Something of an anomaly when it comes to rooftop lounges, Streeterville Social skips the bass thump of the club scene and goes for more of a country club feel. The huge space offers two bars, perfect for after-business drinks or for taking a cocktail to one of the lounge chairs and treating the place like your own tropical getaway. A real-grass play area has games of giant Jenga and pétanque (like bocce). Views in every direction take in the lake and the river, plus city lights at night. A dedicated kitchen serves al fresco dining options like marinated beet salad, fish tacos and a daily flatbread special. Open daily 4-10:30 pm.