The 49 Best Cocktail Bars in Chicago

Julia Momosé's Japanese-inspired dining bar on West Lake holds a James Beard Award for Outstanding Bar and the Spirited Awards title for World's Best Bar, which tells you something before you've even sat down. Staff in sharp black uniforms somehow manage to feel genuinely warm rather than stiff, and the tasting menu now matches the cocktail program's precision, leaning into Japanese flavors and technique. Come for the drinks, stay through dinner, and plan to linger longer than you intended.

1. The Pinnacle Guide 3 Pins
2. Spirited Awards 2025 · Winner · World’s Best Bar
3. James Beard Awards 2025 · Winner · Outstanding Bar

1. VinePair Food & Beverage Program of the Year · The Next Wave Awards
2. The Pinnacle Guide 1 Pin
3. The 50 #27 · North America's 50 Best Bars

1. The 50 #16 · North America's 50 Best Bars
2. Spirited Awards 2025 · Top 4 Finalist · Best U.S. Bar Team
3. Spirited Awards 2025 · Top 4 Finalist · Best U.S. Cocktail Bar

1. Bon Appétit America's Best New Bars
2. The 50 #76 · North America's 50 Best Bars
3. Esquire The Best Bars in America

Velvet booths, globe lights, and wallpaper that belongs in a Left Bank salon set the mood at this Fulton Market cocktail bar, one of the few standalone drinking spots on a street that is otherwise all restaurants. The Paris-in-the-sixties premise runs through everything: French wines, classic martinis, caviar with chips. Named to North America's 50 Best Bars and a James Beard semifinalist, Bisous earns its kisses.

1. The 50 #30 · North America's 50 Best Bars
2. Esquire The Best Bars in America
3. The Banchets Winner · Bar of the Year

1. The 50 #65 · North America's 50 Best Bars
2. Esquire The Best Bars in America
3. The Infatuation The Best Cocktail Bars In Chicago

1. The 50 #80 · North America's 50 Best Bars
2. Esquire Martini Service · The Best Martinis in America
3. Esquire Market Price Martini · The Best Martinis in America

Two buildings knocked into one give Scofflaw two distinct personalities: an industrial front room with the bar counter, and a Victorian-ish back room with wingback armchairs that somehow doesn't feel ironic. It's a gin-focused cocktail bar in Logan Square that also leans dive, with craft beer and pub grub to prove it. Expect a line on weekends; they don't take reservations, and forty minutes is a reasonable opening bid.

1. Difford's Guide 4.5 stars · Difford's Guide
2. Wildsam The 50 Most Essential Bars in America
3. The Infatuation The Best Cocktail Bars In Chicago

The menu at this Bucktown coffee and cocktail bar is split in two: morning drinks for one crowd, evening drinks for another, with cold brew threading through both halves. The food runs from pizza bagels to caviar, which tells you something about the room's sense of humor. A James Beard semifinalist for Best New Bar in 2025, Truce has figured out that the best argument for staying all day is not having to change venues.

1. Eater Best New Bar
2. James Beard Awards 2025 · Semifinalist · Best New Bar
3. The 50 The 50 Discovery

1. The Infatuation The Best Cocktail Bars In Chicago
2. Eater Chicago’s Best Speakeasies and Secret Bars
3. Spirited Awards 2023 · Regional Honoree · Best U.S. Hotel Bar – U.S. Central

You find this tiki bar by following strangers down a narrow alley off Clark Street, which is either a great sign or a terrible one depending on your instincts. A staircase descends under a wall of skulls into a big, dim basement decked out in modern tiki grandeur. The drinks are serious and the room knows it. Difford's Guide gives it five stars, and the wait on weekends is its own kind of endorsement.

