Chicago Criminals, Mobsters and Gangsters Bus History Tour
Your tour will begin in Chicago’s Near North Side, across the street from Water Tower Place, where you will board your coach vehicle. On board, an experienced guide narrates during your tour of Chicago’s famed criminal and historical sights. Listen to thrilling stories of mobsters, violence and crime as your coach winds through Chicago’s historic River North, Gold Cost, Lincoln Park, Old Town, Loop and Magnificent Mile. Snap pictures and enjoy little-known tales of legendary mobsters Al Capone, ‘Terrible’ Tommy O’Conner, and Bugs Moran. Your mafia tour highlights Chicago’s most notorious crime scenes, including the courthouse where some of the most famed mob cases were tried, and the site of the grisly 1929 St. Valentine’s Day Massacre. Other notorious mob haunts you do a drive-by on are the Biograph Theater and Holy Name Cathedral. (Along the way, you can hop out of your ride for pictures.) When it's all over, you'll get a ride back to the Near North Side to end the tour.
Overview
Your tour will begin in Chicago’s Near North Side, across the street from Water Tower Place, where you will board your coach vehicle. On board, an experienced guide narrates during your tour of Chicago’s famed criminal and historical sights. Listen to thrilling stories of mobsters, violence and crime as your coach winds through Chicago’s historic River North, Gold Cost, Lincoln Park, Old Town, Loop and Magnificent Mile. Snap pictures and enjoy little-known tales of legendary mobsters Al Capone, ‘Terrible’ Tommy O’Conner, and Bugs Moran.
Your mafia tour highlights Chicago’s most notorious crime scenes, including the courthouse where some of the most famed mob cases were tried, and the site of the grisly 1929 St. Valentine’s Day Massacre. Other notorious mob haunts you do a drive-by on are the Biograph Theater and Holy Name Cathedral. (Along the way, you can hop out of your ride for pictures.) When it's all over, you'll get a ride back to the Near North Side to end the tour.
Itinerary
Water Tower Place
This world famous tour starts and ends OUTSIDE 163 E. Pearson Street (SE side of Michigan Avenue and Pearson Street). Learn about the history of leading gangster and mobster figures like Al Capone, John Dillinger, Frank Nitti, Dean O'Banion, and Bugs Moran. You'll see famous gangster shootout sites like the St. Valentine's Day Massacre, the handshake murder, and 'The Enforcers'' safe and tunnels. You will be led by a local, informative guide and guests are able to get off the bus and explore these historic crime scenes.
15 minutesWater Tower Place
Meet your guide across from the Water Tower Place shopping mall in Chicago’s Near North Side at your selected time. Hop aboard a luxury climate-controlled coach and begin your 1.5-2 hour tour of the history of Chicago crime, from 19th century to today.
Museum of Contemporary Art
Drive by the Museum of Contemporary Art, a world class institution that offers a rich experience during a visit to Chicago. Just steps from the start and end of the tour, a great opportunity to explore modern art.
The Magnificent Mile
See the Magnificent Mile.
John Hancock Center
View the world famous John Hancock Center in the historic Streeterville neighborhood.
Abraham Lincoln Park
Drive through historic and beautiful Lincoln Park and it's surrounding neighborhood on the tour route.
North Avenue Beach
Drive by on tour bus.
Biograph Theatre
Stake out crime scenes including the Biograph Theatre.
10 minutesOz Park
Drive by en route to the St. Valentines Day Massacre.
Chicago River
Enjoy breathtaking views of the Chicago River, skyline and historic speakeasy from the State Street Bridge.
5 minutesThirty Five E Wacker
The Jewelers Building and historic landmark building.
5 minutesGo inside to see Nitti's vault, a mob museum, and historic bootlegging tunnels.
10 minutesHoly Name Cathedral
Pass by the Holy Name Cathedral, and see the site of the 1929 St Valentine's Day Massacre, one of Chicago's most notorious murder scenes. This Prohibition-era conflict between two powerful Chicago gangs -- the South Side gang led by Al Capone and the North Side gang led by Bugs Moran -- ended in the brutal murder of seven Mob members. In addition to your comfortable, narrated drive through the city, you’ll also hop off the coach to visit some areas by foot for a more immersive experience. Your guide will offer in-depth narration as you follow the path that Chicago gangsters John Dillinger and Hymie Weiss walked right before their deaths. Hop back on the coach and return to the Near North Side to conclude your Chicago crime and gangsters tour.
7 minutesHistoric Water Tower
Conclude the tour across the street from the Historic Water Tower, one of the few surviving structures from the Great Chicago Fire of 1871. This iconic building is often open to the public before or after the tour.
Location
Address
163 E Pearson St, Chicago, IL 60611, USA
Experience
Highlights
Inclusions
- All inclusions are subject to availability.
- Exclusive access to crime quiz
- Spy of secret Prohibition Era tunnels
- Photo opportunities off the bus at infamous crime scenes
- Luxury temperature controlled coach bus
- Storage for 1 foldable wheelchair or stroller
- Mini mob museum
- Live interactive tour guide
- Historic video footage
- Stops on and off the bus
- Keepsake brochure with special offers
Exclusions
- Gratuity: Recommended $5/person gratuity (or more) via cash or Venmo.
- On-board restrooms
- No food & Drinks on board
Additional Information
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Bus departs on time. Arrive at least 15 minutes early for check-in.
- Guests may not join the tour after the bus departs. General seating is on a first-come first-served basis. Joint seating is not guaranteed.
- No restroom breaks. Please go before checking in at the bus.
- No eating or drinking on the bus.
- There is no onsite office.
- Bus is NOT equipped with an electronic lift. Tour includes steps and stairs.
- Audio and video recording and services are not permitted without the express written consent of Chicago Crime Tours and Experiences.
- Kindly refrain from talking or translating on the bus during the tour.
Guide Languages
English
Cancellation Policy
A full refund will apply if you cancel more than 24 hours before the activity start time.
No refund is possible if you cancel less than 24 hours before the activity start time.
Traveler Ratings
See how travelers have rated this attraction. Check out the average rating and read what others have shared about their experiences
4.6 / 5
4.6 out of 5 stars
Based on 2775 reviews
Review histogram
5
- 76%
4
- 14%
3
- 6%
2
- 2%
1
- 2%
Traveler Reviews
Discover what other travelers have to say about this attraction. Read their reviews and get insights into their experiences
Related Attractions
Explore similar attractions that other travelers have enjoyed. Discover more options to enhance your travel experience

