From hearty Chicago deep dish pizza to the classic Chicago Dog, the Windy City offers an endless feast of culinary delights. Why not spice up your meal with a slice of history? Chicago’s dining scene presents a unique blend of flavor and intrigue. Explore eateries that once served as mob hot spots and bars or speakeasies where gangsters like Al Capone once lingered. These storied spots don’t just cater to your taste buds—they invite you to dine and drink like a gangster.
Harry Caray’s Italian Steakhouse
Located near Harry Caray’s Italian Steakhouse, Frank Nitti’s (Al Capone’s enforcer) 4th floor apartment stands just a block away from the Cook County Criminal Courthouse; he reportedly had an escape route in the tunnels beneath it. Visit this restaurant on the Chicago Crime Tour, see through a window into the old tunnels and come back for dinner or a show at Nitti’s Supper Club.
Pro Tip: Make reservations in advance! Try the chicken Vesuvio, a prime steak or the eggplant parmigiana. Also, try an order of their house made Holy Cow! Potato Chips—to die for!
Pizzeria Uno
Pizzeria Uno was a speakeasy during Prohibition. The original bar ran the entire length of the building. Now, only half of the original bar remains. The other half of the bar is located at Pizzeria Due, just a block down the street. They are both unique Chicago restaurants.
Pro Tip: Give yourself a lot of time to eat here. Each pie is handmade, goes through a double baking process in 2 separate ovens, and takes 40-45 minutes. You must try the pizza!
The Berghoff
German delights inspire your old-world tastebuds at the Berghoff. On display, you will find the first liquor license issued at the end of Prohibition. Try a German beer or Berghoff’s root beer with your schnitzel—a winning combination.
Pro Tip: Make a reservation in advance and see the full menu online. Make time to check out the historic furnishings, artwork, and liquor license. Try the root beer, which during Prohibition was called “near beer.”
Burwood Tap
This historic bar was a speakeasy during Prohibition and is a true neighborhood bar. The red and white striped awning reflects the history as a soda shop called “the Noble Experiment.” Bad, Bad Leroy Brown (the man/character from the song) was a longtime regular of the bar until he passed away. The bartender said he was a “kind, nice man & one hell of a pool player.”
Pro Tip: Take public transit or a taxi/ride share to get to the Burwood Tap. Be prepared to hang with the locals at this historic neighborhood spot.
Wiener Circle
If you have a sense of humor and enjoy being insulted, try the Wiener Circle in Lincoln Park. This hot spot has been a staple for Chicago hot dogs for over 40 years.
Pro Tip: Remember to bring cash for a tip and NEVER put ketchup on your dog–it’s illegal. If you like it hot, try the char dog!
Halligan Bar
This classic Irish bar has been serving up drinks for over 100 years. This northside gang bar was rumored to be led by Bugs Moran during the Beer Wars of Prohibition. This is just one of many Chicago gangster locations you will drive by on the Chicago Crime Tour or Night Crimes Tour.
Pro Tip: This bar has a great atmosphere to watch a game and drink with friends.
