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.

5 Star Ratings (based on 65,168 reviews) Read Reviews

Book Your Chicago: Gangs and Mobsters Walking Tour Tonight

Chicago Tour GroupHaunted Golden Dagger or Tonic Room Chicago

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!

Compass graphic

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

Clock graphic

Starting Time: 1PM

dog graphic

Pet Policy: Pets are welcomed!

mug graphic

Alcohol Policy: No Drinking Permitted

face graphic

Adults Only: No

Book Now

Where to Meet, Park, and Directions

100 E Jackson Dr, Chicago, IL 60603

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

Sirius USA Today Huffington Post Country Living INC Travel Featured on KAYAK! Guides Inside Edition CBS MTV Fox Business New York Post Smithsonian Wall Street Journal Yahoo Boston Globe
Sirius USA Today Huffington Post Country Living INC Travel Featured on KAYAK! Guides Inside Edition CBS MTV Fox Business New York Post Smithsonian Wall Street Journal Yahoo Boston Globe

Jackie O'Hara

Five Stars

Loved our tour! It ended up being just me and my son. Our tour guide, Elliot, was very knowledgeable of the area, the ghosts and the local history.

03.14.25

Tony Starr (Fang571)

Five Stars

Was an amazing experience. Got lucky that my partner and I were the only ones on the tour, so we were able to ask lots a questions. Our guide was very...

02.17.25

Hudson

Five Stars

Elliot was a great guide who put on a great tour on a cold February night.

02.11.25

Read All Reviews

Tour Gallery Tour Gallery

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

Icon
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.

Icon
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.

Icon
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.

Icon
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.

Icon
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.

You May Also Like

USGA Shirt Back of Guide Group Ghost Tour

Windy City Ghosts: Hauntings of Chicago

Explore Chicago’s most haunted and chilling locations on the Hauntings of Chicago ghost tour in historic Northside, Chicago.

Meeting LocationTour Meeting Location: All tours meet at the Tin Man statue in Oz Park, 2021 N Burling, Chicago.

Tour TimeTour Times: Daily @ 8PM

Tour LengthTour Length: Approximately 1 hour

Tour WeatherGhost tours are held nightly, rain or shine!

Chicago: Ghosts & Hauntings of the Windy City Walking Tour

Windy City Ghosts Boos and Booze Haunted Pub Crawl

Take this Spirits and Spirits haunted pub crawl tour and add some fun into your work week!

Meeting LocationTour Meeting Location: Meeting Location: Slaughtered Lamb Pub 182 W Fourth St, New York, NY 10014.

Tour TimeTour Times:

Tour LengthTour Length: Approximately 1 hour

Tour WeatherGhost tours are held nightly, rain or shine!

A Chicago Food Venture

Taste of the Windy City: A Chicago Food Venture

Chicago has long been the culinary and cultural capital of the United States.

Meeting LocationTour Meeting Location: Meet your guide in front of Portillo's & Barnelli's at 100 W Ontario St, Chicago, IL 60654

Tour TimeTour Times: Daily @ 11AM

Tour LengthTour Length:

Tour WeatherGhost tours are held nightly, rain or shine!

Two candles by sheets of music

Chicago: Grand Candlelit Symphony

Surrounded by hundreds of flameless candles, enjoy classical renditions of Mozart, The Beatles, Taylor Swift, Broadway hits, and more. This intimate live music event promises a magical and immersive atmosphere.

Meeting LocationTour Meeting Location: Second Unitarian Church of Chicago, 656 W. Barry Ave., Chicago, IL 60657

Tour TimeTour Times: Feb. 14th, 22nd, & 28th. 7 PM & 8:45 PM.

Tour LengthTour Length: Approximately 1 hour

Tour WeatherGhost tours are held nightly, rain or shine!

Check Out Our Blog

Rialto Square Theatre

Rialto Square Theatre

While the Rialto Square Theatre in Joliet, IL., was built as an entertaining phenomenon, it has become a haunting ground known for its para... Read More

03.13.25

Ghost in the haunted Congress Plaza Hotel

The Spirits of the Congress Plaza Hotel

A visit anywhere is only as good as the hotel you’re staying in. That’s why so many of Chicago’s visitors flock to The Congress Plaza... Read More

03.10.25

Woman in white in Bachelor's Grove Cemetery

The Haunted Bachelor's Grove Cemetery

Hidden off the beaten path in Cook County, Illinois, is a graveyard that is often visited by a lady in white searching for a lost loved one... Read More

02.13.25

Chat