Walkin' with Colin: Chicago Tour du JourWalkin' with Colin: Chicago Tour du Jour
Embark on a profound, downtown walk-around led by an "...entertaining, informative and enthusiastic!" guide on a mission to share the most sensational sights, stories and secrets of the Windy City! During our loop around "Da Loop" our group will pee...
$39
per adult
Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and BeerFun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer
Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding a bike. Dive into the atmosphere of the city’s movement and combine it...
$179
per adult
Gold Coast Self-Guided Smartphone Audio Walking TourGold Coast Self-Guided Smartphone Audio Walking Tour
Delve into the rich history and notable architecture of one of Chicago’s most luxurious neighborhoods—and learn insider stories as you go—with this self-led smartphone audio walking tour. Upon booking, download the app and set off at a time a...
$6
per adult

Customizable Private Chicago Scenic Driving TourCustomizable Private Chicago Scenic Driving Tour
Chicago is a very big city with a lot of activities & sightseeing to do. To tour the city quickly, it requires the help of a knowledgeable local driving guide. That's where I step in to assist you. Your Private Chicago Scenic Driving Tour will start...
$281
per adult

The Art Institute of Chicago: Skip The Line Ticket + Exclusive Guided TourThe Art Institute of Chicago: Skip The Line Ticket + Exclusive Guided Tour
Prepare for an enriching experience at The Art Institute of Chicago. With an impressive collection of 300,000 art pieces, this institution is a treasure of creativity and talent. This small group tour is here to guide you through the highlights of ar...
$74
per adult
Chicago Scavenger Hunt and Highlights Self-Guided TourChicago Scavenger Hunt and Highlights Self-Guided Tour
Use clues at each attraction to find your next destination and challenge yourself to use logic, imagination, observation, and team spirit to complete the game. Uncover local information and facts about the city as you explore. Discover hidden...
$13
per adult
Interior Architecture Walking Tour Inside the LoopInterior Architecture Walking Tour Inside the Loop
Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco sp...
$35
per adult
2-Hour Chicago Lakefront & Museum Campus Segway Tour2-Hour Chicago Lakefront & Museum Campus Segway Tour
Explore Chicago by Segway with the benefit of a scenic 7- or 8-mile tour led by your guide. Start with an orientation to operating the Segway and a few minutes to practice. Then roll through the paths of Grant Park to Buckingham Fountain and ...
$64
per adult
Lakefront, Museum Campus Small-Group Segway TourLakefront, Museum Campus Small-Group Segway Tour
Experience Chicago in a new way on this small-group Segway tour. Visit Chicago’s ‘front yard,’ the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths of Grant Park to the famous Buckingham Fountain. Then, tra...
$64
per adult
Art Institute of Chicago Guided Tour and Skip the Line TicketArt Institute of Chicago Guided Tour and Skip the Line Ticket
Make the most of your time at the Art Institute of Chicago by avoiding the crowds to get in. Whether you’re an art aficionado or beginner, this opportunity lets your learn about the museum and its pieces through the eyes of an art historian g...
$74
per adult
Chicago Murder Mystery and Sightseeing Walking TourChicago Murder Mystery and Sightseeing Walking Tour
Bored of traditional walking tours? Try an experience that mixes sightseeing with an engaging game in this murder mystery tour through Chicago. Play as a detective and a suspect as you wander through various neighborhoods and see the city. Le...
$35
per adult
Art Institute of Chicago Small-Group Highlights TourArt Institute of Chicago Small-Group Highlights Tour
Explore one of the country’s great art museums—and discover many of its collection highlights—on this small-group Art Institute of Chicago tour. Meet your guide right out front, and see works from artists the likes of Picasso, Chagall, Seurat...
$90
per adult
Downtown Chicago Architecture, Art, and History Walking TourDowntown Chicago Architecture, Art, and History Walking Tour
This walking tour is a feast for the eyes, combining art, architecture, and history as you navigate through bustling downtown Chicago. In a small group, you’ll marvel at skyscrapers and mosaic murals as you discover stories and secrets about ...
$33
per adult
West Side Neighborhoods Foodie Small-Group Bike TourWest Side Neighborhoods Foodie Small-Group Bike Tour
Make your way to Chicago's Streeterville neighborhood near Navy Pier to meet your guide and group. Get set up with your helmet and bike, then pedal off through the River North neighborhood, across the Chicago River, and over to Fulton ...
$99
per adult
Chicago Small-Group Digital and Polaroid Photo ShootChicago Small-Group Digital and Polaroid Photo Shoot
Don’t leave Chicago without taking home professional digital and polaroid shots of your visit. Starting from the iconic Millennium Park, your photographer guide takes you to some of the city’s most photogenic landmarks to take photos of you t...
$169
per adult
Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline CruisePrivate Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise
Enjoy a private two and a half hour sailing experience for up to four people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make...
$488
per adult
Chicago Lake Michigan Private Sunset Sailing CharterChicago Lake Michigan Private Sunset Sailing Charter
Soak up unbeatable views of Lake Michigan and the Chicago skyline—and stay on the water long enough to watch the lights come on in the city—on this private, sunset sailing tour. This charter is completely customizable, giving you the chance t...
$508
per adult
Historical and Architectural Chicago Fireboat River/Lake CruiseHistorical and Architectural Chicago Fireboat River/Lake Cruise
Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel on Lake Michigan and through the Chicago River seeing the sights. Perfect for Fire enthusiasts, families and everyone in between! Our flagship vess...
$45
per adult
Lincoln Park Hauntings Ghost Investigation TourLincoln Park Hauntings Ghost Investigation Tour
Arrive at Lincoln Park after dark, leaving room in your day to complete other activities on your itinerary. Join forces with your personal paranormal investigator and begin to take a leisurely stroll through the neighborhood.Delve into...
$40
per adult
Chicago River Architecture Cruise History and Sightseeing TourChicago River Architecture Cruise History and Sightseeing Tour
Make your way to either Navy Pier or Michigan Avenue (depending on option chosen) for your cruise departure. Board your riverboat and find a comfortable seat; a restroom is available on the boat. Listen as your guide, an architecture e...
$49
per adult

45-Minute Private Helicopter Flight for 1-3 People45-Minute Private Helicopter Flight for 1-3 People
Enjoy spectacular views of Chicago from an MD500 helicopter. This helicopter flight over Chicago covers all the important highlights of the city from McCormick Place and Soldiers Field in the South to Wrigley Field in the North. Depart from Schaumbu...
$756
per adult
Architecture cruise in Spanish on the Chicago River from Michigan AveArchitecture cruise in Spanish on the Chicago River from Michigan Ave
This picturesque cruise is led by a professional Spanish speaking guide who shares exciting details and the historical significance of the buildings that line the Chicago River. Boarding at the dock on Michigan Avenue, you'll sail down all th...
$54
per adult
Chicago American Writers Museum Skip-the-Line Admission TicketChicago American Writers Museum Skip-the-Line Admission Ticket
Immerse yourself in American literary traditions, and enjoy a wide range of interactive exhibitions, during a visit to Chicago’s one-of-a-kind American Writers Museum. Conveniently located on Michigan Avenue, the museum was established in 201...
$16
per adult

