MOOSE JAW CITY TOUR FIELD GUIDE
Bootleggers Below Main: A 1929 Chase Through Moose Jaw’s Secret Tunnels
An immersive, actor-led 50-minute guided tour that stages Al Capone’s Chicago ties beneath Moose Jaw — this guide distills what to expect, where to meet, and who should (or shouldn’t) join.
Bootleggers Below Main: A 1929 Chase Through Moose Jaw’s Secret Tunnels.
Step into the thriller of 1929 and move beneath Moose Jaw’s streets as costumed characters lead you from a speakeasy into atmospheric underground tunnels, learning the ropes of bootlegging while you try to evade the law.
Highlights
Outing Highlights
Immersive 1929 bootlegger narrative
The Chicago Connection uses live character actors to place visitors in a prohibition-era storyline—become a bootlegger, ally with Capone’s gang and race to safety while surprises keep the suspense high.
From speakeasy to subterranean passages
Expect atmospheric sets that transition from Miss Fanny’s club to the cramped, lit tunnels below the streets—designed to evoke the era and the risks of smuggling.
Surprises and effects that heighten suspense
The tour layers sound and practical effects into the route, producing loud moments and sudden surprises that amplify the chase-and-escape narrative.
What the day feels like
What it feels like to go underground
You begin at a storefront speakeasy, meet costumed guides, then follow the narrative through sets and tunnels as you dodge authority figures and follow characters like Gus to safety—an active, theatrical half-hour that unfolds under Main Street.
Suitability
Who it's for
Who this tour suits — and who should take caution.
Practical planner
Details to review before reserving
The Chicago Connection runs about 50 minutes.
Meet at 18 Main St. North, Moose Jaw, Saskatchewan for tour check-in.
No special gear is required; dress for stairs and confined spaces. Note that photography is prohibited and only service animals are allowed in tour spaces.
The tour includes several flights of stairs and staged loud noises and surprises—guests who have difficulty with stairs or are sensitive to sudden effects should plan accordingly.
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.
Can I take photos during the tour?
No—photography is not allowed inside the tour spaces.
Are service animals allowed?
Only service animals are permitted in tour spaces.
Is the tour suitable for young children?
Families with young children should be aware the tour has several flights of stairs and includes loud noises and surprises that may upset very young guests.