If you’re still remembering the summertime queues snaking past the elevator here, cheer up: Cold weather means no waiting for a perch at this rooftop spot. Like Milk Room (No. 3), it’s part of the Chicago Athletic Association Hotel. Reminiscent of a Great Lakes vacation house, complete with wood and picnic tables, Cindy’s delivers insane gull’s-eye views of the lake, the Bean, and other sights without feeling like a tourist trap. Bartenders are sharp and efficient but never cold. Cocktails start at $14, but they’re potent enough to give you your money’s worth. 12 S. Michigan Ave., 312-792-3502

Crowd Beautiful people and out-of-towners in boat shoes
Food Full menu with lots of seafood and contemporary fare
Top Tipple Hunter’s Moon (Scotch, amontillado, Amaro Meletti, apple saba, smoked red grape, Aleppo pepper), $18