Located on the second floor of an old masonic lodge in Highland Park, Checker Hall is part restaurant, part bar, and a rare spot where any type of night is possible. The cavernous main room is lined with booths suited for intimate date nights, while the Mediterranean-leaning menu is built for big groups with various skewers and shareable mezze plates. But we might love Checker Hall most for its late-night scene, especially when the attached music venue lets out, and the pentagon-shaped bar is suddenly wall-to-wall with people drinking excellent cocktails—the tequila and jalapeno-heavy Carmen #6 is one of the best spicy margaritas in the city—and looking for an afterparty.