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

Viator Rating : 5 (38 reviews)

Dyvarcity Score Icon

Dyvarcity Score : 8.1/10 (Verified Excellent)

Location Icon Chicago

Chicago Mob Tour: Gangsters & Movie Sites

Clock

90

Overview

Experience Intelligence

Highlights

Sentiment Analysis

FAQs

Location

Overview

Quotes Logo The Chicago Mobsters and Movies Walking Tour takes everyone into Chicago's thrilling past! Explore real spots where famous mobsters like Capone and Dillinger lived and see how these places became movie sets. This walking tour shows how Chicago became a big part of American gangster history and movies.

Walk along the Chicago Riverwalk and visit hidden underground tunnels, iconic landmarks, and Chicago's Business District. The tour even makes stops at the Art Institute of Chicago, a famous live music venue, and the Chicago Cultural Center (once the main library). See the spots from movies like 'The Untouchables' and 'Public Enemies.' The guides are experts who know all about true crime, movies, and Chicago history. They'll share exciting stories and behind-the-scenes facts.

This experience includes souvenir photos to remember the adventure. Please note that tips for the tour guide are not included. With small group sizes, everyone can easily hear the guide and feel like they're part of the story. This tour is a unique way to see Chicago's most famous spots and learn about its exciting history. It's more than just a tour; it's a chance to step into the world of gangsters and movies. Quotes Logo

Experience DNA Fingerprint

Scores are shown on a scale of 1 to 10, 1 = lowest score, 10 = highest score.

What People Love

Crowd Density (8 - Empty / Light)

Crowd Density (8 - Empty / Light) : Very few people, free movement

Safety (9 - Secure)

Safety (9 - Secure) : Strong feeling of safety and control

Upsell Risk (9 - Transparent)

Upsell Risk (9 - Transparent) : No upsells or hidden costs

Pacing (8 - Balanced)

Pacing (8 - Balanced) : Smooth and comfortable timing

Guide Quality (9 - Exceptional)

Guide Quality (9 - Exceptional) : Engaging and memorable

Guide Reliability (9 - Dependable)

Guide Reliability (9 - Dependable) : On time with strong follow-through

What to Watch Out For

Logistics (7 - Friction)

Logistics (7 - Friction) : Issues but experience continued

Mobility (7 - Moderate)

Mobility (7 - Moderate) : Some effort required

Instagram Factor (7 - Scenic)

Instagram Factor (7 - Scenic) : Some good photo moments

Highlights

Highlight Icon

Walk in the Footsteps of Mobsters: See the real places where Capone and Dillinger made history.

Highlight Icon

Movie Magic Locations: Visit spots where famous movies like 'The Untouchables' were filmed.

Highlight Icon

Expert Guides: Learn from true crime historians and film buffs.

Highlight Icon

Iconic Chicago Landmarks: Explore the Chicago Riverwalk, Art Institute, and more.

Highlight Icon

Souvenir Photos Included: Take home memories of the mobster movie tour experience.

Highlight Icon

Small Group Experience: Enjoy a more personal tour with a smaller group size.

Sentiment Analysis

  • Positive Highlight Icon Customers loved the knowledgeable and engaging tour guides.

  • Positive Highlight Icon Visitors enjoyed seeing the actual locations of mob history and movie scenes.

  • Positive Highlight Icon Many found the tour to be a fun and unique way to experience Chicago.

  • Positive Highlight Icon The stories and insider trivia were a highlight for many.

  • Negative Highlight Icon Some customers felt the tour could have been longer.

  • Negative Highlight Icon A few mentioned that the weather impacted their enjoyment.

The Journey

1

Chicago Riverwalk

Stroll along the famed Chicago Riverwalk, a vibrant pedestrian promenade showcasing Chicago's architectural beauty and playing host to numerous film locations. Discover captivating mob stories and explore real-life settings featured in movies, experiencing the intersection of Chicago's criminal past and its prominent role in cinematic history. Enjoy the river views while immersing yourself in tales of gangsters and movie magic.

