MOOSE JAW GUIDED TOUR FIELD GUIDE
Bootleggers' Run: Descend into Moose Jaw’s 1929 Underworld
An immersive, guided 50-minute tour that recreates Prohibition-era bootlegging and Al Capone’s ties to Moose Jaw—this guide explains what to expect and where to meet.
Bootleggers' Run: Descend into Moose Jaw’s 1929 Underworld.
Step into 1929 Moose Jaw on a guided, theatrical exploration that dramatizes Prohibition, Al Capone’s connection to the town, and the risky business of moving contraband beneath the streets. The Chicago Connection blends live character actors, atmospheric sets and underground tunnels into an immersive storyline in which visitors learn the ropes of becoming a bootlegger.
Highlights
Outing Highlights
Immersive 1929 bootlegger storyline
The tour stages a narrative in which you join Capone’s operation—complete with live character actors—so you experience the tension and choices of smuggling during Prohibition.
From speakeasy floors to secret tunnels
Atmospheric sets recreate a speakeasy and the subterranean passages beneath Moose Jaw, bringing the era’s underground world to life as you move through staged environments.
Surprises, effects and suspense
The production uses surprises and effects to heighten suspense along the route, amplifying the sense of danger as you try to sidestep law enforcement in the storyline.
What the day feels like
What it Feels Like Underground
You begin at Miss Fanny’s club and are drawn into a live-action narrative: follow Gus, Capone’s goon, into a network of secret tunnels, learn smuggling tradecraft in a speakeasy set, and navigate staged challenges as you attempt to transport illicit cargo while evading the law. The guided experience is theatrical and paced to fit an approximately 50-minute run.
Suitability
Who it's for
Who this tour fits—and who should be cautious.
Practical planner
Details to review before reserving
The Chicago Connection runs for about 50 minutes.
Meet at 18 Main St. North, Moose Jaw, Saskatchewan for the tour departure.
The tour has several flights of stairs, contains some loud noises and surprises, only service animals are permitted in tour spaces, and photography is prohibited.
Bring only what you need; note that only service animals are permitted and photography is not allowed—follow operator instructions while on the tour.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the Chicago Connection tour?
About 50 minutes.
Where do I meet for the tour?
At 18 Main St. North, Moose Jaw, Saskatchewan.
Is photography allowed during the tour?
No—photography is not allowed on the Chicago Connection tour.
Can I bring my pet?
Only service animals are permitted in tour spaces.
Are there any safety concerns or accessibility issues?
The experience includes several flights of stairs and some loud noises and surprises; families with young children should be aware of these elements.
What is the tour’s storyline?
The tour dramatizes Prohibition-era bootlegging and Al Capone’s connection to Moose Jaw: you start at Miss Fanny’s club and follow characters into secret tunnels as part of an immersive guided story.