Adventurous flight attendant Sydney’s plans for a tropical Christmas get delayed when she helps an unaccompanied minor get home to Chicago to her dad Jonathan, a handsome widower and investigative reporter. Faced with a shortage of out-going flights, Sydney is marooned for several days in the Windy City – once her home as a small girl — and tags along with Jonathan, his daughter, and their exuberantly festive family until she can find a connecting flight. Jonathan makes her a deal: he helps her chase down the story of how her late parents met, and she helps him to write the perfect Christmas story and keep his job, and along the way, sparks form between them.

Ethan, always the nice guy, wakes up in a new reality at Christmas. Initially, he is enthralled with his new life but soon realizes that it's not what he thought it would be.