2

Underground Tunnels (Chicago)

Delve into the clandestine world of Chicago's underground tunnels, once utilized by the infamous Chicago Outfit. Visit the poignant location where John Dillinger met his girlfriend for the last time. These hidden passages and historic spots provide a unique glimpse into the city's shadowy past and have served as dramatic backdrops in films like 'The Dark Knight' and 'The Fugitive.'

3

Iconic Chicago Landmark (Various)

Experience an iconic location that has doubled as the stage for some of Chicago's most memorable movie moments. Revisit scenes from 'The Fugitive,' 'The Blues Brothers,' and 'Ferris Bueller's Day Off,' while also uncovering the true crime legends that have haunted this powerful corridor. This location is a crossroads of cinematic brilliance and Chicago's darker history.

4

Chicago's Business District

Explore Chicago's bustling business district, a striking backdrop for exciting movie scenes ranging from 'The Dark Knight' to 'The Untouchables.' Witness stunning architectural interiors while uncovering the stories of famous Chicago mob characters who once operated in these very streets. This district seamlessly blends cinematic drama with the city's notorious underworld.

5

Art Institute of Chicago

Immerse yourself in the history of the Art Institute and Chicago's cultural mile, discovering its surprising connections to some of the city's most famous crimes. Learn how to maximize your visit, focusing on art pieces featured in famous films. The Art Institute offers a unique intersection of art history, cinematic appearances, and intriguing true crime tales.

6

Chicago Landmark (Live Music/Comedy Venue)

Visit a city landmark steeped in Al Capone history, renowned as a filming location for numerous live music and comedy albums. This venue has captivated audiences in movies like 'Public Enemies' and 'The Dark Knight,' offering a potent mix of Chicago's musical heritage, mobster lore, and cinematic significance. Experience a location where legends of entertainment and crime converge.

7

Former Chicago Public Library (Cultural Center)

Conclude your tour at the filming location of the climactic scene from 'The Untouchables,' a perfect blend of mobsters and movies. Explore the architectural wonders inside the former Chicago Public Library, now a cultural center, including the world's largest Tiffany glass dome and other exquisite art exhibits. This location offers a stunning finale, combining cinematic history, architectural beauty, and artistic treasures.

Know Before You Go

This experience includes souvenir photos to remember the tour. Tips or gratuities for the tour guide are not included in the price. Participants should meet at the designated starting point. Be sure to wear comfortable shoes for walking, as the tour covers several city blocks and you will be standing for an extended period of time.

Hot Tip

Wear comfortable shoes, as you'll be doing a lot of walking! Also, consider the weather and dress accordingly. Bring a water bottle to stay hydrated.

Review Summary

Customers generally say the Chicago Gangsters and Movies Tour offers vivid, engaging storytelling combining true crime history with iconic movie locations, guided by knowledgeable insiders. Positive remarks frequently highlight the entertaining, informative guides and the unique access to exclusive interiors. Some travelers noted the walking pace and length as moderate, which may not suit those with mobility issues, and a few wished for more interactive elements or film memorabilia. Overall, it is rated highly for its immersive, behind-the-scenes insight into Chicago's gangster lore and cinematic heritage.

This page is synthesized and developed by Dyvarcity Team

From $35 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

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 Crime & Architecture Walking Tour

Location Icon Chicago

$35

Chicago Crime & Architecture Walking Tour

Architecture Tours Low Supplier Cancellation Rate Low Last Minute Supplier Cancellation Rate

Rating Star 5.0 (326 reviews)

Chicago Architecture and True Crime History Tour offers a thrilling exploration of Chicago's iconic skyline intertwined with its intriguing, sometimes dark, past. Inspired by 'Devil in the White City,' this guided walking tour unveils secrets hidden within architectural marvels and overlooked landmarks that are typically missed by boat tours.

