29 days in Chicago Itinerary

29 days in Chicago Itinerary

Created using Inspirock Chicago trip builder

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Route & dates

1
Chicago
— 28 nights
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28
nights
Chicago

Chicago ©

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 South Bend Regional 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

Side Trips

Oak Park, South Bend, Saint Joseph, Oak Brook, Illinois
Find places to stay Oct 2 — 30:
Hotels on TripAdvisor
Homes on Airbnb
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
1:30pm, Tue Oct 2, 2018
Millennium Park ©
Millennium Park
2:30pm, Fri Oct 12, 2018
Bengtson's Pumpkin Fest ©
Bengtson's Pumpkin Fest
1:30pm, Thu Oct 4, 2018

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