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.
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.
Chicago’s skyscrapers, music scene and massive collection of cultural attractions make it arguably the most exciting city in the US to visit.
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 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.
Why book the Go City Chicago Explorer Pass?
- 🏙️ Skydeck Chicago & 360 CHICAGO: Get high-altitude views of the city from its most famous observation decks, including the glass-bottomed “Ledge” at Willis Tower.
- ⛴️ Architecture River Cruise: Experience Chicago’s world-renowned skyline from the water on a Shoreline Sightseeing cruise, one of the city’s most popular activities.
- 🦕 World-Class Museums: Choose from premier institutions like the Field Museum, the Museum of Science and Industry, the Adler Planetarium, and the Art Institute of Chicago.
- 💰 Save up to 40%: Pay one flat price for your choice of 2 to 7 attractions and enjoy significant savings compared to purchasing individual tickets at each gate.
- 📱 Total Flexibility: You have 60 days to use your pass once it’s activated at your first attraction, and your digital pass is easily managed directly from your smartphone.
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.
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.
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.
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
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.
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.
More Pennsylvania travel
Other Pennsylvania travel articles on Planet Whitley include:
- Planning a visit to the Carnegie Museum of Natural History in Pittsburgh.
- Road trips from Pittsburgh: The best stops on the Pittsburgh to Cleveland drive.
- What to expect inside the Museum of the American Revolution and the Betsy Ross House.
- Visitor guides to Steamtown National Historic Site the Electric City Aquarium in Scranton.
- The best stops on a Scranton to Chicago road trip.
