Big Star What compelled a James Beard Award–winning chef and the owners of the city’s most exclusive cocktail lounge to open a divey bar that slings Tecates and whiskey shots for $3 apiece? A stroke of absolute genius. Brutal crowds harsh the country-music mellow on weekends, but neighborhood hipsters put up with it, dropping by the takeout window to grab a couple of tacos or planting themselves at the bar for a few beers or quality cocktails. 1531 N Damen Ave (773-235-4039). El: Blue to Damen. Bus: 50, 56, 72. Lunch, dinner. Average taco: $3.
D’Noche In the glow of flickering candles, a vibrant crowd throws back fresh fruit cocktails and nibbles on shrimp coctel in citrusy tomato juice. This is the upscale dinner sibling to the adjacent Café con Leche, and while the classic Latin sandwiches like the Cuban and the jibarito are as good as they are next door, hearty entrées (tender pork chops given an al pastor makeover) are the real draw. Except on Wednesdays, that is—then the draw is the $5 margaritas. 2710 N Milwaukee Ave (773-289-4724). El: Blue to Logan Square. Bus: 56, 76, 82. Dinner. Average main course: $13.
Mercadito After opening three NYC locations, this late-night taco-and-tequila parlor entered the Chicago market. The tacos are original—carnitas tacos come with cool coleslaw and rich peanuts; crispy estilo Baja tacos come with an aioli spicy enough to make you sweat—but it’s the lengthy tequila list you’ll linger over. 108 W Kinzie St (312-329-9555, ). El: Brown, Purple (rush hrs) to Merchandise Mart; Red to Grand; Blue, Green, Pink, Orange to Clark/Lake. Bus: 11, 22, 156. Brunch (Sat, Sun), lunch (Mon–Fri), dinner. Average main course $15.
¡Salpicón! This swanky Mexican spot is known for perfect margaritas and chef Priscila Satkoff’s traditional salsas, queso fundido and earthy mole served with handmade tortillas. A weekly specials menu highlights seasonal ingredients, but you can pretty much always count on the trio of small tamales, the lamb chops in garlic-pasilla chili sauce and one of the best tequila selections in town. 1252 N Wells St (312-988-7811, ). El: Red to Clark/Division. Bus: 11, 22, 36, 70, 156. Brunch (Sun), dinner. Average main course: $24.
Twisted Lizard Nothing’s better than kickin’ back at this spot with a potent pitcher of margaritas and baskets of thick chips and homemade salsa. If it weren’t for the big, fat Starbucks sign next door, you might even think you were in a roadside cantina in the Mexican outback. Though, come to think of it, after a few too many of those margaritas, that adjacent coffee chain might come in handy. 1964 N Sheffield Ave (773-929-1414). El: Brown, Purple (rush hrs) to Armitage. Bus: 8, 73. Sun–Thu 11am–10pm; Fri, Sat 11am–midnight. Average cocktail: $6.
Zocalo There’s a lot to choose from on the menu at this after-work spot, which owners Edgar and Marcos Castañeda very much want to be different from their family’s chain of Mexican restaurants, Lalo’s. Make a meal out of starters like a trio of sprightly ceviches; a duo of tamales, one stuffed with fiery strips of jalapeño; and fish tacos that join grilled tilapia with crunchy pickled onions. Or just drink your dinner with selections off the lengthy tequila list. 358 W Ontario St (312-302-9977). El: Brown, Purple (rush hrs) to Chicago. Bus: 11, 33, 65, 66, 125. Lunch (Mon–Fri), dinner. Average main course: $17.