Guide

20 Great Chicago Cocktail Bars

by Fernanda DeSouza

posted on September 13, 2017

Photo Courtesy: Heavy Feather

Did your grandpa have a cocktail every day when he got home from work? We're into his aesthetic, but acknowledge that there are people who know lots more about making drinks than we do. Leave yourself in good hands at any of these Chicago hotspots. From modern tiki creations to reliable classics to boozy experiments in molecular gastronomy, the Chicago bar scene has something for everyone. Check out our guide to get a primer on the best spots to get drunk deliciously.

Queen Mary Tavern

Decked out with mermaid accents and low lighting, this maritime-styled bar focuses on cocktails, fortified wines, and a simple selection of eats for anyone looking to come aboard. Nosh on oysters and splurge on Soft Shock--a punch worth sharing.

Checkout: Soft Shock, Rare Wine Company 'Boston' Bual Madeira, baked oysters

Sportsman’s Club

Chill out with taxidermied decor at this unpretentious, faux old man bar that serves classic spirits, craft beer and wine from behind an Art Deco bar. There are table games to pass the time and linger-worthy patio seating when weather allows.

Checkout: High Life, craft beers and a rotating selection of cocktails, like the Amaro Machine

Deadbolt

At Deadbolt, a hip, casual crowd sips craft cocktails and soaks them up with Chicago hot dogs and hand-breaded chicken nuggets. Get caught up in the party vibe: with live DJs, moody lighting and a good dose of irreverence, you won't want to leave.

Checkout: Chicago style hot dog, burger and chicken nuggets or ramen from sibling Furious Spoon next door

Estereo

You can hang out at this stylish, light-filled corner bar all day: the spot serves as a cafe with Dark Matter coffee by day, and a bar with Latin-inspired cocktails (like the Agricole with coconut, passionfruit, and absinthe) by night.

Checkout: Agricole, coffee, beer cocktails

The Whistler

This bar offers carefully crafted, one-of-a-kind cocktails (think pisco with purple corn and pineapple) served at an L-shaped bar or sipped on the back patio. There's also pop-up art exhibitions and live music (usually jazz or a DJ set) every night.

Checkout: Girl from Ipanema, Ghostwood, Cold Kiss

The Heavy Feather

Idealizing the "fern bar" concept of the '70s, this drink spot features a compact menu of classic and tropical cocktails in cozy digs. Wood and gold accents feature prominently, and a seat next to the fireplace will warm your spirits--literally.

Checkout: Lavern and Sherry, Pisco Inferno, Mudslide

The Barrelhouse Flat

Classic and innovative cocktails abound on the menu at this classically-designed bar outfitted with wooden accents and mood lighting. Order a Sazerac or a Hanky Panky and pull out the chessboard while noshing on truffle popcorn or poutine.

Checkout: Jimmie Roosevelt, Singapore sling, poutine

Hopleaf

This Belgian-inspired 21-and-older spot is the definition of a gastropub. They boast 68 taps. They serve confit chicken wings and a fancy take on pb&j. The industrial, tin-ceilinged space is often packed and the energy's high. Make a night of it.

Checkout: PEI mussels with frites and aioli, duck reuben with cranberry cream cheese spread

Broken Shaker

Eclectic ingredients (like watermelon radish or roasted grapes) are just a glimpse of what goes into the craft cocktails here. Candles and mismatched lamps dot the intimate space, so find your nook and order the renowned, off-the-menu Cocoa Puff.

Checkout: Cocoa Puff, Old Man's Money, Nightmare on Sesame Street

Lost Lake

Party like it’s 1950 with fruity rum cocktails at Lost Lake Tiki Bar. The teak interior might feel kitschy, but the staff is serious about their drinks and has received many awards since opening two years ago. It's no wonder they're always busy.

Checkout: Lost Lake, Tic-Tac-Taxi, Some Days Last a Long Time, Daily Daiquiri, Fogcutter (to share)

Scofflaw

With Victorian settees lining the exposed brick walls, this gin bar has a perfect atmosphere to complement its craft cocktail list, which does include options for the truly gin-averse. Stick around until midnight for a warm chocolate chip cookie.

Checkout: Velero, Caledonia, Sutter's Mill

The Violet Hour

With lush curtains, high stools and bartenders in suspenders, The Violet Hour oozes speakeasy-era glamour. The cocktails, however, are modern with amaros, mezcal and housemade bitters. If you’re hungry, make a meal of focaccia and stuffed dates.

Checkout: Yellow Rose of Texas, Pajama boy, Goodnight Stan, Got Cha, Forlorn Road

Lone Wolf

Whether you're cramming friends into a leather booth or hanging at the bar, Lone Wolf offers fun drinks in a chill setting. Their selection of Old Fashioned twists is impressive, their beer list long and their savory pies are among Chicago’s best.

Checkout: Blanton’s Old Fashioned, Money Train, rotating draft beers, single Depression Dog, featured pie

The Matchbox

Head to this skinny, 460-square-foot tap with brick walls for an elbow-to-elbow experience with a cross-section of tipplers. Set in a vintage building, it's known for its classic cocktails and breezy vibe, which earn it a loyal, local following.

Checkout: Margarita, Cosmopolitan, Pineapple Gimlet and Lemon Drop Martini

Esco Bar

The spirit of Colombia is alive and well in this glamorous speakeasy, courtesy of table-side "cartel cocktail" service. Grab a drink and get ready to conga, thanks to the live music and DJs in low-lit surroundings.

Checkout: Cipitio, Bombilla, Leyenda de Guatemala

Three Dots and a Dash

This glam space fuses LA chic with Polynesian comfort, serving up luau cuisine and tiki cocktails in outrageous glassware. A rum-heavy menu led by mixology master Julian Cox tempts locals and visitors alike with its focus on exotic spices.

Checkout: Kevin Beary's World Famous Third Place Mai Tai, Bluth's Frozen Banana Stand, The Big Kahuna Burger

Flamingo Rum Club

Grab a table on the main floor of this trendy, palm leaf-wallpapered Cuban rum bar with flamingo accents, fixing your gaze on burlesque shows on the lofted balcony. While you watch, enjoy cheekily named cocktails, lamb empanadas and ceviche.

Checkout: Lamb empanadas, Catch a Fire cocktail

Arbella

Grab a spot on a leather banquette in Arbella’s cozy brick room and escape with a travel-inspired cocktail. From perfect pisco sours to the Nagano mule made with Japanese whiskey, there’s a drink for every mood — save room for the taro tacos.

Checkout: Old School, Fraise d’Amour, Chilcano, cha gio, short rib bao, squash chips

The Aviary

Cocktails go modernist at Grant Archatz’s The Aviary, which feels more like a lab than a place to chat up the bartender. From bitters ice cubes to truffle-spiked Negronis, each drink awes. Book ahead for an equally astounding tasting menu.

Checkout: Barrel-Aged Martini, In The Rocks (Second Edition), Ford's Model Tea Party, 90 Miles From Mexico

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