Chicago has been the backdrop for several memorable holiday productions, and when it comes to Thanksgiving films, three titles consistently rise to the top. All are connected in one way or another to John Hughes, whose holiday storytelling shaped some of the most enduring seasonal movies of the last several decades. From road-trip chaos to courtroom drama to the classic struggle to get home, these films have secured their place in the Thanksgiving rotation, and I had the good fortune to work on all three.
Dutch — the underrated Thanksgiving film
The 1991 film Dutch is widely regarded by many film enthusiasts as an underrated Thanksgiving movie and a lesser-known companion to John Hughes’ more famous holiday title, Planes, Trains and Automobiles.
Written and produced by John Hughes and directed by Peter Faiman, the film follows Dutch Dooley (Ed O’Neill), a blue-collar Chicago contractor who offers to drive his girlfriend’s son, Doyle Standish (Ethan Embry), home from his Georgia boarding school for Thanksgiving. Their trip quickly derails into a series of mishaps, personality clashes, and unwanted detours before the inevitable shift toward mutual respect.
As with many Hughes projects, the film centers on a holiday deadline, a road trip, clashing personalities, and the gradual softening of emotional walls. Fans of Hughes’ work often view Dutch as a natural, though less polished, companion to his better-known holiday films.
While not as iconic as Planes, Trains and Automobiles, Dutch has earned a place on many Thanksgiving viewing lists thanks to the chemistry between its leads and its familiar John Hughes structure. For viewers looking beyond the usual holiday titles, Dutch remains a solid and often overlooked choice.
Miracle on 34th Street (1994)
The 1994 remake of Miracle on 34th Street is widely remembered as a Christmas movie, but the story actually opens with the Thanksgiving parade, making it a holiday crossover that bridges both seasons.
Starring Richard Attenborough, Mara Wilson, Dylan McDermott, and Elizabeth Perkins, the film follows the familiar story of a department-store Santa who may be the real Kris Kringle. Although the setting is Manhattan, Miracle on 34th Street was filmed primarily in Chicago, with only a few scenes shot in New York City.
The remake was produced during a period when several Hughes-affiliated projects were moving through Chicago, and although John Hughes didn’t direct this one, the film carries his imprint. The remake keeps the original film’s emphasis on faith, kindness, and belief in things unseen, while introducing a contemporary department-store rivalry and updated courtroom elements. It received a mixed critical response during its theatrical run but has since become a regular part of holiday programming.
Planes, Trains and Automobiles
John Hughes’ Planes, Trains and Automobiles (1987) remains the most widely recognized Thanksgiving movie ever made. The story begins in New York, where marketing executive Neal Page (Steve Martin) tries unsuccessfully to get home to Chicago for the holiday. What follows is a series of travel misfires with shower-curtain-ring salesman Del Griffith (John Candy), leading to one of the most enduring holiday comedies of the last four decades.
The filming was originally planned to take place entirely in and around Chicago, but when the weather didn’t provide the snow needed for the winter scenes, the production later moved to the Buffalo, New York area, where they could reliably capture the snowy sequences the film required.
The film blends comedy with emotional resonance, particularly in its final act, which has helped solidify its place as a Thanksgiving staple. Steve Martin and John Candy’s performances remain central to its enduring popularity, along with Hughes’ familiar themes of unexpected companionship and the desire to get home during the holidays.
Together, these films capture the travel, tension, humor, and heart that define Thanksgiving on screen. Their Chicago connections only add to their appeal for local audiences revisiting them each year.
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