Chicago to Lexington KY drive: Distance, time & best stops
The best road trip stops on the Chicago to Lexington drive are Indianapolis, Louisville and Frankfort KY. The distance from Chicago to Lexington by car is 372 miles, with a 5h37m driving time.
Planning a Chicago to Lexington road trip itinerary
The Chicago to Lexington drive takes you from the biggest city in Illinois to a horse-obsessed city in Kentucky.
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.
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.
Lexington, Kentucky, is renowned as a hub for the world of horse-breeding. However, there is much more to the city than studs.
Interesting Lexington experiences include downtown food tours, guided art walks, zipline tours through the Kentucky River Palisades. You can also try bluegrass cocktail tours, visiting a thoroughbred horse farm and visiting Mary Todd Lincoln House.
Chicago to Lexington distance and driving time
By car, the distance from Chicago to Lexington is 372 miles. That makes for a driving time of around five hours and 37 minutes. The quickest route is along the I-65 and I-64.
The best stops to add to a Chicago to Lexington road trip itinerary are Indianapolis, Louisville and Lexington KY.
For more things to do on the way, check out the guides to the individual road trip sections.
Best stops between Chicago and Lexington: 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 Lexington 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.
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.
Chicago to Lexington KY road trip attractions: Frankfort KY
Frankfort is the relatively small capital of Kentucky. The capitol building is architecturally impressive, but the city’s real strength is its distilleries. The Buffalo Trace distillery offers tours and free tastings. You can do tours at the Castle & Key distillery, too.
For something more on a natural bent, Cove Spring Park is home to wetlands, ravines and picturesque waterfalls.
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