29 days in Chicago Itinerary

29 days in Chicago Itinerary

Created using Inspirock Chicago trip builder

Plan created by another user. Make it yours

Route & dates

1
Chicago
— 28 nights

28
nights
Chicago

Chicago ©
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), National Shrine and Museum of St. Therese (in Darien) 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, 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

Side Trips

Oak Park, South Bend, Saint Joseph, Oak Brook, Illinois
Find places to stay Oct 2 — 30:
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park
Millennium Park
Skydeck Chicago - Willis Tower ©
Skydeck Chicago - Willis Tower

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