Chicago Mobsters Gangsters Ghosts and Prohibition Tour

Imagine strolling through the streets of Chicago, where history’s most notorious gangsters once ruled and spirits are said to still linger in grand hotels. That’s exactly what the Chicago Mobsters, Gangsters, Ghosts, and Prohibition Tour offers—a compelling blend of crime stories, haunted sites, and the city’s vibrant past.

This tour is perfect if you’re curious about Chicago’s underground world of speakeasies, mob shootouts, and ghostly legends, all told through the eyes of an expert historian guide. We loved how it combines engaging storytelling with scenic city sights, making it a memorable experience. That said, it’s a short tour—just 90 minutes—so if you prefer in-depth explorations, you might want to add additional visits elsewhere.

This tour appeals most to those interested in true crime, haunted history, or Chicago’s Prohibition era. It’s fun, informative, and offers a unique way to see the city’s darker stories come to life after dark.

Good To Know

• Historical storytelling: Expert guides share detailed tales of mob activity, speakeasies, and ghosts.
• Haunted landmarks: Visit iconic hotels and sites reputed for paranormal activity and celebrity lore.
• Scenic routes: Walk along the Chicago Riverwalk and explore areas tied to smuggling and mob dealings.
• Concise, engaging format: 1.5 hours packed with stories, perfect for a quick evening activity.
• Affordable price: At just $28 per person, it offers good value considering the rich stories and sightseeing.
• Small group size: Max 35 travelers, ensuring a more personal experience.

An In-Depth Look at the Chicago Mobsters, Ghosts, and Prohibition Tour

What to Expect from the Itinerary

This tour takes you through the heart of Chicago’s historic districts, illuminating the city’s notorious past with lively storytelling and visits to legendary landmarks. It’s designed to give you a taste of Chicago’s gangster era while weaving in ghost stories that add a spooky thrill to the night.

Starting Point: 71 E Wacker Dr, a prime location near public transit and surrounded by shimmering skyscrapers, sets the tone for this city-centered adventure.

Stop 1: The Heart of Downtown Chicago
You’ll begin in an area filled with historic skyscrapers and some of the city’s most haunted locations. Here, your guide, likely a knowledgeable historian, will set the scene, highlighting Chicago’s rise as a crime hub during Prohibition. Expect lively narration about mob influence blending with the city’s architecture and nightlife.

Stop 2: Speakeasies, Crime Scenes, and Mob Hangouts
Next, the tour moves into the South Loop, an area renowned for its speakeasies and historic mob activity. You’ll learn how figures like Al Capone built their empires, with stories of shootouts at famous sites and secret tunnels used for smuggling alcohol. The visit to Death Alley behind the Nederlander Theatre is especially notable—once notorious for ghost sightings after the Iroquois Theatre fire, it adds an eerie layer to the evening.

Stop 3 & 4: Haunted Hotels—Palmer House & Congress Plaza Hotel
Two of Chicago’s most iconic hotels feature in the tour. The Palmer House is famous not only for its luxurious history but also for ghostly tales linked to its elegant halls. The Congress Plaza Hotel, often called the most haunted hotel in Chicago, is known for spooky stories from its 12th floor, where recent visitors have reported strange feelings and unexplained phenomena.

Stop 5: Chicago Riverwalk
The scenic Riverwalk isn’t just a pretty view—it’s a route that was once used for smuggling during Prohibition. Walking along here, you’ll hear stories about mob dealings and covert operations, blending the city’s scenic beauty with its darker past.

What Makes this Tour Stand Out

Knowledgeable Guides: The tour’s reviews consistently praise guides like Chris, who is not only well-versed but also engaging and eager to answer questions. Such narration makes history come alive, especially when the tales involve real-life shootouts or celebrity lore.

Authentic Landmarks: Visiting inside the Palmer House and Congress Plaza Hotel adds a tangible element to the stories—being able to see these historic interiors makes the ghost stories even more real.

City Sights with a Dark Twist: Walking along the Riverwalk with its scenic views is a bonus, but the real highlight is understanding how these locations played a role in mob smuggling and crime during Prohibition.

Value for Money: At $28, this tour offers a lot for a short duration. You get inside visits, expert narration, and a walk through significant landmarks—all within an accessible price point.

Who Will Love This Tour?

This experience is ideal for history buffs, true crime enthusiasts, or anyone intrigued by ghost stories and hauntings. It’s suitable for most travelers since it’s a walking tour of moderate length and doesn’t require strenuous activity. Families with older kids who enjoy spooky tales could find it engaging as well.

However, if you’re seeking an in-depth exploration of Chicago’s entire criminal history, you might find this tour more of a sampler than a comprehensive dive. Still, its engaging storytelling and scenic stops make it a memorable night out.

Practical Details You Need to Know

• Duration: Approximately 1 hour 30 minutes, making it a perfect evening activity without overcommitting.
• Price: $28 per person, which includes visits inside the Palmer House and Congress Hotel, plus expert narration.
• Meeting Point: 71 E Wacker Dr, centrally located near public transit, convenient for most travelers.
• Group Size: Max 35 travelers, ensuring a more intimate experience.
• Accessibility: Most travelers can participate, though walking is involved.
• Booking: Mobile tickets are provided, with a straightforward reservation process.
• Cancellation: Free up to 24 hours before the start, offering peace of mind if your plans change.

Final Thoughts

Chicago’s Mobsters, Ghosts, and Prohibition Tour offers a lively, well-paced glimpse into the city’s shadowy past. With knowledgeable guides and visits inside historic hotels, it balances storytelling with scenic sightseeing, making it suitable for anyone interested in crime history or supernatural tales.

The tour’s small group size and affordable pricing make it accessible and enjoyable, especially for those who appreciate a mix of history, mystery, and some spooky fun. It’s a fantastic way to add a different flavor to your Chicago trip, especially if you’re fascinated by the city’s Prohibition-era underworld and ghostly legends.

If you’re after an evening filled with engaging stories, scenic city views, and a dash of the supernatural, this tour is an excellent fit. Just be ready for some chilling tales and a fun, quick step back in time.

FAQ

Is this tour suitable for children?
While most travelers can participate, the ghost stories and crime tales are geared toward older audiences. Check with the provider if you’re bringing young children.

How long is the tour?
It lasts about 1 hour 30 minutes, making it a quick yet thorough experience.

Can I buy tickets on the day of the tour?
It’s recommended to book in advance, especially during peak times, to secure your spot.

Does the tour include inside visits?
Yes, it includes visits inside the Palmer House and Congress Plaza Hotel, adding a tangible element to the stories.

What should I wear?
Comfortable walking shoes are advised since it’s a walking tour, and dress appropriately for the weather.

Are there any ghost sightings during the tour?
While ghost stories are part of the narration, actual sightings depend on individual experiences. Many guests enjoy the spooky tales and historic ambiance.

Is the tour wheelchair accessible?
Most of the tour involves walking, so it’s best to check in advance if accessibility is a concern.

How many people typically join the tour?
The maximum is 35, ensuring a more personal experience.

What languages is the tour available in?
This detail isn’t specified, so verify with the provider if you need language accommodations.

Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours before the tour, providing flexibility.

In summary, this Chicago Mobsters, Gangsters, Ghosts, and Prohibition Tour offers a fascinating, engaging look at the city’s darker past, with stories that stick with you long after. Whether you’re a history lover, a ghost hunter, or simply looking for a unique night activity, it provides excellent value and plenty of memorable moments.