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The Best Speakeasies in Chicago

Secret Speakeasies in the Windy City


Chicago is one of the most animated and fun cities in the United States. And for travelers that like to experience their destinations to the fullest, Chicago should be at the top of your list. During the Prohibition era, speakeasies popped up all over Chicago. Mobsters and locals would all congregate in these places, sipping booze and hiding from the law. Many of those places are still around to this day and are part of what makes Chicago such an interesting place to visit. Here are some of the best speakeasies in Chicago.


3 of the Best Speakeasies in Chicago



If you’re looking for one of the most intimate and exclusive experiences in all of Chicago, The Milk Room is one for the memory books. This 8-seat micro bar focuses on classic, spirit-forward cocktails. Extremely rare and vintage spirits are accompanied by hard to find ingredients, making for a delicious beverage that any cocktail connoisseur would enjoy. Located in the Chicago Athletic Association, The Milk Room has been featured as one of the Best Bars in America by Esquire as well as the Best Bar in Chicago. Rightfully so, as it’s one of the most luxurious bars in the city.



Just because Violet Hour is one of the most well-known institutions in Wicker Park, doesn’t mean that it isn’t one of the best speakeasies in Chicago. Like most speakeasies with “secret” entrances, you can find the door to this gem by locating the mural along Damen Avenue. If you talk to locals, they’ll tell you that Violet Hour is one of the best mixology experiences around. Violet Hour has even been called “bucketlistworthy” by Thrillist. If you’re looking for an amazing ambiance and some out of this world cocktails, Violet Hour is a great choice.



Take a step into another time when you set foot in The Drifter. This Prohibition era original is everything a speakeasy should be and more. It’s got the right amount of quirkiness with an intimate space, secret entrance, delicious handcrafted cocktails and unique performances. You enter the space through the Green Door Tavern and head down the back to be placed in a waiting room. Since it only has 37 seats, you may have to wait. But we promise, it’s well worth it. There aren’t many places in Chicago that still have the original bones like the Drifter does, so don’t miss out on this Chicago classic.


Don’t Just Travel, Immerse Yourself


When it comes to luxury travel, we don’t just want you to go places, we want you to experience them to the fullest. Every destination is an opportunity for you to see and do everything that your heart desires, and we hope to give you some amazing suggestions along the way. We’re the luxury travel guide you didn’t know you needed but can’t live without. Visit our YouTube channel to see some of our recommendations for drinking, dining and traveling around the world.

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