"Chicago’s mercurial weather patterns meet their match at Boleo, a South American rooftop lounge and restaurant with a retractable glass roof atop the Kimpton Gray Hotel. Designed to create the feeling of al fresco hospitality regardless of precipitation, it specializes in colorful, crowd-pleasing drinks like Passion Puma (Vida mezcal, jequitiba rosa, guava) and Two to Tango (Plantation rum, Giffard banana, Dolin Blanco, huna, melon). Balance out the booze with cevices, empanadas, and large plates like bone-in grilled pork chops." - Naomi Waxman, Ashok Selvam