12 days in Chicago, Pittsburgh & Cleveland Itinerary

12 days in Chicago, Pittsburgh & Cleveland Itinerary

Created using Inspirock United States vacation planner

Make it your trip
Fly
1
Chicago
— 4 nights
Fly
2
Pittsburgh
— 3 nights
Drive
3
Cleveland
— 4 nights
Fly

S M T W T F S
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Chicago

— 4 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, and nightlife. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, take in panoramic vistas at Skydeck Chicago - Willis Tower, engage your brain at Museum of Science and Industry, and observe the fascinating underwater world at Shedd Aquarium.

To see where to stay, traveler tips, other places to visit, and other tourist information, use the Chicago online tour itinerary maker.

Washington DC to Chicago is an approximately 4-hour flight. You can also drive; or take a train. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. Expect little chillier temperatures when traveling from Washington DC in October; daily highs in Chicago reach 65°F and lows reach 49°F. You'll have a few hours on the 24th (Sat) to wrap things up before traveling to Pittsburgh.

Things to do in Chicago

Museums · Childrens Museums · Shopping · Parks

Side Trip

Pittsburgh

— 3 nights

City of Bridges

Known primarily for its steel-related heritage and 446 bridges, Pittsburgh sits at the confluence of the Monongahela and Allegheny Rivers, which meet to form the Ohio River.
Explore the numerous day-trip ideas around Pittsburgh: Imperial Glass Museum (in Bellaire) and Moundsville (Grand Vue Park & Archive of the Afterlife, "A Paranormal Museum"). There's lots more to do: take in the local highlights with Walk the Burgh Tours, get engrossed in the history at Photo Antiquities Museum of Photographic History, take a memorable tour with Go Ape Zipline & Adventure Park, and examine the collection at Bicycle Heaven.

To see maps, where to stay, traveler tips, and more tourist information, go to the Pittsburgh holiday builder app.

Fly from Chicago to Pittsburgh in 4 hours. Alternatively, you can drive; or take a train. The time zone difference when traveling from Chicago to Pittsburgh is 1 hour. October in Pittsburgh sees daily highs of 65°F and lows of 48°F at night. Finish up your sightseeing early on the 27th (Tue) so you can go by car to Cleveland.

Things to do in Pittsburgh

Tours · Museums · Parks · Adventure

Side Trips

Cleveland

— 4 nights

Forest City

A culturally diverse city situated on the shores of Lake Erie, Cleveland boasts many places to visit, such as world-class museums, popular amusement parks, and sprawling recreational areas.
Explore Cleveland's surroundings by going to Oberlin Heritage Center (in Oberlin), Back to the Wild (in Castalia) and Cedar Point (in Sandusky). Next up on the itinerary: examine the collection at Rock & Roll Hall of Fame, admire the masterpieces at The Cleveland Museum of Art, try to win big at JACK Cleveland Casino, and walk around Tinkers Creek Viaduct Park.

To see maps, reviews, more things to do, and more tourist information, go to the Cleveland road trip planning tool.

Traveling by car from Pittsburgh to Cleveland takes 2.5 hours. Alternatively, you can take a train; or take a bus. October in Cleveland sees daily highs of 65°F and lows of 51°F at night. Finish up your sightseeing early on the 31st (Sat) so you can travel back home.

Things to do in Cleveland

Museums · Parks · Wildlife · Fun & Games

Side Trips