13 Chicago Christmas Movies That’ll Transport You to the Windy City

Chicago is known for its state-of-the-art buildings and special deep-dish pizza, but it’s especially rewarding to see the Windy City come to life during Christmastime. Natives might be familiar with festive traditions, like the Magnificent Mile Lights Festival and the annual Tree Lighting Ceremony. But if you’re newer to Chi-Town, then allow us to introduce the best Chicago Christmas movies that’ll transport you to the beloved city and get you in the holiday spirit. Keep reading for the full list, from A Bad Moms Christmas to Home Alone. 

1. National Lampoon’s Christmas Vacation (1989) 

• Who’s in it: Chevy Chase, Beverly D'Angelo, Juliette Lewis
• Rating: PG-13

Determined to pull off the best family Christmas, Clark Griswold goes above and beyond to ensure that things go perfectly. However, he realizes that his efforts might’ve been in vain when he gets a few unexpected visitors. (We dare you to sit through the infamous turkey scene without laughing out loud.)

2. Christmas with the Kranks (2004) 

• Who’s in it: Tim Allen, Jamie Lee Curtis, Dan Aykroyd
• Rating: PG

After realizing how costly it is to celebrate Christmas, Luther and Nora Krank decide to skip the holiday altogether. But the neighbors aren’t too pleased about this. And to make matters even more complicated, their daughter announces on Christmas Eve that she’s returning home to celebrate with them. What could possibly go wrong?

3. The Christmas Chronicles (2018)

• Who’s in it: Kurt Russell, Darby Camp, Judah Lewis
• Rating: TV-PG

Siblings Kate and Teddy have one goal this Christmas: to capture the real Santa Claus on camera. But when their mission goes south, they teleport to the city of Chicago and discover that Christmas is in shambles. Together, the trio embarks on a wild adventure to save the holiday before it’s too late.

4. Happy Christmas (2014)

• Who’s in it: Anna Kendrick, Melanie Lynskey, Mark Webber
• Rating: R

Jenny, a 20-something party girl, decides to move in with her big brother and his family in Chicago. However, her presence causes quite a stir in the family’s quiet home. Expect some solid performances and plenty of smart humor.

5. Fred Claus (2007) 

• Who’s in it: Vince Vaughn, Paul Giamatti, John Michael Higgins
• Rating: PG

Fred Claus tells the story of Santa Claus’s wild and rebellious brother. Thanks to his many crimes, Santa must bail Fred out of trouble. And to pay off his debt, he’s sent to the North Pole to work in his brother's toy factory. This turns out to be counterproductive when he causes even more chaos for St. Nick.

6. A Bad Moms Christmas (2017) 

• Who’s in it: Mila Kunis, Kristen Bell, Kathryn Hahn
• Rating: R

This raunchy comedy follows a trio of suburban moms—Carla, Amy and Kiki—who struggle to create the perfect holiday for their families. But their stress levels reach an all-time high when their overbearing moms join the celebration. 

7. Holidate (2020)

• Who’s in it: Emma Roberts, Luke Bracey, Kristin Chenoweth
• Rating: TV-MA

Sloane, a single woman in her twenties, would rather not spend another Christmas being judged by her family. So, she devises a plan that involves getting an attractive guy to be her “holidate” (or platonic plus-one). Of course, things get complicated when they start to fall for each other. (Fair warning, this isn’t a fairytale Hallmark movie. Expect a host of R-rated jokes and raunchy scenes.)

8. Office Christmas Party (2016) 

• Cast: Jason Bateman, Olivia Munn, T.J. Miller
• Rating: R

When Carol, the CEO of Zenotek in Chicago, informs her brother, Clay, that his failing branch is closing, he enlists the help of his coworkers to throw the office party of the century. The goal? To impress a huge potential client that could potentially save the company.

9. Home Alone (1990)

• Cast: Macaulay Culkin, Joe Pesci, Daniel Stern, John Heard, Catherine O'Hara
• Rating: PG

When his family accidentally leaves him behind on the day of their flight to Paris, 8-year-old Kevin is thrilled to have his family’s home all to himself. His little paradise is interrupted by two dim-witted burglars who want to break into the house. And it’s up to him to protect his home with his unparalleled booby-trap skills.

10. Nothing Like the Holidays (2008)

• Who’s in it: John Leguizamo, Debra Messing, Freddy Rodriguez
• Rating: PG-13

Several members of the Rodriguez family are reuniting for a special Christmas gathering, but it’s only a matter of time before the drama starts to unfold. And to make matters worse, the family discovers that their beloved matriarch is planning to divorce her husband.

11. The Princess Switch (2018)

• Who’s in it: Vanessa Hudgens, Sam Palladio, Nick Sagar
• Rating: TV-G

In this modern-day The Parent Trap film, Hudgens plays both a talented baker named Stacy DeNovo and her royal doppelgänger, Margaret Delacourt. When the women discover that they look identical, they come up with a clever plan to trade places during the holidays.

12. Miss Christmas (2017)

• Who’s in it: Brooke D'Orsay, Marc Blucas
• Rating: TV-G

Everyone can count on Holly Khun, AKA "Miss Christmas," to find the perfect tree for Chicago's annual Radcliffe Tree lighting. But this year, when her tree gets damaged just ten days before the event, she becomes desperate to replace it. Lucky for her, she gets a letter from a young boy who promises his tree can do the job. 

Is it a classic Christmas movie? Maybe not. But this flick starring Lindsey Lohan as Cady Heron, who after being homeschooled for most of her life joins her peers in North Shore High School in a Chicago suburb, does have an iconic holiday scene. Namely when the clique of mean girls (aka “The Plastics”) perform a highly inappropriate, practically burlesque, performance of “Jingle Bell Rock”. A technical issue causes the music to stop, but thankfully Cady comes to the rescue and leads the rest of her crew to sing the song themselves while performing the dance routine.