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We picked the 20 best cocktails in town—and lined them up from bitter (no. 1) to sweet (no. 20). Follow our list to quaffing heaven. For more, visit www.chicagomag.com/drinkersguide.
2537 N Kedzie Blvd (btwn Linden & Logan Sq.), Chicago, IL
Café · Logan Square · 257 tips and reviews
Chicago magazine: Must-try cocktail: 11 a.m. Sunday 54 E. 1st St. The most beautiful Bloody happens to be the most delicious—smoked oysters, caper brine, and all.
New American Restaurant · Lincoln Park · 104 tips and reviews
Chicago magazine: Must-try cocktail: Weston. This drink’s components read like a snapshot of its creator’s day off: Four Roses bourbon, strong coffee syrup, and pipe tobacco.
Chicago magazine: Must-try cocktail at the lounge: Dead Meadow. Named for the seminal stoner-rock band, this combination of bourbon and rye goes psychedelic with walnut bitters and apple whiskey.
2700 N Western Ave (at W Schubert Ave), Chicago, IL
Gastropub · Northwest Side · 147 tips and reviews
Chicago magazine: Must-try cocktail: Victorian Pimm's Cup. The best of three Pimm’s Cup variations at this bar, with pink peppercorn tincture and rose water.
18 S Michigan Ave (at E. Madison St.), Chicago, IL
French Restaurant · The Loop · 36 tips and reviews
Chicago magazine: Must-try cocktail: Henri Presse. "The classic sidecar subs Pineau des Charentes for cognac—with an unexpected wash of Old Overholt rye."
619 W Randolph St (at N Desplaines St.), Chicago, IL
New American Restaurant · West Loop · 127 tips and reviews
Chicago magazine: Must-try cocktail: Carlisle. An abstract tribute to the Manhattan, with a base of applejack and delicate bittersweet vermouth and finished with peach bitters.
Chicago magazine: Must-try cocktail: Cognac. Unfamiliar ingredients (tonka bean, quassia, smoked black pepper) delicately complement the queen of cordials.
New American Restaurant · Near North Side · 196 tips and reviews
Chicago magazine: Must-try cocktail: Transfinite Induction. A complicated blend of rum, apricot brandy, allspice dram, and bitters; pairs well with heady conversation.
840 W Randolph St (btwn Green St & Peoria St), Chicago, IL
French Restaurant · Fulton Market · 104 tips and reviews
Chicago magazine: Must-try cocktail: St.-Germaine Fizz. Death’s Door vodka, Aperol, and everyone’s favorite elderflower liqueur combine for a divine blend of bittersweet.
3659 W Armitage Ave (btwn N Monticello Ave & N Lawndale Ave), Chicago, IL
Cocktail Bar · Logan Square · 24 tips and reviews
Chicago magazine: Must-try cocktail: Wood-Burning Stove. As cozy as it sounds: New Holland amber rum, Koval ginger liqueur, and almond syrup, sprinkled with nutmeg.