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A hand places garnishes on four cocktails at a bar
Photograph: Jaclyn Rivas for Time Out Chicago

The 54 absolute best bars in Chicago

Raise your shot glass of Malört to the best damn watering holes in Chicago

Written by
Morgan Olsen
Contributors
Zach Long
,
Emma Krupp
&
Jeffy Mai
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In a city where faded Old Style signs swing outside of beloved dive bars and lines snake around the block at trendy cocktail lounges, the best bars in Chicago act as meeting places, date locales and venues for celebrations. With so many great places to grab a beverage, our list of our all-time favorite bars around town is expansive—and inclusive of taprooms at Chicago breweries, wine bars uncorking bottles of red and white as well as the finest cocktail bars Chicago has to offer. In a city that's packed with places to belly up and have a drink, these watering holes shine extra bright and boozy. Take a look at the best bars in Chicago and find the perfect destination for your next night out.

RECOMMENDED: The best whiskey bars in Chicago

Time Out Market Chicago
  • Bars
  • West Loop

Named for Time Out founder Tony Elliott, Tony’s is the crown jewel of Time Out Market Chicago. The cozy all-season rooftop bar is decorated in vintage Time Out London covers, twinkling lights and handsome wood beams that stretch the length of the room. The space is anchored by a sprawling bar that serves a curated selection of wines, beers and signature cocktails. If the sun is shining, wander outside to take in skyline views (you can easily peep some architectural gems from here).

Top bars in Chicago

  • Bars
  • Cocktail bars
  • West Loop
  • price 3 of 4

When a regular ol’ G&T simply won’t do, Julia Momose is waiting with splurge-worthy concoctions. Arranged from bright and light to spirituous closers, the drinks here are chock-full of ingredients that reflect Momose’s Japanese heritage, including rice vodka, green-tea shochu and plum saké. The environs are equally intimate, with a bar that offers a peek into the kitchen where chef Noah Sandoval whips up Kusshi oysters, truffle-topped milk bread and other luxurious snacks. Walk-ins are always welcome, but space at Kumiko is limited, so you may want to lock down a reservation before your visit.

  • Bars
  • Cocktail bars
  • Uptown
  • price 2 of 4

In the 1920s, Al Capone and other nefarious gangsters used to sidle up to this very bar, but these days it’s all about the music (and the satisfyingly stiff, old-school cocktails). Owner Dave Jemilo, who returned the club to its original luster in the 1980s, books smart bebop, swing and free jazz every night of the week, so expect to pay a cash-only cover at the door. A candle-topped table up front puts you at the center of the action, but the plush, emerald-hued booths are the best seats in the house.

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  • Bars
  • Cocktail bars
  • Humboldt Park
  • price 1 of 4

Glowing red lights set the mood at beloved Humboldt Park haunt California Clipper, which flickered back to life in 2022 thanks to an acquisition by the hospitality company Orbit Group (Segnatore). Drop in to enjoy weekly live music on red leather booths flanking the walls, or if you’re craving a change of pace, venture to the Clipper’s back room (which previously housed coffee shop C.C. Ferns) for DJ sets and late-night dancing meant to channel the spirit of Danny’s, the iconic Bucktown spot that shuttered in 2020. 

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Emma Krupp
Editor, Time Out Chicago
  • Bars
  • Lounges
  • Logan Square
  • price 2 of 4

Though the hand-drawn menu at this Logan Square gin joint changes with the seasons, every iteration includes a glossary of unfamiliar ingredients, like zucca (smoky amaro) and baijiu (a pineapple-flavored spirit from China). That humble mentality permeates the space, too, guaranteeing a welcoming, inclusive experience every time. Come with a few friends, settle into a high-backed sofa and take your drinks with an order of shareable snacks, like the thrice-cooked Scofflaw Fries served with garlic aioli. 

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  • Bars
  • Cocktail bars
  • West Loop

You won't soon forget an evening at the Office, a tiny speakeasy hidden below lauded cocktail bar the Aviary in the West Loop. Your best bet is to reserve one of four bar stools for the Office Hour, a 60-minute guided experience that includes two bespoke cocktails and food pairings (ideal for pre- or post-dinner tipples). Can’t decide on a drink? Opt for the Dealer’s Choice and let the expert bartenders craft a concoction tailored to your preferences.

