4 days in Cleveland & Chicago Itinerary

4 days in Cleveland & Chicago Itinerary

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Route & dates

4 days in Cleveland & Chicago Itinerary

Start: Cleveland
1
Cleveland
— 1 night
Fly:  3​h 15​min
2
Chicago
— 2 nights
Fly:  3​h 15​min
End: Cleveland

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.
On the 13th (Mon), stroll the grounds of Lake View Cemetery, see the interesting displays at A Christmas Story House, then step aboard USS Cod Submarine Memorial, and finally stroll around The Mall. Here are some ideas for day two: appreciate the history behind Soldiers' and Sailors' Monument, then contemplate the long history of James A. Garfield National Historic Site, then walk around Rocky River Reservation, and finally admire the striking features of Heinen's Downtown.

For more things to do, ratings, reviews, and other tourist information, read Cleveland trip planner .

Use the Route module to see travel options from your home to Cleveland. In July, plan for daily highs up to 79°F, and evening lows to 68°F. Finish your sightseeing early on the 14th (Tue) so you can travel to Chicago.

Things to do in Cleveland

Historic Sites Parks Museums

Side Trip

James A. Garfield National Historic Site
Highlights from your plan
USS Cod Submarine Memorial ©
USS Cod Submarine Memorial
Lake View Cemetery ©
Lake View Cemetery
A Christmas Story House ©
A Christmas Story House

2
nights
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 15th (Wed): sample some tasty brews at a beer tour and tasting, explore the world behind art at The Art Institute of Chicago, and then grab your bike and head to Lakefront Trail. On your second day here, contemplate the waterfront views at Lake Michigan, then get to know the fascinating history of Chicago Riverwalk, then tour the pleasant surroundings at Millennium Park, and finally ponder the design of Crown Fountain.

To find where to stay, other places to visit, traveler tips, and tourist information, use the Chicago road trip planning app .

You can fly from Cleveland to Chicago in 3.5 hours. Alternatively, you can do a combination of flight, bus, and subway; or drive. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. In July in Chicago, expect temperatures between 83°F during the day and 67°F at night. Cap off your sightseeing on the 16th (Thu) early enough to travel back home.

Things to do in Chicago

Parks Tours Museums

Side Trip

Lake Michigan
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Beer Tastings & Tours
Lakefront Trail ©
Lakefront Trail

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