Slideshow SLIDESHOW: Chicago Drinking Guide: The Best Spots for Cocktails Right Now

Where to drink cocktails in Chicago. [Photographs: Emma Janzen]

Looking at the pedigree of Chicago's newest craft cocktail bars is like playing a quick game of Six Degrees of Separation. Many of the new school bars are helmed by alumni of the city's original classics, like the Drawing Room, Violet Hour, and Sable. So what happens when these well-trained bartenders leave the nest to open their own places? A few interesting evolutions...and a few awesome places to get a drink.

Because these bar owners spent years training in the best establishments in town, you won't be surprised to hear that cocktail quality is high and balance and innovation stand at the forefront of recipe creation. But bar atmosphere is also beginning to shift—gone are the suspenders, pocket squares, and stiff attitudes. Chicago's new class of bar owners (and bartenders) wants you to feel relaxed when you pull up a stool. A new sense of saucy irreverence is at play—cocktails on tap, in bottles, and dance nights with shots of Old Fashioneds are all fair game.

Sure, some of Chicago's best bars do take themselves pretty seriously, but the drinks are so delicious that we'd still put them on the must-visit list. Here's our guide to where to drink great cocktails in Chicago—10 bars that will make sure your night out on the town is anything but dull.

Punch House

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At Punch House, the coasters reveal the Pilsen establishment's liquid theme, reading, 'strong, weak, bitter, sour, sweet'—the five necessary components of making a proper punch. The subterranean bar (from the team behind Longman & Eagle) anchors Thalia Hall, which also boasts a soon-to-be-open performance venue of the same name and Dusek's Board and Beer (a beer bar and restaurant with food from Michelin starred chef Jared Wentworth).

Straying from the trendy Edison-bulb chic of many craft cocktail joints, Punch House feels more like a swinging 1970s party in your parents' basement than a vintage speakeasy. Wood-paneled walls adorned with vintage fish mounts, shelving units lined with an assortment of kitschy knickknacks, and an impressive back bar fish tank casting a cool blue hue on patrons sets a nostalgic but jovial tone for the main feature: the punches. The menu features a rotating list of 8 house punches served by the glass, carafe, or bowl, and a quartet of "not punch" options, including a Punch House Negroni with Swedish punsch and the Jamaican Old Fashioned with Appleton X/V rum and allspice dram.

Punch House: 1227 W. 18th Street, Chicago, IL 60608 (map) 312-526-3851; punchhousechicago.com

Celeste

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Located in River North, the building that houses Celeste was originally built as a glass factory in the late 1800s by architect Louis Sullivan. The entry-level bar spans one side of the long, narrow first floor space, which drips with moments of black, silver and oak, evoking the night sky. Upstairs, guests transcend into a gold and beige-hued "Deco Room," inspired by the glamorous 1920s. (An additional third floor concept is rumored to still be in the works, as is a rooftop terrace).

Each floor offers its own beverage program, helmed by former Sable bartender Fred Sarkis and former Carriage House bartender Sterling Field. The entry level space features fun drinks like the Strawberry Sour made with your choice of rum, bourbon or gin, plus an assortment of cocktails in single-serving bottles or on draft (all $10). Above, in the supper club-like Deco Room, an exceptional food menu and substantial drink menu are notably more upscale and luxurious ($13 for most drinks). The best part? Celeste is one of downtown's best late night options, open until 4 a.m. on weeknights and 5 a.m. on Saturdays.

Celeste: 111 W. Hubbard Street, Chicago, IL 60654 (map) 312-828-9000; celestechicago.com

Lone Wolf

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Randolph Street's Lone Wolf might be an ideal spot for pre- or post-dining at the nearby Girl and Goat or Au Cheval, but the convivial neighborhood bar is so welcoming, it also stands as a destination in itself. The latest project from the team behind Bangers & Lace and the Revel Room, the modern, minimalist European-style pub appeals to various crowds and age groups, with craft beer as the main liquid focus. Yet the small but inventive selection of low-alcohol cocktails is equally appealing.

The cocktail menu is split into two sections: the first features a trio of Sgroppinos, pre-dinner refreshers that pair sorbet and sparkling wine. The second focuses on digestif cocktails, which largely center on Italian Amari and other bitters. While both work before or after dinner, skip the evening crowds and visit on a relaxed weekend afternoon, when it's easy to snag a seat in one of the oversized leather banquettes and while away the hours listening to one of the bar's upbeat indie rock playlists with a few low-ABV beverages. A spritzy Sgroppino makes for a great brunch cocktail, especially when paired with any of the English-inspired savory pies and bar snacks brought in from Pleasant House Bakery.

