30 days in Chicago Itinerary

30 days in Chicago Itinerary

Created using Inspirock Chicago route builder

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1
Chicago
— 29 nights

29
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Step out of the city life by going to Silver Beach County Park and Jasper-Pulaski Fish and Wildlife Area. You'll explore and learn at The Art Institute of Chicago and The Field Museum. Explore the numerous day-trip ideas around Chicago: Chesterton (Cowles Bog, Coffee Creek Watershed Preserve, & more), Journeyman Distillery (in Three Oaks) and New Buffalo (Whittaker Woods Golf Club & Galien River County Park). There's lots more to do: wander the streets of The Magnificent Mile, appreciate the extensive heritage of Millennium Park, see what you can catch with a fishing tour, and contemplate the long history of John Deere Historic Site.

For reviews, where to stay, and other tourist information, use the Chicago day trip app .

In May, daytime highs in Chicago are 71°F, while nighttime lows are 52°F. Wrap up your sightseeing on the 30th (Thu) to allow time to travel back home.

Things to do in Chicago

Parks Wildlife Outdoors

Side Trips

Pontiac, Lake Geneva, Saint Joseph, Chesterton, Naperville
Highlights from your plan
Starved Rock State Park ©
Starved Rock State Park
Cantigny Park ©
Cantigny Park

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