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 The Magnificent Mile and Chicago Cultural Center. Get outdoors at Starved Rock State Park and Jasper-Pulaski Fish and Wildlife Area. Get out of town with these interesting Chicago side-trips: Saint Joseph (Silver Beach County Park & Fishing Charters & Tours), Cowles Bog (in Chesterton) and Washington Square Park (in Ottawa). The adventure continues: admire the masterpieces at The Art Institute of Chicago, don't miss a visit to Millennium Park, get a new perspective on nature at Field Museum, 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