img0 img1img2img3img4
Left Arrow
Right Arrow
img1
img2
img3
img4
Rating Star

Viator Rating : 5 (115 reviews)

Dyvarcity Score Icon

Dyvarcity Score : 7.4/10 (Solid Experience)

Location Icon Chicago

Chicago Gangster Bus Tour: Crime History & Sites

Clock

105

Overview

Experience Intelligence

Highlights

Sentiment Analysis

FAQs

Location

Overview

Quotes Logo 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. Quotes Logo

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)

Safety (8 - Secure) : Strong feeling of safety and control

Upsell Risk (8 - Transparent)

Upsell Risk (8 - Transparent) : No upsells or hidden costs

Mobility (8 - Easy / Accessible)

Mobility (8 - Easy / Accessible) : Comfortable for most people

Guide Quality (9 - Exceptional)

Guide Quality (9 - Exceptional) : Engaging and memorable

Guide Reliability (8 - Dependable)

Guide Reliability (8 - Dependable) : On time with strong follow-through

What to Watch Out For

Crowd Density (6 - Standard)

Crowd Density (6 - Standard) : Normal crowd, some waiting or tight spots

Logistics (7 - Friction)

Logistics (7 - Friction) : Issues but experience continued

Pacing (7 - Uneven)

Pacing (7 - Uneven) : Inconsistent or mixed pacing

Instagram Factor (6 - Scenic)

Instagram Factor (6 - Scenic) : Some good photo moments

Highlights

Highlight Icon

Relive Chicago's Roaring 20s: Hear true tales of Al Capone, Bugs Moran, and John Dillinger.

Highlight Icon

Visit Notorious Gangster Sites: See the St. Valentine's Day Massacre site, Biograph Theater, and Holy Name Cathedral.

Highlight Icon

Entertaining Gangster Guides: Guides are actors who bring the gangster era to life.

Highlight Icon

Fun Raffles and Prizes: Participate in raffles and win prizes during the tour.

Sentiment Analysis

  • Positive Highlight Icon Customers loved the guides! They say the guides are funny and do a good job acting like gangsters.

  • Positive Highlight Icon Many people thought the tour was very fun and interesting.

  • Positive Highlight Icon The tour gives a good picture of the gangsters' lives.

  • Positive Highlight Icon Raffles and Prizes were a hit!

  • Negative Highlight Icon Some people said it was hard to see the sites from the bus.

  • Negative Highlight Icon A few people felt the tour could have been longer.

The Journey

1

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.

2

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

From $48 Price

Book Now

As a Viator affiliate partner, we may earn a commission on purchases made through our platform.

Book Now

As a Viator affiliate partner, we may earn a commission on purchases made through our platform.

More like this

Chicago's Dazzling Architecture: Interiors Walking Tour

Location Icon Chicago

$35

Chicago's Dazzling Architecture: Interiors Walking Tour

City Tours Viator Plus Walking Tours

Rating Star 5.0 (1475 reviews)

Duration In Minutes 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.

Details

Book Now

Uncover Chicago's Dark Past: A Murder Mystery Adventure!

Location Icon Chicago

$35

Uncover Chicago's Dark Past: A Murder Mystery Adventure!

Walking Tours Crime Tours Cultural Tours

Rating Star 5.0 (724 reviews)

Duration In Minutes 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.

Details

Book Now

Chicago Art Institute: Skip-the-Line Private Tour

Location Icon Chicago

$85.5

Chicago Art Institute: Skip-the-Line Private Tour

Historical Tours Museums Low Last Minute Supplier Cancellation Rate

Rating Star 5.0 (271 reviews)

Duration In Minutes 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.

Details

Book Now

Chicago Food, History & Architecture Walking Tour

Location Icon Chicago

$100.95

Chicago Food, History & Architecture Walking Tour

Likely to Sell Out Food & Drink Viator Experience Award 2023

Rating Star 4.9 (1152 reviews)

Duration In Minutes 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.

Details

Book Now

Chicago City Tour: Top Sights & Skyline Views

Location Icon Chicago

$47.95

Chicago City Tour: Top Sights & Skyline Views

Low Supplier Cancellation Rate Bus Tours City Tours

Rating Star 4.9 (513 reviews)

Duration In Minutes 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.

Details

Book Now

Chicago Art Institute: Skip-the-Line Small Group Tour

Location Icon Chicago

$85.5

Chicago Art Institute: Skip-the-Line Small Group Tour

Historical Tours Museums Low Last Minute Supplier Cancellation Rate

Rating Star 5.0 (152 reviews)

Duration In Minutes 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.

Details

Book Now

Nearby Events

Labyrinth In Concert 40th at Coronado Theatre

Location Icon Coronado Theatre

Oct 04

7:30 PM

Labyrinth In Concert 40th at Coronado Theatre

Family Miscellaneous Film

Jim Henson's Labyrinth: In Concert 40th Anniversary lights up the Coronado Theatre in Rockford, IL, with a live band performing the iconic score from the 1986 cult classic film starring David Bowie, synced perfectly to the on-screen action while preserving his original vocals. This massive 2026 tour, following a triumphant run across nearly 100 cities, celebrates the film's 40th anniversary by immersing audiences in the Goblin King's fantasy world through epic music and visuals.