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Morgan Olsen
Global Food & Drink Editor
  • Bars
  • Cocktail bars
  • Armour Square
  • price 2 of 4

Chinatown is home to an incredible assortment of restaurants but until last summer, a cocktail bar was missing from the equation. Nine Bar owners Lily Wang and Joe Briglio have given the neighborhood a drinking oasis with this moody, Blade Runner-esque lounge hidden away behind Moon Palace Express. Drop in for Asian-inspired old fashioneds and potent concoctions like the Paradise Lost, made with mango brandy, cachaça, ube, pineapple and Thai coconut milk. There’s also a small menu of snacks, headlined by the terrific McKatsu—breaded pork cutlet—sandwich.

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Jeffy Mai
Editor, Time Out Chicago
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  • Bars
  • Cocktail bars
  • Wicker Park
  • price 3 of 4

When it opened in 2007, the Violet Hour was a pioneer of Chicago’s craft-cocktail renaissance, introducing us to well-built classics, house-made syrups and hand-carved ice cubes. Today, the hushed speakeasy still sets the pace, mixing perfect old-fashioneds and Manhattans alongside groundbreaking new concoctions that use only the finest ingredients. Plus, the bar's notorious "no phones" policy has recently been relaxed to allow for texting and picture-taking—you'll just need to step outside if you're taking a call.

  • Bars
  • Dive bars
  • River West/West Town
  • price 1 of 4

A bistro in France it ain’t, but curiously enough, this tidy, dark dive takes a few traditions from across the Atlantic. The bartender—usually a skinny, older gentleman or at least some variation on the theme—typically dresses in an immaculately crisp white button-down, and you can buy hard-boiled eggs if you need a snack. The larger-than-life posters of De Niro on the wall, however, are completely American. Oh, and smoking is prohibited.

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  • Bars
  • Loop

The first thing you should know about this exclusive micro-bar tucked inside the Chicago Athletic Association is that you need a reservation—mostly because there are only eight seats available. During the two-hour experience, you'll browse a menu of vintage spirits and rare whiskeys, like 1970s Fernet Branca and 1940s Cointreau. Of course, for a taste of the past, you'll pay a pretty penny—the drinks here start around $28 and only go up from there. There's a small food menu with luxe bites (think caviar and foie gras terrine), but the better move is to make a post-tipple reservation at the hotel's Cherry Circle Room so that you don't have to stumble far to pad your belly after all that booze.

  • Shopping
  • Liquor stores
  • Avondale
  • price 2 of 4

True to its name, The Beer Temple is a sanctuary for craft-brew lovers, complete with a spacious taproom where visitors can have a drink and a bottle shop stocked with plenty of interesting brews. Kegs from local, national and international breweries regularly join the menu at the bar (and are sometimes depleted in the course of any evening), so you're likely to find at least a few new selections every time you visit. Not a fan of the latest double IPAs and barrel-aged pastry stouts? Don't worry, this place has cans of Hamm's and shots of Malört, too.

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  • Bars
  • Dive bars
  • Ukrainian Village
  • price 2 of 4

Thanks to a funky, taxidermy-dotted interior, a sprawling backyard patio and excellent drinks, this drinkery attracts folks from far beyond Humboldt Park’s borders. The Low Life—a High Life plus a shot of bourbon, Malört, Fernet-Branca or a house blend of amaro—is just $7. Come summertime, the bar invites Chicago’s top chefs to host cookouts on the patio every Sunday afternoon—$20 gets you a heaping plate of food and a drink.

  • Bars
  • Pubs
  • Bridgeport
  • price 2 of 4

Brothers Ed and Mike Marszewski and his brother remodeled and renamed Kaplan’s Liquors, the Bridgeport bar that was owned and operated since 1986 by their mother, Maria. The chandeliers built out of bottles and the 300-plus microbrews are notable, but the real standout feature is the welcoming scene: People like each other here. You can grab a bite to eat (and find even more tables) next door at Kimski, which serves Korean-ish fare.

