Cleveland to Chicago road trip: Best stops, distance & driving time

The distance from Cleveland to Chicago by car is 344 miles, with a 5h10m driving time. The best Cleveland to Chicago road trip stops are Cedar Point, Toledo and Indiana Dunes National Park.

Planning a Cleveland to Chicago road trip itinerary

A Cleveland to Chicago road trip heads across the bottom of the Great Lakes to perhaps the greatest US city of them all.

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 attractions in Cleveland include the Rock N Roll Hall of Fame and Cleveland History Center. Alternatively, Cleveland tour options focus on neighbourhood food scenes, the city’s best craft breweries and Downtown’s public art.

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. Or the 360 Chicago observation deck at the Hancock Tower. Or the Chicago Architecture Center.

Cleveland to Chicago distance and driving time

By car, the distance from Cleveland to Chicago is 344 miles. That means a driving time of around five hours and ten minutes. The quickest route follows the I-90.

The best stops to add to a Cleveland to Chicago road trip itinerary are Cedar Point, Toledo and Indiana Dunes National Park.

Cleveland to Chicago drive: Cedar Point

Cedar Point near Sandusky is one of the world’s great theme parks – particularly if you’re a rollercoaster fan. Unlike other amusement parks, which maybe have one or two good rollercoasters and plenty of filler, Cedar Point has an extraordinary collection of top grade thrill rides.

Steel Vengeance is the fastest, longest and tallest hybrid coaster, but there are five coasters that top the 200ft height mark here.

Attractions between Cleveland and Chicago: Toledo

The National Museum of the Great Lakes in Toledo, Ohio, really embraces the scale and scope of its subject. The aim is to show how the Great Lakes have shaped America’s cultural, economic and political history, covering everything from the Underground Railroad to Prohibition-era rum-runners.

The highlight of the visit is the Col. James M. Schoonmaker, once an iron ore freighter plying its trade on the lakes, now a museum ship. 

Other Toledo experiences include Toledo Zoo.

Cleveland to Chicago road trip stops: Indiana Dunes National Park

Indiana Dunes National Park stretches for 15 miles along the southern shore of Lake Michigan. While it is primarily adored for its beaches, the mixture of ecosystems is fascinating for those who want to do more than just lie on the sand.

The dunes take the attention, but the hiking trails take in woodland too, and are surrounded by wildflowers in spring. Come in winter, and cross-country skiing and snowshoeing are available.

Fishing for steelhead in the Little Calumet River is also immensely popular, while the birdwatching amongst the quiet dunes is highly productive.

The Chicago skyline from the Buckingham Fountain.
The Chicago skyline from the Buckingham Fountain. Photo by David Whitley/ Best3Stops.

More Cleveland road trips

Cleveland to Atlanta | Cleveland to Baltimore | Cleveland to Buffalo | Cincinnati to Cleveland | Columbus to Cleveland | Dallas to Cleveland | Dayton to Cleveland | Cleveland to Detroit | Indianapolis to Cleveland | Louisville to Cleveland | Cleveland to Nashville | Cleveland to New Orleans | Cleveland to Niagara Falls | Cleveland to Philadelphia | Pittsburgh to Cleveland | St Louis to Cleveland | Toledo to Cleveland.

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 | 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.