“Chasing October” features filmmaker Matt Liston, who quits his job to single-handedly will the Chicago Cubs to a 2003 World Series win through a documentary. Blurring the lines between comedy and heartfelt devotion, the film captures Liston in the bleachers during pivotal games and includes interviews with not only Cubs players like Kerry Wood but also celebrities such as Bernie Mac, Gary Sinise, Joe Mantegna, Jeff Garlin, and Larry King.

As Liston’s passion project unfolds, it strains his personal life, leading to a breakup with his girlfriend, Faline England. Despite these challenges and the Cubs falling short of a World Series title, the film serves as a heartfelt, often comedic exploration of extreme fandom and enduring hope among Cubs supporters.