The 40 absolute best bars in Chicago

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.

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.

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. Pro tip: The double-patty cheeseburger with griddled onions is always a good idea.

This dimly lit, seriously sexy rathskeller is a great bet for those nights when you want to go somewhere where no one knows your name. Bar master Lee Zaremba sweetens the deal with a pièce de résistance of a menu that includes 52 retooled and perfected standards. For the Negroni, for instance, Zaremba mimics the flavor of vintage Campari with a top-secret mixture of bitters, achieving an exquisitely balanced, time-traveling tipple.

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.

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 chefs Noah Sandoval and Mariya Russell whip up sea-kissed nigiri, truffle-topped milk bread and other luxurious snacks.

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 whiskey or a pull from the amaro machine—is just $5. Come summertime, the bar invites Chicago’s top chefs to host cookouts on the patio—$20 gets you a heaping plate of food and one cocktail.

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 the Never Setting Sun with gin, orange liqueur, chai tea, lemon and absinthe. Plus, there are events of interest every night, from the LGBT-friendly Slo ’Mo party to the Relax Attack Jazz Series. It’s always a killer night at the Whistler.

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 and free jazz every night of the week, so expect to pay a cash-only door cover ($4–$15). 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.

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.

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.

At this lovable, red-carpeted Hyde Park haunt, you’re greeted by a sprawling portrait 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.

No Chicagoan’s bar bucket list is complete without 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. Miller holds court at the 27-year-old bar, which is decorated with red Christmas lights, obscure works from local artists, a well-loved pool table and an AC/DC pinball machine. Plan your return visit around one of the bar’s frequent tasting events, when rare spirits and brews are the main attraction.

If far-out installation artist Yayoi Kusama had a cocktail bar, it would probably look a lot like the Ladies’ Room. Hidden inside Fat Rice—just off the hallway that separates the restaurant from the bakery—this sultry, postage-stamp–sized speakeasy throws convention by the wayside in favor of bold new techniques and rule-breaking ingredients that totally work. Case in point: A mezcal-based drink incorporates a Portuguese cheese rind.

Situated near a stretch of Ukrainian Village that constantly churns out shiny, new bars and restaurants, Rainbo Club is an incorruptible constant. 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. There’s no food here—if there were, you wouldn’t want it—but the tamale guy makes regular appearances to pad the bellies of late-night revelers.

First, let’s get one thing out of the way: You don’t have to be a Soho House member to drink at this teensy-tiny bar on the property’s mezzanine level. Just swing through the Western-style saloon doors, secure a chair or two at the communal table and head to the bar for a round of boulevardiers, built with brown-butter scotch and walnut bitters. If you ask nicely, your server will gladly deliver an order of crispy nuggets to your table from the Chicken Shop next door.

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.

Brewmaster Jared Rouben uses his culinary background to dream up beers that excite the palate and pair well with fine-dining eats. The Burnt Caramel Vienna Lager boasts notes of toasty Biscoff cookies, while the Hazy Mango-Pineapple IPA emulates a spoonful of ice-cold sherbet. At the brewery’s new South Side digs, guests can match these pours with upscale bar grub from Jared Wentworth—we’re talking smoked-beet tartare with spruce-infused ricotta.

Equal parts beer bar and music venue, Sleeping Village offers a dynamic lineup of cheap (sometimes free) shows from the likes of Melkbelly and Channel Tres, 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.

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.

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.

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 Monday or Tuesday, when select beers are discounted, and meats and cheeses are complimentary.

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. Choose from a one- or two-hour experience at the bar, where 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.

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 traditional 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.

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.

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.

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. For example, the cheeky Pink Drink blends rum and scotch with spiced pear, purple sweet potato and lemon. As a bonus, the spirit-free menu rocks, offering bold, wildly creative quaffs.

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.

The city's only 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. For a glimpse at who could be the next RuPaul, pony up the cover charge for amateur drag shows Mondays, Thursdays and Saturdays.

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 the wildly talented crew turns out creations that both pay homage to and defy tradition—often simultaneously. Though Billy Sunday is squarely a bar, the food is a worthy companion to the drinks—think deviled eggs, cheddar-dusted popcorn and chocolate-loaded puppy chow.

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 craft cocktails by the ounce, meaning you can put together your very own, highly eccentric flight. The kitchen pulls from all corners of the globe, with okonomiyaki fritters and French onion soup on deck.

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.

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.

This West Loop tavern flaunts a very average-sounding tagline: "It's just a bar." The truth is, of course, it's way more than that. The menu, which is blazoned on the mirrored wall of the bar, boasts 31 classics, like the Last Word, a Sidecar and even a Cosmopolitan. Each is crafted with superior ingredients and hand-crafted syrups and tinctures. The hip-hop music soundtrack doesn't hurt either.

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.

A formidable list of craft beers 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.

A few 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.