30 days in Chicago Itinerary

30 days in Chicago Itinerary

Created using Inspirock Chicago holiday 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.
Take a break from the city and head to Silver Beach County Park and Starved Rock State Park. Eschew the tourist crowds and head to Jasper-Pulaski Fish and Wildlife Area and Coffee Creek Watershed Preserve. Get out of town with these interesting Chicago side-trips: Saint Joseph (Box Factory for the Arts, Whirlpool Compass Fountain, & more), Lake Geneva (Studio Winery & Geneva Lake Shore Path) and Oak Grove Golf Course (in Harvard). There's much more to do: take a stroll through The Magnificent Mile, don't miss a visit to Millennium Park, hike along Cowles Bog, and do a tasting at Carpenter Creek Cellars.

To find reviews, traveler tips, maps, and other tourist information, read our Chicago trip planner .

In May, daily temperatures in Chicago can reach 71°F, while at night they dip to 52°F. Finish your sightseeing early on the 30th (Thu) so you can travel back home.

Things to do in Chicago

Parks Wildlife Outdoors

Side Trips

Pontiac, Chesterton, Saint Joseph, Utica, South Bend
Highlights from your plan
Silver Beach County Park ©
Silver Beach County Park
Cantigny Park ©
Cantigny Park

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