River North isn’t just restaurants and rooftops. Beneath the surface lies a network of speakeasies so fun you’ll forget time (and maybe your Uber password 🤫). Here’s the ultimate local’s crawl — colorful drinks, quirky vibes, and insider doors you’d never think to open.

🔮 The Drifter

Hidden under the historic Green Door Tavern, this is as close as Chicago gets to a real Prohibition speakeasy. Tarot-card drink menus, surprise live acts, and serious “secret society” vibes.

• 📍 Address: 676-8 N Orleans St, Chicago, IL 60654
• 🚪 How to find it: Enter Green Door Tavern → past the restrooms → knock on the bookcase (yes, really).
• 🍹 Must-try: Let a tarot card decide your cocktail fate.
• 💘 Best for: Date nights and small groups who love surprises.

🎭 Untitled Supper Club

A sprawling underground supper club with multiple rooms — dining, a vintage-film library, and a performance lounge. Dramatic, glamorous, and totally cinematic. 🍿

• 📍 Address: 111 W Kinzie St, Chicago, IL 60654
• 🚪 How to find it: The entrance is discreet — look for the quiet line or faint music.
• 🥃 Must-try: A stirred whiskey classic to match the Art Deco glow.
• 🎤 Best for: Dinner, drinks, and a show without venue-hopping.

🌺 Three Dots and a Dash

Skull-lined stairway ✔️. Tiki mugs ✔️. Rum paradise ✔️. A hidden island escape you enter from a Chicago alley. Bring your crew — this one’s pure fun.

• 📍 Address: 435 N Clark St (alley entrance off Hubbard), Chicago, IL 60654
• 🚪 How to find it: Slip into the alley just off Hubbard, then follow the glowing skull staircase 💀.
• 🍹 Must-try: A shareable tiki bowl (umbrella included).
• 🎉 Best for: Birthdays, bachelorettes, and vacation energy.

💃 Lulu’s Speakeasy

Beneath Storyville, Lulu’s leans into moody lighting, DJ nights, and late-night mischief. It’s the after-party you didn’t know you needed.

• 📍 Address: 712 N Clark St (inside Storyville), Chicago, IL 60654
• 🚪 How to find it: Enter Storyville and confidently ask for “Lulu’s.” 😉
• 🍸 Must-try: A seasonal special — playful & potent.
• 🕺 Best for: Dancing, mingling, and letting the night take over.

🎷 The Bassment

A live-music cocktail lounge tucked below The Hampton Social. Think secret entrance, luxe gold accents, and bands that keep the room buzzing.

• 📍 Address: 353 W Hubbard St, Lower Level, Chicago, IL 60654
• 🚪 How to find it: Enter via the “Tobacconist”-style secret door and head downstairs — you’re in the right place when the bassline finds you.
• 🍸 Must-try: A house cocktail before the band hits the stage.
• 🎺 Best for: Live-music lovers who still want craft drinks and a speakeasy glow.

💡 Pro Tips for Your Crawl

1. 📅 Weeknights win: Smaller crowds = more magic.
2. 🛑 Sip slow: These cocktails are sneaky strong.
3. 🚖 Plan your ride: Walking works, but a black car feels on-theme.
4. 📸 Keep it mysterious: Low-light pics, no flash. 😉