Best Bars and Speakeasies of Chicago
Chicago is filled with a rich history from Prohibition. It is the old stomping grounds of Al Capone and Bugs Morgan and some of the old speakeasies from prohibition time are still operating today! My husband and I did a lot of research about the gangs of Chicago during the prohibition and watched a lot of Boardwalk Empire before we went to Chicago.
Here is a list of great speakeasies and bars in Chicago that we went to in the order of my personal favorites.
Speakeasies
The Drifter (inside Green Door Tavern)
This is an original speakeasy that Al Capone and other gangsters have been to in the 1920s. This speakeasy is located in the basement of the Green Door Tavern. The Green Door tavern is one of the few remaining wooden commercial buildings in the central business district that stayed standing after the Chicago fire of 1871.
We went on a Wednesday night so it was not busy which was nice. There are no reservations, first come first served and they get really busy on the weekends, so I would recommend going on a week day or earlier in the night. They have hourly cabaret shows and their drink menu is on a series of tarot cards. We took our chances and randomly chose our drink from a fortune cookie out of a Buddha cookie jar which was cheaper than ordering from the menu. We got really lucky because we both got really good drinks, but we could have been stuck with a shot of Malort. The people next to us did the same thing (following our lead) and ended up with Malort. If you feel lucky try the Buddha, but I would not recommend it (trust me you don’t want Malort).
To get there: Head to the back of the tavern and go down the stairs, don’t look towards the bathrooms, look to right at the bookshelf. We found it because people were coming out of the door, but it is not marked. If you need help finding it you can ask one of the workers in the Green Door Tavern.
Why was this my favorite? The nostalgia factor. It is such an old bar and there is real history from the prohibition era so the fact that I went to a speakeasy that was actually a speakeasy was really cool! Also behind the bar and cash register is a latch and an underground escape that was built for the gangsters (I didn’t get to see it in person, but I saw it in this video)! If you’re unable to get into the speakeasy, the Green Door Tavern is still really cool and you can learn some Chicago history while you’re there. Location is good too.
The Green Mill was originally opened up in 1907. During prohibition, “Machine Gun” Jack McGurn of Al Capone’s crew became part owner. Al Capone frequented this place a lot and his favorite booth is still inside to this day.
Today, this is a Jazz bar that many locals go to. We came here because of the speakeasies of Chicago video and Boardwalk Empire. We came here on our last night a Sunday night (because it was way out of the way, and because they get really busy on the weekends). There was a cash only cover of $10 each even on a Sunday night. When we got there it was really busy because of a Slam Poetry event. We weren’t really into the slam poetry (so be sure to check their schedule ahead of time). Once the show ended, the place cleared out and Al Capone’s booth was empty! The Jazz show started an hour later so we quickly snagged Al Capone’s booth! A traveling comedian and his friends were sat in the booth with us right before the jazz show and we had a really good time chatting with them! The jazz was really good too!
The Good: The nostalgia and the fact that we were able to sit in Al Capone’s booth! The place felt old and had a really cool vibe. The jazz music was really good too! It also helped that we made some friends when they were seated next to us.
The Bad: It is out of the way for sure, north of Wrigley, about a 25-30 train ride from Magnificent Mile. There is nothing around here either, this would be a trip just to go to the Green Mill. We were in Chicago for a week so it was fine, but I would not recommend for a quick trip)
Three Dots and a Dash is a tiki bar hidden underground in River North. This tiki bar has a great atmosphere, well decorated, and good strong cocktails. There is also a speak easy within Three Dots and a Dash called The Bamboo Room. The Bamboo Room has more exotic and more expensive rum and cocktails. The Bamboo Room requires reservations, which can be made online. Three Dots and a Dash is located in an alley and downstairs (use google maps to find this place).
We came here later in the night and it was pretty busy but not too crowded. Drinks average around $15 each but they are delicious and strong. We only had one before ending our night. We didn’t get to go to the Bamboo Room because we didn’t make a reservation, but maybe next time!
