11(ish) Essential Bars in Chicago

The City of Big Shoulders has always been a drinking town. It sits on a solid foundation of local tavern culture built across its 77 diverse neighborhoods. In these watering holes, you’ll catch regulars throwing back $2 PBRs and shots of whiskey or our unofficial spirit mascot, Malört, if you prefer a more bitter brand of masochism.

Community forms the heart of Chicago’s bar culture, but nowadays what’s in the glass takes on equal importance. It started with the craft beer movement in indie breweries and beer bars, but in more recent decades, the city has earned a well-deserved reputation as a serious cocktail and wine destination.

Indeed, these days you can seek out cocktail joints with expertise in gin, amaro, agave or cane spirits; bars that specialize in molecular mixology or house 1,000 different whiskeys. You can also sip a rare Belgian dubbel, delicate junmai sake or funky, fizzy natural wine on a regular old weeknight. While there, you might see some modern art or a joyous drag show, catch a live blues session, dance till you’re out of breath or simply relish the sight of a few friendly faces.

All that said, I balked at first when I was tasked with narrowing down Chicago’s 10 essential bars. How could I possibly do my hometown justice with so small a number?

Then I did what any good Chicagoan would do and hit the pavement—revisiting old haunts and checking off a few I had yet to visit or only been to once. I basked in the soothing sounds of jazz organ over a potent Old Fashioned at the iconic Green Mill. I sampled Trinidadian rum I’d never heard of at The Bamboo Room, the sexy bar within a tiki bar. I sipped an impeccable gin and yuzu koshō cocktail that tasted like the sea at pretty Kumiko. I reconnected with a beloved punk rock joint (and its serious whiskey collection) from my 20s and hugged the Duchess of Bridgeport, Maria Marszewski, in front of her namesake bar. Along the way, I fell in love with the city’s rich bar culture all over again (and might’ve taken a few liberties with the list).

Thus I present my woefully incomplete compendium of 11(ish) essential Chicago watering holes, slowly amassed in the nearly 20 years I’ve lived here—a mix of the seminal neighborhood joints that built us and those, new and old, that keep nudging us forward. No matter how fancy or timeworn the bar you sidled up to from this list, I promise you’ll always find a refreshing lack of pretense, and probably a bottle of Malört hiding somewhere.

Image Courtesy of The Violet Hour

The Violet Hour

Wicker Park

It’s hard to overstate the impact of this velvet curtain-cloaked bar on Chicago’s craft cocktail scene since bartending veteran Toby Maloney and One Off Hospitality debuted it 17 years ago in Wicker Park. The bar’s award-winning, pre-Prohibition drinks menu has spawned numerous copycats. Its alumni have since had a hand in the city’s most exciting beverage programs; not least of which, Abe Vucevich’s Meadowlark, is amassing accolades for playful cocktails that homage the flavors, culture and history of the Midwest behind an unmarked door. All this is not to relegate The Violet Hour into the static annals of history.

Creativity remains the engine behind this iconic bar, where bartenders pull from a vast, still-growing arsenal of spirits, tinctures and seasonings to delight our senses as we nestle into a high-backed banquette or post up at that elegant, mile-long marble bar. Consider bar manager Karli Sandos’s bright, wintery Dressed to the Pines, in which warming Cognac and rye whiskey join herbaceous Fernet and Braulio with puckering notes of lemon, hibiscus, pomegranate and piney rosemary. Like a frothy, holiday-flavored Lambrusco.

Fun fact: A pair of modern classic cocktails were born here: the refreshing, bittersweet Paper Plane (a Last Word riff created in 2007 by Sam Powers), and the also-bitter, rum- and cynar-based Art of Choke aperitif cocktail (created in 2008 by Kyle Davidson). Are you sensing a pattern, Malört lovers?

