Upon entering Roof, The Wit Hotel’s new 27th-floor lounge, most would think they had traveled not up but down—south, that is. The roofless, skyline-level spot smacks of Miami but boasts a view that’s pure Chicago. Where the airy, glass-enclosed bar measures an ample 7,000 square feet, the craft-cocktail menu is thoughtfully petite; we liked the Jalisco Old Fashioned (tequila, orange and cinnamon bitters, and agave nectar; $13). Gluten-free and organic brews, an affordable wine list, and very shareable Italian small plates underscore the lounge’s something-for-everyone approach—a delightfully friendly contrast to a chic space that looks handcrafted for the South Beach elite.

GO: ROOF 201 N. State St.; roofonthewit.therestaurantsatthewit.com

Photograph: Chris Guillen