After years of skipping family celebrations, Whitney Kennison (played by Tiya Sircar), a New York City event planner, heads to Chicago to celebrate Christmas with her Grandma Frances (portrayed by Diane Ladd). Thrilled to have her granddaughter home for the festive season, Frances decides to pass down the cherished Kennison family Christmas ornaments to Whitney. However, when Whitney accidentally discards the box containing the ornaments, Grandma Frances cleverly organizes a delightful Christmas scavenger hunt to teach Whitney the true spirit of the holiday. As Whitney races to recover the family treasures, she also discovers romance and absorbs the valuable lesson her grandmother wishes to impart.