The Roosevelt Hotel

Mad Men fans will recognize the Roosevelt as Don Draper's temporary pied-à-terre in the cult TV series. Occupying an entire city block, the hotel maintains its classic looks in both the chandelier-lit lobby and the bedrooms. Fittingly, there's plenty of choice when the cocktail hour arrives: The old-school Madison Club Lounge, the more modern Vander Bar and mad46 rooftop lounge. Rooms: 1,015.