Best Speakeasies in West Loop, Chicago / Illinois
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- IIsabelChicago / Illinois •2 reviews5.0Dined on Jul 3, 2026I took my sister who was celebrating her 21 as a surprise everthing we experienced was amazing from the host , the dancers the drinks and foodMore infoBordel$$$$• Bar / Lounge / Bottle Service• Bucktown / Wicker Park•4.7
- HHeatherNew York City •6 reviews5.0Dined on Jul 2, 2026Fantastic night. Full house. Met new friends. Had a blast catching up with old friends. New cocktails. Izakaya amuses and amazes—don’t judge til you drink! New bar snacks—Mango Chicken Bites hit the spot. Good time had by all!More infoNightcap$$$$• Speakeasy• Bucktown / Wicker Park•4.9
- JJasonChicago / Illinois •2 reviews5.0Dined on May 25, 2026My wife and I celebrated our 29th anniversary at The Berkshire Room, and it was an outstanding experience from start to finish. The ambiance was exceptional—great music, a wonderful vibe, and the perfect atmosphere for enjoying cocktails and conversation. It felt special without being pretentious, making it an ideal setting for a memorable evening. The mixologist was fantastic, creating custom cocktails tailored to our preferences. Each drink was expertly crafted and showcased both creativity and skill. Our server, Brandon, was attentive, personable, and added to the overall experience with excellent service. The manager was also warm and welcoming, helping make our anniversary celebration even more memorable. As for the food, the kettle chips were very good, but the real standout was the house-made onion dip. It was absolutely delicious and is something I would highly recommend ordering. Overall, this was a 10 out of 10 experience. Between the atmosphere, exceptional cocktails, outstanding service, and thoughtful hospitality, The Berkshire Room exceeded our expectations. My wife and I both agreed that we will definitely be back, and we would highly recommend it to anyone looking for one of the best cocktail experiences in Chicago.More infoThe Berkshire Room$$$$• Cocktail Bar• River North (Chicago)•4.7
- AAlejandraChicago / Illinois •3 reviews5.0Dined on May 7, 2026Service and drinks are amazing! We love Revolver, it’s a hidden gem in wicker park!More infoRevolver$$$$• Speakeasy• Bucktown / Wicker Park•4.6
- FFadChicago / Illinois •2 reviews5.0Dined on May 2, 2026Place is great nice and cozy vibes good place for a date night the 60 dollar all u can eat drink cocktails is worth itMore infoHabibti Chicago$$$$• Mediterranean• West Loop•3.7