5 days in Chicago Itinerary

5 days in Chicago Itinerary

Created using Inspirock Chicago planner

Make it your trip
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Chicago
— 4 nights

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Chicago

— 4 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Do your shopping at Chicago Cultural Center and The Magnificent Mile. Get outdoors at Starved Rock State Park and Cowles Bog. Get out of town with these interesting Chicago side-trips: Saint Joseph (Silver Beach County Park & Fishing Charters & Tours), Washington Square Park (in Ottawa) and Jasper-Pulaski Fish and Wildlife Area (in Medaryville). The adventure continues: admire the masterpieces at The Art Institute of Chicago, engage your brain at Field Museum, don't miss a visit to Millennium Park, and do a tasting at Hickory Creek Winery.

To see other places to visit and other tourist information, you can read our Chicago online trip builder.

Expect a daytime high around 81°F in June, and nighttime lows around 63°F. Finish your sightseeing early on the 17th (Mon) to allow enough time to travel back home.

Things to do in Chicago

Parks · Outdoors · Wildlife · Museums

Side Trips