Interested in a Midwest road trip from the Windy City to the Steel City? The drive from Chicago to Pittsburgh passes through Indiana and Ohio, giving tourists a chance to visit some big cities, historic small towns, and a national park or two.
Pittsburgh and Chicago are both worth exploring. Chicago, of course, has world-famous attractions like the Willis (Sears) Tower, Millennium Park, Wrigley Field, and the Art Institute.
My underrated hometown of Pittsburgh has sights such as the Andy Warhol Museum, the National Aviary, kayaking on the three rivers, and riding the incline up to see the unparalleled view from Mount Washington.
I’ve made this drive many times over the years and have stopped at numerous points of interest along the way. Here’s my personal drive guide!
Map of Two Possible Routes for the Chicago to Pittsburgh Drive
Here’s the basic path from Chicago to Pittsburgh. The top route is what we’re calling Route #1. It mostly sticks to the highway. The bottom path is Route #2, passing through the heart of Indiana and Ohio.
We’re not specifically covering the middle route, which passes through Fort Wayne, but you can always make a short detour to reach that city.
You can get from Chicago to Pittsburgh in 7-9 hours if you really want to. But I suggest doing this as a 2-3 day road trip, so you have time to enjoy all the fun places along the way.
You can visit as many as six different states on this road trip. Four are guaranteed: Illinois, Indiana, Ohio, and Pennsylvania. Route #2 also includes a fifth state, West Virginia. And you could easily detour from route #1 up into Michigan.
How much will this road trip cost you? You can always use a fuel cost calculator, such as Gas Buddy, to estimate the total price.
This drive covers two time zones. You’ll start in Chicago in the Central Time Zone, before moving into the Eastern Time Zone once you reach central Indiana.
Note: If you want to avoid the highway completely, simply follow U.S. Route 20, a coast-to-coast route that is actually the longest road in America! Much of Route 20 parallels the toll highway, so you avoid tolls and see smaller towns.
We’re not specifically covering Route 20 in this article, but we have an entire article about driving U.S. Route 20. Check it out, if getting off the highway interests you!
Route #1: Mostly Highway + National Parks
Distance: 505 miles
Drive Time: 8 hours, 5 minutes
Highlights: Indiana Dunes National Park, South Bend, Toledo, Cedar Point, Cleveland, Cuyahoga Valley National Park
Route #1 generally follows Interstate 90, which is a toll highway. As of fall 2024, you can expect to pay $15 to drive the entire length of the road in Indiana, another $21 for the toll road in Ohio, and another $8 in Pennsylvania.
Fees may vary, depending whether or not you have an EZ-Pass, and how many times you leave the toll route to drive on free roads.
For this route, we’re taking you off the highway to visit two national parks and the cities of South Bend, Toledo, and Cleveland.
List of recommended stops:
Chicago
Gary, Indiana (Michael Jackson birth house)
Indiana Dunes National Park
South Bend, IN
Elkhart, IN (RV Hall of Fame)
Toledo, OH
Sandusky, OH (Cedar Point)
Cleveland
Cuyahoga Valley National Park
Pittsburgh
Let’s go over each recommended stop in greater detail!
Chicago
Obviously, you’ll want to spend some time checking out Chicago’s best activities before getting in the car.
Some of our favorite Windy City attractions include the Bean sculpture in Millennium Park, the Green Mill jazz club, the famous architecture boat tour downtown, Chicago improv clubs, and the Garfield Park Conservatory.
Make sure to try iconic Chicago foods like deep dish pizza, Italian beef sandwiches, chocolate cake milkshakes, and Chicago hot dogs. Take advantage of the city’s public transportation to visit the coolest neighborhoods in the city.
Need more ideas? See our list of the best Chicago museums, the top tourist attractions that are worth visiting, activities to do in Chicago at night, and winter activities in Chicago. We also have a perfect 2-day Chicago itinerary.
Gary, Indiana
Gary has a reputation for being a high-crime area, so it’s not necessary to linger here. The main reason to visit is to see Michael Jackson’s birth house.
