5 days in Chicago Itinerary

5 days in Chicago Itinerary

Created using Inspirock Chicago trip itinerary planner

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1
Chicago
— 4 nights

4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get some cultural insight at The Magnificent Mile and Carpenter Creek Cellars. Step off the beaten path and head to Prarie States Winery and DC Estate Winery. Explore the numerous day-trip ideas around Chicago: St. Julian Winery-Union Pier (in Union Pier), Chesterton (Hunter's Brewing & Butler Winery) and Journeyman Distillery (in Three Oaks). Next up on the itinerary: admire the masterpieces at The Art Institute of Chicago, admire the landmark architecture of Chicago Cultural Center, admire all the interesting features of Millennium Park, and don't miss a visit to Skydeck Chicago - Willis Tower.

To see traveler tips, reviews, ratings, and other tourist information, use the Chicago sightseeing planner.

In December, daily temperatures in Chicago can reach 38°F, while at night they dip to 26°F. Wrap up your sightseeing on the 26th (Wed) to allow time to travel back home.

Things to do in Chicago

Museums Wineries Shopping

Side Trips

Chesterton, Journeyman Distillery, Prairie States Winery, Carpenter Creek Cellars, Horseshoe Hammond
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
The Magnificent Mile ©
The Magnificent Mile
Millennium Park ©
Millennium Park

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