Chicago Mobsters and Movies Walking Tour

Discover Chicago’s Crime and Cinema Heritage for $35

The Chicago Mobsters and Movies Walking Tour offers an engaging journey through the city’s infamous gangster history combined with iconic movie scenes. Priced at $35 per person and lasting about 1 hour and 30 minutes, this tour showcases Chicago’s notorious past as well as its role in Hollywood storytelling. It departs from 238 N State St and ends at the Chicago Cultural Center, conveniently located near Millennium Park and the Bean.

This tour is perfect for history buffs, film enthusiasts, and true crime fans. Led by highly knowledgeable guides who are trained true crime historians and Chicago insiders, the experience provides more than just sightseeing—it offers vivid tales, behind-the-scenes stories, and exclusive access to locations linked to mobsters like Capone and Dillinger. While the tour is primarily walking, the route is accessible, making it suitable for most guests who can comfortably walk at a steady pace.

Key Points

• Affordable and well-reviewed at a perfect 5-star rating based on 5 reviews
• Includes visits to iconic sites like the Chicago Riverwalk and The Art Institute of Chicago
• Highlights both gangster history and famous movie locations across the city
• Led by expert guides with background in crime history and film
• A 1.5-hour walk that covers multiple landmarks with insightful commentary
• Free souvenir photos are included to remember this unique experience

The Tour’s Unique Blend of Crime and Movie Locations

The Chicago Mobsters and Movies Walking Tour stands out by combining true crime stories with Hollywood filming sites in one accessible walking route. It offers a glimpse into Chicago’s infamous mob past, such as the activities of Capone, Dillinger, and The Outfit, while also showing how these streets transformed into iconic film locations.

What makes this tour special is the focus on inside interiors and hidden tunnels used by the Chicago Outfit. Guests explore sites like underground tunnels and places where John Dillinger saw his last girlfriend. The tour also revisits scenes from popular movies like ‘The Fugitive’, ‘The Blues Brothers’, ‘Ferris Bueller’s Day Off’, ‘The Dark Knight’, ‘Public Enemies’, and ‘The Untouchables’.

Starting at the Chicago Riverwalk

The tour begins at 238 N State St, a prime spot along the Chicago Riverwalk, which is itself a famous and frequently filmed landmark. The guide shares mob stories tied to this area and points out filming locations that still stand along the river. The 15-minute stop is perfect for taking in the scenery and snapping photos of this vibrant, historic stretch.

This spot sets the tone for the tour, blending Chicago’s scenic beauty with stories of organized crime and cinematic history. The Riverwalk’s reputation as a highly filmed location makes it a fitting starting point for exploring city legends.

Underground Tunnels and Dillinger’s Last Visit

Next, the tour heads to River North, where visitors discover underground tunnels once used by the Chicago Outfit. These tunnels are part of the city’s secret mob infrastructure. The guide also shows where John Dillinger visited his last girlfriend, adding a layer of personal drama to the criminal tales.

During this 10-minute stop, the focus is on mob secrets and the connection between Chicago’s criminal activities and Hollywood’s portrayal of the city’s underworld. Movie fans will recognize filming locations from ‘The Dark Knight’ and ‘The Fugitive’, enriching the storytelling.

Exploring the Picasso and Movie Scenes

The tour makes a stop at The Picasso, a Chicago icon that also features in major films. Here, the guide revisits scenes from ‘The Fugitive’, ‘The Blues Brothers’, and ‘Ferris Bueller’s Day Off’, emphasizing how Chicago’s architecture and landmarks have played a prominent role in Hollywood.

Guests get a chance to appreciate the city’s artistic and cinematic appeal as the guide explains the significance of this location in both the city’s cultural and film history. The 10-minute stop allows for photos and a deeper understanding of the city’s film-friendly architecture.

Architectural Marvels at The Rookery Building

The next stop is The Rookery Building, a renowned example of Chicago architecture. This historic building serves as the backdrop for scenes from ‘The Dark Knight’ and ‘The Untouchables’. The tour explores its beautiful interior, highlighting art deco details and the building’s role in cinematic storytelling.

In this 15-minute visit, guests learn how Chicago’s distinctive architecture has contributed to film production. The guide shares stories about the building’s history and its appearances in popular media, making it a must-see for fans of both architecture and crime movies.