1. Difford's Guide 5 stars · Difford's Guide
2. The Infatuation The Best Cocktail Bars In Chicago
3. The 50 The 50 Discovery

1. The 50 One to Watch Award
2. Spirited Awards 2025 · Regional Top 10 Honoree · Best U.S. Bar Team – U.S. Central
3. Spirited Awards 2025 · Regional Top 10 Honoree · Best U.S. Cocktail Bar – U.S. Central

The Art Deco bones of this Gold Coast lobby bar date back to the Jazz Age, and the cocktail program leans into that: Cuban classics and Caribbean-inflected originals served under ornate ceilings that most bars would kill for. Sparrow calls itself a neighborhood bar, which is technically true, though the neighbors here wear better shoes than most. A named honoree at the Spirited Awards, it draws people in from well outside the Gold Coast.

1. The Infatuation The Best Cocktail Bars In Chicago
2. The 50 The 50 Discovery
3. Spirited Awards 2023 · Regional Honoree · Best U.S. Cocktail Bar – U.S. Central

1. The Infatuation The Best Cocktail Bars In Chicago
2. Eater Chicago’s Best Speakeasies and Secret Bars

1. The Infatuation The Best Cocktail Bars In Chicago
2. Eater Chicago’s Best Speakeasies and Secret Bars

Taxidermy on the walls, an Art Deco bar, and big comfy booths: Sportsman's Club is a neighborhood tavern that looks like it's been on Western Ave forever but drinks like something that arrived much more recently. The rotating menu leans spirit-forward and serious, even if the vibe emphatically does not. It's the kind of place that made this particular Chicago formula feel worth copying.

1. The 50 The 50 Discovery
2. Spirited Awards 2023 · Regional Honoree · Best U.S. Cocktail Bar – U.S. Central
3. Spirited Awards 2026 · Regional Top 10 Honoree · Best U.S. Cocktail Bar – U.S. Central

1. The 50 The 50 Discovery
2. Spirited Awards 2024 · Regional Honoree · Best U.S. Cocktail Bar – U.S. Central
3. Spirited Awards 2026 · Regional Top 10 Honoree · Best U.S. Bar Team – U.S. Central

1. The 50 The 50 Discovery
2. Spirited Awards 2026 · Regional Top 10 Honoree · Best U.S. Cocktail Bar – U.S. Central
3. Spirited Awards 2023 · Regional Honoree · Best U.S. Bar Team – U.S. Central

1. Spirited Awards 2026 · Regional Top 10 Honoree · Best New U.S. Cocktail Bar – U.S. Central

1. Spirited Awards 2025 · Regional Top 10 Honoree · Best New U.S. Cocktail Bar – U.S. Central

1. Spirited Awards 2026 · Regional Top 10 Honoree · Best New U.S. Cocktail Bar – U.S. Central

1. Spirited Awards 2026 · Regional Top 10 Honoree · Best New U.S. Cocktail Bar – U.S. Central

1. Spirited Awards 2026 · Regional Top 10 Honoree · Best U.S. Restaurant Bar – U.S. Central

1. Difford's Guide 5 stars · Difford's Guide

1. Spirited Awards 2024 · Regional Honoree · Best New U.S. Cocktail Bar – U.S. Central

The back bar holds what might be the most bewildering collection of vintage Italian Fernet you'll encounter outside of Milan. Billy Sunday is a polished amaro and cocktail bar in Logan Square, narrow and dark-wooded, with green walls and vintage lamps that suggest a gentlemen's club that loosened up considerably. The bar stools fill early with people who know their bitter spirits, and the classically built cocktails give them good reason to stay.

1. Difford's Guide 4.5 stars · Difford's Guide
2. The Infatuation The Best Cocktail Bars In Chicago
3. The 50 The 50 Discovery

1. The Infatuation The Best Cocktail Bars In Chicago

1. The Infatuation The Best Cocktail Bars In Chicago

1. James Beard Awards 2022 · Nominee · Outstanding Bar Program
2. The Infatuation The Best Cocktail Bars In Chicago
3. The 50 The 50 Discovery

Tucked into a historic greystone next door to Moreno's Liquors, a southside family institution, Osito's Tap is a neighborhood cocktail bar where the drinks lean hard into Latin American classics, agave spirits, and Micheladas done right. The connection to the liquor store isn't just sentimental; the spirits selection reflects it. Low-key enough that you might walk past it, specific enough that regulars don't want you to find it.

