14. The Irish Oak

City: Chicago
Address: 3511 North Clark St.
Website: irishoak.com

The Irish Oak, located in the Wrigleyville neighborhood of the Chi, is the perfect place to drown your sorrows after a Cubs loss. Nothing helps us get over a real heartbreaker better than a well-seasoned burger and a Guinness. Plenty of room, so bring everyone who feels like crying into their beers.