Table, Donkey and Stick

If you’re game to try the Brooklyn booze trend dubbed the pickleback—a shot of whiskey chased with pickle brine—order one at this Alpine-inspired bar/restaurant with an inviting back patio (enclosed and hearth-heated during winter). Bartenders pair bourbon with rotating brines (cauliflower, onion, leek) for kicky 20-and 30-somethings, whose faces often contort at the chaser’s odd but booze-free aftertaste. Logan Square, 2728 W. Armitage Ave., tabledonkeystick.com

The Dawson

This bar’s after-work set revels in the Chile-Choke, a sweet and spicy shot of chili liqueur and Cynar amaro that leaves a stirring, peppery burn. For something less fiery, opt for the Daily Drip, a shot of bourbon filtered through rotating compost in a cold-brew tea tower. West Town, 730 W. Grand Ave., the-dawson.com

Sportsman’s Club

The icy herbal liqueur swirling in this cozy tavern’s amaro machine (known as Amaro Stoudemire) may conjure mint leaves, sassafras, or licorice—barkeeps Wade McElroy and Jeff Donahue tweak the blend daily. One constant? An extra buck gets you a Miller High Life (the Lowlife), effectively everything you need to blend in with the bar’s grungy art-school crowd. Humboldt Park, 948 N. Western Ave., drinkingandgathering.com