21 days in Chicago Itinerary

21 days in Chicago Itinerary

Created using Inspirock Chicago trip itinerary planner

Make it your trip
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Chicago
— 20 nights

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Chicago

— 20 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Visit Chicago Riverwalk and Cantigny Park for their historical value. Bring the kids along to Lakefront Trail and Lake Michigan. You'll find plenty of places to visit near Chicago: Baha'i House of Worship (in Wilmette), Saint Joseph (Silver Beach County Park & Silver Beach Carousel) and Riverwalk Lot (in Naperville). And it doesn't end there: try out the rides at Fox in a Box Chicago, admire the masterpieces at Richard H. Driehaus Museum, take the plunge with Skydive Windy City, and admire the natural beauty at Garfield Park Conservatory.

For reviews, maps, where to stay, and tourist information, use the Chicago online visit planner.

In July in Chicago, expect temperatures between 83°F during the day and 67°F at night.

Things to do in Chicago

Parks · Outdoors · Wildlife · Historic Sites

Side Trips