There are many lists of “best” Chicago Christmas films. And what’s funny is that some of the same movies show up in “worst of” Chicago Christmas films lists, too.
We’ll note where that is true and it’s also worth mentioning that among a certain subset of Chicago moviegoers, watching terrible Christmas movies ironically is still considered a fun holiday pastime, but you may require a high threshold for pain when doing so.
Some of these movies epically fail in terms of being actually SHOT in Chicago, so those titles are ripe for some special attention in the authenticity department.
This is probably the best cautionary holiday comedy ever. Watching Chevy Chase make what the Brits refer to as a “pig’s breakfast” out of the Christmas holiday is both funny and uncomfortable to watch if you have ever personally experienced the level of holiday obsession some family members succumb to in the winter months.
Set in suburban Chicago and shot between Colorado and California, Chevy Chase isn’t the only reason to try this one–watch for fun performances by Beverly D’Angelo, and Juliette Lewis.
If you haven’t seen a National Lampoon movie before, expect silliness and plenty of slapstick. The standout physical comedy moment in this movie is when Chevy Chase attempts to create the world’s most outrageous outdoor holiday lighting scheme.
You knew Home Alone would wind up on this list. For a start, it’s made by the Chicagoland filmmaker John Hughes, stars Catherine O’Hara, Joe Pesci, Daniel Stern, and of course Macaulay Culkin, who all went on to enjoy a high level of attention thanks to this film.
Home Alone is a story that really needs no explanation, though describing it to the uninitiated as a “funny holiday home invasion movie set in Chicago” does NOT really sell the film on its merits. Don’t miss John Candy in a great supporting role and LOTS of Chicago for a change. Here’s one Chicago Christmas movie NOT shot in Toronto!
Funnier still, this movie takes that notion and turns it inside out–the scenes that are supposed to be in France were actually shot at Chicago’s O’Hare airport. You can always count on John Hughes to show more of the 312 than others.
Set on Christmas Day, Peter Gallagher is saved by Sandra Bullock after he is pushed off the El onto the train tracks; Bullock plays a Chicago Transit Authority employee whose quick action entangles her in a sort of mistaken identity relationship comedy. The real Chicago is the star of many scenes in While You Were Sleeping, filmed in part at Northwestern Memorial Hospital in Chicago as well as scenes set in nearby La Grange. This is described by some viewers as a good old-fashioned rom-com that just happens to be set on Christmas Day, it’s definitely presented as a feel-good movie and may provide some good contrast to other holiday titles that have more snark to them, such as…
It may not be a Christmas movie in the same spirit as Christmas Vacation, but this Lindsey Lohan vehicle has some key scenes set at Christmas…it could be argued in the same breath that Mel Gibson and Danny Glover were in a Christmas movie because the climactic fight scene between Gibson and Gary Busey happens at holiday time.
No matter, this movie has holiday scenes and is set in a Chicago suburb. Co-starring Rachael McAdams, Lacey Chabert, and Amanda Seyfried, this high-school comedy has a couple of fairly WTF moments where people depicted as high schoolers are shown doing something that other reviewers describe as burlesque or “scantily clad” performances to the tune of Jingle Bell Rock.
To add insult to inappropriateness, this Chicago movie was shot in Canada.
For better or worse, the original Bad Moms was released in 2016, starring Mila Kunis, Kristen Bell, and Kathryn Hahn. This trio is back for more Chicago misadventures in this holiday cash-in sequel which includes one character giving Santa Claus a lap dance.
You have to keep Christmas classy, after all. More of a series of setpieces than something with an actual plot, you might hang on to watch Susan Sarandon; while you wait, try to figure out where in Chicago this movie was shot–chances are good you won’t find much as this was shot in Atlanta, Georgia for the most part.
Jamie Lee Curtis tends to class up anything she is in, and this slapstick holiday comedy also features a Chicago favorite–Blues Brother Dan Ackroyd shows up as a mouthy neighbor. And if you don’t read Tim Allen’s Twitter account, you may actually be able to ironically enjoy his turn in Christmas With The Kranks, which is one of those holiday comedies where “the family must unite to save Christmas”.
The real fun in this might be trying to reconcile the movie being set in a Chicago suburb while actually shot near Los Angeles, California. Can you hear the derision of those living in the 312? Christmas in Chicago never knew blue skies like the ones in this movie!
This one shows up in best-of and worst-of Christmas lists, with other reviewers list this movie as “phony” and a “face-plant”. Watch at your own risk!
Other reviewers have labeled Surviving Christmas as “the king of the Chicago Christmas movie tire fires” which is pretty much a recipe for success if you are interested in playing holiday drinking games with your holiday viewing.
“Best” in this case might mean “best/worst” if you aren’t prepared for a black comedy featuring Ben Affleck who hires a family to pretend to have a happy Christmas with him in his former childhood home.
Reasons to hang on for this one include watching the late, great James Gandolfini and SCTV alum Catherine O’Hara, whose career went far beyond those humble SCTV origins…this one might have just been a paycheck for all involved but if your idea of a good holiday movie is one you can snark on Mystery Science Theater 3000-style, you could do a LOT worse than Surviving Christmas.
Kurt Russell has played many iconic characters; Snake Plissken from Escape From New York, Jack Burton in Big Trouble In Little China…and he also plays Santa Claus alongside Judah Lewis and Darby Camp, who cause Russel’s Santa to crash his sleigh on Lakeshore Drive.
The rest of this movie is about finding Santa’s lost presents and magic hat from the crash…yes, this is another “we MUST SAVE CHRISTMAS” story, so buckle up that as well as for a movie that is Chicago-literate, but actually shot in Canada.
Russell actually gets high marks for his on-screen Santa from multiple reviewers and his spouse Goldie Hawn shows up as Mrs. Claus, making this even more heartwarming. This gets higher marks than our next entry, Fred Claus, for overall movie quality, but it’s a shame that the inferior (to some) Fred Claus goes for more on-location authenticity.
Some could argue that on the silver screen, Canada could be considered a suburb of Chicago since it stands in for the Windy City so much.
The film above, The Christmas Chronicles, features Santa, but never mentions his grouchy older brother, who we get to meet in Fred Claus. Vince Vaughn plays the lead as Santa’s older sibling who, among other things, gets arrested for robbing street Santa Clauses. It’s up to Santa, played by Paul Giamatti, to save the day and put everything right. This one gets complaints for being a bit flat, but you can get some good looks at Michigan Avenue. For some, it’s a bit of sport to watch Paul Giamatti in this movie knowing his turn in Sideways was only three years or so prior.