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  • Bars
  • Avondale

Equal parts beer bar and music venue, Sleeping Village offers a dynamic lineup of cheap (sometimes free) shows from locals acts and touring bands, with the occasional comedy gig tossed in for good measure. A projector displays a laundry list of beers on a wall near the bar, and bartenders pour everything from mead and hard kombucha to the latest IPA from Marz Community Brewing Co. During the summer, you'll likely to have to wait your turn for one of the picnic tables on the patio to clear out.

  • Bars
  • Cocktail bars
  • Andersonville
  • price 2 of 4

Be nobody’s darling; / Be an outcast. Named for an Alice Walker poem, Nobody’s Darling made waves when it debuted in 2021 as the second Black-owned LGBTQ+ bar in Chicago, offering an elegant, inclusive space with a high-end cocktail menu to boot. Flip through a selection of riffs on classic cocktails like the fiery Kahlo Margarita (Jon Basil Reposado tequila, passionfruit liqueur, triple sec, lime, agave and spicy bitters) or treat yourself a drink off the bar’s ever-changing Featured Darlings menu.

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Emma Krupp
Editor, Time Out Chicago
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  • Bars
  • Beer bars
  • Uptown
  • price 2 of 4

A formidable list of craft beers and European imports dominates this sprawling two-story spot with multiple bars. It’s an Andersonville staple, pouring local and international brews, both on draft and in bottles or cans. The bar has special tappings and charity kegs, so be on the lookout as you peruse the 60-plus drafts—if you see a rarity, be sure to snag it. There’s also an encyclopedic bottle list, plus a handful of wines on draft if, for some insane reason, you can’t find anything frothy to fit your fancy.

  • Bars
  • Dive bars
  • Sheffield & DePaul
  • price 2 of 4

No Chicagoan’s bar bucket list is complete without a vist to Mike Miller’s no-bullshit establishment, which is known for its extensive collection of whiskey and beer as well as its nightly DJ sets—everything from metal to ska (the good kind) and R&B—and VHS tape screenings. Miller holds court at the three-decade-old bar, which is decorated with red Christmas lights, obscure works from local artists, a well-loved pool table and a pinball machine. If the more than 800 options on the whiskey list are too intimidating, don't be afraid to ask the bartender for a recommendation.

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  • Bars
  • Dive bars
  • Ukrainian Village
  • price 1 of 4

Situated near a stretch of Ukrainian Village that constantly churns out shiny, new bars and restaurants, Rainbo Club has been an incorruptible constant since the early 1930s. The L-shaped neon sign beckons from blocks away, pulling patrons into the no-frills environment to down a can of something cheap and a shot of something strong in its coveted red booths. 

  • Bars
  • Lounges
  • West Loop
  • price 3 of 4

The Alinea family’s drunkest member serves cocktails with a side of whimsy. Though the menu descriptions don’t give much away—it’s better that way, trust us—each drink is a mini science experiment that defies gravity and blows minds. The layered Jungle Bird boasts rum-soaked jelly balls that burst in your mouth, while the crowd-pleasing Loaded to the Gunwalls is served in a bottle with a ship inside. You'll need a reservation (accompanied by a deposit, which is applied to your bill) to drink here, so plan ahead!

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  • Bars
  • Café bars
  • Logan Square
  • price 2 of 4

Leave your worries at the door at this sunny, all-day oasis that’s bumping with whatever vinyl the crew behind the bar is feeling at the moment. The menu is organized by spirit—pisco, agricole, mezcal, tequila—and the sips highlight fresh juices and syrups of the tropical variety, like tamarind agua fresca and horchata. Come summertime, the garage-door–style windows open up to let in a warm breeze, making Estereo an ideal hangout for imbibing the day away—plus it's dog-friendly.