1. The Infatuation The Best Cocktail Bars In Chicago
2. The 50 The 50 Discovery

Parachute HiFi is a Korean listening bar from the Parachute team, built for people who'd rather hear a record than their own thoughts. Vinyl spins while the menu runs street-food mashups, like a burger drowned in Comté fondue and tteokbokki in a pad Thai situation, alongside cocktails. It's casual and dressy-ish in the way a good record collection is, and it takes reservations but still keeps room for walk-ins.

1. James Beard Awards 2022 · Nominee · Outstanding Restaurant
2. The Infatuation The Best Cocktail Bars In Chicago
3. Eater Chicago’s Best Korean Restaurants

1. Midwest Living 2023 · Best of the Midwest
2. Difford's Guide 3.5 stars · Difford's Guide
3. The Infatuation The Best Cocktail Bars In Chicago

1. The Infatuation The Best Cocktail Bars In Chicago

The ground floor runs dark wood and dim light, with a long bar and clandestine booths; upstairs it's velvet couches and armchairs, like someone's very well-stocked living room. This Lincoln Avenue cocktail bar leans into an old-time saloon feel without making it a costume, pulling sixty-plus classics-leaning drinks organized by spirit and style. The Harry Johnson-style etchings on the menu are either charming or insufferable, depending on your mood.

1. Difford's Guide 4.5 stars · Difford's Guide

1. Eater Chicago’s Best Speakeasies and Secret Bars

1. Eater Chicago’s Best Speakeasies and Secret Bars

1. Eater Chicago’s Best Speakeasies and Secret Bars

1. Eater Chicago’s Best Speakeasies and Secret Bars

1. Eater Chicago’s Best Speakeasies and Secret Bars

1. Eater Chicago’s Best Speakeasies and Secret Bars

The bar is in the basement, which is the point. The Drifter is a tiny subterranean cocktail lounge tucked beneath the Green Door Tavern, a speakeasy in the old sense of the word, not just the aesthetic. Low ceilings, dim light, and the general feeling that you've wandered somewhere you weren't supposed to find. The kind of place where a well-made drink tastes better simply because you had to descend a staircase to get it.

1. Difford's Guide 4 stars · Difford's Guide
2. Eater Chicago’s Best Speakeasies and Secret Bars

1. Eater Chicago’s Best Speakeasies and Secret Bars

1. Eater Chicago’s Best Speakeasies and Secret Bars

1. Eater Chicago’s Best Speakeasies and Secret Bars

1. Eater Chicago’s Best Speakeasies and Secret Bars

1. Difford's Guide 4 stars · Difford's Guide

1. Spirited Awards 2023 · Regional Honoree · Best U.S. Cocktail Bar – U.S. Central

By day it pulls coffee; by night the Latin-American vintage vinyl goes on and the mezcal comes out. Estereo is an agave bar on Milwaukee Avenue where the cocktail list is organized by spirit category and the drinks lean toward the unexpected, think cold-brew tea and shochu sharing a glass with pisco. The crowd tends to find it on the younger, cooler end of Logan Square, which is saying something in that neighborhood.

1. The 50 The 50 Discovery
2. Spirited Awards 2023 · Regional Honoree · Best U.S. Cocktail Bar – U.S. Central

You ride a repurposed service elevator to reach this speakeasy-inspired rooftop cocktail bar perched atop the Rafaello Hotel. Dim lighting, dark wood, bronze fixtures, and mushroom-toned walls set a moody, upscale tone, and a resident DJ keeps the energy pointed firmly toward party. The crowd skews young and loud, so if you're after a quiet drink and a view, the elevator goes both ways.

1. Difford's Guide 3.5 stars · Difford's Guide