50 days in Chicago Itinerary

50 days in Chicago Itinerary

Created using Inspirock Chicago route planner

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Chicago
— 49 nights

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Chicago

— 49 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Explore Chicago's surroundings by going to South Bend (Grotto of Our Lady Lourdes, Basilica of the Sacred Heart, &more), Whiskey Acres Distilling Co. (in DeKalb) and Saint Joseph (Silver Beach Carousel, Whirlpool Compass Fountain, &more). And it doesn't end there: admire the masterpieces at The Art Institute of Chicago, appreciate the history behind Cloud Gate, get curious at Museum of Science and Industry, and find something for the whole family at Navy Pier.

Plan a trip to Chicago easily and quickly by telling Inspirock to suggest an itinerary.

Expect a daytime high around 83°F in July, and nighttime lows around 67°F. Wrap up your sightseeing on the 31st (Sat) to allow time to travel back home.

Things to do in Chicago

Parks · Outdoors · Museums · Trails

Side Trips