The Ultimate Guide to Negronis in Chicago

Chicago does Negronis the way it does winter and hot-dogs; Head on, unflinching and unapologetically in its own way.

Bitter is a flavour here, not a warning. Cross the river, steam rising from the grates, and slip into rooms where bartenders stir by instinct and garnishes mean something. Order the house Negroni and let the city square its shoulders.

Acanto

An Italian soul staring down the Art Institute lions. The Negroni Classico does the canon proud: Sipsmith, Cocchi Storico, Campari, orange twist. Cold, taut, elegantly bitter, the page‑one pour that reminds you posture matters and patience is rewarded.

Adorn Bar & Restaurant

Globally curious with Midwestern calm. Their riff, “If a Negroni Practiced Aromatherapy,” layers palo santo, vetiver and pink peppercorn over Tanqueray, Campari and vermouth. It reads spa day, drinks velvet hammer, scented, serious, and unashamedly adult.

Coco Pazzo

White tablecloths and Italian confidence. Order the Negroni Sbagliato, Campari, sweet vermouth, prosecco, and let the bubbles turn the edges soft. A lift instead of a shove, built for long dinners and better stories.

Coda di Volpe

Southern Italy with a Chicago grin. The white‑grapefruit Negroni threads gin, Lillet blanc and Pamplemousse through a kiss of Malört, a local dialect of bitterness that somehow feels like affection. Floral, sharp, unforgettable.

Fig & Olive

Two lanes, same highway. The Noir Café folds coffee‑bean–infused Campari, Punt e Mes, Diplomático rum, Chartreuse and chocolate bitters into a midnight Negroni built for late conversations.
The Rush St. Negroni, Stray Dog Gin, Gentian Amaro, Italicus, Giffard Apricot, is brighter, citrusy, and sly. Choose your trouble.

Hawksmoor

Steakhouse swagger, British sleeves rolled up. The Sour Cherry Negroni (Fords gin, Campari, Martini Rubino, tart cherry) is fruit‑forward without flinching, a big pour for a big room, built to stand next to ribeye.

Rosebud

A city institution pouring a straight‑shooting classic, Tanqueray, Campari, sweet vermouth, orange slice. Old‑school Italian, no apologies; the cocktail that cuts through a plate of red sauce like purpose.

Torali at The Ritz‑Carlton

Tailored skyline swagger. The house Negroni Rosato, Aviation Gin, Balsam Rose Vermouth, Peychaud’s Aperitivo, flamed orange, is floral and poised, like a suit that finally fits. Sip it slow and watch Michigan Avenue glitter.

Château Carbide

An indoor‑outdoor rooftop with a French lilt. The Ichigroni (Sipsmith Strawberry Smash, Carpano Antica, Campari, freeze‑dried strawberries) sounds playful and drinks precise, a sunshine Negroni with charity stitched into the receipt.

Bar Roma

Warm, lively, properly Italian. Go classic or try the Blonde Negroni (City of London Gin, Cocchi Americano, Dolin Dry) strips out the scarlet without losing the spine. Pair with braised beef cheek meatballs and good company; leave happier.

Billy Sunday

Vintage spirits on the shelves, brains behind the stick. Rotate with the Negroni of the Week or grab the bottled house unconventionally using aged Old Tom. Cocktail geekery with a grin, the lecture notes got edited down to the good parts.

“If you’re bored of Negronis, you’re drinking with the wrong people.”

SPEAKEASY APPENDIX

I couldn’t cover Chicago, home of prohibition, home of Capone, without highlighting some of the city’s Speakeasies

The Drifter (under Green Door Tavern)

Down the stairs at the back of the Tavern, through a fake shelf door behind a bathroom sign, you slip into another century. The Drifter’s got legit Prohibition bones, flag-draped walls, flickering lights, and a stage barely big enough for one dreamer with a guitar. At 6:30, the horn blares, the chatter dies, and time folds in on itself. Order from the tarot-card deck, maybe the chocolate Negroni if fate deals it, and toast the floorboards. Every drink tastes like a secret whispered underground.