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Nine Bar

Chinatown

Until 2022, there had never been a dedicated cocktail bar in Chicago’s Chinatown. That summer, work and life partners Lily Wang (Estereo) and Joe Briglio (Blind Barber) took the reins at Moon Palace, the iconic Chinese restaurant and 50-plus-year neighborhood fixture owned by Wang’s parents, Zhong Pei “Jones” and Jennifer Wang. With an eye toward the already thriving neighborhood’s future, they downshifted Moon Palace into a permanent to-go operation and built a sultry bar where the dining room used to be, accessible through a heavy metal door by the carryout counter. Beneath “support your local Chinatown” signage and a neon-lit back bar, bar staff deftly mix cocktails that mingle Japanese, Chinese and tropical influences.

Take the superb, if dangerously drinkable, Nine Bar Mai Tai, with a blend of aged rums, persimmon liqueur, amaretto, almond cookie orgeat and citrus. Or the vanilla- and pithy, citrus-scented Neo Tokyo, with Japanese whiskey, bergamot liqueur, clementine and bracing lemongrass and ginger. Peeking into the kitchen, you may spot the technically retired Jones prepping his namesake “General Jones” wok-fried wings, a sticky, fiery, tangy must-order if you’re here before 8 pm. “I’m not sure if he will ever really ‘retire,’” Lily Wang tells me. It’s a family affair, after all.

Kumiko

West Loop

Even when Kumiko is packed to the gills, abuzz with lively chatter and clinking glassware—as Julia Momosé’s award-winning West Loop “dining bar” almost always is—there’s quiet intention behind each detail and hospitable gesture that soothes me every time I come. It’s a beautiful space, with blond woods and exposed brick aglow in soft, warm light.

Drawing on her Japanese-American heritage and a formidable collection of spirits, sake and shochu, Momosé presides over one of the city’s most impressive and thought-provoking cocktail menus. The zesty, quietly complex Sea Flower (gin, blanc vermouth de chambéry, brackish yuzu koshō, minty kabosu juice and lime) tastes like a gulp of fresh, salty sea air. The sultry Umé Boulevardier (whiskey, Italian bitter liqueur, uméshu and aromatized wine) betrays velvety stone fruit notes to soften its bitterness. Don’t sleep on the spiritfrees, which set the bar for NA drinks in Chicago.

Sophisticated drinking food includes oysters with charred shishito ponzu and karaage chicken with a guttural crunch. Or book ahead for the full pairing menu, in which you’ll wash down seasonal, Japanese-leaning dishes from Chefs Alex Ching and Josh Mummert, alongside a mind-opening range of sakes, cocktails or spiritfrees. However you experience this singular escape, you may well forget where you are altogether—till you step outside and hear the everpresent rumble of the El above.

Maria's Packaged Goods adn Community Bar — Image Courtesy of Maria’s Packaged Goods adn Community Bar

Maria’s Packaged Goods and Community Bar

Bridgeport

Maria’s is the sort of bar that wraps you in a hug the moment you walk in. That might also include a literal embrace from South Korea-born proprietor and namesake Maria Marszewski, who’s held court at this welcoming third place since she opened it in the old Kaplan’s Liquors space in 1987. The bar itself, with a tin-print ceiling, beer bottle chandeliers and a liquor store upfront, embodies the classic Chicago hybrid packaged goods joint and bar, even since her sons Mike and Ed Lumpen (owner of the superb Marz Community Brewing) rehabbed it in 2010, adding an extensive craft beer and cocktail selection and renaming the bar in her honor. There’s a prescriptively good house Corpse Reviver (gin, Cocchi Americano, cointreau, lemon and absinthe) and house Manhattan. However, my go-to order here is a classic Chicago Handshake, Old Style tallboy and a shot of Malört. Cheers to “Mom,” a.k.a. the Duchess of Bridgeport.

Some other essential neighborhood taverns: To overlook Chicago’s no-frills neighborhood joints when you’re in the Windy City is to do yourself a great disservice. Some of my favorite haunts include Rossi’s in River North, L & L Tavern (“the L&L) and Nisei Lounge in Lakeview, West Town’s Archie’s Iowa Rockwell Tavern (get the cheeseballs) and The Chip Inn, Miller’s Pub in the Loop, Simon’s Tavern and Carol’s Pub in Uptown, Logan Square’s Go Tavern & Liquors, Green Eye Lounge in Bucktown, Rainbo Club in Ukrainian Village, Pilsen’s Skylark, Cunneen’s Bar in Rogers Park and Old Town Ale House.

