When ambitious freelance reporter Avery Clark returns to Chicago to spend Christmas with her mom and new stepdad, she's hoping for a little holiday downtime before her next assignment. Instead, she lands a feel-good story profiling Darlene Donnelly, a beloved Chicago Bears superfan about to celebrate an incredible milestone: attending her 500th game. There's just one catch: Avery knows next to nothing about football or Chicago. Enter Darlene's handsome grandson Matt, a Chicago firefighter and die-hard Bears fan who, with a little gentle nudging from Darlene, agrees to show Avery what being a part of Bears Nation is all about.

Alan built a castle in rural Illinois with his late love Adrianne. Facing life alone, he revisits their fantasy through musical reenactments transporting him to the world they shared.