The Best Holiday Movies Set In Chicago
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The windy city of Chicago is famous for its sports teams, world-class museums, and excellent shopping. It’s no wonder why the city remains a popular tourist hotspot. However, Chicago is also famous for something else – being the setting for numerous holiday films.
Perhaps it’s the city’s midwestern feel or the bitter, snowy winters that keeps inspiring screenwriters year after year to set their holiday tales within America’s third-largest city. While it may be called The Second City, Chicago is clearly the king of holiday movies.
Office Christmas Party (2016) – Stream On Paramount+
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In Office Christmas Party, a disastrous year for a company in downtown Chicago leads to threats of numerous layoffs and pay cuts. Desperate to keep the company’s spirits up, an employee puts together an elaborate Christmas party, even inviting the Chicago Bulls’ Jimmy Butler to make an appearance.
However, after hearing that the office is being shut down, all hell breaks loose and the party becomes debaucherous, destructive, and completely hilarious. The movie featured a talented cast including Jenifer Aniston, Jason Bateman, Kate McKinnon, Olivia Munn, and more.
A Bad Moms Christmas (2017) – Stream on Fubo TV
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Though shot completely in Atlanta, A Bad Moms Christmas is set in Chicago. The story follows up on the original film and centers on Mila Kunis, Kathryn Hahn, and Kristen Bell as they spend the holidays with their own moms (played by Susan Sarandon, Christine Baranski, and Cheryl Hines).
Fortunately, according to the Chicago Sun-Times, Kathryn Hahn, who attended Northwestern University, and Mila Kunis, who had spent many holidays in Chicago, helped guide the crew as to what the city would look like in the middle of December, leading to an authentic-looking Midwestern winter, despite being filmed in the South.
Surviving Christmas (2004) – Stream on Paramount+
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Some holiday films are poorly received but become more beloved with age…others, however, just remain poorly received. Surviving Christmas, starring Ben Affleck, Christina Applegate, and Catherine O’Hara, had great potential to be a holiday classic.
The film centers around a neurotic man (Affleck) who pays a family living in his childhood home to spend Christmas with him, hoping to use the opportunity to overcome childhood trauma. Critics and audiences weren’t impressed and the movie became a massive bomb at the box office. However, despite Surviving Christmas’ bad reputation, it’s still referenced by locals since it was based and filmed in the city’s neighborhood of Forest Glen.
Christmas Lost & Found (2018) – Stream on PlutoTV
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No city is safe from the endless array of cheesy made-for-TV Christmas movies, and Chicago has its own with Lifetime’s Christmas Lost & Found. In the film, Whitney, a high-strung busy New York City businesswoman returns home to Chicago for the first time in years.
Her grandmother gives her the family’s precious heirloom ornaments, but Whitney carelessly throws them away. Her grandmother then devises a scavenger hunt that will help Whitney find the missing ornaments, learn the meaning of Christmas…and of course, find a man.
The Princess Switch (2018) – Stream on Netflix
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After seeing the success Hallmark and Lifetime were having with cheesy Christmas films, Netflix decided to get in the game too. Their most notable entry is Vanessa Hudgens’ The Princess Switch, which stars the former High School Musical actress as Stacy, a baker in Chicago (who, of course, is recently single).
She and her baking partner win a chance to compete in a pastry competition in the Kingdom of Belgravia in Europe. Hoping to forget about her ex, Stacy agrees to go. However, she ends up looking identical to a wealthy royal who is dating Belgravia’s prince, and before long, holiday magic gets to work in creating mischief, love, and whacky antics that could only be found in a Christmas movie. Two sequels followed.
Christmas with the Kranks (2004) – Stream on Starz
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Based on Skipping Christmas, the popular novel by John Grisham, Christmas with the Kranks starred Tim Allen and Jamie Lee Curtis as two parents who decide to skip Christmas after discovering their daughter won’t be coming home for the holidays. The movie is set in a Chicago suburb but was actually filmed in a now-demolished studio backlot outside of Los Angeles.
In the film, however, the Kranks reside on Hemlock Street in Riverside, Illinois, a real Chicago suburb that sits directly next to the city, near Chicago’s Midway Airport. Despite being filmed just south of LA, the production did an excellent job of making it look like a midwestern winter. While the movie received lackluster reviews upon release, it’s since become loved for its great dialogue and holiday chaos, cementing it as a modern Christmas classic.
Christmas Vacation (1989) – Stream on HBO Max
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1989’s Christmas Vacation, the third film in the Vacation series, is a perennial favorite that continues to be watched religiously by fans more than 30 years after its release. The film follows the Griswold family in their Chicago suburb home as they host their cantankerous extended family for what’s supposed to be a joyous Christmas.
Naturally, as with all Christmas films worth their salt, everything goes wrong and Clark is pushed to the absolute edge of sanity. The movie is loaded with great lines and endless absurdity that many families can probably relate to during the holidays.
Planes, Trains, and Automobiles (1987) – Rent on Amazon Prime
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1987’s Planes, Trains, and Automobiles is a comedy classic that’s still loved today. It’s about two men in New York City (played by comedy legends Steve Martin and John Candy) who are desperate to make it back to Chicago in time for Thanksgiving.
However, after bad weather diverts thair plane to Kansas, the two try everything they can to get home, traversing three states via every mode of transportation from busses to cars, and even a milk truck. Planes, Trains, and Automobiles also stands as one of the few holiday movies that centers around Thanksgiving instead of Christmas.
Home Alone (1990) – Stream on Disney+
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The world has never quite been the same since Kevin McCalister was left home alone on the days leading up to Christmas back in 1990. As everyone knows, in Home Alone Kevin fights off the “Wet Bandits” using some fantastic one-liners and a few truly creative inventions using household objects ’90s technology.
The movie is based in the Chicago suburb of Winnetka and was actually filmed there. In fact, the “Home Alone House” has become a popular tourist spot (despite the fact that it’s a private residence) as tourists want to see if they can catch a glimpse of McCallisters inside.
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