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

The best road trip stops on the Chicago to Pittsburgh drive are South Bend, Cedar Point and Cleveland. The distance from Chicago to Pittsburgh by car is 461 miles, with a 6h45m driving time.

Finding the best things to do between Chicago and Pittsburgh

The Chicago to Pittsburgh drive takes you from the birthplace of the skyscraper to a seriously underrated city in western Pennsylvania.

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.

Book mobile-friendly tickets here.

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.

You can explore Pittsburgh with a hop-on, hop-off bus pass. Pittsburgh experiences include bike tours full of stories, guided whiskey-themed walks and craft beer sampling on a multi-brewery tour.

To find good deals on Pittsburgh hotels, hunt here.

Chicago to Pittsburgh distance and driving time

By car, the distance from Chicago to Pittsburgh is 461 miles. You can expect a driving time of six hours and 45 minutes. The quickest route heads along the I-90, I-80 and I-76.

The best stops to add to a Chicago to Pittsburgh road trip itinerary are South Bend, Indiana, the Cedar Point theme park in Ohio and Cleveland.

Best road trip attractions between Chicago and Pittsburgh: South Bend, Indiana

South Bend is one of those towns that’s just fun to hang out in. It’s a university city, and the student life gives it the bulk of its energy. Notre Dame University tours take in the campus and key buildings such as the hugely impressive Basilica of Notre Dame.

For car-lovers, however, the key attraction in South Bend is the Studebaker National Museum. Studebaker Cars were made here until 1963. The museum tells their story and has plenty of classics on display.

Find more attractions on the Chicago to South Bend drive, or the Chicago and Toledo drive.

Chicago to Pittsburgh 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.

For more options, check out our guide to the Toledo to Cleveland drive.

Chicago to Pittsburgh road trip stops: Cleveland

There are many strong attractions in Cleveland, including the Cleveland History Center. But the big stand out is the Rock N Roll Hall of Fame. It’s an extremely reverent trawl through rock ‘n roll history, looking at the origins and development of the genre. There’s a massive amount of memorabilia, with sections devoted to several Hall of Fame inductees.

The Rock N Roll Hall of Fame is dense, detailed and capable of sucking up the best part of a day.

Alternatively, Cleveland tour options focus on neighbourhood food scenes, the city’s best craft breweries and Downtown’s public art.