5 days in Chicago Itinerary

5 days in Chicago Itinerary

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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.
When in Chicago, make a side trip to see Bengtson's Pumpkin Farm in Homer Glen, approximately 42 minutes away. There's lots more to do: explore the world behind art at The Art Institute of Chicago, appreciate the extensive heritage of Millennium Park, admire the landmark architecture of Skydeck Chicago - Willis Tower, and enjoy breathtaking views from 360 Chicago Observation Deck.

For photos, traveler tips, reviews, and other tourist information, use the Chicago road trip planner .

In November, daily temperatures in Chicago can reach 50°F, while at night they dip to 35°F. Finish your sightseeing early on the 25th (Sun) to allow enough time to travel back home.

Things to do in Chicago

Outdoors Parks Museums

Side Trip

Bengtson's Pumpkin Farm
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Museum of Science and Industry ©
Museum of Science and Industry

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