Ride a luxury coach through Chicago’s Prohibition-era hotspots with actor-guides who bring Capone, Dillinger and the St. Valentine’s Day Massacre into sharp focus. This 105-minute tour mixes theatrical storytelling with historical sites and easy on-foot stops — ideal for history buffs and city explorers.
More ways to explore the area's outdoor wonders
You step onto a polished coach in downtown Chicago and the city narrows to a ribbon of brick, stone, and river. Buildings lean in like witnesses; the Chicago River dares you to follow its engineered bends as the bus ghosts past storefronts and marked-off lots where headlines were once written in blood.
Difficulty
easy
Duration
1–2 hours
Fitness Level
Suitable for all fitness levels; mostly seated with short, easy walking segments
Wildlife
History
Chicago’s Prohibition-era crime was fueled by bootlegging, ethnic neighborhood rivalries, and rapid industrial growth—figures like Al Capone leveraged both violence and business networks to build power.
Conservation
Many sites are city-owned landmarks or churches—treat memorials and markers with respect and avoid disturbing plaques or adjacent residential areas.
Reserve your spot on the Chicago's Original Gangster Tour by Bus today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Book early
Tours fill fast—reserve online in advance to secure your preferred departure time and seating.
Arrive 15 minutes early
Check in at the meeting point to ensure your spot; buses leave on time and late arrivals may be denied boarding.
Bring a charged phone
Guides reference archival photos and many stops are good for quick photography; a charged device ensures you capture details.
Comfortable footwear
Most of the tour is seated but a couple short walking segments require steady shoes—avoid new or slippery soles.
Comfortable walking shoes
Supportive shoes for short on-foot stops and uneven sidewalks.
Mobile ticket or printed confirmation
Required for entry and fastest boarding—mobile tickets are accepted.
Light jacket or layers
Spring and fall can be chilly; layers let you adjust between bus warmth and outdoor stops.
spring
Portable phone charger
Keeps your device powered for photos and map-checking after the tour.