Get started
Open the door to our private Collection of incredible, spacious homes in highly sought-after destinations.
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.
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.