The modest home sits in a residential neighborhood, Tourists frequently stop by the see the house and leave trinkets or souvenirs.
It’s amazing to think that Michael and his nine siblings all grew up in this little home!
Indiana Dunes National Park
The Indiana sand dunes became a national park in 2019. You can climb on the dunes, explore the shore of Lake Michigan, or hike and camp in the forests.
Most people will be fine just spending a couple hours here, unless you want to camp overnight.
South Bend, IN
The home of Notre Dame University has a lot going for it. First, see the campus, including the famous football stadium and the Basilicia of the Sacred Heart.
Then, see our list of fun South Bend activities, including the chocolate factory, the Studebaker National Museum (an ode to classic cars), and the Potowami Conservatories to see plants of all kinds.
South Bend is a must-visit on a road trip between Pittsburgh and Chicago!
Elkhart, IN
Just off the interstate is another quirky facility, the RV Hall of Fame. This spacious museum features RVs and motorhomes from throughout decades.
They have the most state-of-the-art, brand new ones, and some classics from bygone eras. Anyone who loves road trips will find something interesting here.
Toledo, OH
Toledo has some attractions you may find interesting, including a zoo, an art museum, and the National Museum of the Great Lakes, which educates visitors about the history of Lakes Erie, Michigan, Huron, Superior, and Ontario.
The quirkiest place to visit in Toledo is the Hot Dog Bun Museum. It features hundreds of foam hot dog buns signed by A-list celebrities, from presidents to movie stars! Find it inside Tony Packo’s Cafe.
Sandusky, OH
Sandusky is home of Cedar Point, one of the absolute best amusement parks in the United States. They have an incredible collection of roller coasters and thrill rides, far better than what you’d find at a Six Flags.
Make sure to set aside a full day to experience the park. It’s open from May through September, with additional special weekend events in October leading up to Halloween.
Cleveland
Cleveland, Ohio is a great Midwestern city with a lot to do. I recommend staying overnight here, perhaps at Aloft Cleveland Downtown, and giving yourself several hours to explore.
Start with the Rock & Roll Hall of Fame, probably the greatest museum in the country for anyone who’s a big popular music fan.
For more ideas, see our article on offbeat things to do in Cleveland, such as the grave of President Garfield, the giant ‘FREE’ stamp, the Cleveland Aquarium, the quirky History of Contraception Museum, the Cleveland Police Museum, and the A Christmas Story House, the very house used for exterior scenes of the classic holiday movie.
Cuyahoga Valley National Park
Ohio does have a national park! Cuyahoga Valley NP isn’t as spectacular as Yellowstone or some of the other famous parks, but it does have lots of hiking and biking trails.
And you never know what kind of wildlife you can see there. I once spotted four snakes tangled together hidden in a pile of leaves!
Pittsburgh
Finally, you’ve arrived in Pittsburgh! I grew up here, and still consider it one of the hidden gem cities in the country.
Among the Steel City’s many highlights: The National Aviary, which has dozens of bird species from penguins to bald eagles; the inclines, the cable cars that transport visitors to the top of Mount Washington; the Cathedral of Learning, which has 31 different “nationality classrooms” modeled after countries from around the world;
Be sure also to check out the vibrant South Side neighborhood, and the best Pittsburgh museums, including the Fort Pitt History Museum and the Andy Warhol Museum.
You can also do Pittsburgh-specific activities such as kayaking on the three rivers, or attending a Steeler game or Pirates game.
We have a one-day itinerary for Pittsburgh with plenty more ideas. But hopefully you’ll stay a lot longer than one day!
Route #2: Through the Heart of Indiana and Ohio
Distance: 573 miles
Drive Time: 9 hours
Highlights: Indiana Dunes National Park, Indianapolis, Dayton, Columbus, Wheeling
After hitting Gary and Indiana Dunes National Park, Route #2 heads south down to Indianapolis, and then cuts straight across Ohio. Dayton and Columbus are both worth seeing.
This path also passes through the West Virginia panhandle and the city of Wheeling, before heading east to finish in Pittsburgh.