Jim Henson's Labyrinth captivates with its timeless puppetry, enchanting songs like 'Magic Dance' and 'As the World Falls Down,' composed by Bowie and Trevor Jones, drawing fans into Sarah's quest to rescue her brother. The Coronado Theatre, a historic 1927 movie palace known for its Spanish Renaissance architecture and starry ceiling, provides an atmospheric backdrop for this unforgettable cinematic concert experience.

Details

Book Now

Comedy Bang! Bang! Live! Chicago 2026 Tickets

Location Icon The Chicago Theatre

May 28

8:00 PM

Comedy Bang! Bang! Live! Chicago 2026 Tickets

Comedy Arts & Theatre

Comedy Bang! Bang! Live! brings the Ground Beefing Tour 2026 to The Chicago Theatre with their signature improv comedy mayhem. Hosted by Scott Aukerman, this live podcast-turned-stage spectacle features surprise celebrity guests, absurd sketches, and unscripted hilarity that has fans raving about its unpredictable energy.
Comedy Bang! Bang! Live! stands out for blending top comedians like Paul F. Tompkins and guests from TV and film into interactive bits that feel fresh every show, cementing its status as improv comedy royalty. The Chicago Theatre, an opulent 1920s marquee landmark, elevates the laughter with its stunning auditorium and storied history of hosting legends.

Details

Book Now

Chicago White Sox vs. Atlanta Braves Tickets

Location Icon Rate Field

Jun 09

6:40 PM

Chicago White Sox vs. Atlanta Braves Tickets

Baseball MLB Sports

The Chicago White Sox face off against the Atlanta Braves at Guaranteed Rate Field, bringing together two storied MLB franchises for an electrifying afternoon of baseball. This matchup showcases the competitive spirit of Major League Baseball, with both teams bringing their best talent to one of Chicago's premier sports venues. The White Sox, playing in their historic home stadium, deliver consistent entertainment that draws fans from across the region who appreciate quality professional baseball and the energy of live play-by-play action.

The Atlanta Braves bring their own legacy of excellence to this interstate rivalry, representing one of baseball's most recognizable organizations. Guaranteed Rate Field, located on Chicago's South Side, is renowned for its modern amenities and intimate fan experience, making it an ideal destination for experiencing MLB baseball at its finest.

Details

Book Now

Pete the Cat Live at Metropolis PAC Tickets

Location Icon Metropolis Performing Arts Centre

Mar 15

12:00 PM

Pete the Cat Live at Metropolis PAC Tickets

Arts & Theatre

Pete The Cat brings his groovy adventures to Metropolis Performing Arts Centre in Arlington Heights, IL, captivating audiences with a lively theatrical production based on the beloved children's book series by James Dean and Kimberly Dean. This family-friendly arts and theatre event features catchy songs, colorful costumes, and interactive storytelling that brings the cool cat's tales of positivity and resilience to the stage.
Pete The Cat, the iconic blue cat known from over 70 books, animated series, and now live shows, teaches kids valuable lessons through music and fun antics like rocking in his red shoes. Metropolis Performing Arts Centre, a state-of-the-art venue renowned for its intimate setting and high-quality productions, provides the perfect backdrop for this enchanting performance.

Details

Book Now

Usher & Chris Brown R&B Tour at Soldier Field

Location Icon Soldier Field

Aug 21

7:00 PM

Usher & Chris Brown R&B Tour at Soldier Field

R&B Music

The R&B Tour starring Usher Raymond & Chris Brown lights up Soldier Field in Chicago with an electrifying showcase of smooth vocals, high-energy choreography, and timeless hits. This dynamic duo, both R&B legends with chart-topping albums and sold-out residencies, promises a night of nostalgic anthems and fresh tracks that have fans buzzing about their unstoppable live chemistry.
Usher Raymond, known for his Super Bowl halftime mastery and Las Vegas residency success, pairs seamlessly with Chris Brown’s acrobatic dance moves and multi-platinum hits like 'No Guidance.' Soldier Field, Chicago’s iconic stadium on the lakefront, hosts massive concerts with stunning acoustics amid its historic columns.

Details

Book Now

Liverpool FC vs Leeds United at Soldier Field Tickets

Location Icon Soldier Field

Aug 02

3:00 PM

Liverpool FC vs Leeds United at Soldier Field Tickets

Soccer Sports

Liverpool FC vs Leeds United ignites Soldier Field in a fierce pre-season showdown between two historic English soccer rivals. As Liverpool, the 2024/25 Premier League champions, gear up under Arne Slot, they face a battle-hardened Leeds United side that went undefeated against the Reds last season, promising high-stakes action and tactical previews for the 2026-27 campaign.

This clash highlights the deep rivalry between Liverpool FC, with over 26 million US fans and the fastest-growing Premier League base in America, and Leeds United, returning to the US after 29 years. Soldier Field, Chicago's iconic NFL stadium home to the Bears and Chicago Fire, offers a massive stage with pristine pitch conditions optimized for elite soccer.

Details

Book Now

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