8 days in Chicago Itinerary

8 days in Chicago Itinerary

Created using Inspirock Chicago travel planner

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1
Chicago
— 7 nights

7
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Eschew the tourist crowds and head to Starved Rock State Park and Silver Beach County Park. Get out of town with these interesting Chicago side-trips: Saint Joseph (Whirlpool Compass Fountain & Silver Beach Carousel), Standard Bank Stadium (in Crestwood) and Washington Square (in Ottawa). There's much more to do: admire the masterpieces at The Art Institute of Chicago, appreciate the extensive heritage of Millennium Park, admire all the interesting features of Wrigley Field, and take in panoramic vistas at Skydeck Chicago - Willis Tower.

Planning Chicago trip won't be overwheling when you use's Insprock itinerary maker.

Expect a daytime high around 71°F in May, and nighttime lows around 52°F. Finish up your sightseeing early on the 11th (Sat) so you can travel back home.

Things to do in Chicago

Parks Museums Childrens Museums

Side Trips

Saint Joseph, South Bend, Washington Square, Grayslake Heritage Center & Museum, Anderson Japanese Gardens
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Beer Tastings & Tours
Basilica of the Sacred Heart ©
Basilica of the Sacred Heart

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