29 days in Chicago Itinerary

29 days in Chicago Itinerary

Created using Inspirock Chicago trip builder

Plan created by another user. Make it yours
Start: Chicago
1
Chicago
— 28 nights
End: Chicago
Tue, Oct 2 - Tue, Oct 30 Edit
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See full calendar

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 Bengtson's Pumpkin Fest (in Homer Glen), Cowles Bog (in Chesterton) and National Shrine and Museum of St. Therese (in Darien). 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 · Historic Sites · Museums

Side Trips

Oak Park, Saint Joseph, South Bend, Oak Brook, Illinois
Find places to stay Oct 2 — 30:
Hotels on TripAdvisor
Homes on Airbnb
Highlights from your trip
©
Must see
The Art Institute of Chicago
4.8
Must see
Millennium Park
4.8
©
Observation Deck
Skydeck Chicago - Willis Tower
4.0
See timeline

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