32 days in Chicago Itinerary

32 days in Chicago Itinerary

Created using Inspirock Chicago journey planner

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Chicago
— 31 nights

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Chicago

— 31 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
For shopping fun, head to Chicago Cultural Center or Chicago Premium Outlets. You'll explore and learn at The Art Institute of Chicago and IL Route 66 Association Hall of Fame & Museum. Change things up with these side-trips from Chicago: Butler Winery (in Chesterton), Jasper-Pulaski Fish and Wildlife Area (in Medaryville) and Grotto of Our Lady Lourdes (in South Bend). Spend the 15th (Tue) exploring nature at Indiana Dunes National Park. There's much more to do: admire the masterpieces at Richard H. Driehaus Museum, hit the slopes at Mountain Top at Grand Geneva Resort, admire the natural beauty at Garfield Park Conservatory, and tour the pleasant surroundings at Lakefront Trail.

For where to stay, more things to do, traveler tips, and other tourist information, use the Chicago trip itinerary planner.

In January, daytime highs in Chicago are 32°F, while nighttime lows are 18°F. Finish up your sightseeing early on the 25th (Fri) so you can travel back home.

Things to do in Chicago

Parks · Museums · Wildlife · Shopping

Side Trips