It was a cloudy Sunday morning when I boarded the black bus just off Michigan Avenue with about 30 other passengers. As the tour guide checked our names off a list, he handed us a brochure for the Crime and Mob Tour we were about to take, complete with pictures of some of the most notorious Chicago mobsters. He then wasted no time delving into Chicago’s storied past, starting back in 1840, when the city was already known as a hotbed of crime.
A stop at Frank Nitti’s Vault on a Chicago Crime and Mob Tour
As we drove north on Lake Shore Drive, our guide explained the history of Streeterville, the neighborhood where our tour began. While not connected to crime or the mob, the story of how this former garbage dump site became prime real estate in the city is fascinating.
Our first stop was on Lincoln Avenue in the Lincoln Park neighborhood. Here, we stood outside the former Biograph Theater to hear the story of bank robber John Dillinger and how he was killed by the FBI in a nearby alley. After driving by the location of Dillinger’s favorite speakeasy, we stopped in front of the scene of the infamous St. Valentine’s Day Massacre. While the building where the massacre took place is long gone, a few remnants of it still remain in the building next door.
As we drove around the city in the black bus, our heavily bearded guide told us stories of crime from throughout Chicago’s history, pointing out the drugstore where bottles of tainted Tylenol were found in 1982 and the fast food restaurant with a drive-through that served more than just food in the early ‘90s. We passed the site of the old courthouse and jail and learned about famous prisoners – some who escaped and some who didn’t.
Harry Caray’s
Our penultimate stop was at Harry Caray’s restaurant, a place I have been a number of times in the past. However, something I didn’t know was that mobster Frank Nitti once lived upstairs, and tunnels underneath the restaurant were used for smuggling. Indeed, we had a chance to go inside to visit Frank Nitti’s Vault and see a collection of memorabilia found in the apartment after his death.
The last stop was outside of the Holy Name Cathedral, a spot included on many historical tours of the city due to the fact that gang leader Hymie Weiss was shot to death on the steps. While many say you can still spot bullet holes on the cathedral’s exterior, our guide assured us this is not the case.
We arrived back where we began, near Water Tower Place, just an hour and a half after we’d departed. The tour was short, but packed full of information; our guide didn’t waste a second, pumping us full of stories and weaving them into a chronology of Chicago’s crime and mob history.
– Contributed by Katie Aune