List of recommended stops:
Chicago
Gary, Indiana (Michael Jackson birth house)
Indiana Dunes National Park
Lafayette, IN
Indianapolis
Dayton, OH
Columbus
Zanesville, OH
Wheeling, WV
Washington, PA
Pittsburgh
Let’s run down each of these stops as well.
Chicago, Gary, Indiana Dunes
The first three stops are the same as those in Route #1, so see above for more details. The Michael Jackson birth house and Indiana Dunes National Park are worth seeing before you head south on Interstate 65.
Lafayette, IN
The city of Lafayette has 70k residents and it’s a good spot to stop for a lunch break, with lots of diverse restaurants, breweries, and wineries.
You may also want to pop into the Haan Museum of Indiana Art and its sculpture garden.
Also, in nearby town of Battle Ground, Indiana, see the Tippecanoe Battlefield & Museum, the site of a notable 1811 battle between U.S. and Native American forces.
Indianapolis
Indy has a very cool Cultural Bike Trail that passes through downtown and other popular neighborhoods. You may want to rent a bike and give it a ride, since it’s a great way to get to know the city!
The Indianapolis 500 Museum is a fun way to get to know everything about the famous car race and see old cars that actually competed in it.
Other fun places include the Indianapolis Zoo, 100 Acres Park, and the Kurt Vonnegut Memorial Library. Activities in nearby Hamilton County include seeing the lifelike human statues around town and Conner Prairie Interactive History Park.
My recommended place to stay in Indy is the Alexander Hotel, a cool, modern place with funky art everywhere.
Dayton, OH
The city of Dayton has a lot of niche attractions that some travelers may enjoy. The National Museum of the US Air Force has a huge display of old aircraft, including planes used by U.S. presidents.
The Dayton Aviation Heritage National Historical Park is all about flight pioneers the Wright brothers, who lived in Dayton before traveling to North Carolina to make their historic flight.
Finally, the Packard Museum has a number of classic cars on display, both the Packard brand and other makes as well.
The perfect place for nature lovers is just east of Dayton at Clifton Gorge State Nature Preserve, where you can find hiking trails and waterfalls.
Columbus
Ohio’s capital city is an awesome place. Your best bet is to read our list of 18 cool and unique places to go in Columbus.
Among the highlights: The North Market, the Ohio State University campus, the Arnold Schwarzenegger statue, the Ohio Statehouse, the Otherworld immersive art experience, the Segway tour of the city, and the hip Short North neighborhood.
Zanesville, OH
Zanesville is a traditional working-class Midwestern town with noteworthy spots like the Alan Cottrill Sculpture Studio and the Alpacas of Spring Acres farm.
Wheeling, WV
Route #2 briefly passes through West Virginia. Many road trippers don’t tend to visit West Virginia often, so take advantage of this opportunity to explore a bit!
The city of Wheeling has attractions like the Kruger Street Toy & Train Museum and the Oglebay Institute Glass Museum.
You can even walk across an old suspension bridge from the 1840s over the Ohio River!
Washington, PA
If you care to make one last stop before Pittsburgh, the town of Washington has the Pennsylvania Trolley Museum, a popular racetrack and casino, and a Frontier League baseball stadium.
Pittsburgh
And again, we finish in the Steel City. See the earlier section with a full list of things to do in Pittsburgh, from museums to historic attractions.
Other Possible Detours on This Road Trip
There’s no rule that you have to stick strictly to our Route #1 or Route #2 maps! If you’re willing to drive a bit further, you can find lots of other cool stuff, from celebrity museums to old prisons to sports attractions.
Here are some other spots you can add to your drive with a bit of a detour.
Champaign, IL
The home of the University of Illinois, Champaign has everything you’d expect to find in a college town, from museums and theaters to green spaces, bars, and restaurants.
Champaign is two hours south of Chicago. You could stop here on the way to Indianapolis.
Olney, IL
Southwest of Indianapolis is the town of Olney, Illinois. The main reason to visit here is to see the white squirrels! Olney has a sizable population of white squirrels, which stand out from their gray cousins. Tourists come to view them in local parks.
