Chicago Mobs and Haunts Walking Tour

Following the beaten path of Chicago’s bustling downtown, the Chicago Mobs and Haunts Walking Tour offers a compelling look at the city’s shadowy past. Priced at $34 per person and lasting roughly 1 hour 30 minutes to 2 hours, this tour appeals to history buffs, true crime enthusiasts, and those curious about ghostly legends. It departs from the Congress Plaza Hotel and culminates near N. Michigan Avenue and Wacker Drive, providing easy access to public transportation and central Chicago.

Guided by a professional, engaging local guide, this tour skips standard sightseeing for a closer look at mobsters, haunted hotels, and the alley known as the Alley of Death. The mix of crime stories, ghost tales, and historic sites makes for an immersive experience that brings Chicago’s gritty underbelly to life. While most reviews praise the guides’ knowledge and storytelling, some note that the outdoor stops can be chilly and that a few stories may seem less believable—yet overall, this tour offers a memorable, edgier perspective on the city.

Key Points

• Affordable and concise: Priced at $34, lasting up to 2 hours with a small group of no more than 20 people.
• Deep dive into Chicago’s crime history: Focuses on mobsters, haunted hotels, and supernatural stories.
• Not just sightseeing: Combines historic sites like the Chicago Loop and the Alley of Death with ghost stories from famous locations.
• Starting point: The Congress Plaza Hotel, a haunted hotel with a storied past.
• Ending near Michigan Avenue: Close to shopping and public transit options for easy exploration afterward.
• Highly rated guides: Guides like Lark and Kevin receive praise for their enthusiasm and knowledge.

Chicago’s Dark Side: From the Congress Plaza Hotel to the Alley of Death

The tour begins at the Congress Plaza Hotel & Convention Center, known as one of the most haunted hotels in America. Here, the guide shares eerie tales about the hotel’s ghostly inhabitants, setting a spooky tone for the walk ahead. This stop lasts for about 15 minutes and introduces the supernatural theme that runs through the entire tour.

Next, the group heads to Exchequer Restaurant & Pub, a location once called the 226 Club, which was a favorite hangout of Al Capone. Standing outside this historic spot, the guide recounts stories of mob activity and the city’s vice operations during Prohibition. This stop also lasts around 15 minutes, giving guests a chance to picture the speakeasy era.

The tour continues into the Chicago Loop, where the guide explains how the area beneath the “L” train system was once a hotbed for crime, gambling, and illicit activities. This segment highlights how the city’s underground spaces played a role in organized crime and vice, lasting about 15 minutes.

Then, the walk leads to West Couch Place, also called the Alley of Death. This alley is reputed for supernatural activity and strange occurrences. The guide describes its haunted reputation and the ghost stories linked to this dark corner of Chicago, making this a highlight for those interested in ghostly legends. This stop also takes around 15 minutes.

What You See and Hear During the Tour

The professional guide leads you through central Chicago, providing captivating stories about mobsters like Al Capone, haunted hotels, and notable tragedies like city fires and disasters. The guide’s storytelling style is often described as lively, informative, and humorous, making the walk both educational and entertaining.

Stops are mostly outside, so dressing warmly is recommended, especially during colder months. The walk covers approximately two miles, with a flat terrain suitable for most participants, and requires no stairs or strenuous activity. The group size is kept to a maximum of 20 travelers, ensuring a more personal experience.

Guests appreciate the depth of the stories, often referencing lesser-known tragedies and Chicago’s notorious criminal past that many aren’t familiar with. The lively narration and the way the guide brings history to life are frequently praised, with mentions of guides like Lark and Kevin for their charisma and knowledge.

Accessibility, Logistics, and Booking

The tour departs from the Congress Plaza Hotel at 520 S Michigan Ave. It ends near North Michigan Avenue and East Wacker Drive, placing you within easy reach of shopping districts and public transportation. The mobile ticket system makes booking straightforward, and most travelers find the scheduling flexible, booking on average 17 days in advance.

With a free cancellation policy up to 24 hours before the tour, plans can be adjusted effortlessly. The maximum group size of 20 people helps keep the experience intimate and engaging, despite occasional outdoor stops that might be noisy or chilly.

The Guides and Guest Experience

Reviews highlight guides like Lark and Kevin for their knowledgeable and engaging narration. They keep the group lively with jokes and interesting facts, making the experience fun while informative. Many reviews mention the guides’ ability to deliver stories at a good pace, with stops allowing for photos and brief rests.

However, a few reviews note that outdoor stops can be cold or noisy, and some stories may be less believable or less detailed than expected. In particular, one review mentions a guide who lacked charisma, and others highlight some issues with communication or tour cancellations, emphasizing the importance of confirming arrangements.

Comparing the Tour with Other Chicago Experiences

While the Chicago Mobs and Haunts Tour focuses on crime, ghost stories, and the city’s haunted sites, it offers a different vibe from river cruises or architecture tours. Its edgy, spooky theme appeals to those wanting a darker perspective on Chicago’s history. The tour’s price and duration make it a convenient add-on for a day of exploring downtown, especially given its high ratings and positive reviews.

Similar experiences include river architecture tours and sunset cruises, but none focus specifically on Chicago’s criminal past and supernatural tales. For those interested in legends of the city’s fires, ghosts, and mobsters, this tour provides a unique narrative.

Final Thoughts on the Chicago Mobs and Haunts Walking Tour

This tour offers a solid value at $34, especially considering the enthusiastic guides and interesting stops. It suits visitors who enjoy history, true crime, and ghost stories, and prefer a walking experience that is both informative and spooky.

The small group size and local guides enhance the experience, though outdoor stops mean dressing warmly in colder months. While some reviews suggest the stories could be more detailed, the engaging narration and selection of locations make this a worthwhile adventure for those craving a darker, more mysterious side of Chicago.

For anyone curious about the city’s criminal legends, haunted sites, and dark history, the Chicago Mobs and Haunts Walking Tour delivers a memorable, slightly edgy peek into the city’s past.

Frequently Asked Questions

How long does the tour last?
The tour runs approximately 1 hour 30 minutes to 2 hours, covering about two miles of walking.

What is the starting point?
It begins at the Congress Plaza Hotel & Convention Center at 520 S Michigan Ave.

Is the tour suitable in winter?
Yes, but outdoor stops can be cold, so dress warmly especially during colder months.

Can I cancel the booking?
Yes, free cancellation is available up to 24 hours before the tour starts, for a full refund.

Are guides knowledgeable about Chicago’s crime history?
Absolutely, reviews praise the guides’ enthusiasm and expertise in sharing stories about mobsters, haunted sites, and city disasters.

Is the tour accessible for most travelers?
Yes, the walk is level, with no stairs, making it accessible to most guests with average mobility.