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Gangster Cool with Roaring ’20s Tours

Chicago Crime Tours

Chicago

There may be no city more notorious for its organized crime and liberal Prohibition-era policies than Chicago. A local tour company called Chicago Crime Tours takes visitors around the city to learn about infamous locals such as Al Capone and John Dillinger, as well as events like the St. Valentine’s Day Massacre.

While a number of the company’s tours touch on characters and events of the 1920s, it’s the Speakeasy Bar Crawl that really connects visitors to the wild environment of that decade in Chicago.

“We go to four bars that were speakeasies during prohibition,” said Chicago Crime Tours owner Mark Sanger. “They didn’t have names during Prohibition because they weren’t supposed to exist. But the fact of the matter is that Prohibition didn’t really exist in Chicago in that era. There were over 10,000 speakeasies in Prohibition Chicago. Today, there are 2,400 bars that have liquor licenses, so there were four times more bars then than there are now.”

The most famous establishment that the tour visits is now called the Green Door Tavern. The bar has a basement room that has been decorated to re-create the feel of a 1920s speakeasy. Capone and other mobsters are alleged to have drank there during the days of Prohibition.

Visitors learn a lot about Capone and his contemporaries during the tour and hear about how the Chicago mayor and police department turned a blind eye toward speakeasies

“We go to the Burwood Tap, which was another speakeasy,” Sanger said. “That’s the place that the song ‘Bad, Bad Leroy Brown’ was based on. We talk about the history of each speakeasy and what it was during Prohibition. There was one that was fronted as a Chinese laundromat. Some of the people that work in the bars that we visit don’t even know that they were speakeasies during Prohibition.”

The tour includes a drink at each of the establishments visited.

www.chicagocrimetours.com

 

The Gangster Museum of America

Hot Springs, Arkansas

Even mob bosses need a vacation every once in a while, and during the height of Prohibition, Capone and his compatriots found the ideal getaway in the thermal baths of Hot Springs, Arkansas. Today, the Gangster Museum of America traces the city’s connection to the most infamous characters of the 20th century.

“Capone started coming here as early as the 1920s,” said museum director Robert Raines. “He and his entourage made biannual pilgrimages down here to stay at the Arlington Hotel, where Capone had a suite. They had a lot of things to do here: the thermal baths, fantastic lakes, a lot of fishing and a great Clearwater River.”

The museum’s seven galleries each have a video presentation with a story of gangsters in Hot Springs as told by former FBI agents and attorneys that were familiar with their operations. The galleries also include period artifacts such as an antique roulette wheel, a slot machine and a dice table that came from an underground Hot Springs casino.

“There was plenty of entertainment, plenty of gambling and plenty of whiskey, even during Prohibition,” Raines said. “The ’20s is really when it all cranked up. People had money and were looking for places to go and things to do.”

www.tgmoa.com

Brian Jewell

Brian Jewell is the executive editor of The Group Travel Leader. In more than a decade of travel journalism he has visited 48 states and 25 foreign countries.