30 days in Chicago Itinerary

30 days in Chicago Itinerary

Created using Inspirock Chicago trip itinerary planner

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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.
For shopping fun, head to The Magnificent Mile or Chesterton’s European Market. You'll explore the less-touristy side of things at Silver Beach County Park and Jasper-Pulaski Fish and Wildlife Area. Get out of town with these interesting Chicago side-trips: Chesterton (Butler Winery, Coffee Creek Watershed Preserve, & more), Shrine of the Christ's Passion (in Saint John) and Washington Square (in Ottawa). Next up on the itinerary: explore the world behind art at The Art Institute of Chicago, delve into the lush surroundings at Hawthorn Hollow - Nature Sanctuary and Arboretum, stroll around Millennium Park, and hike along Starved Rock State Park.

For other places to visit, traveler tips, and more tourist information, read Chicago journey planning tool .

In May, daytime highs in Chicago are 71°F, while nighttime lows are 52°F. Finish up your sightseeing early on the 30th (Thu) so you can travel back home.

Things to do in Chicago

Parks Wildlife Outdoors

Side Trips

Chesterton, Pontiac, South Bend, Saint Joseph, Evanston
Highlights from your plan
Chicago Cultural Center ©
Chicago Cultural Center
Cantigny Park ©
Cantigny Park

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