Lone Wolf: 806 W. Randolph Street, Chicago, IL 60607 (map) 312-600-9391; lonewolftavern.com

Analogue

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Violet Hour alumni Henry Prendergast and Robert Haynes opened this new Logan Square spot, where the vibes and intentions are a far departure from their former bar's exclusive scheme. You won't find vintage decor or much in the way of theatrics at Analogue, which aims to attract a younger, more relaxed crowd that's looking to drink well without the hefty price tag (cocktails are only $10, and classic cocktail shots land at $5). The decor is minimal, and includes a late night dance floor and elevated DJ booth to further encourage fun over pretense.

Analogue's menu is divided into three main sections: a modest list of serious, well-crafted cocktails are listed alongside more tongue-in-cheek concepts like the classic-cocktails-in-shot-form, and a rotating selection of hyper-bitter Purls (drinks made with bitter tinctures and beer). An equally as short but thoughtful selection of beer served from the tap, bottle, or can appeals to those not inclined to drink hard spirits. After a few Old Fashioned shots, the desire to throw caution to the wind and hit the dance floor is strong, and luckily, at Analogue, such audacity is encouraged.

Analogue: 2523 N. Milwaukee Avenue, Chicago, IL 60647 (map) 773-904-8567; analoguechicago.com

Revel Room

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An Old Style beer sign marks the entrance to Wicker Park's Revel Room, revealing one of the many features of the casual but hip neighborhood bar. Owned by the team behind Bangers & Lace and Trencherman, Revel Room stocks a wide range of canned beer and a range of drafts (and yes, you can find Old Style under the "value" section for $4). They also mix up a set of seasonal creative cocktails (two of which are always on tap), devised by barkeep Ronnie Higgins, formerly of Bangers & Lace and Bar DeVille.

The decor is understated, with an attractively disheveled back bar and sporadic vintage touches donning the walls, yet the attitude isn't pretentious. The atmosphere is animated on the weekends, and chill on weeknights, with oversized cherry leather booths providing cozy alcoves for guests along one wall, and a Silver Fox den towards the back of the space inviting hushed conversation. Despite their studied ability to mix up top-notch cocktails, the bartenders always seem downright relaxed, even into the late hours on weekends when the bar is jam packed with a fervent crowd.

Revel Room: 1566 N. Milwaukee Avenue, Chicago, IL 60622 (map) 773-278-1600; revelroom.com

Billy Sunday

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History certainly has its place at Billy Sunday, but that doesn't mean it's used as a strict rule book. The petite Logan Square bar, ironically named after the famous baseball-playing Temperance proponent, looks to the turn of the century for inspiration for many things—the decor, with moulded ceilings and vintage photographs; the cocktail list, which often plays home to a few classic cocktails; and the spirit collection, featuring hundreds of vintage and hard-to-find amari.

Yet unlike other modern craft cocktail bars, the staff often turns cliched tropes on their heads—you might find a classic cocktail or two on the menu, like a Bijou or Daiquiri, but they often come with bitter twists of amaro; the "Tonic" section features house-made tonic waters built from the ground up; and other concoctions include the goat's milk-based Box Lunch that tastes like oatmeal cookies, and a series of quirky "booze sodas," served in bottles. Innovation is sacred behind the bar, and not many other places can claim they do it as well as Billy Sunday.

Billy Sunday: 3143 W. Logan Boulevard, Chicago, IL 60647 (map) 773-661-2485; billy-sunday.com

The Berkshire Room

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Some of the best hotel bars are the ones that eclipse the traveling crowd and draw in a set of locals on a regular basis. The Berkshire Room, situated in the lobby of the Acme Hotel downtown, is so idiosyncratic and detailed, it's easy to forget that the craft cocktail lounge anchors a boutique hotel. The space is broken into several areas: the main bar is flanked by two dimly lit alcoves littered with quirky touches like metal cages containing old dusty bottles and a variety of Edison-bulbed light fixtures. Glass partitions create (slightly awkward) extra seating arrangements in the center of the room, which was the hotel's original lobby, for nights when the bar is bustling and seats are hard to come by.

