This Cake Is Full of Surprises
This industrial restaurant-slash-bar in Logan Square does pizza, beer, and general comfort food (fried cheese balls, poutine, mac & cheese) really really well. The pizza options are staggering: aside from simple cheese, pepperoni, and sausage pies, there are more than 15 specials and a build-your-own options. The Boiler Room's real claim to fame is its PB&J special: a slice of pizza, PBR tall boy, and a Jameson. There's plenty of communal tables and a great outdoor patio, and if you couldn't tell from the aforementioned PBR and whisky special, this place is a hipster destination.
Named for the temp difference between rare and well-done, this burger bar from the West Coast offers a robust selection of build-your-own add-ons (jalapeno bacon, burrata, tarragon remoulade), non-burgerness like bacon-wrapped, green chili 'n pinto bean'd Sonoran hot dogs, and boozy Guinness milkshakes.
Nashville comes to River North through the doors at Lettuce Entertain You’s Bub City, whose award-winning barbecue, 100-plus whiskey labels, and live music can make you forget about that deep Chicago chill. The all-American bar brings the heat from down South with dishes like barbecued brisket (get the burnt ends), fried chicken sandwiches (the Original 8 Buck Cluck is best served with a side of those aforementioned burnt ends), spoonbread, and baby back mac & cheese. To drink, you can sip on anything from a can of Bud to a pour of Pappy Van Winkle himself. Enjoy live country music multiple nights a week, and be prepared for a rowdy dance party.
The Jam House is run by a husband-and-wife duo who are making the world a jam-tastic (sorry, sort of) place by serving shaved ice with flavors like caramel, Kahlua, pineapple-chile, guanabana, and mamey. If shaved ice isn't your thing, milkshakes, fresh fruit salads, and tortas have your back.