27 days in Chicago Itinerary

27 days in Chicago Itinerary

Created using Inspirock Chicago route planner

Make it your trip
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Chicago
— 26 nights

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Chicago

— 26 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Appreciate the collections at The Art Institute of Chicago and Chicago Cultural Center. Satisfy your inner culture vulture at The Magnificent Mile and Frank Lloyd Wright Home and Studio. Get out of town with these interesting Chicago side-trips: Whihala Beach (in Whiting), Saint Joseph (Silver Beach County Park & Lions Park Beach) and Grand Mere State Park (in Stevensville). There's still lots to do: stop by Ernest Hemingway Birthplace, try your luck at Horseshoe Hammond, contemplate in the serene atmosphere at Fourth Presbyterian Church, and meet the residents at Shedd Aquarium.

For traveler tips, other places to visit, where to stay, and more tourist information, you can read our Chicago road trip website.

If you are flying in from Thailand, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and Gary Chicago International Airport. In January, daytime highs in Chicago are 0°C, while nighttime lows are -9°C. Wrap up your sightseeing on the 9th (Sat) to allow time to travel back home.

Things to do in Chicago

Parks · Outdoors · Beaches · Wildlife

Side Trips