5 days in Chicago Itinerary

5 days in Chicago Itinerary

Created using Inspirock Chicago planner

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Route & dates

1
Chicago
— 4 nights

4
nights
Chicago

Chicago ©
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 Silver Beach County Park. Get out of town with these interesting Chicago side-trips: Jasper-Pulaski Fish and Wildlife Area (in Medaryville), 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 things with Boat Tours & Water Sports, and do a tasting at Hickory Creek Winery.

To find photos, reviews, more things to do, 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

Outdoors Parks Wildlife

Side Trips

Saint Joseph, Starved Rock State Park, Jasper-Pulaski Fish and Wildlife Area, Cowles Bog, Washington Square Park
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Starved Rock State Park ©
Starved Rock State Park
Silver Beach County Park ©
Silver Beach County Park

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