29 days in Chicago Itinerary

29 days in Chicago Itinerary

Created using Inspirock Chicago trip builder

Make it your trip
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Chicago
— 28 nights

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Chicago

— 28 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 Bengtson's Pumpkin Fest (in Homer Glen), Cowles Bog (in Chesterton) and National Shrine and Museum of St. Therese (in Darien). And it doesn't end there: explore the world behind art at The Art Institute of Chicago, take a leisurely stroll along Navy Pier, engage your brain at Museum of Science and Industry, and take a stroll through The Magnificent Mile.

For reviews, where to stay, maps, and other tourist information, use the Chicago trip planner.

If you are flying in from Israel, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and Gary Chicago International Airport. October in Chicago sees daily highs of 21°C and lows of 11°C at night. Finish your sightseeing early on the 30th (Tue) so you can travel back home.

Things to do in Chicago

Parks · Outdoors · Historic Sites · Museums

Side Trips

Find places to stay Oct 2 — 30: