Chicago to Philadelphia road trip: Best stops, distance & drive time
The best road trip stops on the Chicago to Philadelphia drive are South Bend, Cleveland and Pittsburgh. The distance from Chicago to Philadelphia by car is 759 miles, with an 11 hour driving time.
Planning the best things to do on a Chicago to Philadelphia road trip
The Chicago to Philadelphia drive takes you between two of the most attraction-packed cities in the US. But the are plenty of things to do along the way.
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. Or the 360 Chicago observation deck at the Hancock Tower. Or the Chicago Architecture Center.
Key attractions in Philadelphia include the Museum of the American Revolution, the Independence Seaport Museum and the Penn Museum. For great Philadelphia tour options, try the Old City historic walking tour, a night tour exploring the city’s dark side or an It’s Always Sunny-themed tour of South Philadelphia.
- To hunt down affordable Philadelphia accommodation deals, head here.
Chicago to Philadelphia distance and driving time
By car, the distance from Chicago to Philadelphia is 759 miles. You can expect a driving time of around eleven hours. The quickest route heads along the I-90, I-80, I-76 and I-70. The best stops to add to a Chicago to Philadelphia road trip itinerary are South Bend, Cleveland and Pittsburgh.
Best road trip attractions between Chicago and Philadelphia: 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 and Toledo drive and Toledo to Cleveland drive.
Chicago to Philadelphia 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.
- Discover more on the Cleveland to Pittsburgh drive.
Chicago to Philadelphia drive: Pittsburgh
Pittsburgh in western Pennsylvania is a monstrously underrated city, with a series of stellar attractions. Get great views from the top of the Duquesne Incline, enjoy the globally-themed rooms at the unmissable Cathedral of Learning and become immersed in pop art at the Warhol Museum.
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.
For Pittsburgh hotels with great reviews, try the Italian villa-style Priory Hotel or the often good value Drury Plaza Hotel Pittsburgh Downtown.
- For more possible stops, see the guides to the Pittsburgh to Harrisburg drive and Harrisburg to Philadelphia drive.
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