Hidden Flapper Speakeasies Of Chicago’s Underground

Ever wondered where the flappers of the 1920s went to dance the night away in Chicago? The city, known for its rich history and vibrant culture, hides a secret past filled with speakeasies and underground jazz clubs. During Prohibition, these hidden gems became the heartbeat of Chicago's nightlife, offering a haven for those seeking music, dance, and a good time. Today, many of these historic spots still exist, offering a glimpse into a bygone era. Whether you're a history buff or just looking for a unique night out, exploring Chicago's hidden speakeasies will transport you back to the roaring twenties. Ready to step into the past? Let's uncover the secrets of Chicago's underground scene.

The Allure of Chicago's Hidden Speakeasies

Chicago's underground speakeasies offer a glimpse into the city's Prohibition-era past. These hidden gems transport visitors back to the 1920s, where jazz music, secret passwords, and clandestine cocktails reigned supreme. Let's uncover some of the best-kept secrets of Chicago's nightlife.

Secret Entrances and Hidden Doors

Finding these speakeasies often requires a bit of sleuthing. Many are tucked away behind unmarked doors or hidden within other establishments. Here are some of the most intriguing spots.

1. The Violet Hour

   • Located in Wicker Park, this speakeasy is hidden behind an unmarked door. Once inside, you'll find plush seating, dim lighting, and expertly crafted cocktails.

2. The Drifter

   • Beneath the Green Door Tavern lies The Drifter, a speakeasy with a rotating cocktail menu and live performances. The entrance is through a trap door behind the bar.

3. The Office

   • Hidden below The Aviary in the West Loop, The Office offers an exclusive, reservation-only experience. The intimate setting and bespoke cocktails make it a must-visit.

Jazz and Live Music

Music played a significant role in the speakeasy experience. Many of Chicago's hidden bars continue this tradition with live jazz and other performances. Here are a few places where you can enjoy great tunes.

4. The Green Mill Cocktail Lounge

   • This Uptown gem has been around since the Prohibition era. Known for its live jazz performances, The Green Mill offers a nostalgic trip back in time.

5. Untitled Supper Club

   • Located in River North, Untitled Supper Club features live music, burlesque shows, and an extensive whiskey collection. The entrance is discreet, adding to the speakeasy vibe.

6. The Bassment

   • Found in River North, The Bassment is a speakeasy-style bar with live music and a cozy, underground atmosphere. The entrance is hidden behind a nondescript door.

Unique Cocktails and Ambiance

The charm of a speakeasy isn't just in its secrecy but also in its unique cocktails and ambiance. These spots offer both in spades.

7. Three Dots and a Dash

   • This tiki-themed speakeasy in River North is hidden down an alley and through a back door. The tropical cocktails and vibrant decor make it a standout.

8. The Violet Hour

   • Mentioned earlier for its secret entrance, The Violet Hour also boasts an impressive cocktail menu and a sophisticated, candlelit ambiance.

9. The Berkshire Room

   • Located in the ACME Hotel, The Berkshire Room offers a speakeasy feel with its craft cocktails and vintage decor. The entrance is through the hotel's lobby.

Hidden Gems with Historical Significance

Some speakeasies have a rich history that adds to their allure. These spots offer a blend of historical significance and modern-day charm.

10. The Green Door Tavern

    • Above The Drifter, The Green Door Tavern itself is a piece of history. Established in 1921, it has retained much of its original charm and character.

11. The Violet Hour

    • This speakeasy not only offers a hidden entrance and unique cocktails but also has a historical connection to the Prohibition era, making it a must-visit for history buffs.

12. The Library at Gilt Bar

    • Hidden within Gilt Bar, The Library offers a cozy, book-lined setting reminiscent of a bygone era. The intimate space and classic cocktails make it a perfect speakeasy experience.

Discovering Chicago's Hidden Flapper Speakeasies

Exploring Chicago's hidden flapper speakeasies offers a unique glimpse into the city's vibrant past. These secret bars, once the heart of the Roaring Twenties, still echo with the jazz music and lively spirit of that era. Visiting these spots isn't just about enjoying a drink; it's about stepping back in time to experience a piece of history.

Whether you're a history buff or just looking for a unique night out, these speakeasies provide an unforgettable experience. From the hidden entrances to the vintage decor, every detail transports you to a different time. So next time you're in Chicago, make sure to seek out these hidden gems. They offer more than just a good time; they offer a chance to connect with the past in a way that's both fun and educational.