While You Were Sleeping
Being a romantic comedy While You Were Sleeping seems unconventional for this list, but it takes place in Chicago giving it double points. This movie is chocked full of what makes the holidays great: monologuing, eavesdropping, and miscommunication.
Christmas is a time for family. When your loved one is in a coma. Adopt a complete stranger who says that she knows him intimately. From Lucy’s perspective as long as you keep lying it will all work itself out in the end. All you’ll be engaged twice without showing any actual romantic gestures towards anybody.