5 days in Chicago Itinerary

5 days in Chicago Itinerary

Created using Inspirock Chicago visit planner

Make it your trip
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Chicago
— 4 nights

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Chicago

— 4 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You've now added BIG Bar to your itinerary. Your inner history buff will appreciate Ernest Hemingway Birthplace and Marquette Building. Step out of the city life by going to Starved Rock State Park and Little Red Schoolhouse. Change things up with a short trip to Prairie States Winery in Genoa (about 1h 20 min away). Next up on the itinerary: explore the world behind art at The Art Institute of Chicago, shop like a local with The Magnificent Mile, steep yourself in history at Pleasant Home, and engage your brain at Museum of Science and Industry.

To find maps, photos, ratings, and other tourist information, read our Chicago road trip site.

If you are flying in from Mexico, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and Gary Chicago International Airport. Expect a daytime high around 8°C in March, and nighttime lows around -1°C. Wrap up your sightseeing on the 18th (Mon) to allow time to travel back home.

Things to do in Chicago

Parks · Museums · Childrens Museums · Outdoors

Side Trips