Ever since my husband and I went to The Bletchley in London a few years ago, I have become obsessed with speakeasies. This meant, before we went to Chicago, I did a little digging and found this great site discussing nine speakeasies in Chicago.
Of course, you can go on brewery or even speakeasy tours in Chicago, but I wanted to experience the wonder of finding these places on my own. And, honestly, some of the tour websites were so confusing, I became too frustrated. This lovely Urban Matter article let me do the work and enjoy the hunt myself. After all, that’s half the fun of the speakeasy.
We were in Chicago for five days, five nights, and I can proudly say we made it to three speakeasies. Not so bad when you realize we flew into town late the first night.
We first went to Watershed, which is owned and operated by the same people as its upstairs neighbor, Pops for Champagne, a classy place to grab a drink in River North. Watershed is in the basement, has a low ceiling, and a more relaxed vibe. The mix-matched furniture feel cozy. The menu is small, but it offered a variety of beer (the true speakeasy drink), wine, and my favorite – crafted cocktails. We each ordered ourselves a drink, saluted a great find and drank our, quite strong, drinks in amicable chatter. My only complaint about this bar was how loud the music became as the night wore on. We came to the bar to chat and drink, not get our ear drums blown out. We did have the pleasure of conversing with one of the co-owners who mentioned one of his favorite things about the bar was the lack of televisions. He said it allowed people to actually talk to one another. I whole-heartedly agree but feel if he keeps turning the music up, the fact that there are no televisions will not matter. No one will be talking because they won’t be able to hear each other.
The next night, we ventured to The Violet Hour, which has a somewhat secret entrance. While the entrance is right on the sidewalk of a main road, the door is unmarked and incorporated into a mural that changes periodically. We even missed it the first time we passed it thinking that couldn’t be the bar. I’d say, The Violet Hour gets some points for that. Inside, the feel is more swanky than Watershed and less cozy, but it quickly became my favorite of the three we visited this trip. We were seated at the bar, which I usually don’t like, but this time, it gave me a great chance to meet other people and get to know our amazing bartender, Ruby. Again, they serve beer, wine, and hand-crafted cocktails. These cocktails are up a notch from Watershed because they are served with their own syrups, bitters, and other mixers. The cocktail menu is quite extensive as well. I had no idea what I wanted. A little help from the bartender, I narrowed my options down to four, and ultimately went with the rum old fashioned. A little while later, we were ready for round two. This time, I told Ruby some things I liked, and she said, “oh, I got you, girl,” and served me up with one of the best drinks I’ve had in a long time. She was right, she got me. It was a little husky from whiskey, a little fruity, and just a bit of adventure, as she set some of it to flame just before serving it to me. More because of the bartender and cocktails, The Violet Hour was my favorite speakeasy we visited during this trip to the Windy City.
The final speakeasy we visited, I hesitate to call a speakeasy. To me, Brando’s Speakeasy was more of a dive bar than anything else. It most certainly had that feel. The door is hiding in plain sight with a small sign near the doorknob indicating you’ve found the right location. The menu is decent, and the drinks fine. However, there is nothing particularly special about the place. They do have karaoke, which adds to the dive bar feel for me. In the end, I would rather skip this place on my speakeasy tour of Chicago.
One place I really wanted to explore, but we did not get the chance to go was The Drifter, which of the nine Urban Matter sites, is the only still in operation speakeasy from the Prohibition Era. Mark my words, that place is a must-see for me next time I’m in the city. Till next time, Chi-Town!
World Wanderer 