29 days in Chicago Itinerary

29 days in Chicago Itinerary

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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.
Get out of town with these interesting Chicago side-trips: National Shrine 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. There's lots more to do: admire the masterpieces at The Art Institute of Chicago, take a leisurely stroll along Navy Pier, take in panoramic vistas at Skydeck Chicago - Willis Tower, and wander the streets of The Magnificent Mile.

For more things to do, where to stay, and other tourist information, refer to the Chicago holiday maker site .

If you are flying in from Israel, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. In October, daily temperatures in Chicago can reach 21°C, while at night they dip to 11°C. Finish your sightseeing early on the 30th (Tue) so you can travel back home.

Things to do in Chicago

Parks Outdoors Museums

Side Trips

Oak Park, Saint Joseph, South Bend, Oak Brook, Glen Ellyn Historical Society
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
Millennium Park ©
Millennium Park
2:30pm, Fri Oct 12
Wrigley Field ©
Wrigley Field
2:00pm, Wed Oct 24

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