Chicago to Nashville drive: Best road trip stops, distance & time

Planning a Chicago to Nashville road trip itinerary

The Chicago to Nashville drive takes you from the biggest city in Illinois to the country music capital of the world in Tennessee.

The Chicago architecture cruise has a phenomenal wow factor, with the boat gliding between some of the world’s most legendary skyscrapers.

We found the commentary matches the views, too. Expect a fascinating run-down of the city’s history – and plenty of surprising detail about the buildings you’re seeing. 

Book mobile-friendly tickets here.

Highly recommended Chicago experiences include an architecture river cruise, a gangsters and ghosts tour of famous Mob sites and a bike tour of the lakefront neighbourhoods. It’s also worth paying a visit to the Field Museum, the 360 Chicago observation deck at the Hancock Tower and the Chicago Architecture Center.

Nashville is renowned for its country music, but the National Museum of African American Music is also in the Tennessee capital.

The best Nashville experiences include backstage tours of the Grand Ole Opry House, helicopter flights over the city and tasting tours at the Big Machine Distillery. You can also try line dancing classes, the Country Music Hall of Fame and haunted pub crawls. Or, for lavish old homes, visit Andrew Jackson’s Hermitage, the Travellers Rest Historic House Museum and Belmont Mansion.

Excellent Nashville accommodation choices include the gloriously evocative Belle Air Mansion and Inn, plus downtown’s grand dame, the Hermitage.

You can save money in Nashville by combining a tour ticket with admission to two top attractions. These combo tickets give you a half day tour of the main sights, plus entrance to the Ryman Auditorium and Country Music Hall of Fame. Find out more here.

Chicago to Nashville distance and driving time

By car, the distance from Chicago to Nashville is 471 miles. That makes for a driving time of around seven hours and 20 minutes. The quickest route is along the I-65.

The best stops to add to a Chicago to Nashville road trip itinerary are Indianapolis, Louisville and Mammoth Cave National Park.

For more things to do, check out the guides to the individual legs of the Chicago to Nashville road trip.

Best stops between Chicago and Nashville: Indianapolis

The capital of Indiana marries big city energy with country charm.

Top attractions in Indianapolis include the Indianapolis Motor Speedway Museum and the Children’s Museum of Indianapolis.

Worthwhile Indianapolis experiences include a Fountain Square food tour and a walking tour around the city’s highlights.

Chicago to Nashville drive: Louisville, Kentucky

Louisville is the biggest city in Kentucky, and has a strong range of attractions to enjoy. The Louisville Mega Cavern has underground zipline tours, the Churchill Downs race track hosts America’s most famous horse race – the Kentucky Derby – and the Louisville Slugger Factory makes the world’s most famous baseball bats. You can take factory tours and there’s a museum attached.

Good Louisville experiences include Old Louisville ghost tours, the Kentucky Derby Museum and a tasting tour of multiple bourbon distilleries. The food and history tours are also worth checking out.

Top Louisville accommodation choices include the history-drenched Brown Hotel and the art-packed 21C Museum Hotel.

The Kentucky Derby Museum isn’t just about the nation’s top horse race – it’s about the phenomenon that surrounds it. Museum entry tickets include the chance to see the trophies, learn the backstories of famous winners and watch an immersive theater screening. Best of all, they also include a walking tour of the Churchill Downs Racetrack. Find out more here.

David Whitley, author of Best3Stops.

Chicago to Nashville road trip attractions: Mammoth Cave National Park

You can go to Mammoth Cave National Park for horse riding, hiking, camping and canoeing, but the caves are the key attraction.

The cave system in Mammoth Cave National Park is billed as the longest in the world. A bewildering range of cave tours is available, some of which are wheelchair friendly, with others more physical and aimed at cavers.

The classic Mammoth Cave tour is the two hour historic tour, which heads through underground tunnels that humans have used for thousands of years. Be warned, however – there are hundreds of steps.

Nashville, Tennessee skyline.
Nashville Tennessee skyline. Photo by GingerColwell/ Pixabay.

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