In need of some quick cash for Deb to purchase an ice cream parlor, the trio decides to make some money rather than save the world. But after Chris devises a strategy to cash in on the fixed 1919 Chicago World Series baseball game, their get-rich-quick scheme is derailed when they run into the infamous mobster Al Capone.

Dan, Deb and Chris find themselves stuck in 1920s Chicago, with Al Capone holding their time travel bag hostage. Chris opts for a play-it-safe plan, using history to take out Capone, while Dan and Deb befriend him instead. As they teach him how to be a better mobster - and husband - they quickly realize that proving their loyalty may not be as easy as they thought.