14 days in Chicago Itinerary

14 days in Chicago Itinerary

Created using Inspirock Chicago trip itinerary planner

Make it your trip
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Chicago
— 13 nights

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Chicago

— 13 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Explore Chicago's surroundings by going to Pottawatomie Park (in Saint Charles), Whiskey Acres Distilling Co. (in DeKalb) and SaltTreeYoga (in Ottawa). There's lots more to do: admire the masterpieces at The Art Institute of Chicago, enjoy breathtaking views from Skydeck Chicago - Willis Tower, engage your brain at Museum of Science and Industry, and take a tour by water with Boat Tours & Water Sports.

For more things to do, photos, maps, and more tourist information, you can read our Chicago trip planner.

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

Things to do in Chicago

Museums · Parks · Historic Sites · Childrens Museums

Side Trips