Cincinnati to Chicago road trip: Drive time, distance & best stops

The best road trip stops to add to the Cincinnati to Chicago drive are the Miami Whitewater Forest, Indianapolis and Wolf Park. The distance from Cincinnati to Chicago by car is 295 miles, with a 4h35m driving time.

Finding the best things to do between Cincinnati and Chicago

A Cincinnati to Chicago road trip takes you from southern Ohio to the birthplace of the skyscraper in Illinois.

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.

Top Cincinnati activities include underground tours – some with beer tasting – and food tours by streetcar. You can also try baseball history tours, indoor skydiving and guided ghost walks

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.

Cincinnati to Chicago distance and driving time

By car, the distance from Cincinnati to Chicago is 295 miles. You can expect a driving time of around four hours and 35 minutes. The quickest route heads along the I-74 then the I-65.

The best stops to add to a Cincinnati to Chicago road trip are the Miami Whitewater Forest, Indianapolis and Wolf Park.

Cincinnati to Indianapolis road trip stops: Miami Whitewater Forest

The Miami Whitewater Forest lies to the north-west of Cincinnati, and is a great place to stretch the legs. The 7.8 mile Shaker Trace Trail forms the centrepiece, offering plenty of native trees and a wealth of butterflies. This trail is paved, so it’s suitable for cycling, too.

The Visitor Centre has live animals – popular with the kids – while pedal boats, kayaks and paddleboards are available for hire at the Boathouse.

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 Cincinnati road trips

Akron to Cincinnati | Cincinnati to Atlanta | Cincinnati to Boston | Cincinnati to Buffalo | Cincinnati to Cleveland | Columbus to Cincinnati | Cincinnati to Dallas | Cincinnati to Denver | Cincinnati to Detroit | Cincinnati to Houston | Cincinnati to Kansas City | Cincinnati to Knoxville | Cincinnati to Indianapolis | Louisville to Cincinnati | Cincinnati to Memphis | Nashville to Cincinnati | Cincinnati to New Orleans | Cincinnati to New York City | Cincinnati to Niagara Falls | Philadelphia to Cincinnati | Pittsburgh to Cincinnati.

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 | 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 |Louisville to Chicago | 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.