Sydney, an adventurous flight attendant, finds her tropical Christmas plans disrupted when she assists an unaccompanied minor in reaching her father, Jonathan, in Chicago. Jonathan, a charming widower and investigative journalist, welcomes Sydney into his life. With limited flights available, Sydney is stranded for several days in the city where she once lived as a child. During her stay, she joins Jonathan, his daughter, and their lively family in their festive celebrations. Jonathan proposes a deal: he will help Sydney uncover the story of how her late parents met, while she assists him in crafting the perfect Christmas article to secure his job. As they collaborate, a romantic connection begins to blossom between them.