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Best Speakeasies in Old Town, Chicago / Illinois

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5 restaurants available nearby

How are Featured results ranked

A photo of The Berkshire Room restaurant
1. The Berkshire Room
4.8
Exceptional(87)
$$$$
• Speakeasy • River North (Chicago)
Booked 8 times today
The Berkshire Room, nestled within River North's chic ACME Hotel, offers an unparalleled Bar and Lounge experience with its exceptional craft cocktails. Guests are consistently dazzled by the "Dealers' Choice," where skilled bartenders create personalized concoctions tailored to each patron’s preferences. The retro classy atmosphere provides the perfect backdrop for a memorable night out, whether you're on a date or enjoying a nightcap with friends after a show. Visitors rave about the "best drinks in town" and the engaging mixologists who bring a touch of magic to every glass. For those seeking an authentic and innovative cocktail experience, The Berkshire Room is a must-visit gem.
A photo of Nightcap restaurant
2. Nightcap
4.9
Exceptional(46)
$$$$
• Speakeasy • Bucktown / Wicker Park
Booked 6 times today
A secret speakeasy crafting cocktails rooted in creativity and connection. In Nightcap’s third act BANQUET, the cocktails are inspired by celebratory gatherings across cultures and time. Tucked away behind Class Act in Bucktown just south of the 606, follow the sidewalk behind the black fence to find the black door.
A photo of Revolver restaurant
3. Revolver
4.5
Awesome(66)
$$$$
• Speakeasy • Bucktown / Wicker Park
Booked 1 time today
Co-owners LeQoinne Rice and Chris Scardina (also behind The Duplex in Logan Square) have invoked speakeasy-style concept, drink menu laden with pre-Prohibition classics like Amaretto sours and dirty martinis alongside contemporary cocktails.
A photo of Bordel restaurant
4. Bordel
4.6
Exceptional(116)
$$$$
• Speakeasy • Bucktown / Wicker Park
Booked 13 times today
Bordel, nestled in the vibrant Bucktown/Wicker Park area of Chicago, is an exceptional cocktail bar that has redefined nightlife with its impeccable blend of creative cocktails and captivating cabaret. Celebrating its 10th anniversary, Bordel has earned a reputation for crafting some of the most unique and delicious drinks in the city. With glowing reviews highlighting the cocktail experience as “phenomenal” and “fantastic,” diners are in for an unforgettable evening. Bordel's cocktails are not just drinks; they are an art form, complementing the seductive atmosphere and live performances that have made it a beloved cultural landmark. "Highly recommend" for an unmatched night out!
A photo of Habibti Chicago restaurant
5. Habibti Chicago
3.0
Good(5)
$$$$
• Speakeasy • West Loop
Nestled in the heart of West Loop, Habibti Chi brings the warmth and soul of Mediterranean cuisine to Chicago's most vibrant neighborhood. By day, we serve bold, fire-kissed dishes crafted from family recipes passed down through generations.By night, step through our hidden door and discover a world of handcrafted cocktails in our speakeasy lounge — where every sip tells a story and every evening becomes unforgettable.
‘About the restaurant’ descriptions have been generated using an artificial intelligence model comprised of OpenTable proprietary data that has not been independently verified by OpenTable. The content is presented as-is, for informational purposes only.

See what locals rave about

From verified diners like you
From verified diners like you
  • RuchaGold
    Chicago / Illinois •1 review
    5.0
    Dined 3 days ago
    Amazing experience! Lisa made us incredible drinks and Isaac was very hospitable!
    More info
    Nightcap$$$$• Speakeasy• Bucktown / Wicker Park
    •
    4.9
  • Jason
    Chicago / Illinois •2 reviews
    5.0
    Dined on May 24, 2026
    My wife and I celebrated our 29th anniversary at The Berkshire Room, and it was an outstanding experience from start to finish. The ambiance was exceptional—great music, a wonderful vibe, and the perfect atmosphere for enjoying cocktails and conversation. It felt special without being pretentious, making it an ideal setting for a memorable evening. The mixologist was fantastic, creating custom cocktails tailored to our preferences. Each drink was expertly crafted and showcased both creativity and skill. Our server, Brandon, was attentive, personable, and added to the overall experience with excellent service. The manager was also warm and welcoming, helping make our anniversary celebration even more memorable. As for the food, the kettle chips were very good, but the real standout was the house-made onion dip. It was absolutely delicious and is something I would highly recommend ordering. Overall, this was a 10 out of 10 experience. Between the atmosphere, exceptional cocktails, outstanding service, and thoughtful hospitality, The Berkshire Room exceeded our expectations. My wife and I both agreed that we will definitely be back, and we would highly recommend it to anyone looking for one of the best cocktail experiences in Chicago.
    More info
    The Berkshire Room$$$$• Cocktail Bar• River North (Chicago)
    •
    4.8
  • Taliah
    Chicago / Illinois •2 reviews
    5.0
    Dined on May 16, 2026
    I had the best experience of my life at Bordel. Service was AMAZING! The host of burlesque was entertaining and also polite, very respectful. Had a ton of fun! Will be back.
    More info
    Bordel$$$$• Bar / Lounge / Bottle Service• Bucktown / Wicker Park
    •
    4.6
  • Alejandra
    Chicago / Illinois •3 reviews
    5.0
    Dined on May 7, 2026
    Service and drinks are amazing! We love Revolver, it’s a hidden gem in wicker park!
    More info
    Revolver$$$$• Speakeasy• Bucktown / Wicker Park
    •
    4.5
  • Fad
    Chicago / Illinois •2 reviews
    5.0
    Dined on May 2, 2026
    Place is great nice and cozy vibes good place for a date night the 60 dollar all u can eat drink cocktails is worth it
    More info
    Habibti Chicago$$$$• Mediterranean• West Loop
    •
    3

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