Be taken back to the 1920s by participating in one of the Chicago gangsters’ favorite activities: eating and drinking (illegally). Many Chicago restaurants have been discovered to have once been underground speakeasies. Many of these eateries play up this theme by adding antique Prohibition relics, aged black and white photos of ill-famed criminals, and even specialty gangster menu items.
Green Mill Cocktail Lounge
Opened in 1907, the Green Mill has seen its fair share of change over time. However, its most famed stretch was in the era of Prohibition when Al Capone’s malevolent cohort, Jack “Machine Gun” McGurn owned 25 percent of the club, actually a speakeasy at the time. In order to obtain his share of the nightclub, McGurn was hired to convince the comedian Joe E. Lewis from moving his act to different club, which he succeeded in doing by slitting Lewis’ throat and cutting off his tongue. After obtaining his portion of the club, McGurn hoarded in a continuous flow of the most wanted criminals in the country. The Green Mill today still holds the air of an illegal speakeasy. Live jazz music erupts from musicians embodying the spirit of the 1930s and 1940s, and guests can even sit in Al Capone’s customary booth, which is decorated with pictures of the ring-leaders of prohibition law-breakers. A modern-day entertaining event at the Green Mill is the Uptown Poetry Slam, which occurs every Sunday.
John Barleycorn Memorial Pub in Wrigleyville
During Prohibition, the building where John Barleycorn is now located was used as a Chinese laundry. Oddly enough, clean clothes weren’t the only item the laundry was pumping out in large loads. A small elevator connected the laundry basement to an upstairs saloon with boarded windows so the lively bar looked closed. In fact, gangsters such as John Dillinger used to enter the laundry and end up spending the rest of the night drinking illegal liquor. Now, John Barleycorn Memorial Pub serves traditional tavern food with a variety of sandwiches, salads, and of course burgers.
Enter the domain of one of the most enabling and influential women of the 20th century simply by walking into Lottie’s Pub in Bucktown. The famous Lottie ran what was then Zagorski’s Tavern for over 30 years and hosted parties of strippers and gamblers almost every night. Zagorski’s was a haven for Chicago’s top gangsters, public officials, and Bucktown locals until 1967 when Lottie was arrested for hosting a bookie den and having illegal gambling paraphernalia. With posh new renovations to the upstairs and downstairs bars, Lottie’s still has the flair of a sizzling party spot. If customers get hungry, Lottie’s always keeps the crowd happy with plenty of cheap and greasy bar food with different specials every night of the week.
Tommy Gun’s Garage
If you feel like being transported back to a Roaring Twenties speakeasy, Tommy Gun’s garage is the hotspot to hit up. The interactive dinner theater is packed with gangsters and flappers who serve you delicious food and lead you through a fun-filled night including live music, dance, and comedy performances. Give the password to the bouncer, try to avoid the coppers, and sip on some quality hootch while enjoying all of the excitement of the twenties. This family-friendly downtown joint provides a quality experience for all types and ages.
For more Chicago gangster dinner theater options, visit the Chicago Gangster Tours guide page.