Participants can anticipate venturing to significant sites, including the Marshall Field's Building (Macy's on State Street), a testament to architectural grandeur, and the modern Chase Tower, learning about their historical and cultural impact on Chicago. Along the way, the tour guide will share true crime stories that will transport participants to another time.

This experience includes the expertise of a local guide, and excludes gratuity. This tour is perfect for those seeking a unique perspective on Chicago's history and architecture.

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

Chicago Crime & Ghost Tour: Mob History & Haunted Tales

Location Icon Chicago

$35

Chicago Crime & Ghost Tour: Mob History & Haunted Tales

Walking Tours Crime Tours Ghost Tours

Rating Star 5.0 (54 reviews)

Duration In Minutes Duration: 90 minutes

Chicago Crime and Ghosts Walking Tour takes people back in time to the days of Al Capone and spooky ghost stories. This walking tour explores Chicago's dark past, blending true crime history, ghost stories, and famous buildings.

Walk along the Chicago River, where some of the city's most infamous events happened. Visit old speakeasies from the Prohibition era and spots where John Dillinger hung out. See the Chicago Picasso and the Theater District, a site of gangster activity. Step inside famous hotels and see the Art Institute, where history whispers after dark. An expert historian guides you, sharing stories of beauty and horror from one of America's most famous periods.

This tour gives you special access to places connected to famous events. Learn about the city's architectural landmarks and haunted locations. It includes an expert tour guide, and access inside famous hotels. Tips and gratuities for the tour guide are not included. The tour ends near a convenient location for continued exploration.

Details

Book Now

Chicago Private City Tour: Discover the Windy City in Style & Comfort!

Location Icon Chicago

$539

Chicago Private City Tour: Discover the Windy City in Style & Comfort!

Bus Tours City Tours Car Tours

Rating Star 4.9 (201 reviews)

Chicago Private Custom City Tour offers a personalized exploration of Chicago with hotel pick-up. Enjoy a 3-4 hour chauffeured tour, led by knowledgeable guides. Stops include Millennium Park and Museum Campus. Interactive and entertaining, this tour covers Chicago's history, architecture, and culture. Concludes with drop-off at your preferred downtown location.

Details

Book Now

Nearby Events

Shreya Ghoshal Live at NOW Arena Hoffman Estates

Location Icon NOW Arena

Sep 11

8:00 PM

Shreya Ghoshal Live at NOW Arena Hoffman Estates

World Music

Shreya Ghoshal: The Unstoppable Tour brings the celebrated Indian playback singer to NOW Arena in Hoffman Estates, Illinois on September 11, 2026. Known for her powerful vocals and commanding stage presence, Ghoshal delivers an unforgettable evening of music spanning her vast catalog of hits from Bollywood blockbusters and independent projects. This tour showcases her evolution as an artist and cements her status as one of the most versatile voices in Indian cinema.

Shreya Ghoshal has captivated audiences worldwide with her technical prowess, emotional depth, and ability to transcend traditional boundaries in playback singing. Her performances are marked by intricate vocal techniques and an engaging connection with fans. NOW Arena, located in the heart of Hoffman Estates, provides an intimate yet impressive venue setting that allows attendees to experience her artistry up close while enjoying world-class acoustics and sight lines.

Details

Book Now

ALOK Live Comedy Show at Milwaukee Improv

Location Icon Milwaukee Improv (Main Room)

Sep 17

7:00 PM

ALOK Live Comedy Show at Milwaukee Improv

Comedy Arts & Theatre

ALOK: New Comedy Show at Milwaukee Improv (Main Room) in Brookfield brings Alok Vaid-Menon’s sharp, highly personal comedy to one of the area’s best-known live-comedy rooms. Alok is currently touring in 2026 with a wide run of stand-up and performance dates, and this stop offers audiences a chance to see a bold, contemporary voice in comedy in an intimate club setting.
Alok Vaid-Menon is a comedian, writer, and performance artist known for work centered on gender, identity, and self-expression, blending humor with reflection and audience connection. Milwaukee Improv (Main Room) is designed for close-up comedy, with a room built for strong sightlines and the kind of direct crowd energy that suits a live comedian’s stage presence.