Benjamin Schiller from the Boka Group (Girl and Goat, G&T Fish & Oyster) mans the beverage program at the simultaneously ritzy yet casual bar. Modern cocktails make up the bulk of the menu, with a special section for "dealer's choice," structured into an easy-to-navigate system of base spirit, flavor profile, and glassware. Just like your regular game of cocktail roulette, the bartenders invent new drinks for customers on the spot, which is certainly a gamble, but rest assured that any of the bar staff would be happy to replace a failed experiment should the odds not turn out in your favor.

The Berkshire Room: 15 E. Ohio Street, Chicago, IL 60611 (map) 312-894-0800; theberkshireroom.com

Three Dots and a Dash

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Tiki torches aren't a common sight in Chicago alleyways, unless they mark the entrance to tiki bar Three Dots and a Dash. These flaming markers of the tropics are just the first hint at what lurks behind the unmarked door behind popular barbecue bar Bub City. Guests must pass under a wall of skulls before entering the jungle-like basement bar, erasing any memory of the cold city streets outside the walls, and setting the stage for the "dangerously delicious" drinks to come.

Under the eagle eye of Paul McGee (formerly of The Whistler), the cocktail menu is split between classic tiki drinks and new concoctions, all overflowing with various styles of rum and fresh juice. Fanciful custom tiki mugs and elaborate garnishes express whimsy and a sense of playfulness, but don't be fooled—the drinks all pack a serious punch. If you're not already opting for one of the shared bowls, keep an eye out for cocktails on the menu marked with little skulls—they are "drinks of impressive strength."

Three Dots and a Dash: 435 N. Clark Street, Chicago, IL 60654 (map) 312-610-4220; threedotschicago.com

Longman and Eagle

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The slogan pasted on the windows on Longman and Eagle—eat, drink, sleep, whiskey—isn't just a clever way of promoting the bar's spirited focus. While they house an impressive whiskey selection, this Logan Square spot also serves as a Michelin-starred restaurant and boutique hotel (if you can call 6 rooms a hotel, that is).

Longman and Eagle set the standard for cocktails in the area when they opened back in 2010, and they continue to be a must-visit spot. The welcoming space is dark and cozy at night, but best frequented during the slower off-hours, like a chilly Sunday afternoon when the curvaceous bar buzzes with patrons without turning into a standing room only situation. Come for a whiskey flight selected from their vast collection (150+), and stay for a cocktail or two—they are some of the most thoughtfully concocted in town.

Longman and Eagle: 2657 N Kedzie Avenue, Chicago, IL 60647 (map) 773-276-7110; longmanandeagle.com

Barrelhouse Flat

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Barrelhouse Flat is a little over a year old, but the cocktail tavern feels like it's been part of the fabric of the Lincoln Park neighborhood for much longer. Maybe it's because owner Stephen Cole learned the tricks of the trade at Wicker Park staple the Violet Hour, so the drinks program already feels storied. Or perhaps it's because the space is simply cordial and convenient; glowing globe lights cast a soft glow on patrons, and snug booths provide the opportunity for confidential conversation in the quietly lit corner bar.

While the decor emphasizes an understated, accessible vintage vibe, the cocktail menu boasts complex concoctions that stir intrigue. Between the extensive list of classic cocktails and second menu featuring adventurous house creations and eccentric seasonal cocktails, combing through the options can be time-consuming. The process of reading through drink ingredients and trying to figure out how the sometimes outlandish flavor combinations will mix can prove to be an even harder task. Does bourbon work in the same cocktail as gin and amaro? Will absinthe and tonic water complement sherry and lemon juice? Surprisingly, most of the time the answer at Barrelhouse is yes—more often than not, their creative staff manage to bring together seemingly conflicting flavors together in tranquility—so seamlessly so, in fact, it feels as though they've been doing it for years.

Barrelhouse Flat: 2624 N Lincoln Avenue, Chicago, IL 60614 (map) 773-857-0421; barrelhouseflat.com

Curious about what to order at each of these bars? Head over to the slideshow for our cocktail picks.

About the author: Emma Janzen is a Chicago-based editor who moonlights as a cocktail, spirits and beer writer. You can find her tweeting in the twittersphere or blogging at her personal website when she isn't writing and editing stories about design and music during the day.

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