Chicago to Jacksonville drive: Distance, time & best stops
The best road trip stops on the Chicago to Jacksonville drive are Louisville, Nashville and Atlanta. The distance from Chicago to Jacksonville is 1.058 miles, with a 16h17m driving time.
Planning a Chicago to Jacksonville road trip itinerary
The Chicago to Jacksonville drive connects the biggest city in Illinois to the biggest city in northern Florida.
Our favourite thing to do in Chicago
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.
Chicago’s skyscrapers, music scene and massive collection of cultural attractions make it arguably the most exciting city in the US to visit.
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.
Top Jacksonville experiences include Amelia Island kayak tours, guided art and architecture tours by electric bike and electric skateboard rides along Fernandina Beach.
For cultural attractions, head to the Cummer Museum, where the strength tends to be the rotating temporary exhibitions.
Chicago to Jacksonville distance and driving time
By car, the distance from Chicago to Jacksonville is 1,058 miles. That makes for a driving time of around 16 hours and 17 minutes. The quickest route heads down the I-65, I-24 and I-75.
The best stops to add to a Chicago to Jacksonville road trip itinerary are Louisville, Nashville and Atlanta.
For more suggestions, check out the guides to the individual legs of the Chicago to Jacksonville road trip.
- Chicago to Louisville drive.
- Louisville to Nashville drive.
- Nashville to Atlanta drive.
- Atlanta to Jacksonville drive.
Chicago to Jacksonville drive: Louisville
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.
Why you should visit the Kentucky Derby Museum
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.
Best stops between Chicago to Jacksonville: Nashville
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.
How to see Nashville the smart way
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 Jacksonville road trip attractions: Atlanta
Atlanta played a massive part in the Civil Rights movement, and a black history and civil rights tour is pretty much a must-do.
For more Atlanta experiences, try a sightseeing trolley tour for orientation and overview. Or a guided bike ride to get a better feel for the neighbourhoods.
Other Atlanta favourites include the World of Coca Cola, Midtown food and cocktail tours and multi-brewery beer tours.
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