60 days in Chicago Itinerary

60 days in Chicago Itinerary

Created using Inspirock Chicago trip builder

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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.
Venture out of the city with trips to Shiojiri Niwa (in Mishawaka), South Bend (Basilica of the Sacred Heart, Grotto of Our Lady Lourdes, &more) and Arlington Heights (Arlington International Racecourse & Shalom Memorial Park). The adventure continues: explore the world behind art at The Art Institute of Chicago, walk around Millennium Park, take in panoramic vistas at Skydeck Chicago - Willis Tower, and make a trip to The Magnificent Mile.

To see other places to visit, traveler tips, ratings, and more tourist information, read Chicago online vacation planner.

In April, plan for daily highs up to 59°F, and evening lows to 40°F.

Things to do in Chicago

Parks · Museums · Historic Sites · Breweries & Distilleries

Side Trips