The Milk Room (Chicago Athletic Association)

Eight vintage seats. No more. No less. The Milk Room isn’t so much a bar, more a vault for people who know their way around a glass. Hidden behind stained glass doors on the second floor of the Chicago Athletic Association, it feels like Prohibition never ended; dark wood, low light, and bottles older than your bartender. The spirits here are rare, the pours deliberate, the price unapologetic. Every cocktail lands with the weight of its history, layered, evolving, and dangerous in its simplicity. The bartender knows your name before you finish your prosecco welcome pour, and by the second drink, you’ve forgotten there’s a world outside. Expensive? Yes. But in a city that built its legend on excess and smoke, some things are worth the tab.

The Office (below The Aviary)

Behind a locked door under The Aviary’s gleaming chaos, The Office waits, a speakeasy the size of a confession booth and twice as honest. Twenty-one seats, two bartenders, and no menu. You talk, they listen. Maybe you whisper bourbon, smoke, something clean, and they build it from memory and instinct, using spirits old enough to have seen a war or two. Say ‘Dealer’s Choice’ and let them tailor the Negroni to your exact bitterness. The story goes the room was once an actual office, a forgotten closet on the blueprints until Grant Achatz decided to fill it with secrets and cocktails instead of filing cabinets. Inside, it’s hushed, reverent, lit like a jazz record sounds. Every pour feels personal, every sip a small act of faith. In a city of noise and ego, The Office reminds you what discretion tastes like.

Nine Bar (behind Moon Palace)

Slip past the bustle of Moon Palace and through the back door, and suddenly Chinatown flickers into a different frequency. Nine Bar hums like a Tokyo side street, neon glow, Blade Runner haze, the bass line of a DJ tucked beneath a canopy of umbrellas. Lily Wang and Joe Briglio built it as an “Asian-ish” cocktail club, but that undersells the attitude. This is Chinatown reimagined through a cosmic lens: Midori meets mezcal, plum wine tangles with lemongrass, and a whisper of Sichuan pepper keeps things honest. Order the tight, classic Negroni, bitter, balanced, unapologetic, then drift toward the McKatsu sandwich or the Ma Po Hot Fries if you need ballast. The crowd is young, the energy contagious, and the cocktails have that rare combination of precision and mischief. It’s not a bar you find, it’s one that finds you, glowing from the alley like a secret in electric red.

Golden Teardrops (beneath Lonesome Rose)

Down a back stair and through an unmarked door, Golden Teardrops glows like a secret you weren’t supposed to hear. The neon says WEDDINGS & FUNERALS, and the whole place leans into that contradiction. It’s the kind of bar where silence hums and time folds in on itself. Just candles, gold-threaded mirrors, and the faint echo of a Flamingos song looping in your head.

The Negronis are sharp and deliberate, spirit-forward, no frills, high-proof masterpieces that punch clean and linger like regret. A menu that changes with the season, but the soul never shifts. The team behind Longman & Eagle and Milk Room knows what they’re doing, this is the place you go to feel something, even if you can’t name it.

Gatsby (inside Bourgeois Pig)

Tucked above The Bourgeois Pig in Lincoln Park, The Gatsby isn’t nostalgia, it’s resurrection. A block from where Dillinger was shot, the place hums with ghosts and good bourbon. Wax candles, velvet sofas, and a bar carved in Naples before Capone ever drew breath. The chandeliers sweat light, the jazz leans low, and that speakeasy door you’re stepping through? Dillinger walked it first. Welcome to Chicago, kid.

The Library (beneath Gilt Bar)

Slip through the side door and descend into The Library, and Chicago exhales into a softer, slower rhythm. It’s the kind of basement that feels like a secret you earned, all velvet booths, low chandeliers, and candlelight that burns with the patience of an old soul. The upstairs Gilt Bar might be the headline act, but down here, the story deepens. Whiskey sours come frothy and perfect, Negronis land sharp and cold, and the air hums with Sinatra, gossip, and maybe a little trouble.

The walls bleed crimson under vintage oil paintings; the lighting flatters everyone. You half expect a dame in a red dress to lean over and tell you something that’ll change your life. It’s got that noir pull, the kind that makes you wish you’d brought a notebook, or at least a good alibi, a little cinematic time warp that proves the best rooms in Chicago still hide underground.

