Chicago Crime Tour: 5 Ways to Save Up to 38% Off

Dive into the underbelly of Chicago’s history, where mobsters once ruled the streets, murder was a chillingly common occurrence, and the echoes of massacres still linger.

If you have an insatiable curiosity about the realm of crime and gangsters or a desire to enter the shadowy underworld of the 19th century, then look no further. Follow along to discover the secrets of The Windy City’s notorious past as we list down some of the best Chicago crime tours!

These killer Chicago crime tours are tailor-made for you, promising an unforgettable journey through the city’s most infamous true crime stories and landmarks.

From interactive crime scene explorations to immersive storytelling, these tours offer a unique opportunity to walk in the footsteps of criminals and law enforcement alike.

So, unleash your inner detective, put on your finest fedora, and brace to unearth the hidden corners of the city’s dark side by embarking on these haunting crime tours in Chicago!

Chicago Crime Tours

Step aboard a mesmerizing bus tour through the world-renowned and famous Chicago Crime Tours! Join this spine-tingling journey, which will depart from the meeting point at 163 E. Pearson Street, just across from Water Tower Place.

Plunge into the mysterious depths of Chicago’s history as you immerse yourself in the frightening tales of the St. Valentine’s Day Massacre, and dig deep into the notorious exploits of John Dillinger and Hymie Weiss. And traverse the enigmatic neighborhoods bearing the remnants of the city’s sinister past at:

  • River North
  • Gold Coast
  • Lincoln Park
  • Old Town
  • The Loop
  • and Magnificent Mile

This Chicago crime and mob tour starts and ends outside 163 E. Pearson St. (SE corner of Pearson and Michigan Ave). Arrive at least 10 minutes early to check in with the tour guide of this Chicago mob tour. 

Be forewarned, for the Chicago Crime Bus Tour is in high demand, and tickets vanish into the night supernaturally fast. Don’t fret, though! Rest assured that it would not be a crime if you reserve your Chicago Crime and Mob Bus Tour tickets with Tripster in advance!

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Pro Tip: Chicago’s climate can be unpredictable, so dress accordingly. Bring a light jacket as you’ll hop aboard a climate-controlled bus. While on this crime bus tour Chicago, get ready to step off the vehicle at select stops for an immersive experience.

In addition, take your Chicago visit to a whole new level with Big Bus Chicago: Hop-On Hop-Off Tours! Hop on and off at over ten convenient stops, including popular attractions like the Magnificent Mile, Field Museum, Adler Planetarium, and even the historic Criminal Courthouse.

man standing on steps speaking with a group of people at the CHICAGO CRIME TOURS AND EXPERIENCES-Gangsters, Mobsters and Criminals in Chicago, Illinois, USA
photo credit: Chicago Crime Tours and Experiences via Facebook

Chicago Phobition Tour

Step back in the Prohibition Era, a time of rebellion and defiance against the constraints of the law, as you board the bus through the Chicago Phobition Tour. From the moment you step inside each speakeasy, you’ll be transported to a time of clandestine meetings, illicit deals, and roaring jazz.

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The Chicago Prohibition Tour starts at 27 N Wacker Dr #126 and ends at Harry Caray’s 33 W Kinzie Street in the River North neighborhood.

At this Chicago crime tour, your knowledgeable tour guide will talk about the rise of organized crime, the battles for control over bootlegging and speakeasies, and the consequences of unlawful trade.

Plus, you’ll gain insight into the lives of both infamous gangsters and ordinary people caught in the web of the prohibition era.

This true crime tour Chicago is a must-do for history buffs, crime enthusiasts, and anyone seeking an immersive and educational experience.

And if you’re eager to explore more of the city’s awe-inspiring attractions and activities, Tripster offers the perfect companion for your adventures: the Go Chicago Explorer Pass.

With the Go Chicago Explorer Pass, you can save time and money while experiencing the best of what Chicago has to offer. Simply select the number of attractions you want to visit and enjoy the convenience of skipping the ticket lines at your chosen destinations.

night view of downtown with L Train station in Chicago, Illinois, USA

Crime and Pizza Walk

Does the thought of solving crime make you hungry? If so, get ready to satisfy your appetite for mystery and pizza with one of the best Chicago tours: the Chicago Crime and Pizza Walk!

Embark on an exciting 2-hour walking tour that starts at Pizzeria Uno on E. Ohio Street, where you’ll fuel up with a mouthwatering pizza that is sure to tantalize your taste buds.

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Explore the historic River North and Gold Coast neighborhoods, where secrets of the past come alive with every step. Walk the same streets where these legendary figures once walked, and immerse yourself in the intriguing world of Chicago’s underworld.

The Chicago Favorites Walking & Food Tour starts at Lou Malnati’s Pizzeria, located at 410 N Michigan Ave, Chicago, IL 60611, USA.

