29 days in Chicago Itinerary

29 days in Chicago Itinerary

Created using Inspirock Chicago trip builder
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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), Bengtson's Pumpkin Farm (in Homer Glen) and Cowles Bog (in Chesterton). 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, pause for some photo ops at Cloud Gate, and enjoy breathtaking views from 360 Chicago Observation Deck.

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.
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Parks · Outdoors · Museums · Historic Sites
Side Trips
Find places to stay Oct 2 — 30: