• Biograph Theatre - The historic Biograph Theater is renowned as the site where the notorious gangster John Dillinger was killed by FBI agents in 1934. The dramatic shootout took place just outside the theater after he watched a movie. Today, the building remains a significant landmark tied to Chicago’s criminal history, serving as a reminder of the city’s tumultuous Prohibition-era past.
• Clark Street - St. Valentine’s Day Massacre Site.
  This location marks the site of the infamous St. Valentine’s Day Massacre of 1929, one of the most notorious events in American organized crime history. Seven members of a rival gang were brutally executed in an event widely associated with Al Capone’s criminal empire. The massacre shocked the nation and intensified efforts to combat organized crime. Today, the site stands as a powerful symbol of Chicago’s gangster era.
• Holy Name Cathedral - Holy Name Cathedral.
  Holy Name Cathedral is one of Chicago’s most significant religious landmarks, with an unexpected link to the city’s crime history. In 1926, gunmen attempted to assassinate Al Capone outside the cathedral in a dramatic drive-by shooting. Capone narrowly escaped, adding another chapter to the city’s violent mob conflicts. The cathedral remains today as both a place of worship and a historic site.
• Criminal Court Building - Cook County Criminal Court Building.
  This courthouse played a pivotal role in Chicago’s fight against organized crime. Many mobsters, gang leaders, and criminals were tried here as authorities sought to dismantle powerful criminal organizations. The building became a symbol of the legal battle against the city’s notorious gangster networks. Its history reflects Chicago’s long struggle to restore law and order during the Prohibition era.
• Harry Caray’s Italian Steakhouse - Harry Caray’s Italian Steakhouse (Former Mob Hangout).
  Situated in a historic building once linked to Chicago’s criminal underworld, this location has ties to the city’s mob history. During the Prohibition era, many restaurants and clubs secretly served alcohol and became gathering spots for influential figures. Today, the building houses one of Chicago’s renowned restaurants while preserving its fascinating past.
• Business Locations - Chicago Loop Prohibition-Era Locations.
  The Chicago Loop was once teeming with hidden speakeasies where illegal alcohol was served during Prohibition. Behind ordinary storefronts, secret bars operated throughout the city, often protected by powerful crime syndicates. These underground venues became central to Chicago’s nightlife in the 1920s. Walking through the area today reveals the streets where this clandestine world once thrived.

• Hotel or custom pickup and drop-off
• Professional English-speaking local driver/informal guide
• On-board WiFi
• Fuel and Tolls
• Water
• All taxes and handling charges

• Meals and beverages
• Tips and Gratuities

Explore Chicago’s notorious gangster history on a private, fully customized tour through the city’s historic Prohibition-era streets. Enjoy a comfortable journey with your English-speaking driver, who will share fascinating tales about Al Capone, rival gangs, speakeasies, and legendary crime events from the 1920s and 1930s.

Start at the Biograph Theater, the site of John Dillinger’s shooting, then proceed to the St. Valentine’s Day Massacre location, a significant event in Al Capone’s ascent. Visit Holy Name Cathedral, the Cook County Criminal Court Building, and Harry Caray’s Italian Steakhouse, all connected to Chicago’s mob history.

Finish in the Chicago Loop, discovering hidden speakeasies and secret nightlife venues from the Prohibition era. With a flexible, door-to-door itinerary, this private tour provides an engaging and exciting glimpse into the city’s dramatic gangster past.

• For 1-3 people: A comfortable sedan will be assigned to your group.
• For 4-7 people: A spacious minivan will be assigned to your group.
• Throughout your ride, our drivers serve as informal local guides—sharing stories, history, and local tips at every stop. Please note that drivers are not permitted to enter museums or archaeological areas, but they’ll ensure you make the most of your visit with suggestions and background information before you explore on your own.
• Some stops on your itinerary may be closed on the date of travel due to public holidays, maintenance, or special events. We recommend verifying opening hours on the attraction’s official website or contacting us before your tour. If a stop is unexpectedly closed, we will try to offer a suitable alternative or a refund if the tickets are included in the price.
• Our tours are fully flexible — you decide which attractions to explore inside and which to admire from the outside. Entrance tickets are not included unless clearly specified as a “tickets included” option in the tour selection. Your driver will adjust the itinerary based on opening hours, availability, and your preferences to ensure a smooth and enjoyable experience.

For a full refund, cancel at least 24 hours before the scheduled departure time.