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The Drifter
Photograph: Jaclyn Rivas The Drifter

The 21 best cocktail bars in Chicago

Pick your poison at the top cocktail bars in Chicago. Get ready for some tasty drinks to drink tonight.

By Morgan Olsen

This city isn't shy about its booze obsession—and we have the Chicago breweries and wine bars to prove it. But when you're searching for something stronger, hunker down at the best cocktail bars in Chicago, where some of the world's top bartenders shake, stir and pour excellent drinks with ease. Whether you're in the mood for a classic Manhattan or Negroni or you're hankering for an over-the-top tiki sipper with colorful bendy straws, the best cocktail bars in Chicago will take care of you. The list practically doubles when you factor in all of the amazing rooftop bars Chicago has to offer. Start making your way through the best cocktail bars in Chicago tonight.

RECOMMENDED: Discover more of the best bars in Chicago

Best of the city under one roof

Photograph: Jack X. Li

Secret Sound

Restaurants West Loop

We love the tropical cocktails at Lost Lake so much that we asked co-owners Shelby Allison and Paul McGee to open their own bar inside Time Out Market Chicago (which is why you won't find them on the list below). The hidden cocktail counter specializes in rum-soaked tipples that will transport you to a faraway island. After your first sip, you’ll understand exactly how McGee and Allison won the title of Best Cocktail Bar in America from the discerning Tales of the Cocktail as well as Bar of the Year at Time Out Chicago’s 2018 Bar Awards.

Time Out Market Bar, Chicago
Photograph: Jack Li

Time Out Market Bar

Bars West Loop

Chicago, we know you're thirsty, which is why we put a bar on every floor of the Market in addition to our secret speakeasy from Lost Lake co-owners. The editorially curated beverage program features inspired libations created by leading mixologists at Arbella, Best Intentions, Billy Sunday and Flora Fauna. Plus, beverage director Jonathan Kahn dreamed up a roster of sippers inspired by Chicago markets past and present, like the CH Vodka-based Green City Bazaar with carrot juice and turmeric-ginger-pineapple tea syrup. He rounds out the menu with top-rated wines and a selection of Chicago-made brews from the likes of Pipeworks, Cruz Blanca and Moody Tongue.

Best cocktail bars in Chicago

The Aviary
Photograph: Christian Seel

1. The Aviary

Bars Lounges West Loop

When Grant Achatz does a cocktail bar, it should go without saying that it's no ordinary cocktail bar. At the Aviary, which opened in 2011, cocktails receive the same innovative treatment from beverage director Micah Melton as the food at Next or Alinea. That is to say, you should expect to drink cocktails like the Junglebird, a science experiment in liquid density, with layers of rum, campari, pineapple-lime syrup and rum "pearls" suspended in the drink. O'Doyle Rules comes with a fried banana snack on top of the rum-curry-cognac concoction.

The Violet Hour
Photograph: Michael Robinson

2. The Violet Hour

Bars Cocktail bars Wicker Park

This sleek cocktail lounge is exactly what you’d expect from a bar named after a line of T.S. Eliot poetry: pristine (the carefully constructed cocktails are excellent), pretentious (you won’t find a sign on the door—just look for the long lines) and, ultimately, completely and unarguably gorgeous.


3. Scofflaw

Bars Lounges Logan Square

If gin is your liquor of choice, you've come to the right place. This swanky but understated cocktail bar specializes in the clear booze and offers a seasonally rotating lineup of beautiful gin sippers (which are all lovingly illustrated on the menu). The bar team doesn't discriminate: They also use tequila, rum, mezcal, sake and other spirits to craft their beverages.

Photograph: Jaclyn Rivas

4. The Ladies’ Room

Bars Cocktail bars Logan Square

If you're beginning to feel like you've seen everything Chicago's bar scene has to offer, head to the Ladies' Room to rediscover your senses. The tiny, red-lit space inside Fat Rice in Logan Square offers some of the most intricate, imaginative drinks we've ever encountered. One look at the global-inspired menu and you'll see why: The bar crafts many of its own syrups, shrubs and bitters. If you're looking to go all in, spring for the Grande Royale, a mix of champagne, cassis, cognac, house campari, palm sugar and camo bitters.

