Whitney Kennison (Tiya Sircar), a New York City event producer, is traveling to Chicago to spend Christmas with her grandmother, Frances, after years of missing family events (Diane Ladd). Frances is overjoyed that her granddaughter, Whitney, has finally returned home for the holidays, and she decides to present her with the beloved Kennison family Christmas decorations. Grandma Frances, on the other hand, must design a fun Christmas scavenger hunt in order to remind Whitney what the holiday is all about after she accidentally tosses out the ornament box. Whitney is in a race against time as she reclaims the family ornaments, falls in love, and learns the lesson her Grandma Frances has to teach her.