Looking for an honest Chicago Gangsters and Ghosts Tour review before you book?
Whether you’re a curious local or a wide-eyed tourist hoping to spice up your Chicago trip, you’re probably wondering if this tour is more “thrill ride” or a tourist trap.
I get it—I’ve taken enough city tours to know they can either blow your mind or put you to sleep.
As a local travel writer who thrives on spine-chilling legends and true crime tales, I laced up for this two-hour night tour to find out. And let me tell you: it was part history lesson, part haunted hike—and entirely worth it.
From gangster shootouts to restless spirits, here’s everything you need to know before you go.
Chicago Haunted Walking Tour
Overview
I must say, this tour delivered an experience unlike any other. It plunged me into the city’s dark and mysterious past, where I learned about infamous gangsters and their gruesome crimes and visited the haunted locations their spirits are rumored to still roam.
The tour kicks off in the heart of downtown Chicago, where you’ll gather at the meeting point near the Chicago Riverwalk, where guests are greeted for check-in.
I could tell there were a lot of bookings because our group was at capacity, and we left 30 minutes before the start time.
From there, you’ll venture out to historic hotspots, each with its own eerie backstory and unforgettable lore.
You’ll visit the site of the SS Eastland, where more people perished than on the Titanic, as well as some hidden gems from the Prohibition era that history books often skip.
Key Info 👇
👻 Tour Type: History meets haunted
😱 Spooky Rating: 4.7/5
💵 Cost: $36 (look for seasonal discounts)
⏱️ Length: 2 hours, about 2 miles of walking
📍 Location: The Loop near the Riverwalk
💡 Perfect for: True crime junkies, history buffs, paranormal fans, ghost story lovers, date night thrill-seekers, or curious locals. I recommend this tour for anyone interested in the history and the dark side of Chicago.
Chicago Gangsters and Ghosts Walking Tour
What others are saying:
“We had a wonderful time on this walking tour and learned so much about Chicago.”
“It was fantastic!”
First Impressions: History with a Haunting Twist
This isn’t your average haunted walk.
From the moment we gathered along the Riverwalk, the guide set the tone—equal parts storyteller and historian, leading us through a side of Chicago that most visitors (and plenty of locals) never see.
By the time we left the first stop—the site of the SS Eastland disaster—I already had goosebumps. More people died there than on the Titanic, and some say the river still holds their spirits.
The tour moves fast, but it lingers where it counts. You’ll step through dark alleys, pause at storied buildings, and hear tales that weave together bootlegging, murder, and mystery.
This tour has a 5-star rating and has been frequented and reviewed by over 6,000 visitors – and there’s a reason why!
Stops That Gave Me Chills
Throughout the tour, your guide will share fascinating stories and insights into Chicago’s gangster past, as well as the paranormal activity that is said to occur in some of the city’s most haunted locations.
Here’s a peek at the spine-tingling itinerary:
- Couch Place Alley (aka the Alley of Death) – a claustrophobic passage with a grim history.
- Palmer House Hotel – one of Chicago’s oldest (and reportedly haunted) luxury hotels.
- Chicago Theater – more than just iconic signage; this landmark hides a darker past.
- Congress Plaza Hotel (final stop) – no entry, but plenty of ghost stories just outside the doors.
We even passed a spot tied to H.H. Holmes , America’s first serial killer. The tales were fascinating, as well as the recount of other spine-chilling murders in Chicago.
That story alone is enough to keep you up at night.
The tour is a great way to learn about the historical significance of Chicago’s gangsters and their impact on the city.
It provided a wealth of information about the city’s past, the humble beginnings of Al Capone, the Prohibition era, the rise of organized crime, and its influence on city governance.
Check tickets and Join the Mob… of Tour Guests
Born in 1899 to Italian immigrants in Brooklyn, New York, Capone’s rise to fame was emblematic of the social and economic problems of the early 20th century.
Capone’s move to Chicago in 1919 coincided with the dawn of Prohibition, a nationwide constitutional ban on alcohol production, importation, transportation, and sale.
Under the tutelage of Johnny Torrio, Capone learned the intricacies of racketeering and political corruption.
The transfer of power from Torrio to Capone in 1925 marked a significant shift in Chicago’s underworld, ushering in an era of unprecedented violence and sophistication in organized crime.
The Beer Wars of the late 1920s were a struggle for power, territory, and wealth that played out in the modernization of America. Capone’s eventual downfall in 1931, brought about by federal prosecutors using tax evasion.
One would argue that gang activity that prevailed through the years is why people question safety in Chicago.
Al Capone died in 1947 and is buried in Hillside, a suburb located 30 minutes west of the Loop.
Check tickets for the Chicago Gangsters and Ghosts Walking Tour
Why This Tour Stands Out
It’s not just about spooks—it’s about storytelling.
The tour digs into the gritty legacy of Chicago’s gangster era. You’ll hear about Al Capone’s rise to power, the bloody Beer Wars, and how Prohibition turned Chicago into a battleground for crime syndicates.
The guide didn’t just recite facts—he brought the past to life. Every stop came with atmospheric details: the crack of gunfire in the night, the hush of a backroom deal, the lingering scent of bootleg booze.
The tour was both engaging and entertaining. The guide kept the group interested and involved throughout the entire tour.
The tour included a few surprises, such as a visit to a haunted hotel. The stories piqued our imagination and added to the entertainment value. I felt that the tour was well-paced and kept my attention the entire time.
The tour provided a lot of educational content about Chicago’s gangsters and their impact on the city. I felt that the tour was informative and provided a good overview of the topic.
They were able to provide detailed information about the history of Chicago’s gangsters and their impact on the city. The guide stood ready to answer questions and provide additional information when requested.
Know Before You Go
- Accessibility: Mostly easy terrain, but stairs to/from the Riverwalk could pose challenges if you need wheelchair accessibility.
- Age Suitability: Great for adults and teens. Some stories include mentions of murdered children. Narration of murdered children may not be suitable for the little ones.
- Crowd Tip: Our group was full, and we left about 30 minutes early. Arrive early to get a good spot near the guide.
Was It Worth It?
Absolutely.
The Chicago Gangsters and Ghosts Tour blends eerie storytelling, solid historical insight, and unexpected moments of suspense. I walked away with a deeper appreciation for the city’s past and a few extra shivers.
Bonus Tip: Want one last jaw-dropping photo? Walk east after the tour to Buckingham Fountain. It’s especially stunning between May and September with the water and light display.
Final Thoughts on the Chicago Gangsters and Ghosts Tour
As a local, I’m always up for exploring a tour firsthand to give an opinion from the perspective of someone familiar with the city and its history.
As a reviewer, I was pleasantly surprised by the experience. The tour is a unique way to explore the city’s darker history and learn about the notorious gangsters who once ruled the streets of Chicago.
If you’re looking for an unforgettable night out in the Windy City, this tour delivers.
It’s educational without being dry, spooky without being cheesy, and immersive from start to finish.
This tour is a great way to see the city as it transitions from day to night. The views at the last stop are stunning, and your guide will help with photos. We didn’t go inside the last haunted hotel (Congress Plaza), but if you are looking for one more gorgeous place for night photos, head over to Buckingham Fountain (eastward) between May and September.
Overall, I felt that the tour provided good value for money. It was reasonably priced and provided a lot of educational content and entertainment value. I highly recommend this tour.
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