9 days in Chicago Itinerary

9 days in Chicago Itinerary

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1
Chicago
— 8 nights

8
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll explore and learn at The Art Institute of Chicago and The Field Museum. Get outdoors at Starved Rock State Park and Silver Beach County Park. You'll find plenty of places to visit near Chicago: August Hill Winery & Illinois Sparkling Co. Tasting Room (in Utica), John Deere Historic Site (in Grand Detour) and Ronald Reagan Boyhood Home (in Dixon). There's much more to do: get to know the fascinating history of Millennium Park, learn about winemaking at Prairie States Winery, admire the landmark architecture of Chicago Cultural Center, and get curious at Museum of Science and Industry.

For ratings, other places to visit, traveler tips, and more tourist information, read our Chicago road trip tool .

If you are flying in from Canada, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. In October, daytime highs in Chicago are 21°C, while nighttime lows are 11°C. Cap off your sightseeing on the 19th (Sat) early enough to travel back home.

Things to do in Chicago

Museums Wineries Parks

Side Trips

Pontiac, Utica, Saint Joseph, Domaine Berrien Cellars, Prairie States Winery
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Starved Rock State Park ©
Starved Rock State Park

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