13 days in Chicago Itinerary

13 days in Chicago Itinerary

Created using Inspirock Chicago trip itinerary planner

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1
Chicago
— 12 nights

12
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Explore hidden gems such as Starved Rock State Park and Carpenter Creek Cellars. Get some historical perspective at John Deere Historic Site and Ernest Hemingway Birthplace. Venture out of the city with trips to Prairie States Winery (in Genoa), Rosewood Beach (in Highland Park) and Grayslake Heritage Center & Museum (in Grayslake). And it doesn't end there: explore the world behind art at The Art Institute of Chicago, appreciate the extensive heritage of Millennium Park, stroll through Silver Beach County Park, and learn about winemaking at St. Julian Winery-Union Pier.

To see other places to visit, reviews, maps, and other tourist information, read our Chicago road trip website .

In December, plan for daily highs up to 38°F, and evening lows to 26°F. Finish your sightseeing early on the 17th (Tue) so you can travel back home.

Things to do in Chicago

Museums Parks Wineries

Side Trips

Lake Geneva, Pontiac, Coloma, Saint Joseph, Utica
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Basilica of the Sacred Heart ©
Basilica of the Sacred Heart

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