Viator Rating : 5 (38 reviews)
Dyvarcity Score : 8.1/10 (Verified Excellent)
Chicago
Chicago Mob Tour: Gangsters & Movie Sites
90
Overview
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. 
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) : Very few people, free movement
Safety (9 - Secure) : Strong feeling of safety and control
Upsell Risk (9 - Transparent) : No upsells or hidden costs
Pacing (8 - Balanced) : Smooth and comfortable timing
Guide Quality (9 - Exceptional) : Engaging and memorable
Guide Reliability (9 - Dependable) : On time with strong follow-through
What to Watch Out For
Logistics (7 - Friction) : Issues but experience continued
Mobility (7 - Moderate) : Some effort required
Instagram Factor (7 - Scenic) : Some good photo moments
Highlights
Walk in the Footsteps of Mobsters: See the real places where Capone and Dillinger made history.
Movie Magic Locations: Visit spots where famous movies like 'The Untouchables' were filmed.
Expert Guides: Learn from true crime historians and film buffs.
Iconic Chicago Landmarks: Explore the Chicago Riverwalk, Art Institute, and more.
Souvenir Photos Included: Take home memories of the mobster movie tour experience.
Small Group Experience: Enjoy a more personal tour with a smaller group size.
Sentiment Analysis
Customers loved the knowledgeable and engaging tour guides.
-
Visitors enjoyed seeing the actual locations of mob history and movie scenes.
-
Many found the tour to be a fun and unique way to experience Chicago.
-
The stories and insider trivia were a highlight for many.
Some customers felt the tour could have been longer.
-
A few mentioned that the weather impacted their enjoyment.
The Journey
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.
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.'
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.
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.
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.
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.
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
More like this
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
$35
Chicago Crime & Architecture Walking Tour
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.
Chicago
$79.99
Chinatown Chicago: Food Tour & Hidden Gems
4.9
(599 reviews)
Duration: 180
minutes
Explore Chicago's Chinatown on the Chinatown Food and Walking Tour. This tour shows off tasty food and cool history in one of America's best Chinatown neighborhoods. Bobby’s Bike Hike, known for top food tours recognized by USA Today and Tripadvisor, guides this fun walk. The tour lasts 3 hours.
Guests will walk through Chinatown Square. They'll taste yummy Cantonese dim sum, treats from Portuguese-Chinese bakeries, spicy Szechuan dishes, and Xi'an foods. Expert guides tell how these foods and cultures came to Chicago. You'll discover the unique history and flavors of Chicago's Chinatown.
The tour includes a local guide, dinner, and drinks. It doesn't include a suggested $10-15 tip for the guide, which can be given in cash, Venmo, or PayPal. This culinary adventure guides guests through stops like Dim Sum Restaurants, Noodle Restaurants, Portuguese Egg Tart Shops, and Chinatown Square. Learn about Chicago's Chinatown History & Culture as you enjoy the flavors of the neighborhood.
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.
Chicago
$35
Chicago Crime & Ghost Tour: Mob History & Haunted Tales
5.0
(54 reviews)
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.
Nearby Events
Wrigley Field
Jun 19
1:20 PMChicago Cubs vs Blue Jays at Wrigley Field
Chicago Cubs vs Toronto Blue Jays: #BudFridays Cubs 1930s Replica Jersey at Wrigley Field brings MLB action to one of baseball’s most iconic settings, pairing a National League home crowd with a Blue Jays visit that always adds intrigue. The Cubs remain one of baseball’s most recognizable franchises, and a game at Wrigley Field carries the atmosphere, history, and neighborhood energy that make Chicago baseball a destination in itself.
The Chicago Cubs and Toronto Blue Jays represent two well-known MLB clubs with strong fan followings, and matchups like this often draw travelers looking for a classic ballpark experience. Wrigley Field is famous for its ivy-covered outfield walls and historic character, giving every game a distinctly old-school feel that stands out on any baseball itinerary.
Wrigley Field
July 17
7:05 PMChicago Cubs vs. Minnesota Twins Tickets
Chicago Cubs vs. Minnesota Twins at Wrigley Field brings a classic Midwest MLB matchup to one of baseball’s most iconic settings, where every inning carries the energy of a summer day at the ballpark. The Cubs remain one of Major League Baseball’s most recognizable franchises, and a visit to Wrigley Field adds timeless charm, from the ivy-covered outfield walls to the neighborhood atmosphere that makes every game feel bigger than the score.
Both the Chicago Cubs and Minnesota Twins have deep baseball traditions and loyal fan bases, making this matchup a strong draw for travelers and local fans alike. Wrigley Field is known for its historic design, intimate sightlines, and old-school baseball character, creating a memorable experience for anyone looking to see MLB action in Chicago.
Coronado Theatre
Oct 04
7:30 PMLabyrinth In Concert 40th at Coronado Theatre
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.
Purcell Pavilion at the Joyce Center
Sep 11
7:00 PMJim Gaffigan Live at Purcell Pavilion
Jim Gaffigan: Everything is Wonderful! at Purcell Pavilion at the Joyce Center brings one of America’s most recognizable stand-up voices to South Bend for an evening of sharp observations, clean comedy, and crowd-pleasing storytelling. Jim Gaffigan remains a major live draw thanks to his long-running career, bestselling specials, and signature style that turns everyday life into big laughs.
Gaffigan’s appeal comes from his ability to mix family life, food jokes, and self-aware wit into a set that feels both relatable and polished. Purcell Pavilion at the Joyce Center is a well-known South Bend venue with a large indoor arena setting that supports major live entertainment and a strong audience atmosphere.
Soldier Field
July 24
7:00 PMKarol G Chicago Concert Tickets - Viajando Tour
Karol G brings her electrifying Viajando por el Mundo Tropitour to Soldier Field in Chicago, delivering a high-energy Latin music experience that celebrates reggaeton's global dominance. The Colombian superstar, known for chart-topping hits like "Tití," "Mamiii," and "Ella Baila Sola," continues her momentum as one of the most streamed female artists worldwide, commanding the stage with infectious rhythms and stadium-sized production.
Karol G's rise to international stardom represents a pivotal moment for reggaeton and Latin trap in mainstream music, with her albums consistently breaking streaming records and redefining what Latin music means on the global stage. Soldier Field, Chicago's iconic 61,500-capacity lakefront venue, provides the perfect setting for this powerhouse performance, known for hosting unforgettable concerts and major sporting events that draw audiences from across North America.
American Family Field
Jun 18
1:10 PMBrewers vs. Guardians Tickets at American Family Field
Milwaukee Brewers vs. Cleveland Guardians at American Family Field brings together two competitive MLB clubs in a high-energy interleague matchup in Milwaukee. The Brewers’ home-field atmosphere, paired with the Guardians’ scrappy, disciplined style of play, gives this game strong appeal for baseball fans looking for a lively summer night at the ballpark.
Milwaukee has built a reputation around its passionate fan base and power-driven baseball tradition, while Cleveland is known for resilient, fundamentals-first play and clutch pitching. American Family Field adds to the experience with its retractable roof, fan-friendly layout, and classic Midwest baseball setting that makes it one of the most recognizable stops on the MLB calendar.
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