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 Milwaukee Art Museum. Deepen your sense of the past at sights like Garfield Park Conservatory and Basilica of the Sacred Heart. Explore Chicago's surroundings by going to Milwaukee (Riverwalk, Lakefront Brewery, &more), South Bend (University of Notre Dame, Grotto of Our Lady Lourdes, &more) and Severson Dells Nature Center (in Rockford). And it doesn't end there: explore the world behind art at Richard H. Driehaus Museum, identify plant and animal life at Jasper-Pulaski Fish and Wildlife Area, visit a coastal fixture at St. Joseph Lighthouses, and wander the streets of The Loop.

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