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  • The Waldorf Astoria: The Parisian-style exterior exudes Old World glamour, but inside, the Waldorf Astoria is all about sleek, streamlined luxury. The guest rooms are some of the biggest in town, and include bonuses such as fireplaces and furnished terraces. The Gold Coast location — removed from the traffic of downtown — adds to the feeling of an urban retreat.
  • Park Hyatt: If the thought of overstuffed couches and thick brocade curtains makes you wince, this is the hotel for you. With its focus on modern design and clean lines, the Park Hyatt feels like one of those cool urban spaces featured in Architectural Digest. The coolest feature? Moveable bathroom walls that allow you to soak in the view while you lounge in the tub.
  • Peninsula: Inspired by the elegance of 1920s Shanghai and Hong Kong, the Chicago outpost of this Asian chain is a seamless blend of classic and modern. The grand public spaces may be a throwback to the past, but the hotel's amenities are ultramodern. The top-notch gym, spa, and indoor swimming pool (filled with natural light) make the Peninsula a must for fitness fanatics.
  • The Ritz-Carlton Chicago: Appropriately enough in this skyscraper-packed city, some of the best hotels perch far above the sidewalk. Located above the Water Tower Place shopping center, the Ritz has one of the most welcoming lobbies in town, with light streaming through the windows, masses of fresh flowers, and bird's-eye views of the city. The elegant guest rooms are decorated in Art Deco–inspired shades of silver, black, and gold, and the staff prides itself on granting every wish.
  • Trump International Hotel & Tower: Want to make-believe you've got your own pied-à-terre in the heart of downtown? This is the place to live out your fantasy — the contemporary-cool rooms are actually studio apartments with full kitchens, plenty of space to lounge, and killer views of the skyline.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.