I loved the atmosphere and the drinks. This place is more well known and gets pretty busy. This is a newer speakeasy so it doesn’t have the history that the others have, but still a great place to visit if you get the chance.
UPDATE: Janitor’s Closet – Now Closed
The Janitor’s Closet is a well themed speakeasy located inside the FieldHouse Jones Hotel. This speakeasy only seats 15 people and used to really be a janitor’s closet. The small space is decorated with dim lighting, cleaning products and supplies, and the menu is printed on cleaning rags. The drinks are very good and worth the price, the bar tender was really nice too!
Bars
Terrace 16 is a rooftop bar inside the Trump hotel. This place has incredible views of the city and the Chicago River and Lake Michigan, incredible service and great drinks. All of the employees inside the hotel and the restaurant/bar were so nice and provided impeccable service!
We came here around 5pm after going to a Broadway show to have a drink and enjoy the views. The bar tender was really nice and gave us a lot of recommendations for restaurants in Chicago. He also offered me a coat when it started to get cold! I highly recommend going here even just for the views. This was one of my favorite places in the city because of the service, drinks and views!
The Hampton Social is a great place for happy hour and there are many locations in downtown Chicago. They often have live music and the restaurant is very cute making the atmosphere nice and a great place for pictures. Their frosé is delicious and my husband got “The Bees Knees” which is tea infused with bourbon, apricot, lemon and honey. I had a sip and it was also very good. Their parmesan fries are delicious and a great snack to go with your drinks. You can read more about their food in my Favorite Foods of Chicago post.
The Berghoff is a historic German restaurant in Chicago that has been family owned and operated for 121 years. The atmosphere is like an indoor German biergarten with long tables community sitting style tables. The bar area is original with a wooden bar with intricate designs.
We stopped in for a quick German style beer. We enjoyed the atmosphere and the beer was good. Their food looks really good as well, so hopefully I can try their food next time!
Goose Island is one of the most well known breweries originating in Chicago. They specialize in IPAs but they have other types of beer as well. We like to try local breweries when traveling so we decided we had to visit this Chicago original. The bar tenders were really nice and they gave us free beer glasses! They also had a free sundae station when we went in, so we were lucky to get some ice cream sundaes too!
Trying to find the brewery was a little confusing, because all we could find on the map was the Goose Island Brewhouse (which is more of a restaurant) and the Goose Island Taproom. We decided to go to the taproom. The taproom is located near the West Loop and is a bit of a walk from the L train. It is out of the way, so if you don’t have much time I would skip the taproom and just have a Goose Island at any bar near you. I’m also not a big fan of Goose Island and I hate IPAs so it was just ok to me. If you love Goose Island, it might be worth the trip! There isn’t much else around but industrial buildings and a few other local breweries in the area (so it might be a good place to brewery hop).
Cindy’s is a rooftop bar located in the Chicago Athletic Association hotel. The actual outside area is relatively small with standing room only areas. You must have a reservation to sit down, without a reservation you can stand wherever you can find outside. We had to wait in line to order a drink and the drinks were relatively pricey at $16 each and a limited drink menu outside. The drink I got was nothing to brag about and not worth the $16. We waited around for some people to leave to get a good view (the main reason why we came here). It is truly a great view of Cloud Gate (the Bean) and Millennium Park. Personally, I would skip this place or just go up and get a picture. The views, drinks, and service was much better at Terrace 16.
There is a speakeasy inside the Chicago Athletic Association hotel called the Milk Room which was used by members during the prohibition. The bar only seats 8 people and is reservation only. It is also quite pricey so we did not go here.
Billy Goat Tavern is a Chicago Original and has a lot of history particularly with the Cubs and the “Billy Goat Curse“. This place is also known for the SNL skit Cheezborgor. This is a dive bar for sure (which I like dive bars too, but the vibe wasn’t great). We came here for the nostalgia factor. They have a limited food menu centered around cheese burgers (“cheezborgors”), chips, and Coke. We only stayed here for a short time, it is definitely a dive and underground. The drinks are cheap! The food is not great but it’s fast, cheap, and open late!
