8 days in Chicago Itinerary

8 days in Chicago Itinerary

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1
Chicago
— 7 nights

7
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
The Art Institute of Chicago and Ernest Hemingway Birthplace will appeal to museum buffs. Do some cultural sightseeing at The Magnificent Mile and Prarie States Winery. You'll find plenty of places to visit near Chicago: Little Red Schoolhouse (in Willow Springs), Basilica of the Sacred Heart (in South Bend) and Bengtson's Pumpkin Farm (in Homer Glen). And it doesn't end there: get to know the fascinating history of Millennium Park, admire the striking features of Frank Lloyd Wright Home and Studio, engage your brain at Museum of Science and Industry, and identify plant and animal life at Willowbrook Wildlife Center.

To find other places to visit, photos, maps, and tourist information, you can read our Chicago online road trip planner .

In November in Chicago, expect temperatures between 50°F during the day and 35°F at night. Finish your sightseeing early on the 21st (Wed) so you can travel back home.

Things to do in Chicago

Parks Wildlife Museums

Side Trips

Oak Park, Bengtson's Pumpkin Farm, Cowles Bog, Red Oak Nature Center, Little Red Schoolhouse
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum
The Magnificent Mile ©
The Magnificent Mile

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