10 days in Cleveland & Chicago Itinerary

10 days in Cleveland & Chicago Itinerary

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Route & dates

10 days in Cleveland & Chicago Itinerary

Start: Kingston
Drive:  10​h
1
Cleveland
— 3 nights
Drive:  6​h
2
Chicago
— 6 nights
Fly:  5​h 45​min
End: Ottawa

3
nights
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 19th (Mon), get a new perspective on nature at Cleveland Museum of Natural History and then take a stroll through Historic Little Italy in Cleveland. Here are some ideas for day two: explore the world behind art at The Cleveland Museum of Art, then stroll the grounds of Lake View Cemetery, then stop by b.a. Sweetie Candy Company, and finally admire the landmark architecture of Heinen's Downtown.

To find photos, where to stay, maps, and other tourist information, use the Cleveland road trip planner .

Kingston, Canada to Cleveland is an approximately 9-hour combination of flight and car. You can also drive. Traveling from Kingston in August, you can expect nighttime temperatures to be a bit warmer in Cleveland, with lows of 22°C. On the 21st (Wed), wrap the sightseeing up by early afternoon so you can travel to Chicago.

Things to do in Cleveland

Historic Sites Museums Neighborhoods
Highlights from your plan
Cleveland Museum of Natural History ©
Lake View Cemetery ©
Lake View Cemetery
USS Cod Submarine Memorial ©
USS Cod Submarine Memorial

6
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
For shopping fun, head to Lincoln Park or Chicago Cultural Center. Millennium Park and Richard H. Driehaus Museum are good opportunities to explore the local culture. Explore the numerous day-trip ideas around Chicago: Cantigny Park (in Wheaton), Milwaukee (Basilica of St. Josaphat, Pabst Mansion, & more) and Riverwalk Lot (in Naperville). Next up on the itinerary: admire the masterpieces at The Art Institute of Chicago, see the interesting displays at Volo Auto Museum, take in the architecture and atmosphere at Basilica of the Sacred Heart, and contemplate the long history of Baha'i House of Worship.

To find ratings, other places to visit, where to stay, and other tourist information, read Chicago trip builder website .

You can fly from Cleveland to Chicago in 3.5 hours. Other options are to do a combination of flight, bus, and subway; or drive. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. In August, daytime highs in Chicago are 33°C, while nighttime lows are 22°C. On the 27th (Tue), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Chicago

Historic Sites Museums Shopping

Side Trips

Milwaukee, South Bend, Volo Auto Museum, Riverwalk Lot, Harlem Irving Plaza Mall
Highlights from your plan
Basilica of St. Josaphat ©
Basilica of St. Josaphat
Cantigny Park ©
Cantigny Park
Milwaukee Art Museum ©
Milwaukee Art Museum

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