30 days in Chicago Itinerary

30 days in Chicago Itinerary

Created using Inspirock Chicago route builder

Plan created by another user. Make it yours
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.
Your cultural itinerary includes sights like The Art Institute of Chicago and Studebaker National Museum. You'll explore the less-touristy side of things at Chicago Riverwalk and Silver Beach County Park. Change things up with these side-trips from Chicago: Chesterton (Cowles Bog, Coffee Creek Watershed Preserve, &more), New Buffalo (Whittaker Woods Golf Club & Galien River County Park) and Journeyman Distillery (in Three Oaks). Next up on the itinerary: get to know the fascinating history of Riverwalk Lot, examine the collection at Richard H. Driehaus Museum, wander the streets of The Magnificent Mile, and brush up on your military savvy at Cantigny Park.

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May in Chicago sees daily highs of 71°F and lows of 52°F at night. Wrap up your sightseeing on the 30th (Thu) to allow time to travel back home.

Things to do in Chicago

Parks · Wildlife · Museums

Side Trips

Pontiac, Saint Joseph, Chesterton, Lake Geneva, Naperville
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
IL Route 66 Association Hall of Fame & Museum ©
Cantigny Park ©
Cantigny Park

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