Viator Rating : 5 (380 reviews)
Dyvarcity Score : 7.3/10 (Solid Experience)
Chicago
Chicago Mob & Ghost Tour: Dark History & Haunts
Overview
Chicago Mobs and Haunts Walking Tour invites thrill-seekers to step into the shadows of Chicago's infamous past. This walking tour explores the gritty tales of mobsters and the chilling legends of restless spirits that haunt the city's historic streets and alleys. Perfect for history buffs, true crime enthusiasts, and those who love a good ghost story, this experience offers a sultry and spine-tingling journey through the heart of the Windy City.
Participants will uncover Chicago's darkest secrets as they venture from Grant Park to the notorious Death Alley, located near the site of the tragic Iroquois Theatre fire. An expert local guide will shed light on the city's hidden history, pointing out landmarks like the Congress Plaza Hotel, rumored to be one of the most haunted places in Chicago, and the Green Mill Cocktail Lounge, a former mob hangout with a rich and colorful past. Guests will also walk beneath the Chicago 'L' tracks, visiting specific locations with eerie tales to tell.
This captivating tour includes the insights of a professional and entertaining local guide. Please note that gratuities are not included. It's a journey into Chicago's underbelly. Visitors discover the stories that linger in the city's oldest corners, a true blend of history, crime, and paranormal activity. 
Experience DNA Fingerprint
Scores are shown on a scale of 1 to 10, 1 = lowest score, 10 = highest score.
What People Love
Safety (8 - Secure) : Strong feeling of safety and control
Upsell Risk (9 - Transparent) : No upsells or hidden costs
Logistics (8 - Seamless) : Smooth and well executed
Guide Quality (9 - Exceptional) : Engaging and memorable
Guide Reliability (9 - Dependable) : On time with strong follow-through
What to Watch Out For
Crowd Density (6 - Standard) : Normal crowd, some waiting or tight spots
Mobility (5 - Moderate) : Some effort required
Pacing (6 - Uneven) : Inconsistent or mixed pacing
Instagram Factor (6 - Scenic) : Some good photo moments
Highlights
Explore Chicago's Dark Side: Walk the streets where mobsters once roamed and discover haunted locations.
Expert Local Guide: Hear captivating stories and historical insights from a knowledgeable guide.
Visit Iconic Landmarks: See famous sites like the Congress Plaza Hotel and the Green Mill Cocktail Lounge.
Uncover Hidden Secrets: Learn about the city's most chilling mysteries and forgotten tales.
Sentiment Analysis
Customers loved hearing spooky stories from the guide.
-
The tour guide was entertaining and made the tour fun.
-
People enjoyed the chance to walk around and see places they didn't know about.
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Many visitors said the tour was a good way to learn about Chicago's history.
Some people thought the tour could have had even scarier stories.
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A few visitors mentioned the tour was too long.
The Journey
Congress Plaza Hotel
Dare to stay at the Congress Plaza Hotel, rumored to be one of America's most haunted hotels. Since its opening in 1893 for the World's Fair, guests have reported countless paranormal encounters, from shadowy figures to unexplained noises. Room 441 is particularly notorious, with stories of a child spirit named 'Peg Leg Johnny.' Even if you don't encounter a ghost, the hotel's grand architecture and opulent interiors offer a glimpse into Chicago's gilded age.
Green Mill Cocktail Lounge
Step back in time at the Green Mill Cocktail Lounge, formerly the '226 Club,' a legendary haunt favored by Al Capone and his associates during the Prohibition era. Still boasting its original Art Deco interior, the Green Mill offers nightly jazz performances in an atmosphere steeped in history and intrigue. Explore the rumored secret tunnels beneath the bar, once used to evade police raids. It's not just a bar; it's a living piece of Chicago's mobster past.
Chicago 'L' Tracks (Specific Under-Track Locations)
Venture beneath the elevated 'L' tracks, especially in areas like Uptown and the South Side, where pockets of historical crime and vice once thrived. During the early 20th century, these shadowy spaces were notorious for gambling dens, speakeasies, and other illicit activities. While the areas have largely been revitalized, remnants of this gritty past can still be felt. Explore the architectural details of the viaducts and imagine the vibrant, often dangerous, history that unfolded beneath them. It's an off-the-beaten-path way to experience Chicago's urban landscape.
Death Alley (near the Iroquois Theatre)
Visit 'Death Alley,' located beside what was once the Iroquois Theatre (now the Oriental Theatre), a grim reminder of the tragic 1903 fire that claimed over 600 lives. The alley's dark name stems from the location where many victims perished, trapped by locked fire escapes. Today, some claim to sense residual energy and supernatural occurrences in the alley. A visit offers a moment of reflection and a somber connection to Chicago's history, though it is a poignant and potentially unsettling experience.
Know Before You Go
This walking tour includes a professional, entertaining, local guide who will lead you through Chicago's most haunted and historically significant locations. Gratuities are not included, so please plan accordingly. Prepare to walk for the duration of the tour, as it explores various sites throughout the city. Meeting point details will be provided upon booking.
Hot Tip
Wear comfortable shoes, as this is a walking tour. Some areas may be dimly lit, so consider bringing a small flashlight. Be prepared for potentially spooky stories and a thrilling experience. Dress appropriately for the weather, as the tour takes place outdoors.
Review Summary
Customers generally say this tour is highly engaging and entertaining, praising knowledgeable guides with electric personalities like Bryson who keep groups intrigued with spooky Chicago history and mob stories at night. They appreciate the affordable price under $40, perfect length of about 2 hours, and unique spots like Death Alley. Few negatives mentioned, though some note it's not accessible for mobility issues.[2]
Frequently Asked Questions
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