37 days in Chicago Itinerary

37 days in Chicago Itinerary

Created using Inspirock Chicago trip planner

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Chicago
— 36 nights

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Chicago

— 36 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll enjoy a bit of beach vacationing at Atwater Park & Beach and Rosewood Beach. Change things up with these side-trips from Chicago: South Bend (Studebaker National Museum & Basilica of the Sacred Heart), Saint Joseph (Silver Beach Carousel & Silver Beach County Park) and Hickory Creek Winery (in Buchanan). Next up on the itinerary: shop like a local with The Magnificent Mile, engage your brain at Museum of Science and Industry, brush up on your knowledge of spirits at Whiskey Acres Distilling Co., and stroll around Millennium Park.

To see reviews, where to stay, photos, and more tourist information, read our Chicago tour itinerary site.

May in Chicago sees daily highs of 71°F and lows of 52°F at night.

Things to do in Chicago

Parks · Outdoors · Beaches · Museums

Side Trips