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Nobody's Darling cocktails
Photograph: Susanne Fairfax Media

The 46 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
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July 2022: Plant-filled cocktail lounges, subterranean speakeasies and a James Beard Award-nominated LGBTQ+ bar—after a stultifying few years, it's safe to say that Chicago's drinking scene is once again alive and kicking. Our latest roundup raises a glass to bars new and old, from a rollicking New York City import to the revived (and, thankfully, mostly unchanged) California Clipper. 

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 boutique hotels in Chicago

Best of the city under one roof

  • Bars
  • West Loop

Chicago, we know you're thirsty, which is why we put a bar on every floor of Time Out Market Chicago. The main bar—located on the first floor, as soon as you walk in—is also the largest in the building. Beverage director Jonathan Kahn curates seasonal lineups of thirst-quenching craft cocktails that incorporate local spirits from makers like CH Distillery and Apologue. Expect vibrant and fun flavors at every turn, from housemade lavender cola and activated charcoal to hibiscus salt and coconut liqueur. Kahn rounds out the menu with top-rated wines and a selection of Chicago-made brews from the likes of Metropolitan Brewing, Moody Tongue and Off Color Brewing.

  • 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).

Best bars in Chicago

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

Following a pandemic-era closure, the glowing red lights at beloved Humboldt Park haunt California Clipper flickered back to life earlier this year thanks to an acquisition by the hospitality company Orbit Group (Good Measure, Segnatore)—and we’re pleased to report that things are mostly back to usual at the bar, from weekly live music to the same red leather booths flanking the walls. If you’re craving a change of pace, venture to the Clipper’s new 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
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  • 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 piquant aleppo and lemon aioli. 

  • 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.

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  • 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.

  • 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.

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  • 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.

  • 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.

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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
  • 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—and recently shortlisted for the James Beard Awards’ prestigious Outstanding Bar Program prize—Nobody’s Darling made waves when it debuted last year 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 Lavish Darlings menu, which are crafted with high-end spirits and botanical ingredients.

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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
  • 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 highball made with creme de cassis and 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
  • 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 Appalachian Ass Play—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
  • 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 nearly 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
  • 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 newcomer draped in lush greenery from nearby Sunnyside Plants, some of which is available for purchase. Drinks here have a botanical tilt, too, from the mint-toned Seeing Green (matcha, sweetened condensed milk, soju and vodka) 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
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  • Bars
  • Cocktail bars
  • River West/West Town
  • price 2 of 4

The Silver Palm (Chicago's only restaurant in railcar) remains closed, sadly, but the adjacent Matchbox is still serving a menu of classic cocktails. 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.

  • 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 spanakopita grilled cheese sandwiches. 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.

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  • 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!

  • 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 for a drink with a good cause? The bar also sells a Community Cocktail, which donates $1 from each drink sold to a different community organization each month.  

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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 martini-like Still Life (this place loves a good photography reference) introduces grassy notes with cacti and the Mexican spirit Sotol.

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Emma Krupp
Editor, Time Out Chicago
  • 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 a out of the ordinary, you'll find no shortage of options here.

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  • 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 a 14-inch sourdough crust pie from in-house pizzeria Le Pizza (open Thursday through Sunday), if you're feeling peckish.

  • 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
  • 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 Polish-Korean fusion dishes.

  • 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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  • 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 Whisky Smash, made with single-malt scotch, spiced cordial, amaro, lemon and mole for a bit of a kick). 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 Island Time with gin, sake, pamplemousse, lemon and lychee and ginger liqueurs. 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 Tank Top Tumbler, made with rum, two types of sherry, blackberry lime cordial and lemon. 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, Marz Community Brewing's latest 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 a recent visit, 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 tequila-based Space Juice for Jered has been a mainstay since day one for good reason, with a satisfying mix of grapefruit, lime and sparkling wine.

  • 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. A virtual marketplace makes it easy to browse a slew of wines you've probably never heard of, each of which are marked with fun, approachable tasting notes. 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
  • 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, but the top shelf menu—in which drinks are concoted with vintage spirits, like a 1960s Fernet Pedroni, plus other rarefied ingredients—goes as high as $65 a pop, if you feel like splurging. 

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  • 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. Don't miss out on the kitchen's cheeseburger—griddled to crispy-thin perfection and served with a massive mound of fries—which is one of the best in the city. 

  • 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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  • Bars
  • Lounges
  • Logan Square
  • price 2 of 4

Sick of jostling with hipsters to order a drink in Logan Square? This old-school, soul record–playing, live music-hosting, classic cocktail–mixing bar is a neighborhood classic with a 1940s vibe, down to the vintage photobooth and shuffleboard. Venture out to the back patio when the weather’s nice. 

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

Once your eyes adjust to the dim, sultry lighting inside this North Side spot, you'll realize the Victor Bar is your new ideal date-night destination. Sexy environs? Check. Excellent cocktails? Check, check. Easy access to the bus and train so you don't have to splurge on an Uber home? Big ole check. For one last drink before you close out, consider the trio of old-fashioneds that are always available, in bourbon, rye and mezcal. Cheers!

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  • Bars
  • Lounges
  • River North
  • price 2 of 4

When we need a break from the city’s repetitive cocktail lounges, we descend into the basement of Green Door Tavern to grab a drink at this secret speakeasy. Owner Liz Pearce has more than 100 funky cocktails that are described on custom tarot cards. Each night, the team selects a handful of cards from the deck, allowing for a wildly different experience with each visit.

  • Bars
  • Dive bars
  • Lower West Side
  • price 1 of 4

This speakeasy-esque space—a vacuous room, lined with booths and sprinkled with tables and chairs—is a nightly respite for local artists. The tater tots and mac and cheese are greasy must-haves, and you should wash ’em down with $6 draft beers from the likes of Dovetail, Maplewood and Off Color. 

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