4 days in Chicago and Beyond Itinerary

4 days in Chicago and Beyond Itinerary

Created using Inspirock Chicago and Beyond attractions planner

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Route & dates

4 days in Chicago and Beyond Itinerary

Start: Toronto
ferry + Fly:  4​h 30​min
— 3 nights
Fly + ferry:  4​h 30​min
End: Toronto


Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, nightlife, zoos & aquariums, and childrens museums. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, stroll around Millennium Park, observe the fascinating underwater world at Shedd Aquarium, and enjoy breathtaking views from Skydeck Chicago - Willis Tower.

To find photos, traveler tips, more things to do, and other tourist information, go to the Chicago trip itinerary planning tool .

Toronto, Canada to Chicago is an approximately 4.5-hour combination of ferry and flight. You can also fly; or drive. You'll gain 1 hour traveling from Toronto to Chicago due to the time zone difference. Expect a daytime high around 21°C in October, and nighttime lows around 11°C. Cap off your sightseeing on the 10th (Sat) early enough to travel back home.

Things to do in Chicago

Museums Parks Zoos & Aquariums
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Skydeck Chicago - Willis Tower ©
Skydeck Chicago - Willis Tower