Chicago, Illinois

Discover the Windy City while staying in Inspirato’s chic downtown accommodations. Located along Michigan Avenue, Pendry Chicago lives within the architectural landmark of the Carbide & Carbon Building, steps away from the city's best attractions.

 The Langham Chicago is close to the Loop, just a short walk from the Bean and the Art Institute of Chicago. Situated in the posh Gold Coast neighborhood, The Ritz-Carlton, Chicago offers a refined experience with panoramic views of Lake Michigan and the Navy Pier.

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A World-Class City on the Shores of Lake Michigan

Chicago is a towering triumph of American architecture, good food, renowned museums, and friendly midwesterners, nestled on the bank of Lake Michigan. Take an unhurried stroll through Millennium Park and Grant Park, home to acres of gardens, Buckingham Fountain, and Chicago’s most famous sculpture: the Bean. Catch a Cubs game at Wrigley Field—the second-oldest ballpark in the country—and pop into world-class museums like the Field Museum, the Shedd Aquarium, and the Art Institute. You won’t go hungry; Chicago has exploded as a foodie destination in recent years, where gourmet restaurants and charming dives sit side by side. End your visit with a sunset harbor cruise on Lake Michigan to take in the twilit silhouette of the iconic skyline.

Quick Facts

  • Suggested airport
    O’Hare International Airport (ORD) or Midway International Airport (MDW)
  • Average temperature
    82°F in summer; 32°F in winter
  • Peak season
  • Car recommended?
  • Population
    3 million

Destination Highlights

  • Lakefront Trail

    Walk or bike the 18-mile lakefront trail that hugs Lake Michigan, winding past the skyscrapers in the Loop and the Neoclassical and Art Deco buildings of the museum campus further south. Hop off to explore Lincoln Park and its free urban zoo.

  • The Art Institute

    The Midwest’s most venerable art museum, The Art Institute is home to masterpieces like American Gothic by Grant Wood, Nighthawks by Edward Hopper, and A Sunday on La Grande Jatte by Georges Seurat. You’ll also find works by Claude Monet and Georgia O’Keeffe.

  • Architecture River Cruise

    The Chicago River swoops through the Loop, flowing out of Lake Michigan (thanks to an engineering feat in 1900) and coursing through the city. Learn about Chicago’s famous skyscrapers on an architecture cruise or a kayak tour.



  • Forecasting Your Chicago Vacation

    Chicago experiences all four seasons fully. Hot and humid summer days send locals and tourists alike to the refreshing waters of Lake Michigan; summer nights are balmy, long, and best savored on an outdoor patio. If you don’t like the humidity, fall is a great time to visit, when the leaves change color and average temps in October hover in the crisp mid-50s. Chicago winters can be cold, damp, and overcast, but the chilly weather means much fewer crowds.


Map of Chicago

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