Gayle's Great Sandwich Search

Borinquen, a Chicago neighborhood joint, is another one of Esquire's favorite picks. This small eatery is home to the jibarito—or "the Little Hillbilly."

This Windy City winner is inspired by chef Juan Figueroa's Puerto Rican roots. Juan nestles slow-cooked pork, mayo, lettuce and tomato between two slices of crispy, fried plantains.