
Chicago Crime Walking Tours Guide
Dive into the gritty underworld of Chicago with its most famous crime tours. Explore the historic sites linked to Al Capone, the St. Valentine's Day Massacre, and the Prohibition era. Travelers can compare top-rated walking and bus tours to uncover the dark secrets behind the Windy City's skyline. These immersive experiences bring history to life through storytelling at iconic locations like the Green Mill Lounge and the original mob hideouts. Whether you are a history buff or seeking an adrenaline-pumping adventure, find the perfect tour that matches your interest in true crime and urban legends. Book now to secure your spot on these highly reviewed journeys and discover why Chicago remains the epicenter of American organized crime history.
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Chicago Crime and Movies is a two-in-one true crime and movie locations tour. Learn the real stories of Al Capone and the mafia—then see how the very same streets were turned into movie magic.
Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities. Hear true crime stories about Chicago Gangster Al Capone, The Untouchables, The Chicago Mob, Prohibition, John Dillinger, F...
- Prohibition Era personality profile
- All inclusions are subject to availability.
- Photos ops at infamous crime scenes
- Mini mob museum
- Live interactive tour guide in English
- Historic video footage
- Exclusive crime quiz
- Keepsake brochure with special offers
- Gratuity: Recommended $5/person gratuity (or more) via cash or Venmo.
- There are no translations, audio-guides or headphones.
- Water Tower Place
- Museum of Contemporary Art Chicago
- The Magnificent Mile
- John Hancock Center
- Abraham Lincoln Park
- North Avenue Beach
- Biograph Theatre
- Oz Park
- Chicago River
- Thirty Five E Wacker
- Holy Name Cathedral
- Historic Water Tower
For a full refund, cancel at least 24 hours before the scheduled departure time.
Mobsters and Movies takes you through the real haunts of Capone, Dillinger, and The Outfit—then shows you how the very same streets turned into movie magic. Walk the same corners seen in 'The Untouchables' and 'Public Enemies,' and hear how Chicago wrote the script for American gangster history. Thi...
- Souvenir Photos
- Tip/Gratuity for Tour Guide
- River North
- The Picasso
- The Rookery Building
- The Art Institute of Chicago
- The Chicago Theatre
- Chicago Cultural Center
For a full refund, cancel at least 24 hours before the scheduled departure time.
Embark on a captivating walking tour that delves into the intriguing legacy of the Midwest's most notorious mobsters and gangs. Immerse yourself in the rich history of the Windy City as you stroll through its vibrant streets, where the echoes of a century of Mob activity intertwine with the modern c...
- Well-trained guide
- Excellently researched history
- James R. Thompson Center
For a full refund, cancel at least 24 hours before the scheduled departure time.
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Frequently Asked Questions
Get answers to the most common questions travelers ask before visiting.Most of the options we compare across booking platforms fall between $35 and $49, with a median price of $46. The typical spread ranges from $32 to $55. While prices fluctuate based on the specific operator and date, you can generally expect to pay around this band for a standard guided experience.
If you are looking for the sweet spot between price and quality, the Sightseeing Tour category stands out. These average 4.72 stars while costing around $42, which is at or below the overall median price yet rated higher than the general average. This format offers excellent value for travellers who want high-rated content without paying a premium.
The majority of experiences run between 1.5 and 2.5 hours, with a median duration of 2 hours. This timeframe is designed to cover the key historical crime sites without feeling rushed, allowing enough time for the guide to share detailed stories and for you to take photos at each stop.
About half (50%) of the options we compare offer instant confirmation, which often allows for same-day or next-day bookings. However, because roughly 44% also offer free cancellation, popular time slots can fill up quickly. We recommend booking in advance if you have a specific date or time preference to secure your spot.
Guides are offered in four languages: English, Italian, Portuguese, and French. English is the most widely available, but if you prefer another language, you should check the specific listing details when comparing options to ensure that language support is included for your chosen tour.
Yes, 39% of the options we compare are tagged as eco-friendly. This includes walking-based tours that reduce carbon footprints compared to bus-heavy alternatives. If sustainability is a priority for you, look for these tags when browsing the listings to find operators who align with those values.
With an average rating of 4.61 stars across 5,515 pooled reviews, feedback is overwhelmingly positive. Common themes include descriptions like "great," "amazing," "fun," and "entertaining." Reviewers frequently praise guides for being knowledgeable and engaging, though it is worth noting that some guests mention the groups can be large during peak times.
Use the CTA app or Ventra card. Trains run frequently and cover most major attractions efficiently.
Try Lou Malnati's or Giordano's for classic options. Reserve ahead as lines can be long during peak hours.
The Loop and River North are generally safe with police presence. Stay aware of your surroundings and stick to well lit areas.