Drumbar
Chicago
Cocktail Bar
$$$$
Not only is Drumbar one of the sexiest rooftop lounges in Chicago, the 18th-floor bar atop the Raffaello Hotel has a brag-worthy selection of whiskey, scotch, bourbon, and cognac. The sleek spot has a cozy den-meets-gentlemen's club decor with dark leather couches, wood-paneled walls, and a marble bar. During the summer, the seasonal outdoor patio makes it even more of an after-work drinking destination near the Magnificent Mile.