Chicago: Gangs and Mobsters Walking Tour

Step into Chicago’s seedy past to uncover the hot spots where mobsters once ruled without fear and discover how the Second City earned its tough reputation.

Join the Gangs and Mobsters Walking Tour to hear wild tales of Chicago’s gangland history, from scandalous shootouts to underground tunnels, speakeasies turned battlegrounds, and alleyways turned crime scenes.

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Chicago: Gangs and Mobsters Walking Tour

Take a gritty stroll through Chicago’s dark past and walk the same grounds as the legends who made the Windy City a hotspot for mobsters and mayhem. From Capone’s infamous hideouts to dark corners where deals were made and lives were lost, the Gangs and Mobsters Walking Tour is your all-access pass to the real Chicago. As you follow the trail of notorious gangsters and see where history’s bloodiest shootouts went down, you’ll see how this city became a hotbed of crime and chaos and known for being the gangster capital of America. Book your spot today!

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Meeting location: 100 E Jackson Dr, Chicago, IL 60603

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Starting Time: 1PM

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Pet Policy: Pets are welcomed!

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Alcohol Policy: No Drinking Permitted

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Adults Only: No

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Where to Meet, Park, and Directions

100 E Jackson Dr, Chicago, IL 60603

Visit parkopedia.com for the most up-to-date parking info.

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Five Stars

The ghost tour was amazing and Alex really knew his stuff! He kept us well entertained and intrigued! We learned a lot a lot Chicago’s creepy past!

09.03.24
Jaye Moseley
 

Five Stars

A spooky stroll with tour guide Carrie! Our group had a fun time hunting ghosts and learning about the local haunts. Thanks, Carrie!

09.01.24
Katie P
 

Five Stars

Carrie was a fantastic tour guide!! This was one of the best ghost tours I’ve been on!

09.01.24
Patricia Paul
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Tour Preview: Where You’ll Go

Buildings in Chicago

Palmer House Hotel

The iconic Palmer House Hotel isn’t just a swanky spot for luxury; it’s also a hotspot for scandal. Come along as we uncover Chicago’s most riveting tales of crime and passion, and discover why the longest-operating hotel in the United States wasn't just a hanout for mobsters, but also a backdrop for one of the city’s most sensational murders.

Lion Statue Chicago

Thompson Center

For a building where gangsters once negotiated peace with a side of violence, the historic Thompson Center now stands as a flashy symbol of Chicago’s storied past. Get a front-row seat to the dramatic stories of the bloody “Beer Wars” as you walk through the streets where the city’s most notorious figures tried (and failed) to make peace.

Playing Cards And Drinks

The Exchequer Restaurant

Once the notorious 226 Club of the roaring 1920s, the Exchequer Restaurant was a speakeasy hideout for Capone and his crew, complete with hidden booze and illicit thrills. Hear the stories of the dirty deals and daring escapes with a hidden tunnel that let Chicago’s infamous mobsters slip in and out under the city’s nose.

What is the Gangsters and Mobsters Walking Tour about?

Beneath the shiny skyscrapers and bustling streets you see today lies a story of grit, guns, and the remnants of gangsters. The Chicago: Gangs and Mobsters Walking Tour takes you into the heart of Windy City’s most scandalous stories, where the legends of Al Capone, the blood-soaked Roaring Twenties, and underground speakeasies come alive.

 

Get ready to step into the shoes of the most vicious characters Chicago has ever seen as you trace their footsteps through the city’s mean streets. Prepare to feel the pulse of the Prohibition-era nightlife and discover the secrets behind the scenes that tuned the historic district of Chicago into a crime haven.

 

From the smoky dens of the former 226 Club to the eerie remnants of an underground tunnel network that once served as a lifeline for all sorts of illegal activities, you’ll hear stories of daring heists, notorious gangsters, and the thrill of an era where danger lurked around every corner.

 

Don’t miss your chance to be part of this thrilling journey into Chicago’s bloody past. Book your spot on the Gangs and Mobsters Walking Tour in Chicago to uncover the dark secrets, scandalous stories, and hidden haunts that made this city the gangster capital of America.

Reasons to Take the Gangsters and Mobsters Walking Tour

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You Love a Good Gangster Story

Join us today to get the lowdown on infamous figures like Al Capone and his gangsters who turned Chicago into their playgroun ... d. You’ll hear the juicy details of their ruthless lifestyles, from their raucous parties to their even wilder crimes, all while walking the very streets they once ruled. From Al Capone’s rise to infamy to the brutal St. Valentine’s Day Massacre and other vicious underworld dealings that kept Chicago on edge, you’ll get your fill of legendary mob stories that are just too wild to be fiction.

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You Want to Visit Locations Associated With Significant Events in Chicago’s Criminal History

Sure, you can read about it, but why not walk where the action actually happened? Our Chicago: Gangs and Mobsters Walking Tou ... r takes you to real-life locations where major mob-related events went down, where you’ll see the city through the eyes of the criminals who made it famous and get up close and personal with the places where history’s wildest events took place. Step into the shadows of these infamous spots and feel the thrill of standing where the past was written in blood.

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You Want to Hear the Behind-the-Scene Stories of the Crimes and Atrocities From the Roaring Twenties in Chicago

Get the scoop on all the juicy details of the history books left out! Hear the authentic, unfiltered account of the audacious ... crimes that defined an era and bloody rivalries that turned Chicago into a crime capital. This tour digs deep into the dirty details of mob wars, political corruption, and scandalous affairs, revealing the scandalous and jaw-dropping stories that didn’t make it into the history books.

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You Want to Discover How the Mob Era Influenced Chicago’s Art and Music Scenes

Chicago’s mobsters didn’t just deal in booze and bullets—they made their mark on its art and cultural scenes, too! Disc ... over the unexpected connections between crime and culture, and see how the city’s artistic soul was forged in the fires of its criminal past. From the jazz clubs where Capone’s men mixed with the musicians to the artistic influences that rippled through the city’s nightlife, you’ll see how the city’s artistic legacy was built on a foundation of crime.

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You’re Up For a Thrilling Storytelling Adventure

If you’ve got a taste for adventure and love a good yarn, our tour guides are masters at spinning tales that’ll leave you ... hanging on every word. With each stop, they bring to life the thrilling—and sometimes chilling—stories of Chicago’s most notorious criminals in a way that makes you feel like you’re right there in the thick of the action. Whether it’s the dramatic retelling of a daring heist or a vivid account of a mobster’s last stand, you’ll be hooked from start to finish.

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