60 days in Chicago Itinerary

60 days in Chicago Itinerary

Created using Inspirock Chicago journey planner
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Chicago
— 59 nights

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Chicago — 59 nights

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Eschew the tourist crowds and head to Chicago Cultural Center and Lakefront Trail. Visiting Mountain Top at Grand Geneva Resort and Wilmot Mountain will get you outdoors. Change things up with these side-trips from Chicago: Milwaukee (Milwaukee Art Museum, Concordia, &more), Hilldale Golf Club (in Hoffman Estates) and Bloomingdale Golf Club (in Bloomingdale). Spend the 22nd (Sat) exploring nature at Indiana Dunes National Park. There's still lots to do: see the interesting displays at Richard H. Driehaus Museum, find something for the whole family at Fox in a Box Chicago, browse the different shops at Woodfield Mall, and admire the masterpieces at The Art Institute of Chicago.

To see other places to visit, where to stay, maps, and tourist information, use the Chicago road trip website.

Expect a daytime high around 32°F in January, and nighttime lows around 18°F.
Outdoors · Parks · Museums · Shopping
Side Trips