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Big Chicks

Uptown

Uptown’s beloved, cash-only gay bar is also a welcoming neighborhood joint of the highest order, thanks to proprietor Michelle Fire, who debuted the bar in 1986—at the terrifying height of the AIDS crisis. The place became a refuge, providing nourishing meals for free to those struggling with their finances and a place to connect and hold vigils. In the decades since, it has provided a safe haven for its queer neighbors when they need it and an easygoing third place to all. It has sponsored sports teams and held political fundraisers; hosted art and drag shows and too many raucous dance parties to count. It’s a place where life’s mundane and monumental moments unfold over a stiff, expertly made cocktail or two (I’m partial to their spritzes and mules, season be damned) against a backdrop of Fire’s formidable art collection, which plasters every free inch of wall space.

If you’ve overdone it just a tad, you can always drag yourself back here tomorrow for a fluffy omelet and Bloody Mary at Tweet, Big Chick’s excellent, sibling comfort food restaurant next door.

Delilah’s

Lincoln Park

I didn’t appreciate Delilah’s enough in my 20s. Wait, I take that back. I was too busy drinking $1 PBRs and $2 whiskey shots to appreciate what a singular and serious bar it was—and remains. Of course, Mike Miller’s 31-year-old punk rock bar will always be a no-frills third place to pop by for a (still) $1 Old Milwaukee, on Mondays, and a round of pool. It’s also quietly become one of the best spots in the country to nerd out on whiskey (1,000-odd bottles and climbing!) or beer (300-plus brews), not to mention a fast-growing collection of rum and agave spirits. Come here to sample rare Scotch releases straight from Islay or triple malt Danish whisky, to peruse rare art then dance your face off to hard country or revisit an oldie but goodie live Nirvana show on film.

Lately, I like bellying up at the bar and asking the bartender to make me a Manhattan with whatever whiskey they’re loving at the moment—perhaps a high-rye bourbon or gently smoky mesquite-filtered whiskey. Other times, I stop by simply because my feet led me here after dinner, for one more round in this city kid’s home away from home.

The Bamboo Room

Near North Side

A sexy 22 seater hidden within the ever-bustling tiki juggernaut Three Dots and a Dash, The Bamboo Room is the place to experience rum on a more intimate level. The bar is home to some 275 bottles from nearly every rum-producing country. Beverage director Kevin Beary’s current favorite? The Single Estate Series Release 02 from Mount Gay in Barbados. “This was a very surprising release,” he says. “For 100 percent pot still, it is a wonderfully balanced and enjoyable pour.”

Sip rum neat, in a flight or as a supporting actor in one of Beary’s seasonally shifting list of provocative, ingredient-focused cocktails. (I’m loving the smooth, vegetal Tomato Presidente, in which delicate Trinidadian white rum and grassy, funky rhum agricole from Martinique join white vermouth, pineapple, clarified tomato and strawberry and absinthe.) If you’re new to rum or this bar, Beary suggests starting with the Navy Grog, a remix on a potent classic that blends rare Trinidadian, Jamaican and Barbadian rums with bracing citrus, pimento dram and cane sugar. Don’t stand up too fast after drinking that one.

Hopleaf

Andersonville

Michael Roper’s 32-year-old Andersonville beer bar-turned-pub draws patrons from every corner of the city and beyond with excellent Belgian-style food, a deep list of European craft beers (68 on tap!) and a relaxed, convivial vibe owing partly to the absence of TVs. The bustling front room opens to an airy, two-story back dining area that could just as easily be situated in Brussels, Belgium. To that end, Hopleaf’s beer list rivals that of the best beer bars anywhere, but I stick to Belgium brews when I’m here: rich, complex Westmalle Dubbel and honeyed, funky De Garre Tripel.

If you’re hungry, there’s a top-notch brisket reuben sandwich; and, of course, the famous mussels steamed in wit beer (or rotating seasonal broth), served with phenomenal frites and aioli. In summer, you won’t find a prettier backyard patio, with leafy trees bedecked in twinkle lights—the sort of urban haven that encourages lingering till the sun slips down, immersed in good conversation and a damn good beer.

