11 days in Chicago & Cleveland Itinerary

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.

Deepen your sense of the past at sights like Cantigny Park and Basilica of the Sacred Heart. Appreciate the collections at The Art Institute of Chicago and Chicago Cultural Center. Change things up with these side-trips from Chicago: South Bend (University of Notre Dame & Grotto of Our Lady Lourdes), Whiskey Acres Distilling Co. (in DeKalb) and John Deere Historic Site (in Grand Detour). And it doesn't end there: don't miss a visit to The Magnificent Mile, take in panoramic vistas at Skydeck Chicago - Willis Tower, examine the collection at Swedish American Museum, and stroll around Millennium Park.

To see ratings, photos, where to stay, and more tourist information, you can read our Chicago trip itinerary site.

Ottawa, Canada to Chicago is an approximately 5.5-hour flight. You can also drive; or do a combination of train and car. Due to the time zone difference, you'll gain 1 hour traveling from Ottawa to Chicago. Traveling from Ottawa in August, things will get somewhat warmer in Chicago: highs are around 33°C and lows about 22°C. Wrap up your sightseeing on the 24th (Sat) to allow time to travel to 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.

Get some cultural insight at Rock & Roll Hall of Fame and Rutherford B. Hayes Presidential Library & Museums. Get some historical perspective at Marblehead Lighthouse State Park and West Side Market. Get out of town with these interesting Cleveland side-trips: James A. Garfield National Historic Site (in Mentor), Port Clinton Lighthouse (in Port Clinton) and Akron (Stan Hywet Hall & Gardens, Dr. Bob's Gravesite, &more). There's still lots to do: contemplate the long history of Zoar Village State Memorial, pause for some serene contemplation at St John's Cathedral, take a tour of USS Cod Submarine Memorial, and admire the masterpieces at The Cleveland Museum of Art.

For photos, more things to do, other places to visit, and tourist information, use the Cleveland road trip planning app.

Getting from Chicago to Cleveland by flight takes about 3.5 hours. Other options: drive; or take a train. You'll lose 1 hour traveling from Chicago to Cleveland due to the time zone difference. Expect a daytime high around 31°C in August, and nighttime lows around 22°C. Finish your sightseeing early on the 28th (Wed) to allow enough time to travel back home.