"Chasing October" is a docu-comedy that chronicles one fan's crusade to take the Chicago Cubs to the World Series "by any means necessary." Director Matt Liston quits his job, gets all access to his favorite team, and rallies a city. Perhaps no other fan in the history of sports has gone to such an extreme. See Liston as he helps facilitate a trade, attempts to get a $20 million loan to help team payroll, and takes being a fan to a whole new level. This film is a hilarious must-see for all sports fans and for anyone who has ever chased a dream.
| Actor | Role |
|---|---|
| MMatt ListonSelf | Self |
| CChris KarnakSelf | Self |
 Faline EnglandSelf | Self |
| AAllison KarnakSelf | Self |
| RRay ListonSelf | Self |
| KKathie ListonSelf | Self |
| JJuanita SchoningSelf | Self |
| EEsta-Joy PetersSelf | Self |
| BBill MurphySelf | Self |
| SSusan Gayle WattsSelf | Self |
| SSteven Leslie HorowitzSelf | Self |
 Bill KurtisNarrator (voice) | Narrator (voice) |
| DDominic TocciNarrator (voice) | Narrator (voice) |
| JJ.V. MartinNarrator (voice) | Narrator (voice) |
| BBrandon LinvilleLetter Reader (voice) | Letter Reader (voice) |
| HHallie Faben ComfortLetter Reader (voice) | Letter Reader (voice) |
| NNate CallowayLetter Reader (voice) | Letter Reader (voice) |
| BBen BrimerLetter Reader (voice) | Letter Reader (voice) |
 Bernie MacSelf | Self |
| CChuck GuenoSelf | Self |
 Joe MantegnaSelf | Self |
| DDan RamSelf | Self |
 Larry KingSelf | Self |
| EErin SermeusSelf | Self |
 Gary SiniseSelf | Self |
| EErit YellenSelf | Self |
 Mike DitkaSelf | Self |
| MMary AlbrightSelf | Self |
 Dennis FranzSelf | Self |
| CCynthia SnyderSelf | Self |