7 days in Chicago & Orlando Itinerary

7 days in Chicago & Orlando Itinerary

Created using Inspirock United States travel route builder

Make it your trip
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Chicago
— 3 nights
Fly
2
Orlando
— 2 nights
Fly

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Chicago

— 3 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, nightlife, and parks. Your trip includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, engage your brain at Museum of Science and Industry, admire the local landmark of Buckingham Fountain, and learn about wildlife with up-close encounters at Lincoln Park Zoo.

To find photos, reviews, traveler tips, and other tourist information, read Chicago route planner.

The Route module shows you all the different ways you can get to Chicago. Expect a daytime high around 81°F in June, and nighttime lows around 63°F. Cap off your sightseeing on the 10th (Thu) early enough to catch the flight to Orlando.

Things to do in Chicago

Museums · Parks · Childrens Museums · Zoos & Aquariums
Find places to stay Jun 7 — 10:

Orlando

— 2 nights

Theme Park Capital of the World

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.
Pack the 11th (Fri) with family-friendly diversions at Universal's Islands of Adventure. There's more to do: find something for the whole family at Universal Orlando Resort and make an unforgettable trip to Disney's Typhoon Lagoon Water Park.

To find ratings, traveler tips, reviews, and more tourist information, you can read our Orlando trip itinerary website.

Traveling by flight from Chicago to Orlando takes 4.5 hours. Alternatively, you can drive; or take a bus. The time zone difference when traveling from Chicago to Orlando is 1 hour. Plan for a bit warmer temperatures traveling from Chicago in June, with highs in Orlando at 91°F and lows at 73°F. Wrap up your sightseeing on the 13th (Sun) early enough to fly back home.

Things to do in Orlando

Theme Parks
Find places to stay Jun 10 — 13: