25 days in Chicago, Cleveland & Louisville Itinerary

25 days in Chicago, Cleveland & Louisville Itinerary

Created using Inspirock United States vacation maker

Make it your trip
Fly
1
Chicago
— 6 nights
Fly
2
Cleveland
— 8 nights
Drive
3
Louisville
— 8 nights
Fly
4
Chicago
— 2 nights
Fly

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Chicago

— 6 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Attractions like The Art Institute of Chicago and Millennium Park make great kid-friendly stops. There's still lots to do: engage your brain at Museum of Science and Industry, take in panoramic vistas at Skydeck Chicago - Willis Tower, visit The Magnificent Mile, and laugh and play at Navy Pier.

To see more things to do, ratings, other places to visit, and other tourist information, read Chicago trip maker.

Helsinki, Finland to Chicago is an approximately 12-hour flight. You'll gain 8 hours traveling from Helsinki to Chicago due to the time zone difference. In July, Chicago is somewhat warmer than Helsinki - with highs of 33°C and lows of 22°C. Finish up your sightseeing early on the 7th (Wed) so you can catch the flight to Cleveland.

Things to do in Chicago

Museums · Childrens Museums · Parks · Zoos & Aquariums

Cleveland

— 8 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.
Family-friendly places like Cedar Point and Rock & Roll Hall of Fame will thrill your kids. Explore the numerous day-trip ideas around Cleveland: Holy Angels Catholic Church (in Sandusky), Sugarcreek (David Warther Carvings, The Farm at Walnut Creek, &more) and Burnham Orchards (in Berlin Heights). The adventure continues: explore the world behind art at The Cleveland Museum of Art, contemplate the long history of USS Cod Submarine Memorial, let little ones run wild at Memphis Kiddie Park, and admire the natural beauty at Fellows Riverside Gardens.

For more things to do, photos, where to stay, and other tourist information, refer to the Cleveland day trip app.

Traveling by flight from Chicago to Cleveland takes 3 hours. Alternatively, you can drive; or take a train. Traveling from Chicago to Cleveland, you'll lose 1 hour due to the time zone difference. In July, daytime highs in Cleveland are 30°C, while nighttime lows are 23°C. Finish up your sightseeing early on the 15th (Thu) so you can catch the flight to Louisville.

Things to do in Cleveland

Parks · Museums · Historic Sites · Theme Parks

Side Trips

Louisville

— 8 nights

Derby City

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
You'll visit kid-friendly attractions like Louisville Mega Cavern and Fat Man's Misery. Explore Louisville's surroundings by going to Holiday World & Splashin' Safari (in Santa Claus), Elizabethtown (Brown-Pusey House, Veterans Memorial, &more) and Mammoth Cave (in Mammoth Cave National Park). There's still lots to do: take in nature's colorful creations at Cincinnati Zoo & Botanical Garden, examine the collection at Kentucky Derby Museum, learn about wildlife with up-close encounters at Louisville Zoo, and relax in the rural setting at Old Friends at Dream Chase Farm.

To find out how to plan a trip to Louisville, use our trip itinerary maker.

Getting from Cleveland to Louisville by flight takes about 5 hours. Other options: drive; or take a bus. Traveling from Cleveland in July, expect nights in Louisville to be about the same, around 24°C, while days are somewhat warmer, around 36°C. You will leave for Chicago on the 23rd (Fri).

Things to do in Louisville

Parks · Museums · Nature · Theme Parks

Side Trips

Chicago

— 2 nights

Windy City

Kick off your visit on the 23rd (Fri): browse the different shops at The Shops at North Bridge, then steep yourself in history at Ernest Hemingway Birthplace, and then stroll around Jackson Bark - Dog Park. On your second day here, grab your bike and head to Lakefront Trail, then admire the striking features of Frank Lloyd Wright's Robie House, and then stroll around Grant Park.

To see other places to visit, ratings, more things to do, and tourist information, read our Chicago online tour builder.

Traveling by flight from Louisville to Chicago takes 3 hours. Alternatively, you can drive; or take a bus. Traveling from Louisville to Chicago, you'll gain 1 hour due to the time zone difference. Finish up your sightseeing early on the 25th (Sun) so you can catch the flight back home.

Things to do in Chicago

Parks · Historic Sites · Shopping · Outdoors

Side Trip