Price Point: $14 for The Cuban
Like so many great sandwiches, a textbook Cuban aims to accomplish two very contradictory things at the same time. Loaded with roast pork, ham, and Swiss cheese, a Cuban must feel meaty and substantial—but it also needs to stay fairly thin. Pile on too much roast pork and ham, or use bread that’s too thick, and no amount of mustard or pickles can save it from dryness. Skimp on the fillings, and you’re left with what looks like a sad-looking panini. (If you couldn’t tell, the Cuban and I have a fraught relationship.)
Happily, the recently opened Oak + Char (217 W. Huron St., 312-643-2427, oakandchar.com) in River North joins the club, even if the kitchen takes a few liberties with the formula. While “prosciutto cotto” is simply Italian for boiled ham, the kitchen serves a tender and fatty braised pork collar instead of regular roast pork (a definite plus). While you’ll never get tipsy off the house bourbon pickles, they are crunchy and acidic, making for a nice pairing with the mustard. But the bread really makes this sandwich. Both crisp and very thin, it allows you to appreciate the feast, while containing the chaos.