5 days in Chicago Itinerary

5 days in Chicago Itinerary

Created using Inspirock Chicago sightseeing 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 in touch with nature at Little Red Schoolhouse and Willowbrook Wildlife Center. Millennium Park and Ernest Hemingway Birthplace will appeal to history buffs. Explore the numerous day-trip ideas around Chicago: Bengtson's Pumpkin Farm (in Homer Glen), Cowles Bog (in Chesterton) and Red Oak Nature Center (in Batavia). Next up on the itinerary: explore the world behind art at The Art Institute of Chicago, enjoy breathtaking views from Skydeck Chicago - Willis Tower, admire all the interesting features of Wrigley Field, and wander the streets of The Magnificent Mile.

To see where to stay, other places to visit, traveler tips, and more tourist information, read our Chicago road trip planning app .

If you are flying in from Netherlands, 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. Finish up your sightseeing early on the 9th (Tue) so you can travel back home.

Things to do in Chicago

Parks Wildlife Outdoors

Side Trips

Ernest Hemingway Birthplace, Red Oak Nature Center, Little Red Schoolhouse, Bengtson's Pumpkin Farm, Willowbrook Wildlife Center
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Ernest Hemingway Birthplace ©
Ernest Hemingway Birthplace

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