"The Gwen, located on the city’s famed Magnificent Mile and in the landmark McGraw-Hill building—with its 1928 facade wholly preserved—truly reflects the character of Chicago. Art Deco interiors with taupe- and gold-hued rooms emanate old-fashioned glamour and chic modernity all at once. Drinks at the rooftop bar and restaurant, Upstairs at the Gwen, is the perfect start or end to a romantic weekend. You can also book one of the special romance packages, which include things like prosecco at check-in and a rose petal turndown."