Photograph: Martha Williams

5. Matchbox

Bars Cocktail bars River West/West Town

If the thought of being crammed in this tiny boxcar of a bar makes you nervous, relax. The patio practically doubles the capacity of the place, and it’s the perfect spot to throw back one of its margaritas, made with fresh lemon and lime juice, top-shelf liquors and powdered sugar, and poured with a heavy hand.

Three Dots and a Dash Dead Reckoning cocktails
Photograph: John Khuu

6. Three Dots and a Dash

Bars Cocktail bars River North

The menu at Three Dots and a Dash—and its bar-within-a-bar concept, the Bamboo Room—features exquisite tiki cocktails crafted with fresh pressed juices and house-made syrups. The arsenal of garnishes is next level, with tropical flowers, colorful bendy straws and fresh herbs and citrus. First-timers should start with the namesake cocktail, an agreeable blend of rums, allspice, falernum, orange and lime. After a few drinks, flag down your waiter and ask for the king crab rangoons, which are packed with cream cheese and hunks of tender crab meat.

Photograph: Kailley Lindman

7. Kumiko

Bars Cocktail bars West Loop

Star bartender Julia Momose presides over this beautiful West Loop cocktail den that's steeped in Japanese heritage. Her menu flows from light and bright to dark and stirred, allowing guests to sip rare liquors and fun ingredients like elderflower syrup, orange-saffron bitters and cashew orgeat. Expect to pay a premium—$16–$21 per cocktail—for some of the best booze you've ever tried.
Photograph: Nick Murway

8. Weegee’s Lounge

Bars Lounges Logan Square

Ten years from now, when this strip of Armitage is populated with coffee shops and vintage clothing stores, this old-school, soul record–playing, classic cocktail–mixing bar will be overrun with hipsters vying for their turn in the photo booth. Start hanging out here now so you can say you knew it in the good, old days.

Photograph: Jaclyn Rivas

9. Vol. 39

Bars Hotel bars Loop

It feels weird to call Vol. 39 a hotel bar, but that's exactly what it is—and all other hotels should take note. Located inside the Kimpton Gray, this sophisticated cocktail lounge is decorated like a library with handsome leather furniture and volumes and volumes of books neatly lining shelves that section off the room. It should come as no surprise, then, that there are eight different old fashioneds on the menu—like one made with mezcal, agave, hibiscus and lime.

Fino Sherry at The Whistler
Photograph: Jason Little

10. The Whistler

Bars Cocktail bars Logan Square

From the outside, this place looks like a gallery (which, technically, it partially is). On the inside, it’s open and loft-like, with a permanent stage set up for weekly live music and performance. But behind the bar, the drink-slingers have perfected the art of the cocktail, skillfully crafting colorful refreshments that pack a punch. One sip and there’s no doubt that despite everything else going on here, the drinks are the reason to stick around.

martini at Best Intentions
Photograph: Courtesy Best Intentions

11. Best Intentions

Bars Pubs Logan Square

Back in 2015, brothers Chris and Calvin Marty bought the old Marble Bar and reopened it as Best Intentions. The dive bar charm remains, though the bar is a touch sleeker and the drinks are much better. When the weather agrees, the backyard patio is the perfect place to lounge and sip an ice-cold Wondermint malted shake (mint liqueur, gin and Luxardo hazelnut). Inside, the dimly lit bar serves excellent classic cocktails in an unassuming setting; we're big fans of the gimlet and lesser-known Bobby Burns. But perhaps what we admire most about Best Intentions is its ability to nail the neo-dive vibe without feeling forced.

Photograph: Jaclyn Rivas

12. Moneygun

Bars Cocktail bars West Loop

If classic cocktails and ’90s hip-hop are your jam, Moneygun might just be your dream bar. The small, dark space features all the originals—from mojitos and mai tais to sidecars and sazeracs. Every drink involves a perfected recipe and quality, often house-made ingredients. Balance out the booze with bar upgraded snacks like loaded waffle fries, English pea croquettes and a chocolate chip cookie.

