Chicago Mysteries & Crime Tour

Delve into Chicago's intriguing history of deception and intrigue with this guided exploration of the city’s infamous crimes and puzzling mysteries. Prepare for a spine-tingling experience filled with captivating tales.

Tour Overview

Upon booking, you will have the option to select between two distinct tours that commence and conclude at 163 E Pearson St. . Each tour includes transportation via bus and is led by an English-speaking guide. Below, you will find a concise overview of each available tour:

Day Tour (1.5–2 Hours)

Board the bus as we embark on a chilling journey to uncover chilling stories and locations that will send shivers down your spine. We will traverse the lesser-known corners of the Windy City, a stronghold for the Mafia, where gangsters operated outside the law. This tour will encompass six notable neighborhoods, including Streetville, River North, Lincoln Park, and Old Town.

At each stop, compelling narratives await us, leaving us questioning: Who was the elusive Al Capone? What was concealed behind the façade of Frank “The Executioner” Nitti? We will view the Biograph Theater, the site of John Dillinger’s dramatic end after a betrayal. A visit to the Holy Name Cathedral will recount a notorious mafia vendetta marked by violence.

Next, we will arrive at the Cook County Criminal Courthouse, a critical venue for landmark trials that shaped the legacy of Chicago's crime saga. A stop at Harry Caray's Italian Restaurant will unveil fascinating connections to the Mafia's legacy. What role did this restaurant play in its storied past?

Additionally, we will recount the grim exploits of H. H. Holmes, a notorious serial killer whose heinous actions ignited widespread fear, and whose charm masked his dark nature. Did you know he was regarded as one of the most attractive men of his era? We will also reflect on the notorious St. Valentine's Day Massacre, where numerous men met their tragic fate in a clandestine setting on the North Side.

• Schedules: this tour is available daily at 10 am, 12 pm, 2 pm, and 4 pm

Night Tour (2–2.5 Hours)

Prepared to witness the city lights obscure the remnants of crime? This tour follows the same path as the daytime experience but allows us to dive deeper into the tales at the locations marked by Chicago’s criminal history.

As a highlight, there will be a surprise stop revealed during our journey. Can you guess what it might be? One hint: it promises to be a delightful interlude.

This tour represents not just a walk through the city but a journey into its shadowy past. And remember, the truth often resides within the shadows.

• Schedule: this tour is conducted on Mondays, Thursdays, and Fridays at 7:30 pm