Top 10 Speakeasies in Chicago

Direct Answer

The Best Overall speakeasy in Chicago is The Violet Hour, the pioneering Wicker Park cocktail den behind an unmarked, ever-changing mural wall, which set the standard for the city's hidden-bar scene with world-class drinks and a hushed, chandelier-lit room. The Best Value pick is Room 13, a genuinely tucked-away basement bar where the drinks are strong, the cover is nonexistent, and the discovery costs you nothing but the hunt.

This list is built for cocktail lovers, date-night couples, and visitors who want the real hidden-bar experience across Wicker Park, River North, the Loop, and Logan Square. Every spot below is a real, currently-operating Chicago bar.

How We Ranked the Top 10

We weighed each hidden bar against what makes a speakeasy worth finding, drawing on Eater Chicago, Thrillist, Time Out Chicago, The Infatuation, Chicago Magazine, and thousands of Yelp and Google reviews. The weighting:

• Atmosphere and vibe — 25%
• Drinks and menu — 20%
• Secrecy and entrance — 20%
• Crowd and service — 15%
• Value — 10%
• Location and access — 10%

A bar with a clever door but weak drinks drops fast; so does a great cocktail room with no sense of discovery. The winners balance all six.

1. The Violet Hour 🏆 BEST OVERALL

Type: Cocktail bar / Speakeasy | Price: $$$ | Best for: Serious cocktails in a hushed hidden room

Hidden behind an unmarked, ever-changing mural on Damen Avenue in Wicker Park, The Violet Hour is the bar that launched Chicago's modern speakeasy era and still leads it. You enter through a curtained doorway into a tall, candlelit room of blue walls, high-backed chairs, and crystal chandeliers, where house rules ask for hushed voices and no cell phones on the bar.

The cocktail program is among the best in the country — a multiple James Beard Award recipient — with a rotating menu of meticulously balanced originals and classics. The crowd is dressed-up but relaxed, the service is precise, and the no-standing, no-reservations policy keeps the room civilized.

It is the complete hidden-bar experience.

Pros:

• James Beard Award-winning cocktail program
• Unmarked, ever-changing mural entrance
• Hushed, chandelier-lit room with real house rules
• Polished, knowledgeable bartenders

Cons:

• Waits can be long on weekends
• Premium cocktail pricing

Verdict: The original and still the best — Chicago's definitive speakeasy night.

2. The Office (Aviary)

Type: Cocktail bar / Speakeasy | Price: $$$$ | Best for: A special-occasion luxury cocktail experience

Hidden beneath The Aviary in the Fulton Market/West Loop area, The Office is the most exclusive speakeasy in the city — a small, reservation-only lounge from the team behind Alinea. The room feels like a private study, leather and dark wood, and the cocktail list runs deep into rare and vintage spirits alongside flawless craft drinks.

Service is impeccable and bespoke, with bartenders tailoring drinks to your taste. The crowd is celebrating something, and the prices reflect the pedigree. It is less a night out than an event — but for a milestone, nothing in Chicago tops it.

Pros:

• Alinea-team pedigree and flawless execution
• Deep rare and vintage spirits selection
• Intimate, private-study atmosphere
• Bespoke, world-class service

Cons:

• Reservations are hard to get
• The most expensive room on this list

Verdict: The luxury splurge — book it for a once-in-a-while special occasion.

3. Milk Room

Type: Cocktail bar / Speakeasy | Price: $$$$ | Best for: An ultra-intimate vintage-spirits tasting

Inside the historic Chicago Athletic Association hotel on Michigan Avenue facing the Loop and Millennium Park, the Milk Room is an eight-seat micro-bar specializing in rare and vintage spirits. With only a handful of seats and a reservation-only policy, it is one of the most intimate drinking experiences in the country — the bartender pours and narrates obscure bottles you will not find elsewhere.

The room is tiny, jewel-box dim, and meant for slow, attentive sipping. It is not a place to bring a big group; it is a place to taste history one glass at a time.

Pros:

• Eight-seat micro-bar focused on rare spirits
• Reservation-only intimacy
• Knowledgeable, narration-driven service
• Stunning historic hotel setting

Cons:

• Only a handful of seats, so hard to book
• High prices on vintage pours

Verdict: The connoisseur's pick — a tiny, vintage-spirits tasting room like nowhere else.

4. Bordel

Type: Cocktail bar / Cabaret lounge | Price: $$$ | Best for: A glamorous date with live entertainment

Above Black Bull in Wicker Park, Bordel is a plush, bordello-themed lounge reached by an easy-to-miss staircase. The room is all velvet, low light, and Old World glamour, and the draw is the pairing of a strong craft-cocktail list with live cabaret, burlesque, and music on select nights.

The crowd dresses up, the energy is romantic and theatrical, and reservations are recommended for show nights. It is the most entertainment-forward speakeasy on this list — a great pick when you want drinks and a show in one hidden room.

Pros:

• Live cabaret, burlesque, and music programming
• Plush, glamorous bordello-themed room
• Strong craft-cocktail list
• Romantic, dressed-up atmosphere

Cons:

• Show nights can carry a cover or ticket
• Books up fast for performances

Verdict: The glamour-and-show pick — best for a theatrical date night.

5. Berkshire Room 💎 BEST VALUE

Type: Cocktail bar | Price: $$ | Best for: A great hidden hotel bar without the premium

Inside the ACME Hotel in River North, the Berkshire Room delivers a serious cocktail experience at a friendlier price than the city's marquee speakeasies. The room is handsome and clubby, and the signature move is the "Dealer's Choice" — tell the bartender a spirit and a mood, and they build a custom drink on the spot.

The crowd is a relaxed mix of hotel guests and locals, the service is warm, and you can usually walk in without a reservation or a wait. For the quality of the drinks, it is the best bang-for-buck hidden bar in Chicago.

Pros:

• "Dealer's Choice" custom cocktails on request
• Strong drinks at a gentler price point
• Walk-in friendly with little wait
• Comfortable, clubby River North room

Cons:

• Less hidden than a true speakeasy
• Can fill with hotel-guest traffic

Verdict: The value champion — top-tier drinks without the splurge or the wait.

6. Room 13

Type: Cocktail bar / Speakeasy | Price: $$ | Best for: A genuinely tucked-away no-cover hideout

Room 13 is a basement speakeasy hidden beneath the Hotel St. Clair in Streeterville/River North, reached through an unmarked door and a downstairs walk that delivers real discovery. Inside, the room is dim, low-key, and free of pretense, with a solid craft-cocktail list and a relaxed neighborhood feel rather than a scene.

There is no cover, the prices are fair, and it rarely carries the long waits of the bigger-name spots. For people who want the thrill of finding a hidden bar without paying a premium for it, this is the sweet spot.

Pros:

• Genuine unmarked-door, basement entrance
• No cover and fair pricing
• Solid, unpretentious craft cocktails
• Relaxed, scene-free atmosphere

Cons:

• Easy to walk past if you do not know it
• Smaller drink menu than the marquee bars

Verdict: A great low-key find — real speakeasy discovery without the premium.

7. Watershed

Type: Cocktail bar / Speakeasy | Price: $$$ | Best for: A cozy underground date in River North

Watershed sits in a basement beneath River North, an underground cocktail bar built around a focus on American spirits and regional producers. The space is intimate and cavern-like, with exposed brick and low light that make it feel like a secret hideout below the busy streets above.

The cocktails lean thoughtful and spirit-forward, the crowd is couples and small groups, and the service is friendly without being stuffy. It is a warm, romantic underground room — a great mid-night stop when you want to descend out of the River North bustle.

Pros:

• Cozy, cavern-like underground setting
• Focus on American spirits and regional makers
• Thoughtful, spirit-forward cocktails
• Romantic, low-key atmosphere

Cons:

• Small space fills on weekends
• Basement location can be easy to miss

Verdict: A warm underground date spot — descend for spirit-forward drinks.

8. Untitled

Type: Cocktail bar / Live music | Price: $$$ | Best for: A big speakeasy with whiskey and live jazz

Untitled is a sprawling, multi-room subterranean spot in River North that pairs a massive whiskey and bourbon selection with regular live jazz and blues and even burlesque on some nights. Unlike the city's tiny hidden bars, this one is large and lively, with several distinct rooms that range from intimate to social.

The drink program is deep, the entertainment calendar is busy, and the crowd is a mix of groups, dates, and after-work parties. It is the speakeasy for people who want scale, music, and a serious brown-spirits list under one roof.

Pros:

• Huge whiskey and bourbon selection
• Regular live jazz, blues, and performances
• Multiple rooms for different moods
• Lively, group-friendly energy

Cons:

• Larger and louder than a classic speakeasy
• Cover or minimum on big show nights

Verdict: The big-room pick — whiskey and live music at speakeasy scale.

9. The Drifter

Type: Cocktail bar / Cabaret lounge | Price: $$$ | Best for: A vintage tarot-card cocktail night with a show

Beneath the Green Door Tavern in River North, The Drifter is a Prohibition-era basement bar with a delightful gimmick: drinks are presented on vintage tarot-style cards, and you pick by the card's art rather than a written menu. The room is small, vintage, and atmospheric, with live cabaret and burlesque on select nights adding to the throwback charm.

