9 days in Chicago & Orlando Itinerary

9 days in Chicago & Orlando Itinerary

Created using Inspirock United States holiday maker

Make it your trip
1
Chicago
— 1 day
Fly
2
Orlando
— 7 nights

S M T W T F S
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Chicago

— 1 day

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 18th (Tue): explore the world behind art at The Art Institute of Chicago, walk around Millennium Park, then admire nature's wide array of creatures at Shedd Aquarium, and finally take in panoramic vistas at Skydeck Chicago - Willis Tower.

To see ratings, reviews, traveler tips, and more tourist information, read our Chicago route builder tool.

The Route module shows you travel options from your home to Chicago. May in Chicago sees daily highs of 71°F and lows of 52°F at night. Wrap up your sightseeing on the 18th (Tue) early enough to fly to Orlando.

Things to do in Chicago

Parks · Zoos & Aquariums · Museums
Find places to stay May 18 — 19:

Orlando

— 7 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.
Bring the kids along to Walt Disney World Resort and SeaWorld. Step out of Orlando with an excursion to Blue Heron River Tours Inc in DeLand--about 56 minutes away. Pack the 25th (Tue) with family-friendly diversions at Universal Orlando Resort. Pack the 20th (Thu) with family-friendly diversions at Universal's Islands of Adventure. There's much more to do: make a splash at Discovery Cove, discover the magic at Disney's Animal Kingdom Theme Park, look for gifts at Tharoo & Co, and find something for the whole family at Magic Kingdom Park.

For maps, traveler tips, photos, and other tourist information, read our Orlando trip planner.

You can fly from Chicago to Orlando in 4.5 hours. Alternatively, you can drive; or take a bus. 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 May, things will get somewhat warmer in Orlando: highs are around 88°F and lows about 69°F.

Things to do in Orlando

Side Trips

Find places to stay May 19 — 26: