The Best Speakeasy Bars in Chicago

A hidden gem in Little Village, Osito’s Tap blends speakeasy vibes with Latinx flair, offering craft cocktails, rare spirits, and a cozy, historic setting.

Hidden beneath the Green Door Tavern, The Drifter is a vintage speakeasy offering tarot card-inspired cocktails and eclectic live performances in an intimate, Prohibition-era setting.

Descend into The Office, The Aviary’s clandestine speakeasy—only 21 seats, vintage-inspired cocktails crafted with precision, and a rich whisky collection. It’s Chicago cocktail culture distilled into a cozy, exclusive hideaway.

Hidden beneath River North, this speakeasy-style tiki bar offers exotic cocktails, vibrant décor, and an immersive tropical escape in the heart of Chicago.

A clandestine tiki‑tropics speakeasy tucked away down a River North alley—an intimate 22‑seat rum haven where rare bottles, expert bartending, and refined daiquiris take center stage.

Hidden behind a record-shop façade in Wicker Park, Dorian’s is a sleek cocktail lounge & live-music speakeasy where vinyl DJs spin and crafted drinks flow into the early hours.

A hidden-gem cocktail lounge in the Gold Coast with 1920s art-deco vibes, sultry lighting, and a rum-heavy menu that transports you straight to a vintage Havana-era speakeasy.

Enter the roaring ’20s at The Gatsby Speakeasy — a hidden book-case door, candlelit library vibe, bespoke cocktails and jazz in Chicago’s Lincoln Park.

Hidden behind a blank bird sign, Meadowlark is Logan Square’s moody cocktail den: vintage bricks, leather couches, rotating themed menus, and intimate vibes for serious drinkers.

Gilt Bar is a moody River North hideaway — dim lights, a gilded bar, craft cocktails and hearty American fare in a speakeasy-style setting. Perfect for a date night, late dinner or cocktail-focused evening.

Descend into the basement lounge of The Hoxton and step into Lazy Bird — a moody, music-filled cocktail hideaway where classic drinks, plush seating, and soulful live sets make every night feel like a secret soirée.