Discover Chicago's Most Interesting Bars

Experience the Windy City's stunning architecture, lakefront parks, and renowned food scene

$$$$

The Drifter

676 N Orleans St Chicago, IL 60654 United States

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.

$$$$

tiki

speakeasy

Three Dots and a Dash

435 N Clark St (Entrance in the alley) Chicago, IL 60654 United States

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

$$$$

Craft Beer

Speakeasy

Cocktails

Osito’s Tap

2553 S. Ridgeway Avenue Chicago, IL 60623

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.

$$$$

Cocktails

Fancy

Experience

The Aviary

955 W Fulton Market, Chicago, IL 60607, USA

A cocktail laboratory by Grant Achatz, The Aviary redefines mixology with theatrical presentations, molecular techniques, and a kitchen-style bar experience in Chicago’s West Loop.

Know an Interesting Bar?

Help us grow our collection by submitting your favorite bars. Share the unique spots that make your city special.