Chicago: Gangsters and Ghosts Guided Walking Tour

Chicago’s Gangsters and Ghosts Guided Walking Tour takes visitors on an engaging 2-hour journey through the city’s captivating vice history. Led by knowledgeable historians, the tour explores the South Loop’s notorious past, including the reign of Al Capone and the area’s haunted landmarks. For $35 per person, this family-friendly experience offers a unique opportunity to uncover the city’s eerie and intriguing secrets. Whether you’re a history buff or simply curious about Chicago’s dark side, this tour promises to leave you…

This experience made our article of The 16 Best Walking Tours In Chicago.

Key Points

• Provides a 2-hour guided walking tour in Chicago’s South Loop, covering 1.5 miles and highlighting the area’s history with gangsters and ghosts.
• Includes a 20-minute break at a former gangster hangout, allowing participants to enjoy the city’s dark past.
• Offers a family-friendly experience, with free admission for children aged 6 and under, and is wheelchair accessible.
• Focuses on significant landmarks tied to Al Capone’s criminal activities, delivering captivating narratives of the area’s vice history.
• Features positive traveler feedback, with an overall rating of 4.7 out of 5 stars and high praise for the knowledgeable guides and unique storytelling.

You can check availability for your dates here:

Tour Overview

The Chicago: Gangsters and Ghosts Guided Walking Tour is a 2-hour exploration of Chicago’s South Loop, known for its seedy underbelly during the 1920s and 1930s.

Chicago’s South Loop was once home to a seedy underbelly during the 1920s and 1930s, as explored in this 2-hour guided walking tour.

Priced at $35 per person, the tour covers 1.5 miles with a 20-minute break at a former gangster hangout.

Led by a historian, it’s family-friendly, uncovering mysteries of Chicago’s dark past. Participants will engage with stories of gangsters and ghosts, visiting significant sites like the Chicago Riverwalk, Palmer House, and Congress Plaza Hotel.

The tour is wheelchair accessible and has positive traveler feedback, with guides praised for their knowledge and entertaining presentations.

Booking Information

Free cancellation up to 24 hours in advance allows travelers to reserve their spot risk-free and receive a full refund if plans change.

Booking is flexible, with the option to reserve now and pay later. Children aged 6 and under can join the tour for free, though it’s not recommended for those with infants or mobility issues.

The tour is wheelchair accessible, making it inclusive for a wide range of participants.

Itinerary Highlights

Beginning in downtown Chicago, the tour explores the South Loop, a neighborhood known for its vice during the 1920s and 30s.

Guests visit the Chicago Riverwalk, Palmer House, and Chicago Theatre, learning about the area’s dark history. The tour focuses on Al Capone’s criminal empire, uncovering mysteries and ghost stories at historic landmarks like the Congress Hotel.

Along the 1.5-mile route, guests enjoy a 20-minute break at a former gangster hangout.

Tour Experience

How does the tour experience unfold? The tour is guided by a historian who brings the city’s dark past to life.

Participants engage with stories of gangsters and ghosts as they visit significant sites throughout the South Loop. The family-friendly experience uncovers the mysteries of Chicago’s vice-filled history during the 1920s and 30s.

Travelers commend the knowledgeable and entertaining guides, who skillfully weave together tales of the city’s notorious characters and ghostly inhabitants.

With a mix of historical insights and spooky legends, the tour offers a unique perspective on Chicago’s storied past.

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Customer Reviews

Travelers have overwhelmingly positive reviews for the Chicago: Gangsters and Ghosts Guided Walking Tour, with an overall rating of 4.7 out of 5 stars based on over 1,300 reviews. Guests praise the knowledgeable and engaging guides, like Max and Sophia, who bring the city’s dark past to life. The tour also earns high marks for value, with reviewers noting the reasonable price for the quality experience.

| Metric | Rating |

| — | — |

| Overall | 4.7/5 |

| Guide | 4.8/5 |

| Value | 4.6/5 |

Travelers commend the tour’s ability to uncover Chicago’s mysteries in a family-friendly manner, making it a must-do activity for those seeking an immersive look into the city’s notorious gangster and ghost history.

Exploring Chicago’s South Loop

The Chicago: Gangsters and Ghosts Guided Walking Tour takes visitors on an immersive journey through the South Loop, a neighborhood once notorious for its criminal underworld during the 1920s and 1930s.

Guides lead participants to explore the district’s haunting past, stopping at key landmarks linked to Al Capone’s empire.

From the historic Chicago Riverwalk to the legendary Palmer House and Chicago Theatre, the tour uncovers the shadowy tales of gangsters and ghosts that once inhabited these streets.

Guests engage with the stories, gaining a deeper understanding of Chicago’s captivating and sinister history.

Al Capone’s Empire

As the tour progresses, guides explore the intricate details of Al Capone’s criminal empire that once thrived in Chicago’s South Loop.

The notorious gangster’s operations controlled much of the area’s illegal activities, including bootlegging, gambling, and prostitution.

Guides share stories of Capone’s rise to power, his lavish lifestyle, and the brutal violence that maintained his grip on the city.

Captivating tales of Capone’s rise to power, his extravagant lifestyle, and the ruthless violence that secured his hold on the city.

Visitors learn how Capone’s empire ultimately unraveled, leading to his downfall and imprisonment.

Through these captivating narratives, the tour provides a glimpse into the darker underbelly of Chicago’s past.

Haunted Landmarks

What haunting tales await visitors on the Chicago: Gangsters and Ghosts Tour?

Guides lead guests to historic landmarks rumored to be haunted. At the Congress Plaza Hotel, hear the story of a young woman who died under mysterious circumstances. Legend has it her ghost roams the halls.

The Palmer House also has a ghostly reputation, with tales of a bride who died on her wedding night. Visitors may feel a chill or hear unexplained noises as they explore these haunted sites.

The tour offers a chilling glimpse into Chicago’s supernatural side.

Frequently Asked Questions

Can We Take Photos During the Tour?

Participants are generally allowed to take photos during the tour, though some sites may have restrictions. It’s best to check with the tour guide at the start of the tour for any specific guidelines.

Is the Tour Suitable for People With Hearing Impairments?

The tour may be suitable for people with hearing impairments, as it’s wheelchair accessible. However, it’s best to inquire about specific accommodations, as the tour relies heavily on the guide’s commentary and storytelling.

Do We Get to Interact With Any Real-Life Gangsters?

No, participants won’t interact with any real-life gangsters on this tour. The tour focuses on exploring historical sites and learning about Chicago’s gangster past through the guide’s narration and stories, rather than any live reenactments or encounters.

Are There Any Restroom Breaks During the Tour?

The tour includes a 20-minute break at a gangster hangout, which provides an opportunity for restroom access. Participants can use restrooms during this intermission to ensure a comfortable experience throughout the 2-hour walking tour.

Can We Purchase Snacks or Drinks Along the Way?

Yes, tour participants can purchase snacks or drinks during the 20-minute break at a gangster hangout. There are also opportunities to grab a bite to eat or grab a beverage at other stops along the 1.5-mile walking route.

The Sum Up

The "Chicago: Gangsters and Ghosts Guided Walking Tour" offers a compelling 2-hour journey through the South Loop, immersing visitors in the city’s captivating vice history. Led by knowledgeable historians, the tour covers 1.5 miles and includes a stop at a former gangster hangout, making it a must-do for anyone intrigued by Chicago’s rich and eerie past. At $35 per person, this family-friendly experience provides an engaging exploration of the area’s notorious figures and haunted landmarks.

You can check availability for your dates here: