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
Five great things to do in Chicago
- 🏙️ Marvel at the skyscrapers – on a Chicago River architecture cruise.
- 🖼️ Take an interiors architecture tour – to see stunning glass art and mosaics.
- 🍕 Taste Chicago’s favourite dishes – on a city favourites food tour.
- 🌆 Visit the Willis Tower observation deck – and see the city from above.
- 🕵️ Discover Chicago’s gangster heritage – on a crime and mob tour.
The Chicago to Philadelphia drive takes you between two of the most attraction-packed cities in the US. But there are plenty of things to do along the way.
Highly recommended Chicago experiences include an architecture river cruise, a crime and gangsters tour of famous Mob sites and a bike tour of the lakefront neighbourhoods.
Key Chicago attractions such as the Chicago Architecture Center, the Art Institute of Chicago, the Shedd Aquarium and the Griffin Museum of Science and Industry are worth visiting. But save time for smaller delights like the Frank Lloyd Wright architecture and the Tiffany Dome in Preston Bradley Hall.
Recommended Chicago hotels include the Club Quarters Central Loop for astonishingly good value. Also consider the Intercontinental Chicago Magnificent Mile for its amazing, historic pool, and the entertainingly science-themed Hotel EMC2.
Philadelphia is drenched in historic sites, such as the Liberty Bell Center, Christ Church Burial Ground and Betsy Ross House.
The Museum of the American Revolution tells of the country’s birth, but the city’s superb museum collection delves into other areas. The Rodin Museum, the Barnes Foundation, and the Philadelphia Museum of Art are top tier art museums, while the the Franklin Institute, Mutter Museum and Academy of Natural Sciences look at various branches of science. For maritime heritage, plump for the Battleship New Jersey and Independence Seaport Museum.
However, it’s likely to be the Eastern State Penitentiary – the model for prisons around the world – that sticks in your memory long afterwards.
5 great things to do in Philadelphia
- 🥖 Taste the best of Philly on a food tour – including historic Reading Market.
- 🏛️ Get to know Philadelphia’s heritage sites – on a guided walking tour.
- 🍻 Go on a pub crawl – but learn the history between beers.
- 🎨 Let a guide show you Philadelphia’s best murals and street art – including Magic Gardens.
- 🌙 Discover Philly’s dark side – on an adults-only night tour.
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
5 Great Cleveland Experiences to Book
- 👻 Cleveland Ghost Tour: Hear spooky stories from the city’s past and explore haunted landmarks on a guided evening walking tour.
- 🌲 Cuyahoga Valley National Park: Link together the best viewpoints and trails on a self-drive visit with a comprehensive smartphone audio guide.
- 🎸 Rock & Roll Hall of Fame: Explore the history of music legends through iconic artifacts and immersive exhibits at this world-famous lakeside museum.
- 🌮 Ohio City Neighborhood Food Tour: Experience one of the city’s trendiest districts through multiple food tastings and expert drink pairings.
- 🍎 West Side Market Food Tour: Get to know the best local stalls and the history of Cleveland’s oldest operating indoor/outdoor market.
Top attractions in Cleveland include the Rock N Roll Hall of Fame, Great Lakes Science Center and Cleveland History Center. Alternatively, try the Cleveland Metroparks Zoo and the Cleveland Museum of Art.
Cleveland tour options focus on neighbourhood food scenes and ghostly tales after dark.
Best stops between Chicago and Philadelphia: Pittsburgh
5 great Pittsburgh experiences worth booking
- 🏙️ Take an incredibly well-reviewed private Pittsburgh highlights tour.
- 🍽️ Go on a downtown food tour, with 6 fantastic food and drink stops.
- 👻 Hear spooky tales in the evening on a Pittsburgh ghost tour.
- 🥃 Discover Pittsburgh’s whiskey-soaked history – with two cocktails thrown in.
- 🛴 Visit Pittsburgh’s top photo stops – on a fun-packed Segway tour.
Pittsburgh is surprisingly beautiful – take a ride up the Duquesne Incline for the best views out over the city, Point State Park and Fort Pitt. After that, check out the Warhol Museum, National Aviary or the Nationality Rooms in the gigantic Cathedral of Learning.
Pittsburgh experiences include 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.
More Chicago and Philadelphia road trips
- Road trips to Chicago from Indiana: Guides to the Indianapolis to Chicago drive and South Bend to Chicago drive.
- Getting to Chicago from Ohio: What to see on the Cincinnati to Chicago drive, Cleveland to Chicago drive, Columbus to Chicago drive and Toledo to Chicago drive.
- Getting to Philadelphia: Guide to the Harrisburg to Philadelphia drive and Pittsburgh to Philadelphia drive
- Driving to Philadelphia from interstate: Plan your stops on the Cleveland to Philadelphia drive, Columbus to Philadelphia drive, Indianapolis to Philadelphia and St Louis to Philadelphia drive
- Road trips from Philadelphia: The best stops on the Philadelphia to Detroit drive.
