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National Lampoon's Christmas Vacation
Photograph: Courtesy Warner Bros.

The 11 best holiday films set in Chicago, ranked

They may not be cinematic masterpieces, but these Chicago Christmas movies will warm your heart this holiday season.

Emma Krupp
Written by
Emma Krupp
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Ah, Christmas in Chicago. We may not have Rockefeller Center, or the Rockettes, or Central Park in the snow, but we sure do have a (surprisingly) long list of holiday movies that take place among our city's string light-bedecked streets. In honor of the holiday spirit, we've assembled a roster of the all-time best holiday movies set in Chicago for your viewing pleasure this winter.

First of all, some ground rules: This list is not exhaustive, especially insomuch as it does not include the overwhelming swell of Lifetime and Hallmark movies set in Chicago. That's not to say these movies don't have merit; rather, we simply don't have the stamina to wade through hours of Jingle Around the Clock, Christmas Lost and Found and their ilk. Second and perhaps more importantly: Understand that "best" is a descriptor used loosely here, more indicative of fond feelings than cinematic quality. Christmas movies are meant to bring warm and festive cheer, after all, not win awards! And hey, if you squint, that film studio set in Atlanta—or Toronto, or Vancouver—starts to look more and more like the Christmastime Chicago we know and love. Furnish a warm beverage, gaze up at the dazzling Chicago Christmas tree on your screen and settle in for a night of the best holiday movies set in Chicago.

RECOMMENDED: The best things to do during the holidays in Chicago 

The best holiday movies set in Chicago, ranked

Fred Claus (2007)
Photograph: Courtesy Warner Bros. Pictures

11. Fred Claus (2007)

Hey, remember Vince Vaughn? The Chicago-area native stars as Santa Claus' down-on-his-luck brother, a repo agent named Fred, in this almost universally panned (and weirdly star-studded) comedy. After winding up in jail, Fred must travel from Chicago to the North Pole to earn back his brother's bail money, where he makes mayhem among elves and eventually learns the true spirit of the season. Know this ahead of time: Fred Claus is a bad, frequently off-color movie, but if you have any kind of nostalgia for mid-budget late-2000s comedies, it's a tenable watch.

Where to stream: Available for rent on Amazon Prime, Google Play and YouTube

The Holidate (2020)
Photograph: Courtesy Netflix/Steve Dietl

10. The Holidate (2020)

The most recent entry on our list makes a limpid attempt at being a real "Chicago" movie, complete with a heroine raised in Logan Square, shots of glittering Michigan Avenue and a handful of local name-drops. Unfortunately, it also sucks. Centered around two lovelorn characters who decided to platonically date on major holidays, the plot is suffused with the kind of "men are from Mars, women are from Venus"-esque gender dynamics that typified rom-coms of the late 2000s, complete with a predictably pat conclusion just in time for Christmas. Still, Chicagoans will find plenty of satisfaction in calling out the movie's failings (at one point it displays a map depicting Logan Square somewhere in the interminable middle between Bridgeport and Beverly), and that brings its own kind of holiday cheer.

Where to stream: Netflix

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9. Christmas with the Kranks (2004)

Instead of paying for expensive Christmas light installations, empty-nesters Luther (holiday movie icon Tim Allen) and Nora Krank (Jamie Lee Curtis) eschew tradition and decide to blow their holiday budget on a cruise for the first time, a move that enrages their obsessive neighbors in the fringe suburb of Riverside, Illinois. Complicating matters, their daughter returns home for a spontaneous visit, requiring the Kranks to fabricate an elaborate holiday celebration in a matter of hours. Does this movie have a 5 percent score on Rotten Tomatoes? Yes, it does. Will we watch it anyway this season? Probably!

Where to stream: Hulu

A Bad Moms Christmas (2017)
Photograph: Courtesy STXfilms

8. A Bad Moms Christmas (2017)

You'd be forgiven for having missed this holiday sequel to the 2016 movie Bad Moms, starring Mila Kunis, Kristen Bell and Kathryn Hahn as the titular bad moms. Like its predecessor, it's set somewhere in the suburbs of Chicago, complete with massive and festively-decorated suburban homes—but this time, Christine Baranski, Cheryl Hines and Susan Sarandon make appearances as the bad (and overbearing) moms of the bad moms. The movie is about as over-the-top raunchy as most gal-pal comedies come, but you've gotta love Sarandon sashaying around as Hahn's freewheeling, cowboy hat-wearing mother.

