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Discover the Best Trendy Speakeasies in Chicago Now

If you’re someone who loves secret doors, vintage vibes, and unique cocktails, then trendy speakeasies in Chicago are exactly what you need to experience. These hidden bars bring the charm of the 1920s to modern times, offering guests not only great drinks but also an unforgettable atmosphere.

In a city rich in Prohibition-era history, Chicago has embraced the speakeasy culture with a modern twist. Many of these bars are tucked away behind unmarked doors, inside restaurants, or beneath the streets. Whether you’re a local or a visitor, finding and experiencing these speakeasies can be a fun, immersive adventure.

Let’s dive into the most talked-about and must-visit trendy speakeasies in Chicago, complete with insider tips on how to find them.

1. The Violet Hour – A Stylish Hideaway in Wicker Park

Focus Keyword Used: Trendy Speakeasies in Chicago

Located in the heart of Wicker Park, The Violet Hour is a modern take on the classic speakeasy. The exterior is intentionally plain — just a painted wall that changes regularly. But once you find the hidden door and step inside, you’ll be greeted by a cozy, candlelit room with high-backed chairs and elegant cocktails.

What Makes It Special:

Award-winning cocktails with a focus on fresh, seasonal ingredients.
A strict “no phones, no hats” policy for a more intimate vibe.
Weekly rotating menu for cocktail lovers.

📍 Address: 1520 N Damen Ave, Chicago, IL 60622
🕒 Hours: 5 PM–1 AM (Sun–Thurs), 5 PM–2 AM (Fri–Sat)

2. Three Dots and a Dash – A Hidden Tiki Treasure

This tropical-themed speakeasy is tucked behind an alleyway in River North. You won’t find a big sign — just look for the small blue light in the alley next to Clark Street. Once inside, you’ll feel like you’re on a beach vacation with rum-based drinks, Polynesian decor, and bamboo booths.

Highlights:

Known for creative and colorful tiki drinks served in unique mugs.
Great for groups or date nights.
Excellent small plate menu with tropical flavors.

📍 Address: 435 N Clark St, Chicago, IL 60654
🕒 Hours: 4 PM–12 AM (Sun–Thurs), 4 PM–2 AM (Fri–Sat)

3. The Office – The Ultimate Secret Experience

Located below The Aviary (a well-known cocktail bar), The Office is an exclusive speakeasy that offers a truly luxurious cocktail experience. This is one of the most trendy speakeasies in Chicago if you’re looking for something upscale.

Why You’ll Love It:

Reservation-only with limited seating for a private feel.
Custom cocktails tailored to your preferences.
Antique furniture, rare spirits, and personalized service.

📍 Address: 955 W Fulton Market, Chicago, IL 60607
🕒 Hours: 5 PM–12 AM (Daily)

4. The Drifter – A Bar With Vintage Flair and Burlesque Vibes

Found beneath The Green Door Tavern (one of Chicago’s oldest bars), The Drifter is an actual speakeasy from the Prohibition era. It keeps the old-school vibe alive with a rotating cocktail menu printed on tarot cards and live performances like burlesque, magic, and jazz.

What to Expect:

Hidden entrance behind a bookcase.
Ever-changing cocktail list (no repeats).
A performance almost every night.

📍 Address: 676 N Orleans St, Chicago, IL 60654
🕒 Hours: 5 PM–2 AM (Wed–Sat)

5. The Booze Box – Underground Japanese Speakeasy

If sushi and sake are more your style, head to The Booze Box beneath Sushi Dokku in the West Loop. It’s a Tokyo-inspired trendy speakeasy in Chicago that combines Japanese bar culture with American underground aesthetics.

Standouts:

Rare Japanese whiskies and sake cocktails.
Graffiti-covered walls and hip-hop background music.
Hidden vibe perfect for late-night chills.

📍 Address: 823 W Randolph St, Chicago, IL 60607
🕒 Hours: 6 PM–12 AM (Wed–Sat)

6. Bordel – Parisian Boho Meets Chicago Speakeasy

Located on the second floor of a Spanish tapas restaurant, Bordel is a plush, sexy bar filled with velvet furniture, chandeliers, and Parisian flair. It feels like a blend of 1920s Chicago and old-world Europe.

Why It’s Trendy:

Live DJs and jazz bands in a cabaret setting.
Elegant cocktails with dramatic presentation.
Dim lighting for a romantic ambiance.

📍 Address: 1721 W Division St, Chicago, IL 60622
🕒 Hours: 6 PM–2 AM (Wed–Sat)

7. Room 13 – The Password-Protected Gem

You can’t just walk into Room 13. This members-only speakeasy is located in the basement of the Old Chicago Inn and requires a password. You’ll need to stay at the inn or join the club to gain access.

Features:

True to the Prohibition vibe — vintage furniture and dress code.
Signature drinks with a historical twist.
Private and classy, ideal for special nights.

📍 Address: 3222 N Sheffield Ave, Chicago, IL 60657
🕒 Hours: Open Fri & Sat (reservations required)

How to Find Trendy Speakeasies in Chicago

Finding these secret bars is part of the fun. Here are some tips to help you get in:

Look for Hidden Entrances:

Many of these bars are disguised behind:

Alleys
Bookcases
Unmarked doors
Inside restaurants or hotels

Use Instagram or Local Blogs:

Search hashtags like #ChicagoSpeakeasy or follow nightlife bloggers for the latest hidden gems.

Make a Reservation:

Some places like The Office or Room 13 require advance booking. Don’t assume you can just walk in.

Dress to Impress:

Most speakeasies have a classy or smart-casual dress code. Avoid overly casual outfits like flip-flops or sportswear.

Why People Love Speakeasies

So what makes these trendy speakeasies in Chicago so special?

Unique Atmosphere: The vibe is unlike any regular bar — it’s more personal, intimate, and mysterious.
Creative Drinks: Bartenders here are more like artists, crafting one-of-a-kind cocktails you won’t find anywhere else.
Instagrammable Decor: From velvet couches to neon signs and vintage glasses, these places are a visual treat.
Live Music & Entertainment: Some venues also offer jazz bands, burlesque shows, and more — making your night unforgettable.

Chicago’s Speakeasy Culture: A Modern Tribute

Back in the 1920s, speakeasies were illegal bars hidden from police during Prohibition. Today, they’re legal (of course!) but they keep the secrecy alive with hidden doors and moody vibes.

In Chicago, the speakeasy trend is more than just a gimmick. It’s a celebration of creativity, design, and craft cocktails. It’s a way to experience nightlife in a more exciting and unexpected way.

Whether you’re planning a romantic date night, a fun weekend with friends, or a solo adventure, these secret bars will surprise you in the best way.

Final Thoughts: Your Guide to Trendy Speakeasies in Chicago

If you’re ready to ditch the loud sports bars and try something unique, trendy speakeasies in Chicago are your answer. These spots mix mystery, elegance, and top-tier cocktails — all wrapped in vintage charm. So grab a friend, do a little digging, and step into a hidden world that’s waiting just behind the next unmarked door.

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