Chicago is a city with a storied past, and there’s no better way to dive into its rich (and sometimes dark) history than by taking the Chicago Crime and Mob Tour. On a cold wintery day, we found ourselves comfortably seated on a tour bus, grateful for the warmth as we explored the city’s infamous crime scenes, learning about its legendary gangsters and Prohibition-era secrets.
A Comfortable and Immersive Experience
One of the best aspects of this tour was that it was conducted on a bus, making it an ideal option for those visiting Chicago in the winter. Instead of braving the icy winds on foot, we enjoyed a comfortable ride through the city, passing by locations we likely wouldn’t have explored otherwise.
The tour provided a fascinating glimpse into the past, complete with engaging storytelling and stops at some of the most significant crime-related landmarks in the city.
A Front Row Seat to History
The tour provided an in-depth look at the life, crimes, and eventual demise of one of America’s most notorious criminals—John Dillinger. We stood at the very spot where he was killed in front of the Biograph Theater, imagining the intense manhunt that led to his capture. It was surreal to walk in the footsteps of a figure so deeply entrenched in the country’s criminal history.
Another highlight was seeing a speakeasy where Dillinger once spent time, offering a glimpse into the underground world of Prohibition-era Chicago. The rich history and atmospheric locations made it feel like stepping back in time.
Hidden Secrets in Harry Caray’s Vault
One of the most unexpected and fascinating stops was Harry Caray’s Italian Steakhouse, located in a 100-year-old building with a history as intriguing as its menu.
In 1998, an electrician made a stunning discovery—a hidden room, now known as Nitti’s Vault. This secret space was used as a hiding place and a passage during Prohibition, providing a direct connection to Chicago’s vast underground tunnel system.
We had the chance to stop and explore the Harry Caray Museum, stepping off the bus to take pictures and get a closer look at the fascinating exhibits. Inside, we saw incredible artifacts that brought the city’s mob history to life. Some of the most intriguing items included:
A phone book from the 1920s containing the addresses and phone numbers of both mobsters and government officials, an eerie reminder of how intertwined crime and politics were at the time.
News clippings from Al Capone’s sentencing shed light on the downfall of one of the most infamous gangsters in American history.
A safe was found within the vault, along with various other artifacts that were hidden away for decades.
Photos of the sealed vault and secret room, offering a glimpse into the hidden underworld that once thrived beneath the streets of Chicago.
An opening in the wall where you can peek inside and see the hidden room, providing a firsthand look into the past and the secretive world of Prohibition-era Chicago.
A Chicago Crime Tour Worth Taking
This tour was an unforgettable way to experience Chicago from a unique perspective. The mix of historical storytelling, significant crime scene locations, and rare artifacts made for an engaging and educational journey through the city’s notorious past. We appreciated that we were able to step off the bus at key locations, take pictures, and truly immerse ourselves in the experience.
Whether you’re a history buff, a true crime enthusiast, or just looking for an interesting way to explore Chicago, this tour is well worth adding to your itinerary. For anyone interested in the darker side of Chicago’s history, the Chicago Crime and Mob Tour offers an up-close look at the city’s gangster past—without having to step into the cold for too long!
For more fun in Chicago, check out 36 Hours in Chicago: A Whirlwind Adventure.
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Las Vegas Nevada also has a very interesting and informative museum that tells an interesting and informative story of organized crime in the Al Capone days.