27 days in Chicago Itinerary

27 days in Chicago Itinerary

Created using Inspirock Chicago trip planner

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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.
Shop till you drop at The Magnificent Mile and Chicago Cultural Center. Step out of the city life by going to Willow Crest Golf Club and Bloomingdale Golf Club. Explore Chicago's surroundings by going to Grand Mere State Park (in Stevensville), Lake Opeka (in Des Plaines) and Whihala Beach (in Whiting). There's still lots to do: admire the masterpieces at The Art Institute of Chicago, try your luck at Horseshoe Hammond, take in the spiritual surroundings of Fourth Presbyterian Church, and pause for some serene contemplation at Basilica of the Sacred Heart.

To find photos, where to stay, other places to visit, and other tourist information, you can read our Chicago tour itinerary tool.

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, plan for daily highs up to 0°C, and evening lows to -9°C. Finish your sightseeing early on the 9th (Sat) so you can travel back home.

Things to do in Chicago

Parks · Outdoors · Beaches · Wildlife

Side Trips