50 days in Chicago Itinerary

50 days in Chicago Itinerary

Created using Inspirock Chicago route builder

Make it your trip
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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.
Change things up with these side-trips from Chicago: South Bend (Warren Golf Course, Basilica of the Sacred Heart, &more), Rockford (Sinnissippi Park & Anderson Japanese Gardens) and Historical Auto Attractions (in Roscoe). The adventure continues: explore the world behind art at The Art Institute of Chicago, observe the fascinating underwater world at Shedd Aquarium, get in on the family fun at Navy Pier, and stop by The Magnificent Mile.

To find reviews, ratings, more things to do, and tourist information, go to the Chicago trip itinerary maker tool.

In June, plan for daily highs up to 81°F, and evening lows to 63°F. Cap off your sightseeing on the 31st (Fri) early enough to travel back home.

Things to do in Chicago

Parks · Outdoors · Museums · Historic Sites

Side Trips