Cocktail Bars in Chicago

The Barrelhouse Flat

20s / Artsy Dresses / Blouses / TVs

Party Earth Review Helmed by a former bartender from The Violet Hour and a GM whose previous ventures include The Aviary, The Barrelhouse Flat is a temple to craft cocktails located in an area better known for rowdy packs of college kids. The first floor has a saloon feel, with weathered exposed brick and a vintage jukebox that plays this ... more

2624 North Lincoln Avenue
Chicago, IL 60614

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Longman & Eagle

Artsy / Artsy / Artsy Dresses

Party Earth Review Its motto is “Eat, Sleep, Whiskey,” which pretty much sums up the hipster and foodie paradise – and Michelin star-rated restaurant – that is Longman & Eagle. Unlike venues that normally get Michelin’s approval, however, L&E is devoid of white tablecloths and crystal glasses; instead, the vibe is casual, the décor minimal ... more

2657 North Kedzie Avenue
Chicago, IL 60647

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Big Star

20s / ATM / Artsy / Blues / Cash Only

Party Earth Review Just a few steps from the lively Wicker Park intersection of North and Damen Avenues, a large black and red star shines over what looks like a former gas station – and that’s because it is. The funky exterior of Big Star, however, belies the lively and energetic vibe within, as loud honky-tonk music blares from the stereo ... more

1531 North Damen Avenue
Chicago, IL 60622

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The Whistler

20s / Acoustic / Blues / Couples / DJ

Party Earth Review Free nightly concerts and an intense but unpretentious dedication to mixology distinguish The Whistler, a small bar popular with a young crowd of hipsters, musicians, and connoisseurs of classic cocktails. Once patrons pass through the door hidden in the storefront façade – which doubles as a gallery featuring an ever-changing ... more

2421 North Milwaukee Avenue
Chicago, IL 60647

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Delilah's

Anything goes / Arcade Games

Party Earth Review With over four hundred types of whiskey, one hundred brands of beer, and a jam-packed roster of events every night of the week, Delilah’s keeps both the drinks and the DJ tracks flowing 365 days a year. Once past the image of the evil queen out front, the collection of goth kids, leather-clad bikers, and even a few local ... more

2771 North Lincoln Avenue
Chicago, IL 60614

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The Aviary

Affluent / Ambient / Blazers / Jazz

Party Earth Review Opened to much fanfare in mid-2011, The Aviary draws a mix of sophisticated patrons and dedicated foodies of all ages into an intricate cocktail realm; a place where the creations behind the bar showcase the same intense attention to detail as Owner/Chef Grant Achatz's world famous dishes. Known for his work ... more

955 West Fulton Market
Chicago, IL 60607

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Le Bar

30s / Absinthe / Ambient / Blazers

Party Earth Review Tucked inside the ultramodern Sofitel Hotel, Le Bar is a stylish and intimate lounge best known for its French fusion snacks, intricate cocktails, and assortment of gourmet cheeses. Early in the evening, upscale hotel guests and fashion-conscious couples sink into warm velvet chairs by a roaring fire to work their way through ... more

Sofitel Chicago Water Tower
20 East Chestnut Street
Chicago, IL 60611

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Chicago basically invented prohibition-era chicanery with a plethora of illegal speakeasies and hidden drinking dens popping up throughout the city in the 1920s. Today, those drinking traditions remain (although now legally) with a wide array of artisanal cocktail joints and mixology masters concocting new creations on a nightly basis.

There are so many great cocktail bars in Chicago that it can be hard to know where to start. Just know that no matter what neighborhood you’re in, chances are there’s a cocktail bar waiting for you.

One of the best Chicago cocktail bars is The Barrelhouse Flat in Lincoln Park. Here, an extensive list of cocktails as well as signature punches keep a diverse clientele boozed up in the most unique ways possible.

Three of Chicago’s finest whiskey bars are Longman & Eagle, Big Star, and Delilah’s. Longman’s motto is “Eat, Sleep, Whiskey” which is fitting since there’s Michelin star cuisine, perfectly crafted cocktails, and 6 guest rooms above the bar to sleep it all off in. Big Star, meanwhile, serves up out-of-this-world Mexican fare with their whiskey, whereas Delilah’s carries over 400 types of the brown stuff to mix and match in whichever way you want.

Prohibition is long gone and the art of drinking is in full force in Chicago. And while there are still crazy laws regarding happy hour, it’s easy to find one-of-a-kind cocktail bars to serve up artisanal libations any time of day and any day of the week.