Santa Claus, IN
The famous town of Santa Claus is worth a visit. Almost everything in the town is totally Christmas-y. It’s quite a long detour, though — Santa Claus is three hours south of Indianapolis.
Fort Wayne, IN
The city of Fort Wayne has historic mansions, art museums, a zoo, a minor league baseball field, and vibrant shopping and dining areas.
Peru, IN
Located a bit north of Indianapolis, the town of Peru has the Circus Hall of Fame, the Miami County Museum, and the Cole Porter Inn, the birthplace of the famous composer, which now serves as a bed and breakfast.
Fairmount, IN
The town of Farmount in central Indiana is where you’ll find the James Dean Museum, the largest collection of artifacts from the icon’s life.
Fairmount is also the hometown of Jim Davis, the creator of the Garfield cartoon. There’s actually a Garfield Trail here with statues of the animated cat.
Findlay, OH
Findlay is a small town, but it’s a college town, so it has more cool bars and restaurants than you’d expect. It’s also the home of the Flag City Balloon Fest each August.
Fremont, OH
Ohio has produced more U.S. presidents than any other state! In Fremont, you can visit the Rutherford B. Hayes Presidential Center.
Wapakoneta, OH
The Armstrong Air & Space Museum focuses on the career of legendary astronaut Neil Armstrong. It’s open every day and features really cool artifacts, including a Moon Rock that Neil brought back from his mission to the Moon.
Mansfield, OH
The historic prison known as the Ohio State Reformatory was used for nearly a century, until 1990. Most of the acclaimed movie The Shawshank Redemption was filmed here.
Today, in honor of its history, the prison is open for tours everyday. You can see many of the spots where movie scenes were shot.
Cincinnati, OH
One hour south of Dayton, Cincy has all the big-city amenities you could want. Visit Findlay Market, the fascinating American Sign Museum, and the insightful National Underground Railroad Freedom Center.
Also take some time to explore the Riverwalk and the Carew Tower observation deck. And the William Howard Taft National Historic Site, if you’re into presidential history.
Detroit, MI
See our full itinerary for one day in Detroit. In that short time, you can see some of the city’s most fascinating spots, like the Heidelberg Project, a neighborhood art installation; the Joe Louis fist statue, located in the park looking out towards Windsor, Canada; and the famous Motown Museum, where dozens of soul music legends once recorded.
Berlin, OH
Berlin is the heart of Amish Country! More Amish actually live here than in Lancaster, Pennsylvania.
The town welcomes tourists and has museums, gift shops, and other businesses that can educate guests about the Amish lifestyle and offer the chance to interact with Amish locals. Heini’s Cheese Chalet is a must-visit!
Canton, OH
Sports fans will want to make this detour. The primary point of interest in Canton is the NFL Hall of Fame, where the best football players in history are enshrined.
Niles, OH
Visit the National McKinley Birthplace Memorial Museum to learn about the life of the 25th president of the United States.
Steubenville, OH
The town of Steubenville has a Nutcracker Village with dozens of life-size nutracker statues around town. Come during the holiday season for special nutcracker-related events near historic Fort Steuben.
Erie, PA
If you’re traveling on Route #1, you could consider driving from Cleveland over to Erie, Pennsylvania. The main place to visit is Presque Isle State Park, which juts out into Lake Erie and offers numerous outdoor activities.
Chicago to Pittsburgh Wrap-Up
Of course, you could always fly between these cities. Southwest, in particular, often has very affordable direct flights between Chicago O’Hare International Airport and Pittsburgh International Airport.
Amtrak trains also exist between these two cities. But a road trip is always a lot more fun. And it gives you a chance to make stops along the way!
You could even make a longer detour with alternate routes and explore places like Louisville, home of the Kentucky Derby and Muhammad Ali Center; Mammoth Cave National Park; and New River Gorge National Park in West Virginia.
Do you have any other suggestions for places to add to the Chicago to Pittsburgh drive?
