Geek Travel: Chicago Crime Tour

The 1920’s and 1930’s were a wild time for the country, and not in a good way. A combination of Prohibition and the Depression wore down on America’s soul providing the perfect breeding ground for crime. In the Windy City of Chicago, Illinois the underworld became a particularly powerful force in the lives of citizens. A number of the gangsters, robbers, and serial killers throughout the city’s history have attained a level of infamy that their names are recognized throughout the world. While the city proper tries to hide its past of sin and vice, it is still there and true crime is always a popular topic. Ensuring the Second City’s criminal past is never forgotten, the Chicago Crime Tour is here to lead you through the historic dark corners of Chicago.

While my time in Chicago as a whole was only a few days it was long enough to learn that the city’s traffic is a monster of sluggishness and pain. With that in mind, while I tip my hat to all the Lyft drivers I had during my time there, I full on bend the knee to the driver who navigated downtown traffic in our full-sized tour bus for the morning. Our guide through the Chicago Crime Tour was Leah who had the perfect mix of gleeful enthusiasm for the topic with just enough of an edge necessary for the macabre subject matter that made her perfect for this event. The tour began driving along an area of the city named in honor of the shifty man who incidentally founded the area during a shady business deal following the Great Chicago Fire, “Cap” George Streeter. What we now saw as a prestigious neighborhood running alongside Lake Michigan was once a mere junkyard Streeter founded the profiteer off the disaster.

The first stop on the tour was an absolute highlight on this drive around Chicago. On the surface it appears to be the Biograph Theater, but a nearby new-ish mural in the neighboring alley serves as a testament to its historical importance. In 1934 “Public Enemy Number One” went here to take in a Clark Gable and Myrna Loy film and upon leaving was ambushed by G-Men who gunned him down in the alley. As the tour guide Leah recounted the grand story of the charming bank robber she revisited the idea that the powers-that-be in the Second City were not keen to memorialize the darker side of their history and that the magnificent mural of Dillinger would likely be covered up in a short amount of time. In fact the only plaque commemorating what happened sited the Biograph as the site where the FBI solved the case that legitimized them as a federal agency. After a good chunk of time exploring the area and taking the requisite pictures for social media cred, it was time to once again board the Crime Bus (or whatever you wanna call it…..Transport of Evil?….Bus to Hell?..) and continue the exploration of the city’s underworld.

Along the way to our next stop we were regaled with stories of Chicago criminals from the big namers like HH Holmes and Leopold & Loeb to the obscure like a drug dealing ring of fast food employees. Given the nature of the beast there was a focus on Chicago during the bleak and horrifying time of Prohibition. Driving through historic neighborhoods, Leah pointed out the older buildings which were marked with green on the doorframes which denoted its status as a Speakeasy during this dark time. Of course, no discussion of Prohibition would be complete without bringing up Al Capone and his Southside Gang. The gangster’s rise and fall and everything in-between was covering, naturally with a focus on his war his Northside Gang rivals as we drove pas the vacant lot where the St. Valentine’s Day Massacre occurred. The bus even made a brief stop so we could get out and get a good look at the ornate tower where Capone ran his empire.

The final stop on our tour was perhaps the coolest. On the surface it was a restaurant named for its founder, and famed Chicago Cubs announcer, Harry Caray. But following the death of Al Capone his successor Frank “The Enforcer” Nitti took over the gang and set up his headquarters in what is now this Italian steakhouse. Upon doing the necessary remodeling work to convert a gangster’s hideout into a restaurant they discovered a treasure trove of Nitti’s goods. In a move that makes history buffs like me incredibly grateful, they did not throw anything out, rather they used a small section of the basement as a small crime museum. Though the coolest discovery is not in this museum, but rather right there by the front door of Harry Caray’s for all to see. It is a small notebook where the Enforcer kept record of every gunsel, lawyer, cop, judge, government official etc. who were on the take from him.

Few cities have a history filled with gangsters, serial killers, grifters, and all around crumb bums like Chicago. True, other cities have had heavy crime problems, but none have had these criminals reach the level of notoriety like Chicago criminals. There is no denying, that despite their actions, there is a certain coolness associated with figures like Al Capone, “Bugs” Moran, John Dillinger, and more. Given the prevalence of true crime entertainment currently it is surprising that the city does not do more to promote this as a means to attract tourists. Many cities see the value of their seedy pasts as a means to bring in out-of-town dollars, I mean look at Salem, Massachusetts. That being said the Chicago Crime Tour is there to carry that forward and make sure the dark side of the Windy City is uncovered for those seeking it out. The comfortable bus ride takes you comfortably past a number of fascinating historic sites while knowledgeable and entertaining tour guides showcase a skill for storytelling that grabs your attention and does not let go.