7 days in Chicago Itinerary

7 days in Chicago Itinerary

Created using Inspirock Chicago holiday builder

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1
Chicago
— 6 nights

6
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Eschew the tourist crowds and head to Silver Beach County Park and St. Julian Winery-Union Pier. Get some cultural insight at The Magnificent Mile and Millennium Park. Get out of town with these interesting Chicago side-trips: Geneva Lake Shore Path (in Lake Geneva), Exploration Station...a children's museum (in Bourbonnais) and Carpenter Creek Cellars (in Remington). And it doesn't end there: admire the masterpieces at The Art Institute of Chicago, learn about winemaking at August Hill Winery & Illinois Sparkling Co. Tasting Room, trek along Starved Rock State Park, and try to win big at Four Winds Casino.

To see more things to do, where to stay, photos, and other tourist information, read our Chicago visit planner.

If you are flying in from Mexico, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. In October, daytime highs in Chicago are 21°C, while nighttime lows are 11°C. Finish your sightseeing early on the 1st (Thu) so you can travel back home.

Things to do in Chicago

Wineries Parks Outdoors

Side Trips

Utica, Hickory Creek Winery, Silver Beach County Park, Geneva Lake Shore Path, Carpenter Creek Cellars
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Silver Beach County Park ©
Silver Beach County Park
Millennium Park ©
Millennium Park

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