Millennium Knickerbocker Hotel Chicago

Formerly Hugh Hefner’s swinging Playboy Towers, this regal property now caters to a more refined crowd. Guests and locals populate the renovated two-story lobby bar, which has a jazz piano soundtrack and a choice of more than 50 Martinis. Bathrooms have been upgraded in a bid to keep the historic property up to speed. *High-speed internet ($9.95 wireless in public spaces & via cable in rooms).