31 days in Chicago Itinerary

31 days in Chicago Itinerary

Created using Inspirock Chicago travel route planner

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.
You'll find plenty of places to visit near Chicago: Historical Auto Attractions (in Roscoe), Wheaton (Wheaton Public Library, First Division Museum at Cantigny, &more) and Edwards Apple Orchard (in Poplar Grove). There's still lots to do: admire the masterpieces at The Art Institute of Chicago, head outdoors with Outdoor Activities, take in the waterfront at Navy Pier, and get up close and personal with brilliant marine life at Shedd Aquarium.

For other places to visit, where to stay, photos, and more tourist information, you can read our Chicago day trip planning app.

October in Chicago sees daily highs of 65°F and lows of 49°F at night. Finish up your sightseeing early on the 31st (Sat) so you can travel back home.

Things to do in Chicago

Parks · Museums · Historic Sites · Childrens Museums

Side Trips