Photograph: Jason Little

13. Punch House

Bars Cocktail bars Lower West Side

Located below Dusek’s Board & Beer, this dark, ’70s-themed bar is decorated with a fish tank, wood paneling and a huge fish on the wall. Think of it as an upgraded, boozy version of your grandparents' basement. Like its name suggests, punch is the main draw here—and you can order most cocktails by the glass, carafe or bowl. Whether you go big or small, you'll experience the genius and precision happening behind the bar at Punch House. If you're looking for a good place to start, order Space Juice for Jered, a blend of tequila, grapefruit, lime, Luxardo bitters, black pepper, sparkling wine and sage. After a few glasses, you'll be ready to head upstairs to piano bar Tack Room.

Old Fashioned at Billy Sunday
Photograph: Matthias Merges

14. Billy Sunday

Bars Cocktail bars Logan Square

Who would have guessed longtime Trotter's chef Matthias Merges would find his calling checking IDs at the door of a Logan Square bar? Granted, his is not just any bar: Here, beverage director Stephanie Andrews creates a menu with original cocktails and twists on classics packed with loads of amari. Though Billy Sunday is squarely a bar, the food is a worthy companion to the drinks: Don't miss any of the snacks in jars.

Photograph: Jaclyn Rivas

15. The Drifter

Bars Lounges River North

Located under the Green Door Tavern, the Drifter is a cozy bar from Liz Pearce (Gage, Drawing Room, Aviary), who serves up a rotating selection of cocktails (printed on a tarot card menu). Your order depends on the cards she deals each night, so keep your fingers crossed for the velvety chocolate negroni or South American Mistress, a smooth blend of pisco, vermouth and Fernet, balanced with chocolate liqueur and blackstrap bitters. The space is a former speakeasy and much of the original decor remains; the occasional performances, like a belly dancer, feel right at home amidst the vintage vibe.

Chicken Milanesa at Cindy's
Photograph: Jason Little

16. Cindy's

Restaurants Contemporary American Loop

Chicago's unofficial Best Rooftop Bar for Your Out of Town Visitors also boasts fantastic beverage program. Order the Jillian—with vodka, vermouth, spiced clementine and lemon—and secure a spot on the sprawling rooftop deck, which offers sweeping views of Millennium Park, the Bean and the surrounding skyline.

Beg Your Pardon at Drumbar
Photo: Jason Little

17. Drumbar

Bars Cocktail bars Streeterville

The gorgeous 18th-floor bar of the Raffaello Hotel boasts three prime sections: a handsome, dim interior full of tufted leather banquettes; a chic exterior deck lounge with open fire pits; and (our favorite) a narrow indoor-outdoor corridor where the marble floor and arched windows play against contemporary green stools. Drumbar serves excellent twists on classics, like the brandy old fashioned and the meyer lemon vodka martini.

18. The Sixth

Bars Cocktail bars Lincoln Square

Beverage director Benjamin Schiller (Fifty/50 Group) balances quality and whimsy at the Sixth in Lincoln Square. Expect playful garnishes (like sparklers) as well as flavored ice cubes and fresh flowers suspended in ice. An order of the duck wings plays nicely with just about everything on the menu.

Ambiguous Smile at Celeste
Photograph: Martha Williams

19. Celeste

Bars Cocktail bars River North

As one of Chicago's latest late-night bars (open till 5am on Saturdays), Celeste is equally suited for date night and last call. The welcoming first-floor bar slings killer cocktails that are easy to love, like the White Flower, a delicate mixture of gin, elderflower, lemon, cava and raspberry. After a few rounds, boogie on up to Disco to hit the dance floor and order bottle service.

Grapefruit and Mint Gintonic at Sable
Photograph: Jason Little

20. Sable Kitchen & Bar

Restaurants Contemporary American River North

The bar is the main draw at Sable, where bartenders turn out excellent cocktails, including lively Spanish gin and tonics garnished with fruit and herbs. The food menu is a nice match, with snacks, seafood, roasted bone marrow and a burger.


21. The Heavy Feather

Bars Cocktail bars Logan Square

We weren't around to bar hop through the ’70s, but we're pretty sure the drinks were not quite as good as Heavy Feather bartender Doug Phillips (Scofflaw) makes them seem. At the sleek fern bar located above the raucous dance floor of Slippery Slope, Phillips brings back cocktails from the era and greatly improves upon them. With choices like a Fantasy Island, The Bunny Man and Mudslide ice cream drink, we can't wait to travel back in time.


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