10 days in Chicago Itinerary

10 days in Chicago Itinerary

Created using Inspirock Chicago vacation planner

Make it your trip
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Chicago
— 9 nights

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Chicago

— 9 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll discover tucked-away gems like Lakefront Trail and Chicago Riverwalk. Venture out of the city with trips to Milwaukee (Milwaukee Soldiers Home, Chudnow Museum of Yesteryear, &more), Anderson Japanese Gardens (in Rockford) and Cantigny Park (in Wheaton). There's lots more to do: find something for the whole family at Fox in a Box Chicago, make a trip to Chicago Skyline, contemplate the waterfront views at Lake Michigan, and admire the masterpieces at Richard H. Driehaus Museum.

For traveler tips and tourist information, read our Chicago day trip site.

June in Chicago sees daily highs of 81°F and lows of 63°F at night.

Things to do in Chicago

Parks · Historic Sites · Museums · Shopping

Side Trips