The Alderman (inside Pilsen Yards)

Slip behind the wall at Pilsen Yards and you’ll find The Alderman, sixteen seats, a velvet banquette, and the kind of hush that feels earned. This isn’t a bar you stumble into; it’s one you’re invited to, a dim little theatre where the cocktails play the lead. Winner of the 2022 Jean Banchet Award for Best Bar, it trades flash for precision, every pour measured, every garnish intentional.

The drinks riff on American classics, a Manhattan tuned low, an Old Fashioned sharpened just right and rotate with the seasons, but the negroni is a constant as if they dare not start a family war by cancelling it. The room itself glows ink-black and intimate, equal parts mystery and midwestern charm. It’s the kind of place you go when you’re not done with the night but ready to stop pretending otherwise.

The Rose Lounge (beneath Adalina)

Take the golden elevator down and the world above drops away, noise, neon, the whole performance of the Gold Coast. What waits below is softer, slower: The Rose Lounge, Adalina’s secret bloom of candlelight and velvet. The bar curves in a horseshoe, all dark marble and murmured conversation, the air perfumed with walnut bitters and good intentions.

This is where the night exhales. The cocktails are refined but unpretentious. The chandeliers throw a low, flattering light, and the floral art feels less decorative than devotional. It’s not big, reservations are tight, conversations closer. Down here, beneath the glitter of the city, The Rose Lounge reminds you that luxury isn’t loud, it’s whispered, one perfect drink at a time.

Brando’s Speakeasy

Slip through the doors of the Fisher Building and into Brando’s, Chicago’s longest-running secret that everyone somehow knows. It’s part karaoke bar, part fever dream, dressed in vintage swagger and humming with the ghosts of the Roaring Twenties. You can still feel the Prohibition bones under the neon.

Since 2007, Brando’s has been where bad days go to die and good nights get louder. The crowd’s a glorious mix, tourists, locals, off-duty bartenders, and the brave souls who think Sinatra’s “My Way” is still unclaimed territory.

Stars have sung here, George Lucas, Cuba Gooding Jnr, and the entire cast of Jersey Boys, but it’s the regulars who own the room, crooning into the early hours like it’s their last call on Earth. Brando’s isn’t about perfection; it’s about participation. Order a drink, grab a mic, and remember: in this city, even the shy ones eventually sing. The Negroni is honest; the mic is inevitable.

Booze Box (below Sushi Dokku)

Down a back-alley stairwell under SushiDOKKU, past what looks suspiciously like a maintenance door, you drop into Tokyo after dark. The beats are low and smooth, the room glows red, and the air smells faintly of soy and sake. It’s small, just enough bar, a few booths tucked into shadow.

This is a place for night owls and insomniac romantics, for those who’d rather sip cocktails or Japanese whisky than shout over a DJ set. The staff pour with precision, the sashimi arrives like art, and the regulars all seem to know each other by nod. Get there early, by 7pm it’s standing room only, or do the smart thing and reserve.

The Bassment (beneath The Hampton Social)

Music lounge under The Hampton Social; part Speakeasy, part full-blown secret party. Hidden behind an unmarked door and down a stairwell that looks like it might lead to storage, it’s Chicago’s only true underground dance den, equal parts prohibition fantasy and rock-and-roll fever dream.

Once inside, the space hits you like a bass line, low ceilings, gold accents, plush leather, and a stage that hums with live music instead of the usual DJ churn, sliding from funk to soul to full-tilt rock like they’re reading the crowd’s pulse. Drinks are polished but potent, the negroni as punch as the bass you feel.

Chicago doesn’t coddle you. It hands you a heavy glass, a big cube, and a colour that looks like a stoplight you chose to ignore. In return, you get clarity, the bite, the bloom, the sigh after the second sip. Whether you’re in a glitzy rooftop bar or a hidden underground speakeasy, the contract is the same: you bring the night; the Negroni brings the honesty.

If New York’s Negroni is a wink, Chicago’s is a stare. Either way, bottom of the glass comes too fast.