  • Bars
  • West Loop

This dimly lit, seriously sexy rathskeller beneath the Hoxton hotel is a great bet for those nights when you want to go somewhere where no one knows your name. The deal is sweetened by a pièce de résistance of a cocktail menu that includes 52 retooled and perfected standards. The Negroni, for instance, mimics the flavor of vintage Campari with a top-secret mixture of bitters, achieving an exquisitely balanced, time-traveling tipple. Whether you want something familiar or out of the ordinary, you'll find no shortage of options here.

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  • Bars
  • Cocktail bars
  • Logan Square
  • price 2 of 4

Helmed by the restaurant group of longtime Trotter's chef Matthias Merges, this Logan Square bar takes an almost culinary approach to its cocktail list. Most drinks will run you around $14-$16, but the top shelf menu—in which drinks are concocted with vintage spirits, like 1980s Gordon Gin, plus other rarefied ingredients—goes as high as $35 a pop, if you feel like splurging. 

  • Bars
  • Avondale

Flipping a beloved dive is no easy task, but enterprising bar dudes Wade McElroy and Jeff Donahue (Sportsman’s Club, Estereo) nailed it with the old Orbit Room space in Avondale. The bar’s laid-back spirit remains intact, but the forward-thinking menu proffers classic craft cocktails alongside cans of High Life and a reasonably affordable draft beer menu. If you need sustenance, there's usually a pop-up slinging delicious eats out of the kitchen.

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  • Bars
  • Cocktail bars
  • South Lawndale

Located in the back of Moreno’s Liquors—a destination for hard-to-find tequila and mezcal in Little Village for more than 40 years—this lofty speakeasy leans into its locale with a robust selection of agave-focused cocktails spiked with ingredients like ancho chile and jamaica, plus an impressive draft beer list to boot. Look for a neon Chihuahua sign at the back of the liquor store (that’s the likeness of Osito, the bar’s namesake) and slide into high-backed booths in the bar’s historic interior, or grab seats on the patio and soak up the sunshine.

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Emma Krupp
Editor, Time Out Chicago
  • Bars
  • Beer bars
  • Bucktown
  • price 1 of 4

If the cartography, flags and copious copies of National Geographic didn’t tip you off, this Bucktown bar honors wanderlust, and it has a beer list to match. In the morning, the Map Room is a café that serves lattes and cortados, but, come sunset, the regulars hunker down to travel the world through suds, hopping from Chicago to Germany to Quebec. Stop in on a weekday to enjoy discounts on beer from various regions of the world. 

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Cove Lounge
  • Bars
  • Dive bars
  • Hyde Park
  • price 1 of 4

At this lovable, red-carpeted Hyde Park haunt, you’re greeted by a sprawling mural of a younger Barack Obama, backed by Chicago’s famous skyline. On any given night, a nice mix of University of Chicago students and blue-collar workers sip PBR tall boys and play darts in total harmony amid the picnic tables. It may not have an Old Style sign swinging from its facade, but the Cove is a classic Chicago dive.

  • Restaurants
  • American creative
  • River West/West Town
  • price 1 of 4

All Together Now bills itself as a cafe (which is true; pop in at brunchtime for coffee and egg sandwiches, plus bagels on the weekends), but we prefer to sidle up to a window-facing bar stool or patio table in the evening for locally-sourced charcuterie plates and natural wine by the bottle or glass. Don’t leave without perusing the miniature grocery and bottle shop, which is stocked with splurge-y kitchen treasures—think tinned fish, homemade granola and hunks of funky cheeses—and a lean-yet-sophisticated selection of wine.

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Emma Krupp
Editor, Time Out Chicago
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  • Bars
  • Cocktail bars
  • Ukrainian Village
  • price 2 of 4

Tucked away beneath Split-Rail sits this LGBTQ+ cocktail den that’s decked out in vintage furniture and ‘70s-style decor. You’ll find good vibes all around and a rotating selection of intriguing libations, such as the Bad Poetry made with coffee liqueur, mezcal, campari and egg white. There are also regular events and programming like Fruit Salad, Dorothy’s monthly queer open mic night.

