The Resy Guide to the Best Cocktail Spots in Chicago

This gin-centric cocktail bar manages to exude both elegance and come-as-you-are ease, making it one of our favorite early-evening hangs. You’ll find cocktails that change with the seasons but always match the wryly chic vibe — like the Neptune with genever, falernum, orgeat, passion fruit and lemon. New this summer, a walled-in back patio is all dressed for a garden party in pretty white wicker and fringy white umbrellas.

For more than eight decades, this teeny cocktail bar perched on the hectic corner of Milwaukee, Ogden and Chicago Avenues has been slinging among the city’s best (and wallet-friendliest) cocktails — with sidecars! Headlined by a perfect lemon-lime margarita counterintuitively rimmed with powdered sugar (trust us), the tight list features a dozen-odd throwbacks done right, from daiquiris to cosmos to gimlets. The diminutive wedge-shaped interior remains closed for obvious reasons, but the partially covered patio more than doubles the Matchbox’s capacity.

This cheerful, family-owned Mexican spot offers all sorts of Jalisco-inspired bites, from colorful ceviches to hand-pressed tacos. But we may love the cocktails even more, owing to La Josie’s deep selection of agave spirits. Go bright and floral with the mezcal marg — with fruity Banhez mezcal, dry curacao, organic agave, and gusano salt rim — or botanical and quenching with El Guapo with mezcal, aloe liqueur, agave, grapefruit, lime, jalapeño, cucumber, and habanero salt.

Up the stairs at Mama Delia and behind a hidden door, this sumptuous, candlelit cocktail den and cabaret beckons with nightly live entertainment and sexy drinks to match. Time travel back to Montmartre during the last golden age of cocktails with a frothy Lost in Pearadise, with Scotch, spiced pear brandy, lemon, and demerara as you take in a burlesque show. Be warned: It’ll take you a minute to reorient yourself to present-day Wicker Park when you leave.

This handsome Midwestern tavern is the place to go for spirited, impeccably balanced tipples, like the Longman Manhattan with Wild Turkey, Punt e Mes, and aromatic bitters, and the Paper Plane with Evan Williams bourbon, amaro, Aperol, and lemon. You’ll want a snack with that boozy sipper; we’d suggest broiled oysters with crab butter and warmed smoked trout dip for starters. While it’s warm, take advantage of Longman’s serene sidewalk patio — set back on a tree-lined side street.

Choose from a lively subterranean cocktail den or an alleyway jungle oasis at this top-notch cocktail bar from Rick Bayless’s daughter Lanie Bayless. Here, Mexican medicinal herbs, condiments and chiles in every guise imaginable infuse the stellar cocktail lineup, like the Mango, Chamoy with Espolón blanco tequila, mango, spicy-tangy chamoy, lime, and a splash of Topo Chico. Unsurprisingly, you can’t go wrong with the food, from drinking snacks to ceviches to specialty tacos (ahem: carnitas taquitos ahogados in spicy tomato broth).

Owner and bartender Julia Momose helms this elegant cocktail bar steeped in Japanese influences. Cocktails run from light and supple — think the Matcha Cointreau, with shochu, cointreau, Oleo Saccharum, soda, and fresh matcha — to boozy and provocative, as in the Legent Manhattan with bourbon, umeshu (plum liqueur), Bénédictine, and two kinds of bitters. (Heads up: most sips will set you back $18 or more.) Pair with impeccable bites, from tempura nori to pristine sashimi and katsu sandos.

This tribute to Americanized Chinese fare from Team Giant has become one of our go-tos when we’re craving nostalgic crab rangoon and fiery dan dan noodles. But don’t sleep on the colorful, tropically tinged takes on classic cocktails. The gin-based Lemongrass Gimlet with shochu is a quenching partner to the spicy dishes. Or take a tiki direction with the Galaxy Whistle, a rich, sorta Zombie blending falernum, rums, absinthe, and genepy.

Named for the photography term for the out-of-focus look from a fast-moving lens, this moody, brick-walled cocktail den feels at once sultry and neighborhood-y. The cocktails — which shift seasonally — tend toward bold, herbaceous, and vegetal. The namesake Bokeh perfumes a classic egg white sour with fernet, and notes of citrus and cardamom; while the Still Life is a grassy, vegetal take on the martini featuring sotol and nopales.

Perched high above Michigan Ave at the Chicago Athletic Association hotel, this is the place you always want to bring out-of-town friends to show off our beautiful Lake Michigan — though Cindy’s also just so happens to serve killer cocktails. Case in point: the lush, funky Tierra Roja with single-blended Mexican rum, mezcal, passion fruit, and lime.

This cozy, taxidermy-filled watering hole is one of the coolest places in the city to drink. Classics done right include the lemony, honeyed Bee’s Knees and a deliciously no-nonsense old fashioned. Rotating specials include clever sips like the Haitian Daiquiri with funky rums, oloroso sherry, and lime. Out back a glorious patio awaits — roomy and stone-paved, complete with a fire pit and mobile bar beneath a canopy of twinkly lights.

This elegant, high-ceilinged bar pours seriously alluring cocktails, often pulling from local and house-made tinctures for inspiration — as in the gin-based Van Down by the River, with hibiscus, lime and Arbella peach tea sipping vinegar. Heads up, whiskey lovers: A Traveling Old Fashioned menu features global takes on this classic cocktail, like the Lagos, Nigeria with smoked, spiced ginger whiskey, habanero honey and elderflower liqueur. Check the site and socials often for weekly happy hour specials and DJ sets.