Mob / prohibition

Question

Hi all

I’m travelling to the Windy City this year and really want to see some of the organised crime / prohibition sites without taking an organised tour. Is there anything I can do or see on my own? Tried researching but can’t see much past the bus tours.

Thanks in advance

Answer

Chicago is a great city for anyone interested in organized crime history, especially from the Prohibition era. While many people opt for organized tours to explore these sites, there are still plenty of fascinating places you can visit on your own to get a taste of the city's colorful mob past. Here are a few spots and ideas for exploring Chicago’s mob and Prohibition history independently:

The Green Mill Cocktail Lounge: Located in the Uptown neighborhood, this historic bar is a must-see for anyone interested in Chicago's Prohibition history. The Green Mill was a notorious mob hangout during the 1920s and 1930s and still maintains its old-school atmosphere. You can grab a drink here while soaking up the ambiance, which still retains the feel of its Prohibition-era roots. The famous backroom booth is where Al Capone was known to hold court.
Holy Name Cathedral: This cathedral is significant because it was the site of the funeral for one of Chicago’s most infamous mobsters, George “Bugs” Moran, who was involved in the St. Valentine’s Day Massacre. Although it's a place of worship, visiting the cathedral allows you to reflect on the intersection of the city’s history with organized crime.
The St. Valentine’s Day Massacre Site: Located at 2122 N. Clark St., the site of the infamous 1929 massacre is one of the most well-known locations tied to Chicago's mob history. While there’s no grand marker, you can visit the building and learn about the tragic event that played a pivotal role in the downfall of the North Side Gang. There’s a plaque at the site, and the neighborhood is rich in mob lore, with a number of nearby locations tied to the events of that time.
Reagan’s Pub: Known for its speakeasy vibes, Reagan’s Pub in the River North neighborhood offers a throwback to the days of Prohibition, with its secretive atmosphere and history of serving alcohol during the dry years. It’s a fun place to grab a drink and feel the historic ambiance.
Chicago History Museum: While the museum itself doesn’t focus solely on organized crime, it does have exhibits related to Chicago’s Prohibition history and the infamous mob figures that shaped the city. It’s a great starting point for learning about the city’s past, and you can easily explore it on your own.
Speakeasy Bars: Many modern bars in Chicago have adopted a Prohibition-era theme, offering a fun way to experience the city's hidden history. Examples include The Violet Hour, a secretive bar in Wicker Park that gives a nod to the Prohibition era, and The Paper Moon, which evokes the style of an old speakeasy.

If you're interested in a more detailed dive into Chicago’s Prohibition and mob history, a visit to the Chicago Outfit museum or even a trip to some of the city’s historic gangster haunts might be worth your while, but they often require booking ahead or being part of a tour. Still, there’s plenty to see and explore on your own to get a great sense of the city's colorful history with organized crime!

Enjoy your trip to Chicago and happy exploring the Windy City’s fascinating past!