The crowd is in on the fun, the cocktails are well made, and the discovery of the descent below a historic tavern adds to the appeal. It is playful, theatrical, and genuinely old-Chicago.

Pros:

• Tarot-card cocktail menu gimmick
• Historic Prohibition-era basement setting
• Live cabaret and burlesque on select nights
• Playful, in-on-the-fun crowd

Cons:

• Small room fills quickly
• Show nights may carry a cover

Verdict: The playful, theatrical pick — pick a card and enjoy the throwback.

10. Bernard's

Type: Cocktail bar / Speakeasy | Price: $$$ | Best for: A polished, design-forward hidden bar

Bernard's is a stylish hidden bar tucked into the River North area, reached past a discreet entrance into a warm, design-forward room of rich wood and soft lighting. The cocktail program is refined and seasonal, with carefully composed originals and a tidy spirits list, and the service strikes a balance between attentive and easygoing.

The crowd is stylish but not stuffy, and the room works equally well for a date or a small group. It rounds out the list as a more contemporary, design-driven take on the Chicago speakeasy.

Pros:

• Refined, seasonal cocktail program
• Warm, design-forward room
• Attentive but easygoing service
• Works for dates or small groups

Cons:

• Pricing runs toward the high end
• Can get busy on weekend nights

Verdict: A polished modern hideout — the design-forward speakeasy pick.

Where Should You Go Out?

What to Look For in a Night Out in Chicago

• Decide splurge versus discovery first — Some hidden bars like The Office and Milk Room are luxury events; others like Room 13 are about the thrill of finding a no-cover hideout. Pick your lane before you go.
• Reserve where you must — The Office, Milk Room, and Bordel's show nights book up; the Berkshire Room and Room 13 welcome walk-ins.
• Know the entrance — Half the fun is the door, from The Violet Hour's mural to Room 13's unmarked basement. Look up the entry so you do not walk past it.
• Match the crowd size — Eight-seat Milk Room is for two; Untitled's many rooms suit a group. Bring the right party for the room.
• Check for shows — Bordel, Untitled, and The Drifter run cabaret, jazz, and burlesque on select nights, which can change the cover and vibe.
• Plan your transport — River North and Wicker Park parking is tight on weekends; the CTA and rideshares save the night.

What matters less than the hype: how exclusive the door feels, how viral the bar is on social media, and bottle-service status. A genuinely great drink, a room with character, and a good crowd beat all of it.

FAQ

What is the best speakeasy in Chicago overall? The Violet Hour in Wicker Park is our top pick — the bar that launched the city's hidden-bar scene, with a James Beard Award-winning cocktail program and an unmarked, ever-changing mural entrance.

What's the best-value speakeasy in Chicago? The Berkshire Room in River North offers top-tier drinks, including custom "Dealer's Choice" cocktails, at a gentler price with little wait. Room 13 is another no-cover favorite.

Which Chicago speakeasy is best for a special occasion? The Office beneath The Aviary, from the Alinea team, is the city's most exclusive reservation-only lounge, while the eight-seat Milk Room offers an unmatched rare-spirits tasting.

Where can I find a speakeasy with live entertainment? Bordel and The Drifter run cabaret and burlesque on select nights, and Untitled pairs a huge whiskey list with regular live jazz and blues.

Do I need a reservation for Chicago speakeasies? For The Office, Milk Room, and Bordel show nights, yes — book ahead. The Violet Hour is walk-in but can have long waits, while the Berkshire Room and Room 13 welcome walk-ins.

Which Chicago neighborhood has the best speakeasies? River North has the densest cluster, including the Berkshire Room, Untitled, Watershed, and The Drifter, while Wicker Park is home to The Violet Hour and Bordel.

Bottom Line

For a hidden-bar night in Chicago, The Violet Hour is our Best Overall — the pioneering Wicker Park den with a James Beard-winning bar program and an unmarked mural door that still defines the genre. The Berkshire Room in River North is our Best Value, delivering custom cocktails and a warm room without the splurge or the wait.

If you want a special-occasion luxury bar, a rare-spirits tasting, or a speakeasy with a live show, use the decision tree above to route yourself to The Office, Milk Room, or Bordel instead. Know the door, match the room to your party, and the night becomes an adventure.

Sources

• Eater Chicago — bar and speakeasy guides
• Thrillist — best Chicago speakeasies
• Time Out Chicago — bars and nightlife
• The Infatuation — Chicago bar guides
• Chicago Magazine — bars and nightlife
• Yelp — Chicago speakeasies
• Google Reviews — Chicago bars
• The Violet Hour — official site
• The Aviary / The Office — official site
• Choose Chicago — nightlife guide

*best speakeasies in Chicago review — best hidden bars and cocktail lounges, where to go out, ratings, and a review of the top speakeasies.*