Chicago Gangster History Walking Tour of River North
Step beyond the usual stories of Al Capone and discover a deeper, more intense side of Chicago's gangster history. An expert guide will lead you through the streets of River North, revealing stories of the Beer Wars, daring ambushes, and brutal rivalries that played out right where you walk.
This 2-hour walking tour offers a vivid glimpse into the city's turbulent past, highlighting landmarks that have witnessed some of the most infamous moments in Chicago crime history. From surviving fire-era structures to locations tied to organized crime, you'll get a true sense of how these streets became the battleground for power and violence.
Perfect for history buffs and curious explorers alike, this tour combines storytelling with a walk through historic neighborhoods. Whether you're traveling with family or friends, you'll find plenty to fascinate and educate on this immersive journey into Chicago's gangster era.
Frequently asked questions
How long is the Chicago Gangster History Walking Tour of River North?
The tour lasts approximately 2 hours, giving you plenty of time to explore the key sites and hear the stories behind them.
Is the tour suitable for children?
Yes. The tour is appropriate for all ages, including infants, children, and teenagers. It’s wheelchair accessible, and small children can ride in strollers or prams.
What is included in the tour?
You’ll enjoy a curated 2-hour route through major landmarks, guided by a knowledgeable local who provides historical context and stories.
Are there any exclusions I should know about?
Gratuities for your guide are appreciated but not required. The tour price does not include tips.
Where do I meet the guide?
Meet at the base of the Old Chicago Water Tower, on the corner of Michigan Avenue and Chicago Avenue. Look for your guide on the east side of the Water Tower, facing Michigan Avenue.
Can I cancel if my plans change?
Yes. You can cancel for a full refund if you do so at least 24 hours before the scheduled start time. Cancellations made within 24 hours are non-refundable.
Free cancellation
You can cancel for a full refund if you do so at least 24 hours before the scheduled departure time.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 2 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Planned route: a curated 2-hour walk through major landmarks
- Professional guide: a local expert providing history and stories
Not included
- Gratuities for your guide (appreciated but not required)
Itinerary
-
Stop 1
One of the few structures to survive the Great Chicago Fire of 1871, this limestone landmark marks the heart of what would become the most contested and bloodiest turf in Prohibition-era Chicago.
-
Stop 2
This stunning Catholic cathedral, dedicated in 1875, still bears evidence of a 1926 machine gun ambush that took down one of Al Capone's most feared rivals just steps from its entrance.
-
Stop 3
This Gilded Age mansion showcases the immense legitimate wealth flowing through River North—creating a stark contrast to the illegal fortunes made on these streets.
-
Stop 4
Former location of the Celano Tailor Shop—a seemingly ordinary shop that served as a key meeting point for Outfit members, blurring the lines between legitimate business and organized crime.
Meeting point & pickup
Meet at the starting point
Meet your guide at the base of the Old Chicago Water Tower, on the corner of Michigan Avenue and Chicago Avenue. Look for your guide on the east side of the Water Tower, facing Michigan Avenue.
Open in Google MapsCancellation & confirmation
Free cancellation
You can cancel for a full refund if you do so at least 24 hours before the scheduled departure time.
- 100% refund if canceled at least 1 day in advance
- No refund if canceled within 24 hours of the start time
Instant confirmation
Your booking is confirmed immediately after checkout.
From $39.99 per person
- Free cancellation
- Secure checkout with our booking partner
