31 days in Chicago Itinerary

31 days in Chicago Itinerary

Created using Inspirock Chicago trip itinerary maker

Make it your trip
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Chicago
— 30 nights

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Chicago

— 30 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Change things up with these side-trips from Chicago: St. Joseph Catholic Church (in Joliet), Ottawa (Washington Square Park & SaltTreeYoga) and Pontiac (Museum of the Gilding Arts & Livingston County Courthouse). The adventure continues: admire the masterpieces at The Art Institute of Chicago, get to know the resident critters at Lincoln Park Zoo, enjoy breathtaking views from Skydeck Chicago - Willis Tower, and get curious at Museum of Science and Industry.

For other places to visit, photos, reviews, and other tourist information, go to the Chicago trip itinerary planning app.

Expect a daytime high around 32°F in January, and nighttime lows around 18°F.

Things to do in Chicago

Museums · Historic Sites · Parks · Shopping

Side Trips