Louisville to Chicago road trip: Distance, drive time & best stops

By car, the distance from Louisville to Chicago is 298 miles, with a driving time of 4h56m. The best road trip stops on a Louisville to Chicago road trip are Brown County State Park, Indianapolis and Wolf Park.

Planning a Louisville to Chicago road trip

A Louisville to Chicago road trip connects Kentucky to Illinois – and the home of the Kentucky Derby to one of America’s greatest cities.

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.

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.

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.

Louisville to Chicago distance and driving time

By car, the distance from Louisville to Chicago is 298 miles. That makes for a driving time of around four hours and 56 minutes. The quickest route is along the I-65 and I-90.

The best stops to add to a Louisville to Chicago road trip are Brown County State Park, Indianapolis and Wolf Park.

Louisville to Chicago road trip attractions: Brown County State Park

The ravines of Brown County State Park were created by glacier meltwater. If picking just one walk, make it the 0.75 mile Ogle Hollow Nature Preserve Trail, where you can see rare yellowwood trees.

The park’s focal point is the Abe Martin Lodge, which has a swimming pool and small water park, although the Nature Center is the best bet for understanding the natural environment.

The best views, however, come from the top of the 90ft Fire Tower.

Best stops between Louisville and Chicago: 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.

Louisville to Chicago drive: Wolf Park

Near Lafayette IN, Wolf Park is a conservation and education facility that aims to change public attitudes towards wolves and learn more about them.

General admission allows visitors to see the animal exhibits, but there’s no guarantee you’ll actually see wolves. For that, book on to a guided tour – they run both in the day time and at night.

Skyscrapers around the Chicago River in Chicago.
Skyscrapers around the Chicago River in Chicago. Photo by David Whitley/ Best3Stops.

More Louisville road trips

Atlanta to Louisville | Bowling Green to Louisville | Louisville to Cincinnati | Louisville to Cleveland | Columbus to Louisville | Louisville to Dallas | Louisville to Detroit | Evansville to Louisville | Louisville to Gatlinburg | Louisville to Indianapolis | Knoxville to Louisville | Louisville to Lexington KY | Louisville to Memphis | Louisville to Nashville | Pittsburgh to Louisville.

More Chicago road trips

Albany NY to Chicago | Ann Arbor to Chicago | Chicago to Asheville | Chicago to Aspen | Chicago to Atlanta | Chicago to Baltimore | Chicago to Birmingham AL | Bloomington IL to Chicago | Chicago to Boston | Chicago to Buffalo | Cedar Rapids to Chicago | Charlotte to Chicago | Chattanooga to Chicago | Cincinnati to Chicago | Cleveland to Chicago | Chicago to Colorado Springs | Columbus OH to Chicago | Davenport IA to Chicago | Dayton OH to Chicago | Denver to Chicago | Des Moines to Chicago | Detroit to Chicago | Chicago to Fargo | Fort Wayne to Chicago | Chicago to Gatlinburg | Grand Rapids to Chicago | Chicago to Green Bay | Indianapolis to Chicago | Iowa City to Chicago | Chicago to Jacksonville | Kalamazoo to Chicago | Kansas City to Chicago | Chicago to Knoxville.

Lafayette IN to Chicago | Lansing MI to Chicago | Chicago to Lexington KY | Chicago to Lincoln NE | Chicago to Little Rock | Chicago to Madison WI | Chicago to Memphis | Chicago to Milwaukee | Chicago to Minneapolis | Moline IL to Chicago | Chicago to Nashville | Chicago to New Orleans | New York City to Chicago | Chicago to Niagara Falls.

Chicago to Omaha | Chicago to Peoria IL | Chicago to Pigeon Forge | Chicago to Pittsburgh | Chicago to Philadelphia | Chicago to Richmond VA | Rockford IL to Chicago | Chicago to San Antonio | Scranton to Chicago | Chicago to Sheboygan | Chicago to Springfield IL | South Bend to Chicago | St Louis to Chicago | Syracuse to Chicago | Toledo to Chicago | Chicago to Tulsa | Chicago to Washington DC | Chicago to Wichita | Chicago to Wisconsin Dells.