Ride Through Chicago's Darkest Chapters With Chicago Crime Tours

Chicago Crime Tours and Experiences operates a bus tour through Chicago's most infamous crime neighborhoods, covering H.H. Holmes, Al Capone, John Dillinger and other notorious figures, departing year-round from 163 East Pearson Street in the Streeterville district.

The "Chicago Crime and Mob Bus Tour" is one of the city's most established true crime experiences, weaving together more than a century of murder, mob violence and Prohibition-era corruption into a single guided ride. Rather than focusing on a single villain, the tour traces a chronological arc of Chicago's criminal history with on-and-off stops for photographs.

America's First Serial Killer

The inclusion of Herman Webster Mudgett — better known as H.H. Holmes — is what sets this tour apart from standard gangster routes. Holmes confessed to 27 murders and is widely regarded as America's first documented serial killer. During the 1893 World's Columbian Exposition, he operated a purpose-built hotel on Chicago's South Side that later became known as the " Castle." The building was fitted with soundproof rooms, gas lines, trapdoors and a basement designed for the disposal of human remains.