Moose Jaw calls itself Canada's Most Notorious City, and the nickname Little Chicago appears on signs, in shop windows and on the tunnels tours. The story behind it is one of the best-loved pieces of local folklore in the country, and it is worth understanding before you go underground. This guide explains what is known, what is legend and how to experience the tunnels today.
Why Prohibition mattered here
Between the 1910s and the early 1930s, parts of North America banned the sale of alcohol. In the United States, nationwide Prohibition ran from 1920 to 1933, while Canadian provinces had a patchwork of rules that changed over the years. Where alcohol was banned, a lively illegal trade grew: smuggling, bootlegging, hidden bars and corrupt arrangements. Railway towns were natural hubs for this trade because goods and people moved through them constantly, and Moose Jaw, on the main line of the Canadian Pacific Railway, was one such town.
The tunnels themselves
Beneath downtown Moose Jaw there are real underground passages. Early buildings were heated by steam, and tunnels connected boilers to basements, giving workers a way to maintain the systems. Over time, the basements and passages were used for storage, work and, according to local stories, other purposes. These are the spaces that today host the tours.
The Capone legend
The most famous tale says that Al Capone and his Chicago associates used Moose Jaw as a hideout and a base for smuggling, and that the tunnels were their secret route. There is no firm documentary evidence that Capone ever visited, and historians treat the claim with caution. The tunnels tours acknowledge this, presenting the story as local legend and theatre rather than proven fact. What is well documented is that Prohibition-era smuggling was widespread, that the railways were important routes, and that the city's reputation for tolerance toward illicit activity was part of its character.
The Chicago Connection Tour
This is the tour that tells the Prohibition story. Costumed actors lead small groups through sets built into real underground spaces, and the group moves from room to room as the plot develops. It lasts about fifty minutes, starts at the ticket office at 18 Main Street North and is one of the most popular activities in the city. Book ahead in summer and on holiday weekends.
Bunker 24
The same operator offers a second tour set in the Cold War. In a 1950s-style bunker, costumed guides explain what life would have been like for people in a shelter during the nuclear standoff. It is not part of the Prohibition story, but it makes a good counterpart for visitors who want a second tunnels experience.
Beyond the tunnels
Other experiences continue the theme above ground. The True Crime Trolley Tour tells documented stories of crime and scandal, the Ghost Trolley Tour covers the haunted side of the old downtown and the Murder Mystery Detective Experience lets you play detective on your own. The murals and heritage buildings of Main Street show the city that grew up around these stories, and the Grant Hall Hotel offers a night in a building that has been part of that history since the 1920s.
Tips for the tunnels
Wear comfortable shoes, because there are stairs and uneven floors. Arrive ten minutes early and check accessibility with the operator, particularly if you use a mobility aid or dislike confined spaces. Photography rules vary, so follow your guide's instructions. The tunnels are underground, so the temperature is steady and the tours work in any season, which makes them an excellent choice on a very hot or very cold day.
A short reading list in spirit
If the subject grabs you, spend an extra hour at the Moose Jaw Museum and Art Gallery, where local history is presented with objects and photographs, or ask the Visitor Centre staff about books on prairie Prohibition and railway history. Seeing the documented material beside the theatre of the tours is the best way to appreciate how much of the Moose Jaw story is solid, how much is polished and why the city has been so good at telling it.
How to take the story
Enjoy it as entertainment built on a solid base of history. The best tours mix documented facts with cheerful embroidery, and the best visitors accept both. If you want to separate the two, ask your guide or the staff at the Visitor Centre, who are used to the question and often have a good answer.