Ride Through Al Capone's Chicago on This Mob Bus Tour
In 1929, seven men stood up for the last time in a garage at 2122 N Clark Street in Chicago — and ever since, the city has never quite shaken its reputation as America's capital of crime. The Chicago Crime and Mob Bus Tour takes you through the very neighborhoods where Al Capone, John Dillinger and serial killer H.H. Holmes left their bloody marks, and the tour still runs today for those who want to see the geography of crime with their own eyes.
What you experience on the tour
The tour lasts between 90 minutes and two hours and departs from the meeting point at the corner of Pearson Street and Michigan Avenue — just outside 163 E Pearson St, Chicago, IL 60611. You are asked to arrive at least 15 minutes before departure. The tour ends at the same location, so there is no need to worry about getting back.
Along the way, the bus travels through neighborhoods including Gold Coast, Lincoln Park, Old Town, the Loop and the Magnificent Mile, while a guide unfolds Chicago's criminal history from the speakeasies of the Prohibition era to today's tourist attractions with a dark past.
The St. Valentine's Day Massacre — Chicago's bloodiest day
On February 14, 1929, seven members of the North Side Gang were shot dead in a garage by men who were presumed to be working for Al Capone's Chicago Outfit. The site at 2122 N Clark Street is today one of the most iconic crime scenes in American criminal history. The garage itself no longer exists, but the bus drives past the location and the guide places the massacre within the broader power struggle over Chicago's underworld during Prohibition.
John Dillinger and the Biograph Theater
On the same tour you pass the Biograph Theater, where the FBI shot and killed wanted bank robber John Dillinger on July 22, 1934, as he was leaving a movie screening. At the time, Dillinger was the most wanted man in the United States and had evaded police on numerous occasions. The theater still stands as a building in the Lincoln Square neighborhood, and the brief drive-by creates a strange sensation that history has suddenly become tangible.
H.H. Holmes and the Murder Castle
No account of Chicago's criminal history is complete without Herman Webster Mudgett — better known as H.H. Holmes. In the 1890s he constructed a three-story building on 63rd Street, which he himself called a hotel, but which investigators later revealed to be a purpose-built killing site fitted with gas chambers, secret passageways and a crematorium in the basement. The number of victims remains unknown — estimates range from 27 to more than 200. The tour includes the story of Holmes as one of America's first documented serial killers.
Holy Name Cathedral and the bombing
Holy Name Cathedral is another stop on the route's drive-by list. In 1926, the site was struck by a bombing linked to the killing of gangster Hymie Weiss, who led the North Side Gang. The cathedral facade bore the marks of the gunfire for decades, and the site stands as a quiet testament to how deeply mob violence penetrated everyday life in Prohibition-era Chicago.
Practical information
Ticket prices start from around 35 dollars with free cancellation available, though prices and availability vary by season and booking type. You can check current prices and reserve your spot directly through Viator's overview of Chicago Crime Tours, where you will also find information about any variations of the tour. Contact the organizer for questions about accessibility for visitors with reduced mobility or group discounts.
Who is the tour suited for?
The tour is ideal for travelers with an interest in American history, the Prohibition era or the true crime genre in general. The physical demands are minimal, as most of the experience takes place from your seat on the bus — making it accessible for most people. If you have already read Erik Larson's The Devil in the White City about H.H. Holmes, or followed documentaries about Al Capone, seeing the actual locations where those stories unfolded will make for a particularly satisfying experience.
Chicago still hides its scars well — but this bus tour knows exactly where to look.
