# 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 "Murder Castle." The building was fitted with soundproof rooms, gas lines, trapdoors and a basement designed for the disposal of human remains.

The Holmes segment of the tour discusses sites linked to his crimes during the World's Fair era, when thousands of visitors poured into Chicago and many were never seen again. The case inspired Erik Larson's bestseller *The Devil in the White City* and remains one of the most studied criminal cases of the 19th century.

Capone, Nitti and the Outfit

The tour then moves into the Prohibition years, when Chicago became synonymous with organized crime. Stops and stories cover Al Capone, who ran the Chicago Outfit until his 1931 conviction for tax evasion, and Frank "The Enforcer" Nitti, who succeeded him. The St. Valentine's Day Massacre of 14 February 1929, in which seven men associated with Bugs Moran's North Side Gang were gunned down in a garage, is a central part of the narrative, as is the era of Eliot Ness and *The Untouchables*.

The route passes through River North, the Gold Coast, Lincoln Park, Old Town, the Loop and the Magnificent Mile — neighborhoods that look polished today but once housed speakeasies, mob hideouts and crime scenes that made international headlines.

Dillinger, Leopold and Loeb

The Lincoln Park portion of the route is closely tied to John Dillinger, the bank robber gunned down by FBI agents outside the Biograph Theater on 22 July 1934 after being betrayed by the so-called "Lady in Red." The tour also covers Nathan Leopold and Richard Loeb, the two University of Chicago students whose 1924 kidnapping and murder of 14-year-old Bobby Franks became one of the most sensational "thrill killing" cases in American legal history, defended by Clarence Darrow.

Practical Information

The tour is operated by Chicago Crime Tours and Experiences and departs from 163 East Pearson Street, Chicago, IL 60611. It is bookable through the official operator and partner platforms, including Viator, Expedia and Tripadvisor, with 2026 dates currently listed.

Exact pricing is not publicly fixed and varies by season and platform. Comparable Chicago crime tours start from around $37 per person on Viator, but for current pricing on this specific tour you should check the booking platforms directly or contact the operator. Tour duration is not specified in public listings — confirm with the operator at the time of booking.

Because this is a bus tour with photo stops rather than a long walking experience, it is suitable for travelers who want to cover a lot of ground in one go. Comfortable shoes and a charged camera are recommended; Chicago weather can shift quickly, so a layer for cooler lake winds is wise even in summer.

Why This Tour Stands Out

Most crime tours specialize in a single era — either Prohibition gangsters or Victorian-era murder. The Chicago Crime and Mob Bus Tour is unusual in connecting Holmes's 1890s Murder Castle, the 1924 Leopold and Loeb case, the 1929 St. Valentine's Day Massacre and the 1934 killing of Dillinger into a single coherent route. For true crime travelers, it offers a rare chance to see how one American city produced such a dense concentration of criminal history within a few square miles.