Dutch Dooley, a rough-around-the-edges but well-meaning construction worker, is dating a wealthy woman named Natalie. When Natalie’s ex-husband leaves their son, Doyle, at boarding school for Thanksgiving, Dutch offers to bring him home. Doyle, a snobby and uptight pre-teen, resents Dutch and his blue-collar demeanor, and he initially refuses to leave with him. However, Dutch insists, and they begin a contentious journey from the school back to Chicago, fraught with numerous misadventures.

Throughout their road trip, the relationship between Dutch and Doyle shifts from outright hostility to reluctant camaraderie. Dutch employs unconventional methods to break through Doyle's highfalutin attitude, exposing him to life's grittier, more humorous side. As they traverse various towns, facing obstacles and unexpected situations, Doyle begins to see Dutch's genuine character and learns valuable life lessons. Both characters evolve, redefining their perspectives on family, responsibility, and acceptance. The trip becomes a transformative experience, reshaping the bond between Doyle and his mother, and offering Dutch a deeper connection with them both.