Chicago, Illinois

Discover the Windy City while staying in chic Inspirato accommodations in the heart of downtown. Enjoy floor-to-ceiling views of Chicago River and Lake Michigan from the aptly named Lakeview, our two-bedroom spacious suite in trendy River North.

Near the lake, in Chicago’s posh Gold Coast neighborhood, the Thompson Chicago is walking distance from the city’s premier attractions including the shops along the Magnificent Mile, Oak Street Beach, and Lincoln Park. The Langham Chicago is closest to the Loop, just a short walk from the Bean and the Art Institute of Chicago.

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Second City? Second to None

With its gourmet restaurants, popular museums and renowned sports teams, Chicago boasts the kinds of urban attractions that rival any city. What the new visitor may not realize is that the "Windy City" is also ideal for strolls to take it all in: on its 29 miles of lakefront paths, through festive Millennium Park, and around the bustling Navy Pier area. You'll likely want to walk the eight blocks of world-class shopping on the Magnificent Mile, and in the summer, eat a hot dog in the sun at Wrigley Field or compare Chi-town's deep-dish pizza to your own favorite. The best way to see this classic city is from the spectacular Trump International Hotel & Tower™.

Quick Facts

  • Suggested AIrport
  • Average Temperature
    Summer: 74° F; Winter: 29° F
  • Taste of Chicago
    Second week of July
  • Lollapalooza
    First weekend in August
  • Magnificent Mile Lights Festival

Fresh Things To Do

Featured Activity

  • Miles of Magnificent Shops

    From visiting quaint boutique emporiums to luxury brand stores, any Chicago vacation should include a stroll down the busy storefront boulevards and avenues. You'll find treasures aplenty at these top locations.

    Magnificent Mile.  Between four multilevel shopping malls and a mile-long stretch of the most densely concentrated shopping found in the continental U.S., you'll need a good pair of walking shoes to make a dent in this shopper haven. Hang on the north end to find well-known department stores and household names, or venture further south to discover the likes of Chanel, Louis Vuitton, Armani and Burberry. 

    American Girl Place.  One of the most visited attractions in Chicago, just exploring this shop is an experience in itself. This historic site reveals the story of the American Girl legacy and sells memorabilia for America's favorite doll.

    Hershey's.  Indulge in the world's favorite decadence. Here you can pick up some unique souvenirs and interact with the brand by creating new chocolate recipes yourself or placing your face on a candy wrapper. This is a great spot to take the kids or just celebrate life's simple pleasures.

    Pratesi Linens.  This family-owned linen company only uses the most superior materials. Each product is hand-woven from the finest cotton available in their Italian mill. The gold standard in fine bed, bath and table linen, Pratesi guarantees both luxury and class.

    Tod's.  This Italian shoemaker is renowned for top-of-the-line driving shoes and is globally recognized for superior comfort and style.

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    For more information about vacationing in this destination, contact your Care team.



  • Forecasting Your Chicago Vacation

    Chicago's climate has mild springs; warm, humid summers; crisp autumns; and cold, windy, snowy winters. Weather can be unpredictable, with frequent, short fluctuations in temperature, humidity, cloudiness and wind direction. Each season is distinct and uniquely enjoyable; however, many visitors consider the moderate weather in spring and fall to be the city's most pleasant.


Map of Chicago, Illinois

Google Maps satellite images are not always up-to-date, especially in non-U.S. destinations. Some Inspirato accommodations are located in developments built after images were last updated. Our pin placements represent our best location estimates, but actual locations may vary.

We're here to help.
Our expert travel advisors will help you find the perfect trip.
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