Chilam Balam Chuy Valencia’s brightly hued Mexican restaurant is not the least bit serious—it’s more underground dinner party than fine dining. Except you’d be hard pressed to go to a dinner party with food like this: Memelas—masa tarts—are filled with smoky black-bean puree and goat cheese; hunks of halibut make for a rustic ceviche; and hanger steak comes out with a brilliant guajillo-chile sauce. It’s food that conveys the energy of its young chef but is executed with the craft of someone twice that age. 3023 N Broadway (773-296-6901). El: Brown, Purple (rush hrs), Red to Belmont. Bus: 22, 36, 77, 156. Dinner (closed Tue). Average main course: $13.
Curio Head to the subterranean restrooms of Gilt Bar and you’ll stumble upon a candlelit room, decked out with Prohibition-era pieces such as a rickety antique phonograph. This is the restaurant’s riff on a speakeasy, where you’ll find carefully crafted cocktails like the amarena cherry–garnished Martinez and the smoky-spicy Mezcal Mule. The cocktails are worth the modern-day price tag ($12)—even if you have to interrupt the time warp by hitting the hallway ATM to follow cash-only rules. 230 W Kinzie St (312-464-9544). El: Brown, Purple (rush hrs) to Merchandise Mart. Bus: 65, 125, 156. Thu–Sat 8pm–2am. Average cocktail: $12.
Di Sotto Enoteca Old World wine list and Mediterranean small plates: Scott Harris has nailed the formula at Purple Pig and Davanti Enoteca, so why mess with a good thing? Admittedly, the scales at DiSotto (in the cellarlike basement of Francesca’s on Chestnut) tip toward drinking—the food is limited to antipasti, bruschette, cheeses and salumi. But when you’re spreading thick ricotta and fragments of honeycomb on toasted bread, sampling warm, marinated olives or indulging in the toast with a truffled egg yolk at its center, the appeal of this wine bar can’t help but feel unending. 200 E Chestnut St (312-482-8727). El: Red to Chicago. Bus: 66, 125, 157. Sun–Thu 5pm–1am; Fri 5pm–2am; Sat 5pm–3am. Average glass of wine: $9.
Double A Tiny, exclusive and saunalike (windowless, with banquettes lining the walls), the tequila lounge beneath Mercadito is the kind of place you really want to get into and will never want to get out of. Spicy, strong concoctions are designed by NYC cocktail consultants the Tippling Bros. and executed in front of (rather than behind) the bar. 108 W Kinzie St, lower level (312-329-2444). El: Brown, Purple (rush hrs) to Merchandise Mart; Red to Grand; Blue, Green, Pink, Orange to Clark/Lake. Bus: 11, 22, 156. Tue–Fri 6pm–2am; Sat 6pm–3am (closed Sun, Mon). Average cocktail: $14.
The Drawing Room Chef Nick Lacasse might be cooking for patrons with clubbing on their minds, but he’s keeping them well fed with contemporary, seasonal dishes like braised radishes with wild-boar pastrami. Mixologist Charles Joly and his team adjust their impressive “culinary cocktail” menu accordingly, ensuring that everything on your table is as au courant as the Gold Coast regulars. 937 N Rush St (312-255-0022). El: Red to Chicago. Bus: 10, 36, 143, 144, 145, 146, 147, 151. Dinner (Tue–Sat). Average small plate: $12.
Half Shell “We close when we feel like closing” and “Nothin’ but cash, no exceptions” are among the oh-so-perfect-for-the-setting sayings overheard one night at this 40-year-old subterranean spot. Grab a table in the tiny, Christmas light–strewn room, and start out with the “Mulligan stew” and an order of crispy calamari. For more fried goodness, have the “Thirty-Two Pointer” for an entrée—a crunchy pile of smelts, perch, frog legs, clam strips and fat shrimp. And if you’re looking to crack some crab, splurge on the meaty king legs. 676 W Diversey Pkwy (773-549-1773). El: Brown, Purple (rush hrs) to Diversey. Bus: 18, 22, 36, 76. Lunch, dinner. Average main course: $15.