Where to stream: Netflix

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Office Christmas Party (2016)
Photograph: Courtesy Paramount Pictures

7. Office Christmas Party (2016)

Office Christmas Party is the bawdy Chicago office comedy that no one really needed, with a plot revolving around the excesses of a bunch of tech employees (played by a coterie of A-listers that includes Jennifer Aniston, Olivia Munn, Jason Bateman and more) around the holidays. Even so, it's good for a few laughs in that sleazy Bateman comedy kind of way, plus some obligatorily classic Chicago shots. Might we suggest a double feature paired with A Bad Moms Christmas?

Where to stream: Available for rent on Amazon Prime

The Christmas Chronicles (2018)
Photograph: Courtesy Netflix/Michael Gibson

6. The Christmas Chronicles (2018)

Two siblings are teleported from Massachusetts to Chicago—with Santa and his sleigh in tow—after a Christmas Eve spying venture goes awry, where they scramble to save the holiday among aerial city shots and brief glimpses of CTA stations. The movie, though clearly shot in Canada, is sweet and family-friendly; plus, Kurt Russell makes a satisfyingly wry Santa Claus (Goldie Hawn, Russell's longtime partner, even makes a cameo as Mrs. Claus). Looking for more Christmas Chronicles? Netflix dropped a sequel in late November.

Where to stream: Netflix

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The Princess Switch (2018)
Photograph: Courtesy Netflix

5. The Princess Switch (2018)

Arguably the best addition to the Netflix royal Christmas movie cinematic universe—other entries include A Christmas Prince and A Christmas Prince: The Royal BabyThe Princess Switch plucks small-time baker Stacy DeNovo (Vanessa Hudgens) out of her humble Chicago life and transports her to a baking competition in the fictional kingdom of Belgravia, where she meets the identical-looking Lady Margaret Delacourt (also Vanessa Hudgens). Chaos, romance and princess-switching ensue. Regrettably, the film takes place in Chicago for all of two scenes—during which Stacy wanders among placeless streets and sports an embarassing "CHICAGO"-emblazoned hat—but it's a whole lot of fun nonetheless.

Where to stream: Netflix

4. Nothing Like the Holidays (2008)

Facing an impending divorce, a Puerto Rican family gathers in their longtime Humboldt Park home for what might be their final holiday together. Strong performances from actors like Alfred Molina and Elizabeth Peña bolster a tender-yet-saccharine plot—and unlike most of the movies on this list, Nothing Like the Holidays gets props for having actually been shot in Chicago, and largely in Humboldt Park, too. Keep an eye out for snow-covered glimpses of Paseo Boricua, the Humboldt Park Fieldhouse and other neighborhood mainstays.

Where to stream: Free on YouTube

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Happy Christmas (2014)
Photograph: Courtesy Magnolia Pictures

3. Happy Christmas (2014)

Even if you've never seen or heard of this movie before, it should come as little surprise that Chicago mumblecore king Joe Swanberg (of Easy fame) has tried his hand at a holiday version of the low-key genre. The resulting film stars Anna Kendrick as the reckless Jenny, who upends the life of her brother Jeff (Swanberg) when she comes to stay in his family's Chicago home during the holidays. Avoid if you're not into mumblecore slowness, but the simple story makes for a refreshing change of pace among the sometimes-trite roster of holiday films (and, like most of Swanberg's work, was shot wholly in Chicago).

Where to stream: Free on YouTube

National Lampoon’s Christmas Vacation (1989)
Photograph: Courtesy Warner Bros.

2. National Lampoon’s Christmas Vacation (1989)

The third installment in National Lampoon's Vacation series is a veritable Christmas classic, chronicling the misadventures of the Griswold family as they prepare for the holidays in the suburbs of Chicago. Chevy Chase has a memorably slapstick turn as overeager family man Clark Griswold, who spends much of the movie's runtime uprooting trees, sparking Christmas light-induced power outages and embarrassing his family in the pursuit of holiday bliss—an ode to hapless, holiday-loving dads in Chicago and beyond.

Where to stream: Available for rent on YouTube, iTunes, Google Play and Amazon Prime

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Home Alone (1990)
Photograph: Courtesy 20th Century Fox

1. Home Alone (1990)

Is it really the holiday season if you haven't watched Kevin McCallister (Macauley Culkin, of course) run amok in his family's sprawling Winnetka home, accidentally forsaken by his Paris-bound relatives? The John Hughes-penned comedy tops our list not only because of its enduring place in the Christmas film canon—you're liable to hear that iconic John Williams score even on FM Christmas radio—but also for its distinctly rewatchable qualities. Even if you've seen those Rube Goldberg machines a million times, or have grown misty-eyed at the touching Kevin-and-family reunion (sorry, spoiler alert!), the story still holds: and that, folks, is the true magic of Christmas movies.

Where to stream: Disney+

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