Dine Like a Gangster at These 5 Mob Hangouts

During prohibition, this restaurant belonged to gangster Bugs Moran. However, now that it has become Twin Anchors, it’s more famous for its BBQ ribs than its gangster past. Frank Sinatra was one of many celebrities who frequented the restaurant, which has been featured in TV shows and movies through the years. Come here to eat where the Blues Brothers ate!

Located in an historic Old Town building that dates back to 1881, Twin Anchors Restaurant & Tavern is one of the oldest restaurants in the city of Chicago, founded in 1932.

Famous for its PIZZA POT PIE, you’ve likely heard of this restaurant if you’re a Chicago native or frequent visitor. What you might not know is that there’s a little gangster history here: On February 14, 1929, the guttural yammering of submachine guns in a garage almost directly across the street brought the notorious “St. Valentine’s Day Massacre” to headlines around the world. Rumor has it that the house at 2121 North Clark served as a lookout post for hoodlum henchmen of the Valentine gunners.

In the roaring ’20s, this restaurant was called the 226 Club. Rumor has it that the restaurant was a speakeasy patronized by none other than Al Capone. After all, Big Al lived just a few blocks south.

Located in the heart of the Chicago Loop, this blast from the past restaurant continues to win awards for its food. Come inside and enjoy the over 500 pieces of memorabilia on the walls including historic newspapers, photos, and posters.

This restaurant is full of gangster history: bullet holes that still line the bar, the St. Valentine’s Day Massacre get-away car found in a neighboring garage, and the diners who still sit in the corner-window booth that only “close friends” can approach. The basement speakeasy has been vacant for 80 years, yet the gangster vibe pervades today.

Club Lucky features the hearty pastas, fresh seafood and classic dishes of Southern Italy and Sicily; not to mention the Chicago classic, Chicken Vesuvio. A mainstay in the Bucktown neighborhood of Chicago, upon entering you find brick walls, formica tables, and naugahyde booths that provide a genuine design element to compliment “grandmother’s recipes” on the Italian menu. But most of all, the history that exudes from the walls that don’t speak is what everyone who dines here really thinks about.

Did you know that during Prohibition a green door signified a speakeasy? This amazing piece of Chicago history was built in 1871 after the great fire, but before the city prohibited wooden structures.  Today, the building has settled and has a bit of a lean to it. During Prohibition it’s said that the Irish-Italian mob frequented the joint. This time it’s not Al Capone who visited there, but his bitter rival Dean O’Banion.

At The Green Door Tavern, you’ll find memorabilia and a true sense of Chicago history alongside delicious pub fare including salads, sandwiches, burgers, and more.

Christine Feehan is the #1 New York Times bestselling author of several series, including the Chicago-set Shadow Riders series, which features the mafia-style Ferraro family.