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Thrillist ChicagoNothing gives you a sense for a neighborhood's needs like being a drug dealer living in it, which is exactly how the longtime Old Town resident/dining industry vet behind Flight 1551 knew his 'hood needed a quaint wine bar with rippled white walls, coffee-colored tables, and a 15-seat semi-circular oak bar you'll never want to leave.
The D.O.C.-vet sommelier presides over a 225-strong global wine program whose emphasis is on small producers and esoteric vintages, with 51 glass pours including 24 on tap, so expect Kiefer Sutherland to jump out late-night and start shouting "There's not enough time!!!". Naturally there're wine & cheese flights, but the kitchen -- helmed by a former Fountainhead chef -- is kicking out vino-friendly trios as well, from burgers (beef w/ cheddar & onion marmalade; lamb w/ curry creme & arugula; salmon w/ caper aioli & frisee) to grilled cheese, which counts aged cheddar & roasted tomato, brie & lemon confit, and Manchego & fig jam (clearly made at a Farmhouse).
Independent foodage comes in the form of stone oven-fired 'zas, including a blanco topped w/ smoked pork belly, pine nuts, and a fried egg, plus small-plate snackery from blue cheese-and-chorizo-stuffed, bacon-wrapped dates w/ Sriracha cream, to mussels swimming in cilantro-sunflower pesto, andouille, and Sauvignon Blanc, because nothing really gives you a sense for a neighborhood's needs like listening to the rants of its wine-filled citizens.