Please note that the Chicago Crime and Pizza Walk is available exclusively on Fridays, Saturdays, and Sundays. Alternatively, you may also opt for the quintessential Chicago Favorites Food and Walking Tour to savor Chi-town’s favorite eats and visit some iconic landmarks.

Looking down at the Wolf Point fork in the Chicago river with the city around it in Chicago, Illinois, USA
photo credit: Wolf Point West via Facebook

Night Crime Tours

Leave the kiddos at home and prepare for an evening of intrigue, scandal, and a touch of mischief as you join Night Crime Tour Chicago. This adults-only true crime Chicago tour will take you through the moonlit streets of Chicago. Where you’ll visit historic bars that have witnessed the whispers of mobsters and the clinking of glasses in secret rendezvous.

Immerse yourself in the ambiance of the very bars that once catered to the city’s underworld elite. The legendary Burwood Tap and the iconic Harry Caray’s are just a glimpse into the alluring world you’ll explore at Chicago Night Crimes Tour.

The tour starts and ends outside 163 E. Pearson St. (SE corner of Pearson and Michigan Ave). Be sure to arrive at least 10 minutes early to check in with your tour guide.

Pssst…how many people can say they’ve set foot in a famous crime scene before? Earn some bragging rights by making sure to fully charge your smartphone or bring a camera to capture one-of-a-kind moments of your tour!

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While this bus tour brings you to renowned bars and venues, it’s important to note that drinks are not included in your ticket. However, the unforgettable experiences and memories you’ll create are worth every moment as they offer an extraordinary blend of history, entertainment, and excitement.

Pro Tip: Before booking, checking out Chicago crime tour reviews is essential. Explore firsthand accounts praising the captivating narrations and knowledgeable guides, ensuring an unforgettable journey through the city’s underworld history.

nightshot of cars passing under the Chicago Chinatown Gate in Chinatown, Chicago, Illinois, USA
photo credit: Chicago Chinatown via Facebook

Gangsters and Ghosts Tour in Chicago

Gangsters, ghosts, and ghouls. Are you ready to confront these elements of the past?

Stop scouring the Internet for the best Chicago gangster tour or Chicago mobster tour because the Gangsters and Ghosts Tour in Chicago has got you covered.

But beware, as this is a Chicago true crime tour that’s not for the faint of heart! Visit the authentic hangouts of notorious gangster Al Capone, where he plotted his schemes, and revel in the stories that bring the roaring 1920s to life.

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As you pause at the legendary Palmer House Hotel, rumored to be haunted, you may encounter restless spirits that are said to roam the halls. Feel an unsettling tingle in the air as you continue your journey through Death Alley, an infamous location associated with gangland violence.

You will depart from the meeting location next to the Royal Sonesta Hotel at 71 E. Wacker Drive on the corner of Wacker Drive and N. Wabash. With this Chicago Al Capone tour, you’ll discover a side of Chi-town that few have witnessed and tales that will send chills down your spine.

Pro Tip: While the killer tours are family-friendly, it may be worth considering whether your little ones would fully appreciate the content. Due to its nature, these tours are generally recommended for ages six and up.

exterior of Congress Plaza Hotel at night with neon red sign and street lamps on ground and statue of man on horse in foreground in Chicago, Illinois, USA
photo credit: Pam Pole via Facebook

Book Chicago Crime Tours and Experiences – Gangsters, Mobsters and Criminals History Awaits

Prepare to be captivated, intrigued, and transported back in time as you roam the very streets where history was made and delve into the mysteries that will captivate your imagination.

Whether you’re a true crime aficionado or simply seeking a unique and thrilling adventure, these killer Chicago crime tours will not disappoint.

Immerse yourself in the gritty world of the eerie and wicked past of Chicago with Tripster! Book your Chicago hotels, attractions, and vacation packages with us today so you won’t miss your chance to explore the dark side of The Windy City like never before.

Don’t let your chance slip away into the night like a phantom, but only if you dare!

Chicago Crime Tour FAQs

The Chicago Crime Tour typically lasts between 1.5 to 2 hours, immersing participants in the fascinating history of the city's underworld.

With engaging narration and notable stops, this tour offers an insightful glimpse into Chicago's criminal past within a compact timeframe.

Yes, Chicago hosts various crime museums and attractions delving into its infamous history of organized crime and violence.

These include the Chicago History Museum, the Medieval Torture Museum, the Field Museum, and the Frank Lloyd Wright Home and Studio.

Tell us, What Other Crime Tours Chicago Did We Miss?

What’s your favorite crime tour Chicago? Let us know in the comments below!

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Written by Archie Villaflores

Over the years, he has won numerous national contests for news and editorial writing, but he has recently discovered that his true passion...

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