2 days in Chicago & Ohio Itinerary

2 days in Chicago & Ohio Itinerary

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Route & dates

2 days in Chicago & Ohio Itinerary

Start: Philadelphia
Fly:  4​h
1
Chicago
— Few hours
Fly:  3​h 15​min
2
Cleveland
— 1 night
Fly:  3​h 45​min
End: Philadelphia

few
hours
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Start off your visit on the 14th (Mon): explore the world behind art at The Art Institute of Chicago, then don't miss a visit to Cloud Gate, then appreciate the extensive heritage of Millennium Park, and finally admire the striking features of Skydeck Chicago - Willis Tower.

For more things to do, photos, traveler tips, and other tourist information, read our Chicago trip planner .

Philadelphia to Chicago is an approximately 4-hour flight. You can also do a combination of train and flight; or drive. Traveling from Philadelphia to Chicago, you'll gain 1 hour due to the time zone difference. Traveling from Philadelphia in January, expect Chicago to be a bit cooler, temps between 32°F and 18°F. Finish up your sightseeing early on the 14th (Mon) so you can travel to Cleveland.

Things to do in Chicago

Museums Historic Sites Parks
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Skydeck Chicago - Willis Tower ©
Skydeck Chicago - Willis Tower

1
night
Cleveland

Cleveland ©
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.
Start off your visit on the 15th (Tue): see the interesting displays at Rock & Roll Hall of Fame, admire the masterpieces at The Cleveland Museum of Art, and then try your luck at JACK Cleveland Casino.

To find traveler tips, maps, and other tourist information, read Cleveland trip planner .

You can fly from Chicago to Cleveland in 3.5 hours. Other options are to do a combination of subway, bus, and flight; or drive. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. In January, daytime highs in Cleveland are 34°F, while nighttime lows are 22°F. Wrap up your sightseeing on the 15th (Tue) to allow time to travel back home.

Things to do in Cleveland

Museums Fun & Games Casinos
Highlights from your plan
The Cleveland Museum of Art ©
The Cleveland Museum of Art
Rock & Roll Hall of Fame ©
Rock & Roll Hall of Fame
JACK Cleveland Casino ©
JACK Cleveland Casino

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