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Jeffy Mai
Editor, Time Out Chicago
  • Bars
  • Wine bars
  • Logan Square

Transport yourself to the streets of Paris at Soif, a speakeasy-inspired 24-seat wine bar housed in the basement space below Testaccio in Logan Square. Named after the French word for “thirsty,” Soif (pronounced “swaf”) centers around a rotating wine list of 50 to 60 bottles, with an emphasis on small batch and limited production wines—like grower Champagne, which is produced in small volumes by the same person who grew the grapes—as well as natural and orange wines. The bar’s lean cocktail list highlights French spirits in traditional drinks, like a martini made with Maurin dry vermouth, while the beers are mostly French or Belgian (with a Dovetail brew thrown in for good measure). 

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Emma Krupp
Editor, Time Out Chicago
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  • Bars
  • Pubs
  • Logan Square
  • price 1 of 4

When brothers Chris and Calvin Marty reopened the old Marble Bar space, we didn’t know what to expect. Since then, the self-proclaimed “fancy cocktail bar” has become a booze-slinging Logan Square institution, complete with balanced drinks and elevated snacks, like calf-liver mousse and port-wine cheese spread. But perhaps Best Intention’s greatest accomplishment has been to find a way to emulate the archetypal Chicago dive bar in all its nitty-gritty splendor. The lived-in space, outfitted in wood paneling and checkered floors, effortlessly looks beyond its years.

  • Bars
  • Avondale

Mother’s Ruin arrives in Avondale by way of New York City (with an additional satellite location in Nashville), bringing its signature spiked slushies and craft cocktails to a spacious storefront on Milwaukee Avenue open 365 days a year. Drink names on the rotating cocktail menu offer an irreverent touch—recent entrants range from Viagra Triangle to Pickle Me Elmo—and pack a boozy punch that’s well-matched against the joint’s genuinely unmissable selection of bar snacks, including one of the best burgers in Chicago. Sidle up to a high-top table beginning at 11am daily, when the bar starts slinging hearty brunch mains, for daytime cocktails and a breakfast burrito.

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Emma Krupp
Editor, Time Out Chicago
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  • Bars
  • Cocktail bars
  • Portage Park

Sure, plenty of bars are decked out in plants—but how often can you actually buy those plants alongside your old-fashioned or G&T? That’s part of the concept at Moonflower, a Portage Park watering hole draped in lush greenery from nearby Sunnyside Plants, some of which is available for purchase. Drinks here have a botanical tilt, too, from the Sittin' Pretty with jasmine-infused gin to the fruit-forward No Brainer (rum, strawberry, banana, lime, Angostura), plus a handful of creative riffs on classic drinks. On weekends, venture downstairs to the speakeasy-style cocktail bar Nightshade, where you’ll find a tight menu that includes—among other treats—a fanciful array of sippers made with fluffy shaved ice. 

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Emma Krupp
Editor, Time Out Chicago
  • Bars
  • Cocktail bars
  • River West/West Town
  • price 2 of 4

As its name suggests, this boxcar bar can feel a bit cramped, but come spring, the sidewalk patio practically doubles the capacity. No matter the season, though, the house margarita hits the spot: Crafted with top-shelf liquors, fresh-squeezed lemon and lime juices, it’s served in a glass that’s rimmed with powdered sugar. Delish.

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  • Bars
  • Breweries
  • Irving Park

There are just a few cideries located in Chicago, but Eris Brewery and Cider House is easily the most beautiful of the bunch, housed in a retrofitted church that dates back more than a century. Snag a seat at a sleek booth in the two-level space (or outdoors on a parking lot patio) and sample some of the house ciders, which range from crisp, dry selection to sweeter options blended with cherry or cranberry juice. The kitchen serves a formidable menu of pub grub, including fried cheese curds, burgers topped with bacon jam and pork belly gyros. And if you're not a fan of cider, Eris brews beer, too! Make sure to try the award-winning Foiken Haze IPA if it's on tap.

  • Bars
  • Cocktail bars
  • Ukrainian Village
  • price 2 of 4

Named in honor of building owner and former bar maven Mary Kafka, Queen Mary Tavern is a self-proclaimed time capsule that introduces modern-day imbibers to the old-time drinking traditions of sailors. Set down an anchor and stay for a glass or two of the Daily Grog, a rotating punch that's garnished with fresh citrus and just enough spice to thaw your weary bones. In the mood to get wild? Order a Miller High Life with a shot of dark rum for just $6.

