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 National Shrine and Museum of St. Therese (in Darien), Cowles Bog (in Chesterton) and Bengtson's Pumpkin Fest (in Homer Glen). Plan for a day of cool, family-friendly fun on the 30th (Tue) at Six Flags Great America. The adventure continues: admire the masterpieces at The Art Institute of Chicago, walk around Millennium Park, take in the waterfront at Navy Pier, and get to know the resident critters at Lincoln Park Zoo.

For traveler tips, more things to do, where to stay, and tourist information, use the Chicago road 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. In October in Chicago, expect temperatures between 21°C during the day and 11°C at night. Finish your sightseeing early on the 30th (Tue) to allow enough time to travel back home.

Things to do in Chicago

Parks · Outdoors · Museums · Historic Sites

Side Trips

Find places to stay Oct 2 — 30: