Viator Rating : 5 (115 reviews)
Dyvarcity Score : 7.4/10 (Solid Experience)
Chicago
Chicago Gangster Bus Tour: Crime History & Sites
105
Overview
Chicago's Original Gangster Tour by Bus takes you back to the roaring 20s and 30s, when gangsters ruled the city. This bus tour isn't just a history lesson; it's an entertaining ride through Chicago's dark past, led by guides who are also actors playing the part of real gangsters.
Expect to hear true stories of infamous figures like Al Capone, Bugs Moran, and John Dillinger. The tour visits the sites of their most notorious deeds, including the St. Valentine's Day Massacre. You'll also see the Biograph Theater, where Dillinger met his end, and Holy Name Cathedral, forever marked by a shootout outside Schofield's Flower Shop.
This experience includes raffles and prizes to make the tour even more interesting. It doesn't include food or drinks so make sure to bring your own! Reservations are strongly recommended to secure your spot on this unforgettable journey into Chicago's gangster era. 
Experience DNA Fingerprint
Scores are shown on a scale of 1 to 10, 1 = lowest score, 10 = highest score.
What People Love
Safety (8 - Secure) : Strong feeling of safety and control
Upsell Risk (8 - Transparent) : No upsells or hidden costs
Mobility (8 - Easy / Accessible) : Comfortable for most people
Guide Quality (9 - Exceptional) : Engaging and memorable
Guide Reliability (8 - Dependable) : On time with strong follow-through
What to Watch Out For
Crowd Density (6 - Standard) : Normal crowd, some waiting or tight spots
Logistics (7 - Friction) : Issues but experience continued
Pacing (7 - Uneven) : Inconsistent or mixed pacing
Instagram Factor (6 - Scenic) : Some good photo moments
Highlights
Relive Chicago's Roaring 20s: Hear true tales of Al Capone, Bugs Moran, and John Dillinger.
Visit Notorious Gangster Sites: See the St. Valentine's Day Massacre site, Biograph Theater, and Holy Name Cathedral.
Entertaining Gangster Guides: Guides are actors who bring the gangster era to life.
Fun Raffles and Prizes: Participate in raffles and win prizes during the tour.
Sentiment Analysis
Customers loved the guides! They say the guides are funny and do a good job acting like gangsters.
-
Many people thought the tour was very fun and interesting.
-
The tour gives a good picture of the gangsters' lives.
-
Raffles and Prizes were a hit!
Some people said it was hard to see the sites from the bus.
-
A few people felt the tour could have been longer.
The Journey
Biograph Theater (Dillinger Shooting Site)
Stand on the very spot where John Dillinger, Public Enemy Number One, met his demise outside the Biograph Theater. Though the original Biograph has been repurposed, the location on Lincoln Avenue remains a potent reminder of Chicago's turbulent past and the relentless pursuit of notorious criminals. Imagine the scene: the flashing lights, the swarm of agents, and the hail of bullets that ended Dillinger's reign of terror. It's a chilling but captivating glimpse into a bygone era of gangsters and G-men.
Holy Name Cathedral & Former Schofield's Flower Shop Site
Visit Holy Name Cathedral, where a young Dean O'Banion once sang in the choir, a stark contrast to his future life as the ruthless leader of the North Side Gang. Across the street, imagine Schofield's Flowers, O'Banion's legitimate business and a front for mob activities. This flower shop supplied the elaborate arrangements for many mob funerals. It was also the site of O'Banion's assassination in 1924, a pivotal event in Chicago's gangland history. The cathedral and its surroundings offer a fascinating juxtaposition of piety and violence, a testament to the complex layers of Chicago's past.
Know Before You Go
This experience includes raffles and prizes. It excludes food and drinks. Reservations are highly recommended to guarantee a spot on the tour.
Hot Tip
Bring a snack or drink since this experience doesn't include any food or refreshments. Wear comfortable shoes because you will be walking a little bit. Keep an open mind and be ready to have some fun with your actor-guide!
Review Summary
Customers find this tour engaging and entertaining, appreciating the theatrical costumed guides who bring Chicago's Prohibition Era history to life with dramatic flair and knowledgeable commentary.[1] The tour is highly rated for its blend of education and entertainment, with visitors particularly enjoying the visits to iconic crime sites like the St. Valentine's Day Massacre and the Biograph Theater.[1] The small group size (maximum 10 travelers) and accessible climate-controlled minibus transportation are frequently praised features that make the experience comfortable and immersive for most participants.
This page is synthesized and developed by Dyvarcity Team
More like this
Chicago
$35
Chicago's Dazzling Architecture: Interiors Walking Tour
5.0
(1475 reviews)
Duration: 120
minutes
Original Chicago Architecture Interiors Tour: Dazzling Interiors takes guests on a journey through some of the city's most breathtaking interior spaces. Many people pass by these hidden gems every day without realizing what's inside. This walking tour, led by an experienced local guide, reveals the stunning beauty within.
Guests will explore architectural wonders, from turn-of-the-century stained glass mosaics to soaring Art Deco designs from the Roaring 20s. Key stops include the iconic Art Deco Building, Surprise Interiors, and the Chicago Cultural Center. Each location offers a unique glimpse into Chicago's rich history and artistic heritage.
The tour includes a knowledgeable local guide who provides insights and stories about each location. Gratuities are not included. Prepare to be amazed by the hidden beauty that lies within Chicago's architectural treasures.
Chicago
$35
Uncover Chicago's Dark Past: A Murder Mystery Adventure!
5.0
(724 reviews)
Duration: 120
minutes
The Chicago Murder Mystery Tour blends history and intrigue as you solve a fictional crime. Explore famous neighborhoods, delve into true crime legends, and play detective. Enjoy interactive gameplay and souvenir mugshot photos. Perfect for history buffs and true crime fans seeking a unique, immersive city experience, requiring walking and observation skills.
Chicago
$85.5
Chicago Art Institute: Skip-the-Line Private Tour
5.0
(271 reviews)
Duration: 150
minutes
Private Art Institute of Chicago Skip-the-Line Guided Tour. This is a special walking tour for people who love art and want to see the best pieces at the Art Institute of Chicago without waiting in long lines. The tour is just for the group and a guide, so it feels personal.
What to Expect: The tour visits famous artworks like 'Paris Street, Rainy Day' and 'Sunday on La Grande Jatte'. People will also see 'Nighthawks' and 'The Old Guitarist'. The guide shares stories about the art and artists. The Art Institute of Chicago is a very big museum with lots of famous art. It has art from all over the world and different times in history.
This private tour lasts for 2.5 hours and includes a professional tour guide just for the group. It also includes all entrance fees. The tour is wheelchair friendly. This tour does not include hotel pickup or drop-off, but the guide suggests using UBER or a taxi. Gratuities (tips) are not included in the price.
Chicago
$100.95
Chicago Food, History & Architecture Walking Tour
4.9
(1152 reviews)
Duration: 270
minutes
Chicago in a Day: Explore Food, History, and Iconic Architecture. This walking tour takes people through the heart of Chicago, showcasing its food, history, and buildings. It's a tasty way to see the city and learn some fun facts.
Visitors will walk along the Riverwalk, see the Wrigley Building, and snap photos at Millennium Park by Cloud Gate, also known as 'The Bean'. The tour also explores hidden spots like the Chicago Pedway and the bustling energy of Chicago's Main Artery. Expert local guides share stories about Chicago's past, from the Prohibition era to the Great Fire.
This tour includes stops at the Chicago Theatre, City Hall-County Building and the Loop. It includes Chicago's famous eats like deep-dish pizza, a Chicago-style hot dog, and Italian beef. The tour is limited to a small group of 12, making it personal and relaxed. This experience is run by a certified B Corp, which means they care about ethical and responsible tourism.
Chicago
$47.95
Chicago City Tour: Top Sights & Skyline Views
4.9
(513 reviews)
Duration: 120
minutes
Chicago City Minibus Tour lets one see Chicago’s famous sights and skyline views on an award-winning, small-group tour. Travel with an expert guide on a comfortable minibus, stopping at iconic locations like the early skyscraper "The Rookery" with Frank Lloyd Wright architecture, and Museum Campus for the best skyline view. You'll also see Buckingham Fountain.
Along the way, the guide shares historical, informational, and sometimes humorous stories about the area and its attractions. The small-group atmosphere, with a maximum of 13 people, ensures a personal experience. Expect to discover The Magnificent Mile, Millennium Park, the Marquette Building, Skydeck Chicago (Willis Tower), Lincoln Park, River North, the Art Institute of Chicago, Chicago Riverwalk, and Lake Michigan.
This tour includes transport by a 13-passenger, air-conditioned minibus and four photo stops. Gratuities are not included.
Chicago
$85.5
Chicago Art Institute: Skip-the-Line Small Group Tour
5.0
(152 reviews)
Duration: 150
minutes
Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max. This tour lets people see amazing art without waiting in long lines. It is a walking tour that is great for people who like art and history.
What to Expect: The Art Institute of Chicago is a very popular museum, just like the Met in New York or the Louvre in Paris. On this 2.5-hour tour, a friendly guide will take a small group (8 people max) to see the most famous artworks. Some of the art you might see includes *Paris Street, Rainy Day*, *Sunday on La Grande Jatte*, and *Nighthawks*. But sometimes, art is not there because it is being fixed or moved.
This tour includes all entrance fees and a guide who knows a lot about art. It does not include tips for the guide or rides to and from your hotel. It's easy to get to the museum by taxi or UBER.
Nearby Events
George Van Dusen Theatre at North Shore Center
Nov 18
7:30 PMFran Lebowitz
Navy Pier
Aug 30
2:00 PMNora En Pure Live at Navy Pier Chicago
Nora En Pure at North Beer Garden @ Navy Pier brings the Swiss electronic music star’s lush, melodic house sound to one of Chicago’s most recognizable lakefront destinations. Nora En Pure is actively touring in 2026, with multiple concert dates listed across North America and Europe, making this Chicago appearance part of a busy live run for one of electronic music’s most sought-after names.
The artist is known for atmospheric sets that blend deep grooves, uplifting melodies, and a polished club-to-festival energy that has earned a loyal global following. Navy Pier adds a scenic setting on Lake Michigan, and its reputation as one of Chicago’s most visited attractions gives the event a memorable backdrop for fans looking for both music and skyline views.
Ravinia
Sep 17
7:00 PMZiggy Marley & Thievery Corporation at Ravinia
Ziggy Marley with Thievery Corporation lights up Ravinia in Highland Park, IL, blending reggae royalty with downtempo electronica in a world music fusion that promises rhythmic transcendence. Ziggy, son of Bob Marley, brings his Grammy-winning vibes from recent albums like 'Love Is the Drug,' while Thievery Corporation delivers their signature global beats, creating a collaborative setlist of hits like 'Three Little Birds' and 'Lebanese Blonde.'
This pairing celebrates Ziggy's legacy of positive messages and Thievery's innovative soundscapes, drawing fans of conscious lyrics and chill grooves. Ravinia, the legendary outdoor venue, enhances the magic with its pavilion and lawn seating amid lush gardens.
Donald E. Stephens Convention Center
Oct 10
10:00 AMBuy Collect-A-Con Tickets: Chicago Rosemont Pop Culture Expo
Collect-A-Con, the nation's largest trading card and pop culture convention, returns to the Donald E. Stephens Convention Center in Rosemont, IL, offering a vibrant expo for hobby enthusiasts. Known for its extensive vendor tables, exclusive collectibles, and live performances, Collect-A-Con attracts fans of trading cards, anime, vintage toys, and more.
Collect-A-Con is a premier gathering spot in the collectibles community, featuring over 900 vendor tables and special guests from the pop culture world. The Donald E. Stephens Convention Center, recognized for hosting major expos and conventions, provides an ideal venue with ample space and accessibility, enhancing the event’s appeal.
The Chicago Theatre
Feb 26
7:30 PMProfessor Brian Cox Emergence at Chicago Theatre
Professor Brian Cox presents Emergence at The Chicago Theatre, a captivating lecture exploring the profound mysteries of the universe through cutting-edge science. Renowned for his BBC series like Wonders of the Universe and Human Universe, Cox blends awe-inspiring visuals with accessible explanations, making complex concepts thrilling for all ages.
Professor Brian Cox, a particle physicist and celebrated science communicator, has enthralled global audiences with his passion for cosmology and quantum mechanics. The Chicago Theatre, an iconic 1920s landmark famed for its lavish marquee and opulent auditorium, elevates this intellectual journey into an unforgettable spectacle.
SeatGeek Stadium
Aug 16
6:00 PMNitro Circus Live Tickets at SeatGeek Stadium
Nitro Circus Live brings the world's most electrifying extreme sports action to SeatGeek Stadium in Bridgeview, Illinois, featuring jaw-dropping stunts, high-flying tricks, and pulse-pounding entertainment. The legendary action sports collective delivers an unforgettable experience combining motocross, BMX, skateboarding, and acrobatics in one explosive show. Known for pushing the boundaries of extreme sports entertainment, Nitro Circus has captivated millions worldwide with their fearless performances. SeatGeek Stadium, a premier multi-use venue in the Chicago area, provides the perfect setting for this high-energy spectacle.
Chicago Best Things to Do: Concerts, Helicopter & Food Tours
The Chicago skyline is hiding a secret- a ton of them, actually. It’s more than a view: it’s got adventures you're meant to explore. Breathe in the winds and excitement of a helicopter tour, party at top concerts, or dive into food and pizza tours. Walk beside history on a gangster mob tour, take a fireboat or bus tour. Looking to get wild tonight? Find events going on sooner than tomorrow, from EDM to country concerts. Check all your bucket list boxes, and live stories you’ll remember forever.
View Chicago Activities