Chicago St. Valentine's Day Massacre Pub Crawl Is Back for 2026

Chicago's Most Infamous Ghost Tour - Fri Feb 13 2026

Chicago has no shortage of love stories, but on Valentine’s week, the city also remembers one of its darkest: the St. Valentine’s Day Massacre. If you’re looking for a night out that’s equal parts history, chills, and cocktails, our Chicago St. Valentine’s Day Massacre Ghost Tour Pub Crawl is built for exactly that.

This is not a “sit and sip” kind of evening. It’s a moving, story-driven crawl through Lincoln Park and into the heart of Chicago’s gangster era, where Prohibition turned bars into battlegrounds and headlines into body counts.

We kick off at Chicago Oven Grinder (1850 N Lincoln Ave) to get everyone settled in with your first drink special and the big-picture setup: Chicago in the late 1920s, when organized crime wasn’t just in the city, it was part of how the city worked.Then we start walking straight into a story that still doesn’t feel real.

The history: what happened on February 14, 1929

The St. Valentine’s Day Massacre was the bloody peak of Chicago’s gang war. Seven men were lined up inside a garage and gunned down in a burst of machine-gun fire.The attack is most often linked to the rivalry between Al Capone’s organization and George “Bugs” Moran’s North Side gang, and it helped cement Chicago’s reputation worldwide as the capital of American gangland violence.

Standing at the site, it’s easier to understand why this case became legend. Even people who know the facts by heart still get quiet there. It’s one of those rare spots where the city’s “then” and “now” feel stacked on top of each other.

The hauntings: what people say lingers at the massacre site

This is where our tour shifts from history you can verify to stories Chicago refuses to let die.

Over the years, visitors and locals have reported strange experiences tied to the old garage location:

• Phantom gunfire that seems to come out of nowhere.
• Screams and shouting that vanish as quickly as they appear.
• Barking dogs and animals acting unsettled, as if they sense something people cannot.

There are even local stories about winter nights when fresh snow seemed to hold “body outline” shapes in the wrong place, like the scene replayed itself when nobody was looking. Believe it or not, it’s the kind of claim that has kept this location in Chicago’s paranormal lore for decades. Click below to watch your tour guide tell the story on video!

The encore: Dillinger at the Biograph Theatre

We will visit another Chicago true-crime landmark: the Biograph Theatre, where John Dillinger was shot and killed by federal agents after leaving a movie in 1934. It’s one of the most famous “walked-out-and-never-made-it-home” moments in American crime history, and it’s a perfect final stop for a tour that lives in the overlap between legend and real-life violence.

You’ll get gangster-era history, ghost stories, and can get drinks as we go. If you’re 21+ and want a Valentine’s season night that’s more guns than roses, come take the crawl with us.

Bring a date! Use the code BUGS2026 to get 2 tickets for only $60!

Stock photos provided by depositphotos.com