The Art Institute and Chicago’s Cultural Mile

At the Art Institute of Chicago, the tour delves into the city’s artistic and criminal history. This stop offers insights into how Chicago’s cultural institutions relate to notorious crimes and Hollywood filming. Guests also hear tips on how to best enjoy a visit to the museum and surrounding Cultural Mile.

This 15-minute segment enhances the tour’s depth, connecting art, crime, and film in one of Chicago’s most celebrated cultural areas. The Art Institute’s historic interiors and nearby landmarks tie together Chicago’s creative and criminal legacies.

The Chicago Theatre and Mobster History

The Chicago Theatre is a key highlight, noted for its Al Capone history and its role as a filming location for ‘Public Enemies’ and ‘The Dark Knight’. The guide discusses the theater’s rich entertainment history and the city’s mob influence on its development.

The 10-minute stop allows visitors to appreciate the architecture and film significance of this iconic venue. It’s a fitting site to reflect on Chicago’s mobster legends and its role in Hollywood’s portrayal of organized crime.

The Grand Finale at The Chicago Cultural Center

The tour ends at the Chicago Cultural Center, famous for its stunning architecture and as the location for the climactic scene in ‘The Untouchables’. Inside, visitors explore beautiful interior spaces and learn about the intersection of mob history and Chicago’s cultural scene.

This 10-minute finale caps off the experience with a look at the city’s architectural beauty and its ties to mobster legends. The Cultural Center’s central location makes it easy for guests to continue exploring nearby attractions like Millennium Park and the Bean.

Practical Details and Accessibility

The tour departs at 2:00 pm from 238 N State St and concludes at 78 E Washington St within walking distance of major landmarks. No transportation is provided, but the route is fully accessible, suitable for most guests who can walk comfortably at a steady pace.

It caters to up to 25 travelers, ensuring a personal and engaging experience. Confirmation is immediate, and free cancellation is available up to 24 hours before the tour starts, adding flexibility to planning.

What Makes This Tour Stand Out

The combination of crime stories, movie locations, and iconic Chicago landmarks sets this tour apart. The guides’ expertise as true crime historians and film buffs ensures that the stories are both accurate and engaging. The inclusion of exclusive interiors and hidden tunnels offers a richer understanding of Chicago’s mobster past.

The free souvenir photos add a memorable touch, letting visitors take home a keepsake of their exploration. The tour’s moderate pace and accessible route make it a great choice for a broad range of visitors, especially those interested in Chicago’s cinematic and criminal legacies.

Authentic and Informative Experience

Based on high praise, the guides’ knowledge and enthusiasm are key strengths. The tour offers vivid tales and insider trivia that deepen the connection to Chicago’s history. The stops at famous landmarks and filming locations provide both visual appeal and storytelling richness.

This is not just a sightseeing walk; it’s a history lesson wrapped in Hollywood stories, making it ideal for those who want both entertainment and education in one compact experience.

Final Thoughts on the Chicago Mobsters and Movies Walking Tour

The $35 price point offers excellent value considering the richness of stories, the variety of locations, and the expert guidance. It’s a well-rounded tour that caters to fans of organized crime, film, and Chicago architecture alike. The small group size helps foster a personal atmosphere, and the accessible route ensures most guests can participate comfortably.

This tour is especially recommended for anyone seeking a deep dive into Chicago’s mob history intertwined with Hollywood’s depiction of the city. Its blend of interactive storytelling, historic sites, and film locations makes it a memorable way to explore Chicago’s fascinating past.

Frequently Asked Questions

How long does the tour last?
The tour lasts approximately 1 hour and 30 minutes.

Where does the tour start and end?
It begins at 238 N State St and ends at the Chicago Cultural Center at 78 E Washington St.

Is the tour suitable for all walking levels?
Yes, the route is fully accessible and suitable for most guests who can walk comfortably at a steady pace.

Are tickets available in advance?
Yes, tickets can be booked 7 days in advance on average, and immediate confirmation is provided.

What’s included in the price?
The tour includes souvenir photos; tips for guides are not included.

Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours before the scheduled start.

Who leads the tour?
The guides are trained true crime historians, film buffs, and Chicago insiders.

Is this tour good for children?
Most travelers can participate, but the content may be more engaging for adults interested in crime history and movies.

Is transportation provided during the tour?
No, this is a walking tour without vehicles; it is designed to be fully walkable and accessible.

How popular is this tour?
With an excellent 5-star rating from 5 reviews, it is highly recommended for a quality, insider experience of Chicago’s criminal and cinematic history.