The 11 best holiday films set in Chicago, ranked

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: Hulu, Disney+

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

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: Prime, Hulu, Disney+, Philo, Sling TV

The Chicago suburbs are a breeding ground for bad moms, from moms who can’t seem to remember how many kids they have while rushing to catch a flight to the lusty lushes of 2016’s Bad Moms. But bad moms beget bad moms, as this holiday-themed sequel to the aforementioned women-behaving-badly comedy reminds. Christine Baranski, Cheryl Hines and Susan Sarandon are the mothers of, respectively, Mila Kunis, Kristen Bell and Kathryn Hahn, who show up weeks early to Christmas and ignite a generational battle of wills. No one really needed an expansion of the Bad Moms Cinematic Universe, but Sarandon’s performance, as a much-too-free spirit in a leather jacket and cowboy hat, sparks a certain joy.   

Where to stream: Netflix

Yes, it’s the seasonal trope from every workplace sitcom, stretched to feature length. Jason Bateman plays yet another ‘strait-laced and miserable’ guy, in this case the middle manager at a Chicago tech company who must help throw the holiday rager of a lifetime in order to land a big client and save the branch from closing. The plot gets even more convoluted, but no matter: the film’s marginal success relies on gung-ho performances from its ensemble cast of omnipresent comics, including Kate McKinnon, Vanessa Bayer, Rob Corddry, Sam Richardson, Randall Park and the now-canceled TJ Miller. And when the action leaves the office, you get your fill of Second City scenery, including a climatic set piece involving the Bataan-Corregidor Memorial Bridge.

Where to stream: Hulu

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

Arguably the best addition to the Netflix royal Christmas movie cinematic universe—other entries include A Christmas Prince and A Christmas Prince: The Royal Baby—The 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

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: Starz, Hulu, Prime, YouTube, Roku, Philo, VIX

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: AMC+, Paramount+, Prime, Philo, Sling TV, Roku, YouTube TV

There is no vacation in the third instalment of the Vacation franchise. Instead, the beleaguered Griswold clan opts to spend the holidays at home in suburban Chicago, which is probably a good idea given how things go whenever they decide to leave Illinois. Of course, that doesn’t mean overzealous patriarch Clark Griswold (Chevy Chase) can’t find a way to make things more difficult than they need to be. His light display causes a city-wide power outage. He electrocutes a cat. He falls off several roofs. He eventually kidnaps his boss and demands a Christmas bonus. Made by future Home Alone duo of writer John Hughes and director Chris Columbus, there’s a sentimental streak running through all the disaster, but for those who like their holiday schmaltz delivered with a kick to the ’nads, it’s a classic.  

Where to stream: Hulu, Max, Disney+, Roku, YouTube, YouTube TV, Sling TV, Prime

It’s technically set in the suburb of Winnetka, the next town over from Northbrook, where John Hughes, who wrote the script, grew up. But c’mon: what other movie could possibly top this list? A box office smash upon release, it’s endured as a yearly must-watch for its ability to appeal to basically every demographic that could possibly occupy the couch during the holidays. At its core, though, Home Alone’s legacy is as the ultimate example of little-kid wish fulfilment. Left behind on a family vacation, young Kevin McCallister (Macaulay Culkin, the coolest ten-year-old of the early ’90s) eats huge bowls of ice cream, rifles through his older brother’s stuff, pranks the pizza delivery guy – and, of course, defends his massive house against a pair of burglars. Yeah, its ultimate message is about how we all need family, even when we think we don’t, but what keeps kids and adults coming back is Joe Pesci and Daniel Stern getting smacked in the face with paint cans. And also the hilarious John Candy cameo.

Where to stream: Disney+, Sling TV