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Speakeasy Chicago Style: The Best Underground Bars in Chi-town

Dim lights, Sinatra, and prohibition-era cocktails coming right up.

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Chicago is a wine and dine town, to be sure, but their Michelin-starred dining options and foodie hotspots distract travelers so much so that they forget one crucial truth: it’s a cocktail town, too. And Chicago’s best neighborhoods—from Old Town to Logan Square to the West Loop and Wicker Park—are home to cozy pubs, tucked-away bars, and hidden speakeasies.

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For the best speakeasy in Chicago, look no further—we’ve rounded up our seven favorites.

The Violet Hour, Wicker Park

The bar program at The Violet Hour has James Beard award under its belt. Blink and you’ll miss the entryway to this Wicker Park hotspot: “The Violet Hour’s exterior facade features an ever-changing mural with a discrete single entryway,” says their website. Once you’ve identified the mural and passed through the door, three intimate rooms, candlelight, and a majestic marble bar greet you. And that’s when your evening begins. The cocktail program at The Violet Hour continuously rotates to blend in-season flavors with often lesser-known spirits. With your cocktails—actually served in a pre-prohibition style—sample their lighter fare, which puts most bar food to shame.

Milk Room, The Loop

Unexpectedly housed in the Chicago Athletic Association, the Milk Room serves rare cocktails and rare spirits under low light. The Chicago Athletic Association actually has four bars—Cindy’s, Cherry Circle Room, Game Room, and Milk Room. Milk Room is the smallest and most sought after. Enter through sliding stained glass doors where you’ll find only eight seats. Make an hour or a two-hour reservation, and prepare to be amazed by their selection of high-end rarely seen whiskies, vintage liqueurs, and of course, small bites that cater to an elevated palette (think: caviar and foie gras).

Booze Box, West Loop

If you didn’t go to the basement of a West Loop Japanese restaurant, did you even go to a speakeasy Chicago style? Booze Box is in the basement of sushiDOKKU, and offers a relaxed atmosphere in a darkened room with light Japanese-style bites (the perks of having a full restaurant upstairs). Their cocktails aren’t messing around, and adopt a distinct Japanese flair. In addition to their Japanese whisky selection, Booze Box has an entire sake cocktail list, and a variety of “Japanese-inspired cocktails,” like their Atari Tochi with “Hennessy VSOP, Sweet Vermouth, Peach Nectar, Cranberry Juice, Peychaud’s Bitters,” and the Lychee Club with “Roku Gin, St. George Raspberry, Lychee, Lemon, Egg White.”

Room 13, Lakeview

Nestled in the Old Chicago Inn, Room 13 is the classic prohibition-style speakeasy. The decor is low-key to mirror the prohibition backroom aesthetic, but there’s a dress code and reservations are required. Be ready for a long conversation with the bartender to hone in on your cocktail tastes before choosing a beverage, here. It’s all about mixing cocktails with high-end ingredients and finding the right libation for your palette. Guests of Old Chicago Inn can even add a Room 13 cocktail flight to their reservation where the resident bartender will customize a boozy array of mixed drinks to suit your tastes.

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The Office at The Aviary, West Loop

When was the last time you saw Inception, where Leo DiCaprio and Ellen Page visit a dream within a dream within a dream? This is a similar concept; it’s a bar within a bar within a restaurant. The hottest restaurant in Chicago is, hands down, Alinea, by Grant Achatz and Nick Kokonas—and connected to Alinea is The Aviary, a bar serving revelatory cocktails with upscale ingredients. In The Aviary’s basement, you’ll find The Office, an invitation-only speakeasy of Chicago. The Office is intimate and exceptionally chic, focusing on a cocktail program blending vintage, hard-to-find spirits with unexpected ingredients. Pro tip: instead of ordering off the menu, ask the bartender for their dealer’s choice cocktail.

The Library at Gilt Bar, River North

Gilt Bar is one of the spaces you walk into and instantly feel like you’re in the right place—it’s something about the warmth radiating off candlelight and the sparkling chandelier that makes this upscale bar feel simultaneously inviting and chic. For speakeasy Chicago vibes within Gilt Bar, head for The Library—it’s another Inception-esque bar within a bar moment. Downstairs from Gilt Bar, The Library has walls lined with old books and classically red velvet mid-century couches. The cocktail program is focused on serving the best version of classic cocktails, and the entire Gilt Bar menu is available downstairs, too.

The Ladies Room, Logan Square

If you've ever been to The Garret in the West Village, where you enter through a Five Guys, you're no stranger to the concept of walking through an entirely unrelated business to end up inside a little cocktail club. Well, to find The Ladies Room, you'll walk through Super Fat Rice Mart (previously Fat Rice Bakery) and voilà, you've made it to this Chicago speakeasy, a favorite amongst locals. The Ladies Room is known for their house made spirits and infusions, quintessential red lighting, and altogether memorable decor.

Punch House, Lower West Side

Dusek’s Board & Beer is a farm-to-table-type restaurant, certainly worth reserving for one of your meals while in Chi-town. Dusek’s is actually a three-story restored community hall, and within these walls, you’ll find three separate concepts. On the top floor, Thalia Hall is now a live music venue—a nod to the building’s musical roots. Below that, Dusek’s Board & Beer, a perfect dinner spot beloved by locals and out-of-town visitors. And on the lower level, you’ll find Punch House, with 70s-esque decor and an extensive punch menu. This might not come as a surprise, but the punches are flavorful and rather potent—so evenings get a little spirited down at Punch House.


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