60 days in Chicago Itinerary

60 days in Chicago Itinerary

Created using Inspirock Chicago visit planner

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Chicago
— 59 nights

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Chicago

— 59 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get a sense of the local culture at The Art Institute of Chicago and Richard H. Driehaus Museum. Deepen your sense of the past at sights like Garfield Park Conservatory and Chicago Riverwalk. Explore Chicago's surroundings by going to South Bend (University of Notre Dame, Grotto of Our Lady Lourdes, &more), Milwaukee (Riverwalk, Lakefront Brewery, &more) and Severson Dells Nature Center (in Rockford). And it doesn't end there: examine the collection at IL Route 66 Association Hall of Fame & Museum, contemplate the waterfront views at Geneva Lake, enjoy the sand and surf at New Buffalo Public Beach, and visit a coastal fixture at St. Joseph Lighthouses.

To see traveler tips, ratings, more things to do, and tourist information, you can read our Chicago route planning tool.

In April, daily temperatures in Chicago can reach 59°F, while at night they dip to 40°F.

Things to do in Chicago

Parks · Museums · Wildlife · Historic Sites

Side Trips