2: Louisville to Nashville

We’re now more than halfway through the trip, with just 175 miles left between Louisville and Nashville, but the adventure is just starting to heat up…

Segment 2 Highlight: Louisville

chicago to nashville road trip - louisville
Photo: Hendrickson Photography

Louisville offers lots of museums, restaurants, distilleries, arts, culture, and more. The city is especially great for those who are interested in exploring Kentucky’s bourbon scene. You can find outposts for several famous distilleries within the city itself, and many countryside-set distilleries are located just a short drive away.

The city’s other claim to fame – the Louisville Slugger – also attracts lots of visitors, thanks to the famous factory offering tours and showcasing baseball history at its adjacent museum.

If you don’t take the side trip from Indianapolis to Cincinnati, you’ll find that the trip between Indianapolis and Louisville takes just under two hours.

Related Read: 12 Exciting Weekend Road Trips From Louisville, Kentucky

Segment 2 Highlight: Mammoth Cave

chicago to nashville road trip - mammoth cave
Photo: Wangkun Jia

Mammoth Cave National Park is Kentucky’s sole national park. But this isn’t just any ol’ cave. It’s the largest cave system in the world.

Visit and dive deep into the underbelly of the earth to see what awaits you in the darkness. You’ll find all sorts of tours and experiences that are designed to fit varying skill levels and types of adventurers, from families with kids to hardcore caving fanatics. If you’re not keen on caves or caving, though, you’ll find other fun things to do here, including a large selection of above-ground outdoor activities.

It’ll take you about an hour and a half to get between Louisville and Mammoth Cave, and will place you about halfway to Nashville!

Related Read: 9 Beautiful Swimming Holes in Tennessee to Beat the Summer Heat

Segment 2 Highlight: Arriving in Nashville

chicago to nashville roadtrip
Photo: Shutterstock

Once you arrive in Nashville (which is about an hour and a half from Mammoth Cave), you’ll have lots to explore. Obviously, there’s the city’s country music scene.

But beyond that, Nashville has so much more to offer. From the Cheekwood Gardens and Art Museum to snapping skyline photos at Cumberland Park, the city is a booming and vibrant metropolis.

Related Read: 8 Impressive Glamping Spots Near Nashville, Tennessee

Segment 2 Side Trip: Lexington

chicago to nashville road trips - lexington
Photo: Shutterstock

If you want to take a side trip during the second leg of your journey, consider visiting Lexington after you leave Louisville. You’ll find it’s a smaller, charming city that’s a little more accessible to some than Louisville, given its more compact downtown. It’s got lots of shopping, historic sites, restaurants, and breweries.

But it’s best known for being “The horse capital of the world” thanks to its many stables, museums, and parks dedicated to horses. Be sure to sign up for a guided horseback journey during your visit.

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