25 days in Chicago Itinerary

25 days in Chicago Itinerary

Created using Inspirock Chicago visit planner

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Route & dates

1
Chicago
— 24 nights

24
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Change things up with these side-trips from Chicago: Standard Oil Gas Station (in Odell), Valentino Vineyards (in Long Grove) and St. Joseph Catholic Church (in Joliet). There's lots more to do: relax in the rural setting at Whiskey Acres Distilling Co., do a tasting at Carpenter Creek Cellars, relax and rejuvenate at some of the best spas, and explore the world behind art at The Art Institute of Chicago.

For ratings, traveler tips, photos, and other tourist information, you can read our Chicago trip planner.

In January, daytime highs in Chicago are 32°F, while nighttime lows are 18°F. Finish your sightseeing early on the 31st (Fri) to allow enough time to travel back home.

Things to do in Chicago

Wineries Museums Neighborhoods

Side Trips

Milwaukee, Oak Park, South Bend, Union Pier, Sri Venkateswara Swami Temple
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Whiskey Acres Distilling Co. ©
Whiskey Acres Distilling Co.
Prairie States Winery ©
Prairie States Winery

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