60 days in Chicago Itinerary
Created using Inspirock Chicago trip planner
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Chicago
— 59 nights
End at...
Wed, Oct 26 - Sat, Dec 24
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Chicago — 59 nights

Windy City
Bring the kids along to The Art Institute of Chicago and Shedd Aquarium. Explore the numerous day-trip ideas around Chicago: Historic Auto Attractions (in Roscoe), Edwards Apple Orchard (in Poplar Grove) and Pioneer Sholes Historic Site (in Saint Charles). And it doesn't end there: get curious at Museum of Science and Industry, get a new perspective on nature at Field Museum, let your taste buds guide you at a local gastronomic tour, and wander the streets of The Magnificent Mile.
For maps, ratings, reviews, and more tourist information, you can read our Chicago online trip itinerary builder.
October in Chicago sees daily highs of 65°F and lows of 49°F at night.
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For maps, ratings, reviews, and more tourist information, you can read our Chicago online trip itinerary builder.
October in Chicago sees daily highs of 65°F and lows of 49°F at night.
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