8 days in Chicago & Orlando Itinerary

8 days in Chicago & Orlando Itinerary

Created using Inspirock United States trip itinerary planner

Plan created by another user.Make it yours

Route & dates

Start: New York City
Fly:  4 h 45 min
1
Chicago
— 2 nights
Fly:  5 h
2
Orlando
— 5 nights
Fly:  6 h
End: New York City

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kids will appreciate attractions like Museum of Science and Industry and Shedd Aquarium. And it doesn't end there: learn about wildlife with up-close encounters at Lincoln Park Zoo, ponder the design of Buckingham Fountain, stroll around Millennium Park, and admire the masterpieces at The Art Institute of Chicago.

To find other places to visit, photos, ratings, and tourist information, you can read our Chicago day trip planning website.

New York City to Chicago is an approximately 5-hour flight. You can also drive; or take a bus. Traveling from New York City to Chicago, you'll gain 1 hour due to the time zone difference. Plan for slightly colder temperatures traveling from New York City in December, with highs in Chicago at 38°F and lows at 26°F. Finish your sightseeing early on the 23rd (Mon) so you can travel to Orlando.

Things to do in Chicago

Parks Zoos & Aquariums Museums
Highlights from your plan
Fox in a Box Chicago ©
Fox in a Box Chicago
Museum of Science and Industry ©
Museum of Science and Industry
Shedd Aquarium ©
Shedd Aquarium

5
nights
Orlando

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Bring the kids along to Universal Orlando Resort and Magic Kingdom Park. Next up on the itinerary: make an unforgettable trip to Walt Disney World Resort, try out the rides at Disney’s Hollywood Studios, explore the world behind art at Charles Hosmer Morse Museum of American Art, and get your game on at The Void.

For traveler tips, other places to visit, and other tourist information, read Orlando visit planner.

You can fly from Chicago to Orlando in 5.5 hours. Alternatively, you can drive; or take a train. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. Traveling from Chicago in December, expect Orlando to be much warmer, temps between 77°F and 59°F. Finish your sightseeing early on the 28th (Sat) to allow enough time to travel back home.

Things to do in Orlando

Theme Parks Museums Fun & Games

Side Trip

Charles Hosmer Morse Museum of American Art
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure

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