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

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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 Riverwalk Lot. Eschew the tourist crowds and head to Milwaukee Art Museum and Lakefront Trail. Change things up with these side-trips from Chicago: Severson Dells Nature Center (in Rockford), Milwaukee (Riverwalk, Lakefront Brewery, &more) and South Bend (University of Notre Dame, Grotto of Our Lady Lourdes, &more). There's much more to do: examine the collection at IL Route 66 Association Hall of Fame & Museum, contemplate in the serene atmosphere at Baha'i House of Worship, don't miss a visit to Chicago Skyline, and admire the majestic nature at Matthiessen State Park.

To find reviews, where to stay, photos, and more tourist information, go to the Chicago trip planning app.

Expect a daytime high around 71°F in May, and nighttime lows around 52°F.

Things to do in Chicago

Parks · Museums · Wildlife · Historic Sites

Side Trips