The Art Institute of Chicago: Fast PassThe Art Institute of Chicago: Fast Pass
Home to some of the world's most recognizable artworks, the Art Institute of Chicago is America's second-largest art museum. Seeing famous art at the Art Institute of Chicago is a reliable way to ensure your day in the Windy City is nothing short of ...
$40
per adult
The Art Institute of Chicago: Fast PassThe Art Institute of Chicago: Fast Pass
Home to some of the world's most recognizable artworks, the Art Institute of Chicago is America's second-largest art museum. Seeing famous art at the Art Institute of Chicago is a reliable way to ensure your day in the Windy City is nothing s...
$40
per adult
Chicago History Museum: Entry TicketChicago History Museum: Entry Ticket
Explore the history of Chicago and United States through permanent and temporary exhibitions drawn from more than 20 million items in the Chicago History Museum. Showcasing photography, documents, artifacts, and interviews, the permanent and ...
$17
per adult

Chicago CityPASS®: Save up to 49% at 5 Top AttractionsChicago CityPASS®: Save up to 49% at 5 Top Attractions
Experience 5 must-see attractions and save up to 49% with Chicago CityPASS® tickets. One simple purchase removes the stress of planning, so you can relax and enjoy your memories in the making. With 9 days to use your tickets, you’ll have plenty of ti...
$126
per adult

American Writers Museum Flexible Date Entry TicketAmerican Writers Museum Flexible Date Entry Ticket
Learn about the history of writing and how it has shaped American culture with a ticket to the American Writers Museum in Chicago. Stroll through exhibits that appeal to all 5 senses, explore the intricacies of language through games, and write your ...
Go City | Chicago All-Inclusive PassGo City | Chicago All-Inclusive Pass
Welcome to the windy city! Home to world-famous art museums, iconic architecture and delicious food, Chicago is a perfect blend of midwestern hospitality and dynamic urban metropolis all set against the beautiful backdrop of Lake Michigan. Do...
$139
per adult

Color Factory Chicago General Admission TicketColor Factory Chicago General Admission Ticket
Voted the #1 Immersive Art Experience in America by USA Today readers in 2024, Color Factory Chicago celebrates the joy of color. Embark on a bright and colorful journey through 14+ immersive installations that inspire joy and human connection, expa...
$32
per adult
360 Chicago Observation Deck: Skip The Line Entry Ticket360 Chicago Observation Deck: Skip The Line Entry Ticket
It might be called the Windy City but from the 94th floor of downtown Chicago's John Hancock Center, you'll see a lot more than windswept trees. 360 Chicago offers incredible views of the city and Lake Michigan, plus four neighboring states. ...
$30
per adult

Willis Tower Skydeck and The Ledge TicketWillis Tower Skydeck and The Ledge Ticket
Enjoy an unrivaled view over the city of Chicago on a trip up the city's Willis Tower. This famous building, once known as the Sears Tower, is not only home to a Skydeck on the 103rd floor, but it also features The Ledge, a series of 4 glass-paneled ...
$29
per adult

Navy Pier Centennial Wheel TicketNavy Pier Centennial Wheel Ticket
Experience the views from the Centennial Wheel at the Historic Navy Pier in Chicago with this attraction ticket. Be suspended over Lake Michigan at the mouth of the Chicago River. Marvel at the Chicago skyline and gaze out over the sparkling waters o...
$20
per adult

360 Chicago Observation Deck Fast Pass Ticket360 Chicago Observation Deck Fast Pass Ticket
Travel to the 94th floor of the former John Hancock Center in just 40 seconds on one of North America’s fastest elevators. Step foot onto the observation deck to experience breathtaking views of the Chicago Skyline and Lake Michigan. Take in the cit...
$49
per adult

360 Chicago Observation Deck Sip and View Ticket360 Chicago Observation Deck Sip and View Ticket
Take in the beautiful views of Chicago as you enjoy a drink from our carefully curated Sip menu. 360 CHICAGO Observation Deck sits 1,000 feet over Chicago’s legendary Michigan Avenue. Located on the 94th floor of 875 N. Michigan (formerly the John Ha...
$39
per adult

Chicago Skyline PassChicago Skyline Pass
From stuffed pizza crusts to windswept walks, Chicago is one American city that wants to entertain you! This specially curated package has been designed to tick-off sky-high views and the city's best architecture from your to-do list. Get easy ac...
$120
per adult

360 Chicago Observation Deck General Admission360 Chicago Observation Deck General Admission
360 CHICAGO Observation Deck sits 1,000 feet over Chicago’s legendary Michigan Avenue. Located on the 94th floor of 875 N. Michigan (formerly the John Hancock Center), 360 CHICAGO gives you the opportunity to experience the best views of the Chicago ...
$27
per adult
360 Chicago Observation Deck Tickets360 Chicago Observation Deck Tickets
360 CHICAGO’s concourse level includes an interactive exhibit highlighting the history of Chicago and the vibrant cultures and businesses across Chicago neighbourhoods. Get inspired to explore Chicago beyond downtown after watching a short do...
$30
per adult