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  • Bars
  • Albany Park

This Albany Park lounge takes its name from a photography term for the dreamy, out-of-focus look achieved by fast-moving lenses, and its interior—all dim lights, sleek furniture and brick walls—offers a similarly sexy aesthetic. Cocktails rotate based on the season, but the core menu favors bold and vegetal spirits; the signature Bokeh cocktail, for example, uses Fernet and cardamom to enliven a traditional sour, while the Camera Obscura (this place loves a good photography reference) consists of mint-infused bourbon and watermelon juice.

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Emma Krupp
Editor, Time Out Chicago
  • Bars
  • Breweries
  • New City

Don't come to the Whiner Beer Co. expecting extremely bitter IPAs or hefty stouts—co-founders Brian Taylor and Ria Neri are more interested in barrel-aged Belgian-style beers and hard kombucha. Ask for a taste of Whiner's signature Le Tub (a blended barrel-aged wild saison) and you'll have an idea of just how funky the brews can get at Whiner's taproom, which is housed inside the Plant, a nonprofit net-zero energy food production space situated in an old warehouse in the Back of Yards neighborhood. Grab a seat at a table with a built-in planter while you enjoy your beer—and order smoked meats from Heffer BBQ (open Thursday through Sunday), if you're feeling peckish.

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  • Bars
  • Cocktail bars
  • Logan Square
  • price 2 of 4

The team behind Logan Square spots Union and Lardon also operates this intimate and swanky cocktail bar. Housed in the same century-old building as the other two concepts, Meadowlark provides guests with a cozy den to hang out in—complete with low lighting, comfy leather couches and book-lined shelves. The drinks are all named after birds and there’s also an accompanying menu of small bites. Seating is limited, so get there early to snag a spot.

  • Bars
  • Dive bars
  • River West/West Town
  • price 1 of 4

Once known primarily as a ramshackle country-rock roadhouse in an industrial stretch of the city, the Hideout has become a place where new musicians, veteran performers and outspoken personalities of all stripes dominate the stage. It can be difficult to reach this out-of-the-way spot by public transportation, but it’s worth the trip for the cheap beer, fresh sounds and DJs dropping nostalgia, from Prince to Devo. 

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  • Bars
  • Cocktail bars
  • River West/West Town

Unlike some of the flashier cocktail bars on our list, drinks at this jewel-toned River West hangout are elegant but unfussy, consisting of a mostly-pronounceable list of ingredients (like the Devil in the White Negroni, made with gin, vermouth, grapefruit and Malört). Come summer, nab a seat at the bar’s expansive patio studded with trees, flowers and punchy murals, where you’ll often find live music on the weekends.

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Emma Krupp
Editor, Time Out Chicago
  • Bars
  • Cocktail bars
  • Logan Square
  • price 2 of 4

The Whistler felt like a mainstay from day one. That’s partly because it embraces the community in a big way: You'll find the work of local artists in the window, and local DJs and bands play most nights. Next to the list of bottles and cans, guests will find a lineup of fantastic cocktails, like Red Diamond with mezcal, cognac, hibiscus and absinthe. Plus, there are events of interest almost every night, from themed dance parties to the Relax Attack Jazz Series. 

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  • Bars
  • Cocktail bars
  • River North
  • price 2 of 4

You'll find the not-so-secret entrance to this subterranean tiki bar in an alley east of Clark Street, between Hubbard and Illinois streets. Once your eyes have adjusted to the dark interior, you'll notice the colorful drinks parading around the room: The cocktails here are served in tiki glassware and accented with fresh flowers, colorful straws and skewers of fruit. Nudge your way to the crowded bar to try classics like the Painkiller, with Caribbean rum, tangerine, pineapple and coconut—it goes down a little too easy after a long day.

