60 days in Chicago Itinerary

60 days in Chicago Itinerary

Created using Inspirock Chicago trip maker

Make it your trip
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Chicago
— 59 nights

S M T W T F S
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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.
Your inner history buff will appreciate Chicago Riverwalk and Holy Name Cathedral. Eschew the tourist crowds and head to Milwaukee Art Museum and The Loop. Change things up with these side-trips from Chicago: 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: admire the masterpieces at The Art Institute of Chicago, examine the collection at Volo Auto Museum, get to know the fascinating history of Riverwalk Lot, and walk around Millennium Park.

For where to stay, photos, other places to visit, and more tourist information, read our Chicago online holiday builder.

In May in Chicago, expect temperatures between 71°F during the day and 52°F at night.

Things to do in Chicago

Parks · Museums · Wildlife · Historic Sites

Side Trips