Another great beer bar: Map Room in Bucktown boasts 25 tap beers plus many more bottles. The best time to visit this cafe by day, bar by night is late in the afternoon, when neighborhood denizens quietly sip their choice brews as golden light pours in through the west-facing windows.

Easy Does It

Logan Square

As its name suggests, this part wine shop, part bar born at Covid’s height in August 2020 doesn’t take itself too seriously. And honestly, it’s about time a wine bar met that description. Co-owner Zach Eastman said it best in 2022, the year the second-floor bar debuted: “Part of making wine more casual is taking it outside of its usual confines of the dinner table or high-end restaurant and putting it next to a High Life or a Negroni. We set out to create a space that has something for everyone.”

Eastman and co-owner Blake Witman’s multifarious spot in the former home of late-night bar East Room does indeed. It can guide you toward a rad minimal-intervention bottle to go with dinner in the diminutive shop. It can pour you a crunchy Zin-Palomino rosé from California on its sprawling back patio, as you drink in every drop of Chicago summer. Or perhaps you don’t know or care much about wine, and simply want to shake your butt to the DJ all night, with a High Life or tart, melony orange wine in hand. If searching for the latter, head to the upstairs bar around 11 pm on a Saturday when the place comes alive like no wine bar before.

Green Mill Cocktail Lounge

Uptown

“Is the Green Mill a bar?” my friend (a restaurant critic no less!) asked me recently after I declared this historic Uptown—ahem—lounge an essential Chicago bar without a shadow of a doubt. I stand by this claim if only to reinforce the importance of taking in a show at this iconic, 89-year-old joint (purportedly loved by Al Capone), whether you’re passing through or you call Chicago home.

It’s cash only, and you won’t find any fussy egg white cocktails here, so the bar’s website deadpans, but rather high-octane Midwestern staples and unfussy, everyday beers like PBR and Bell’s Two Hearted IPA. Barkeeps are the unflappable sort to don “Be a Sport, Drink Malört” T-shirts; I wouldn’t suggest getting too persnickety with your order. Keep it simple (I like a Manhattan or sweet, bitters-heavy Old Fashioned); then scooch into a half-moon booth and drink in this legendary old place as the rich sounds of jazz and blues wash over you.

Pro tip: Every Friday night from 5 to 7 pm, Chicago’s best jazz organist, Chris Foreman, eases Green Mill patrons into the weekend with soulful, bluesy jazz from the likes of Duke Ellington and Nat King Cole, with a side of warm, pithy commentary. There’s no cover, but please tip generously.

The Whistler

Logan Square

Open since 2008 in Logan Square, managing partner Billy Helmkamp’s pioneering cocktail bar hides in plain sight behind a storefront gallery display on harried Milwaukee Avenue. Assuming you find it (I still walk by it by mistake on occasion), this tiny indie bar, gallery, music and performing arts venue will magnetize you with its pulsating creative energy and oft-changing menu of classic and modern cocktails. Said cocktails are near impossible to read, thanks to stubbornly low lighting that makes everyone look good. Maybe you want a fizzy, plummy Red Wine Supernova with vodka, red wine syrup, lemon, rosemary and soda water, or a rich, bittersweet Old Fashioned with wheated bourbon, Zucca Rabarbaro and Ramazzotti amaro. Like the drinks, the crowd and vibe vary, whether an electronic DJ set, poetry reading or jazz quintet takes the small stage. But fast forward to every Saturday at midnight, the thumping tunes won’t accommodate conversations below a shout and the line snaking down Milwaukee Ave. tells you that this is (still) the only place to be.

Close by and very worth drinking in:

Best Intentions: I don’t trust myself when I go to this aptly named Logan Square bar in the best way possible. Unflappable staff pour superb, inventive cocktails and solid wines alongside one of the city’s best burgers.

Queen Mary: This pretty, nautically-tinged boîte (i.e. nightclub) in nearby Wicker Park makes a killer Martini, and houses an impressive offering of gin, rum and fortified wines. I like to sip red vermouth while perched with a friend at the end of the peninsula-style bar, which allows seating on both sides.

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