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200 mWestin Michigan Avenue Chicago
909 N Michigan Ave Chicago United States (the) 60611
¥820.73View
250 mPark Hyatt Chicago
800 N Michigan Ave Chicago United States (the) 60611
¥2,426.21View
280 mThe Drake A Hilton Hotel
140 East Walton Place Chicago United States (the)
¥871.13View
300 mFour Seasons Hotel Chicago
120 East Delaware Place Chicago United States (the) 60611-1443
¥3,023.76View
310 mThe Peninsula Chicago
108 EAST SUPERIOR ST CHICAGO IL 60611
¥2,001.44View
390 mOmni Chicago Hotel
676 N Michigan Ave Chicago United States (the) 60611
¥1,259.90View
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Chicago’s skyline is a testament to architectural ambition, but its soul resides in the historic elegance of the Gold Coast and the shimmering allure of the Magnificent Mile. To experience "Old Money Opulence" is to step into a world where high ceilings, marble lobbies, and white-glove service are the standard, not the exception. This curated collection guides you through the city's true "Grande Dames"—properties like The Langham and The Peninsula that define sophisticated living. Nestled between the upscale boutiques of Oak Street and the historic mansions of the Gold Coast neighborhood, these hotels offer more than just sleep; they offer a pedigree. Whether it represents the Art Deco grandeur of the Roaring Twenties or the timeless European flair of the Waldorf Astoria, each property invites you to inhabit a legacy of wealth, taste, and unparalleled hospitality in the Windy City.
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In the architectural canyon of Chicago, true relaxation is found not on the streets, but in the sky. Our curated selection of urban sanctuaries focuses on luxury properties that elevate wellness literally and figuratively. From the Asian-inspired serenity of The Peninsula Chicago on the Magnificent Mile to the modernist elegance of The St. Regis in Lakeshore East, these hotels offer a respite from the Windy City's energy. Experience the tranquility of the Gold Coast and the bustle of River North from a vantage point of total peace. Whether it's the panoramic pool at The Langham or the refined treatments at the Waldorf Astoria, these spas define high-altitude luxury.