Step Back Into Chicago’s Prohibition Era: The Ultimate Gangster Tour Experience
Difficulty
moderate
Duration
2–3 hours
Fitness Level
Reasonable walking fitness required to cover distance comfortably, no steep terrain.
Overview
Explore Chicago’s gritty Prohibition-era past on an immersive gangster tour through Berwyn’s authentic neighborhoods. Discover real stories of mobsters, speakeasies, and the battle between law and outlaws just outside the Windy City.
Chicago Prohibition Gangster Tour
$40 per Person l 10 years of age and older l 2.5 Hours
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Adventure Photos
About This Adventure
Join author John Binder for a captivating 2.5-hour bus tour through Chicago's Prohibition Era crime history. Explore notorious sites linked to Al Capone and John Dillinger, including the St. Valentine’s Day Massacre. Engage with the expert and uncover thrilling tales of gangland intrigue without the hassle of walking.
Chicago's Underground Revealed!
Rates
People (Ages 10 and older): $40
Duration
2 Hours and 30 Minutes
About
John Binder, author of Al Capone’s Beer Wars and The Chicago Outfit and the consultant on numerous organized crime related documentaries, conducts this in-depth, two and a half hour tour of Chicago’s Prohibition Era crime history. It visits notorious sites associated with Al Capone, his North Side rivals, and John Dillinger, including where the infamous St. Valentine’s Day Massacre took place, where Dillinger was killed, and the locations of other gangland hits and near misses. John welcomes questions from the audience over the entire two and a half hours. The tour is by luxury bus and there is no walking (except for a few stops where passengers may exit the bus to get a closer look).
Additional Information
The bus leaves promptly at the scheduled time, from the Southeast corner of Michigan Ave. and Monroe St. in downtown Chicago (across from Millennium Park), so please try to arrive early to allow for variability in travel times.
Adventure Tips
Wear comfortable shoes for urban walking
The tour involves 2–3 miles on paved streets and sidewalks, so sturdy shoes will keep you comfortable.
Bring a light jacket year-round
Chicago weather can change quickly; layering helps you stay warm during cooler evenings or indoor stops.
Arrive on time to get the full tour experience
Groups are small and tours start promptly to keep the narrative flow engaging and complete.
Capture photos but respect private property
Many sites are visible from public spaces; stay aware of boundaries and privacy during your walk.
Local Insights
Wildlife
- Urban birds like peregrine falcons and red-tailed hawks
- Seasonal sightings of river otters along nearby waterways
History
The tour explores Chicago’s violent Prohibition era from 1920 to 1933, highlighting key figures who influenced the city’s criminal underworld.
Conservation
The tour encourages responsible urban tourism by respecting local neighborhoods and supporting small businesses in Berwyn.
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Frequently Asked Questions
Recommended Gear
Comfortable walking shoes
Essential for navigating city streets comfortably throughout the year.
Light jacket or layers
Fall weather can be cool and windy; layers provide warmth without overheating.
fall specific
Portable phone charger
Keep your devices charged for photos and navigation during the tour.
Camera or smartphone
Ideal for capturing the historic architecture and tour highlights.