Details

Book Now

Labyrinth In Concert: 40th Anniversary at Pabst

Location Icon Pabst Theater

Oct 03

8:00 PM

Labyrinth In Concert: 40th Anniversary at Pabst

Family Miscellaneous Film

Jim Henson's Labyrinth In Concert brings the cult classic film to Pabst Theater in an immersive live experience. Fans watch the 1986 fantasy on a stunning HD screen while a live band performs the full soundtrack in perfect sync with David Bowie’s iconic vocals, celebrating the movie’s 40th anniversary on a global tour hitting over 60 North American cities.

Jim Henson’s Labyrinth, directed by Henson himself and starring Jennifer Connelly and David Bowie as the Goblin King Jareth, captivates with its magical world of fantastical creatures from Henson’s Creature Shop and timeless songs like “Magic Dance.” This fusion of film and live music revives the sweeping score by Bowie and Trevor Jones like never before. The historic Pabst Theater, a Milwaukee landmark, provides an intimate setting for this nostalgic spectacle.

Details

Book Now

Bassem Youssef: The Belly of the Beast Tour

Location Icon The Chicago Theatre

Sep 26

7:00 PM

Bassem Youssef: The Belly of the Beast Tour

Comedy Arts & Theatre

Bassem Youssef: The Belly of the Beast Tour brings the Egyptian-American comedian and satirist to The Chicago Theatre for an evening of sharp political commentary and observational humor. Known globally as the "Egyptian Jon Stewart," Youssef has captivated audiences worldwide with his fearless approach to comedy that blends social critique with intelligent wit. This tour marks his continued expansion into English-language stand-up, where he applies the same uncompromising satirical lens that once drew 40 million weekly viewers to his groundbreaking television show.
Youssef's journey from cardiac surgeon to internationally acclaimed satirist has made him one of the most influential comedians of his generation. His ability to tackle complex political and social issues with humor has earned him recognition as one of Time magazine's 100 most influential people. The Chicago Theatre, one of America's most iconic performance venues, provides the perfect backdrop for an artist who has spent his career challenging authority and sparking meaningful conversation through comedy.

Details

Book Now

Book Tickets: J. Cole Live at United Center Chicago

Location Icon United Center

Aug 11

8:00 PM

Book Tickets: J. Cole Live at United Center Chicago

Hip-Hop/Rap Trap Music

J. Cole: The Fall-Off Tour brings the Grammy-award winning rapper to United Center in Chicago for an electrifying hip-hop and rap performance. This event supports his seventh and final studio album, 'The Fall-Off', released in February 2026, marking a major milestone in his career as he headlines a global tour spanning over 50 cities across 15 countries.

J. Cole is celebrated for his lyrical depth, record production skills, and emotional storytelling that resonates with fans worldwide. United Center, Chicago's iconic 20,000-seat arena known for hosting legendary concerts and Chicago Bulls games, provides the ultimate venue for this unforgettable musical experience.

Details

Book Now

Brewers vs. Rangers: Milwaukee Showdown!

Location Icon American Family Field

Aug 28

6:40 PM

Brewers vs. Rangers: Milwaukee Showdown!

Baseball MLB Sports

Brewers vs. Rangers at American Family Field: Get ready for an exciting Major League Baseball game as the Milwaukee Brewers take on the Texas Rangers at the iconic American Family Field. This contest will feature a thrilling display of athleticism and tactical maneuvers on the diamond. Expect to witness powerful hitters launching balls into the stands, swift runners stealing bases, and skilled pitchers delivering masterful performances.

American Family Field, the Brewers' home stadium, boasts a distinctive open-air design complemented by a retractable roof, guaranteeing that the game will proceed regardless of weather conditions. The stadium's architecture provides fans with intimate and engaging viewing angles, ensuring an immersive experience. This event is tailored for attendees seeking a relaxed and family-friendly sporting atmosphere, perfect for fans of all ages.

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