  • Bars
  • Wine bars
  • Logan Square

You don’t have to know the difference between cheverny and chardonnay to feel right at home at this vino bar that feels like a broken-in neighborhood hangout. Though the menu offers easy-to-understand descriptions of 20 or so natural, low-intervention pours, it’s best to lean on your server for a quality rec: These funky wines are more unpredictable than the stuff at your corner liquor store.

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  • Restaurants
  • Contemporary American
  • Loop
  • price 3 of 4

Whenever we want to impress out-of-towners, we book a table at the Chicago Athletic Association Hotel’s rooftop bar, from which Millennium Park, Lake Michigan and the city skyline are on glorious display. The drink lineup complements the vistas with easy-sipping selections that are best enjoyed in the sun—like Very Necessary, made with vodka, amaro, pineapple juice, lime and orgeat. As a bonus, the spirit-free menu rocks, offering bold, wildly creative quaffs.

  • Bars
  • Breweries
  • Logan Square

Building on the success of its Bridgeport outpost, this Marz Community Brewing taproom sits between Logan Square and Bucktown, taking up residence in the same building that houses the Margie's Candies ice cream parlor and the Snakes & Lattes board game café. Dubbed the Life on Marz Community Club, the space is a bit smaller than the original Bridgeport taproom, but its decor is as stylish as the art that graces the brewery's various beer cans. Dangling lights and multi-colored walls complement a cooler stocked with cans of Marz creations and taps pouring drafts (including a few exclusive brews). If you need a snack while you knock back some hazy IPAs and Chug Life lagers, you'll find an ever-changing menu of salty bar snacks—think flamin’ hot popcorn, curry chips and beef jerky—sourced from vendors near and far. 

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  • Bars
  • Pubs
  • South Shore
  • price 2 of 4

This Black-owned gay bar has been holding it down in South Shore since the 1960s. On past visits, we watched the crowd groove to hip-hop and house while also chatting and canoodling on the sidelines. Swing by on the weekends for DJ nights and dance parties that go until the early hours of the morning. 

  • Bars
  • Lounges
  • Avondale
  • price 1 of 4

Only in Chicago is the name Alice synonymous with raucous late-night karaoke. Don’t come expecting to sing more than one song on a busy night—the regulars rule the mic here, but the majority of them are pretty entertaining to watch. Plus, after a few beers (and a shot or two) you’ll be yelling along to most of the lyrics anyways.

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  • Bars
  • Cocktail bars
  • Lower West Side
  • price 2 of 4

Below Dusek’s Board & Beer, this ’70s-themed bar is decorated with a fish tank and yards of wood paneling—think of it as a deluxe 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. The milk punches are beloved for good reason, with a satisfying mix of rum, coconut and chai tea.

  • Bars
  • Wine bars
  • Logan Square

Late-night spot East Room closed back in 2019, but co-owner Zack Eastman (Dorian's, Saved by the Max) has resurrected the space as a bar and bottle shop with a sprawling back patio where you can sip pét-nats and rosé beneath shade canopies by the Blue Line. Appropriately named Easy Does It, the storefront is a casual, laid-back shop where folks can stock up on natural wines, local beers and liquor. And when the temperatures drop, the drinking moves indoors to a second floor bar with open seating and plenty of room for events like wine tastings and DJ sets.

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  • Bars
  • Cocktail bars
  • Lower West Side

Try searching for “The Alderman Chicago” online and you’ll be lost in a sea of city websites—and maybe that’s intentional. This 16-seat speakeasy-style bar, tucked away in an inky black side room of Pilsen Yards, offers an intimate hideaway for sipping your way through beverage director Lance Bowman’s sophisticated cocktail menu, plus a long list of spirit pours. A word to the wise: Don’t show up without a reservation, especially on the weekends.

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Emma Krupp
Editor, Time Out Chicago
  • Bars
  • Dive bars
  • Old Town
  • price 1 of 4

Knock back stiff drinks with a gloriously diverse cast of characters from grizzled old timers to tourists from nearby Second City at this late-night watering hole. It’s a favorite of many cultural icons, from the late Anthony Bourdain and actor Michael Shannon (he watched the Oscars here in 2018) to Chicago film critic Roger Ebert—and should be a fave of yours, too.

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