Guides And Explainers

Experience the Magic: Chicago's Top Christmas Movies

Hello there, movie buffs! It's that time of the year again when we're all craving some festive cheer, and what better way to get into the spirit than by watching some fantastic...

Mara Ellison
Experience the Magic: Chicago's Top Christmas Movies

Experience the Magic: Chicago's Top Christmas Movies

Hello there, movie buffs! It's that time of the year again when we're all craving some festive cheer, and what better way to get into the spirit than by watching some fantastic Christmas movies set in the Windy City itself? So, grab your hot cocoa, get comfy, and let's dive into the best Chicago Christmas movies that'll make your holidays truly special. Guys, explore more in Guides And Explainers and chicago christmas movie.

Home Alone 2: Lost in New York (1992)

Kicking off our list is a classic that's become a holiday staple, Home Alone 2: Lost in New York. While the title might suggest otherwise, our beloved Kevin McCallister (Macaulay Culkin) indeed finds himself in the Windy City this time around. After mix-ups at the airport, Kevin ends up in Chicago, where he encounters an old adversary, the Wet Bandits, and saves the day in true Kevin fashion.

The movie showcases some iconic Chicago landmarks, such as the Art Institute of Chicago and the Chicago River. It's not just a hilarious Christmas comedy but also a fantastic love letter to the city. Plus, who can resist watching Kevin outsmart those bumbling bandits?

The Family Stone (2005)

Next up, we have a heartwarming family drama set during Christmas, The Family Stone. The story revolves around the Stone family, who live in Chicago's Lakeview neighborhood. When the family's eldest son brings his uptight girlfriend, Meredith (Sarah Jessica Parker), home for the holidays, chaos ensues as she struggles to fit in with the eccentric clan.

The movie offers a charming look into a typical Chicago family's Christmas celebrations, complete with snowball fights in Lincoln Park, cozying up by the fireplace in their brownstone, and even a visit to the Chicago Botanic Garden for some festive ice skating. It's a delightful watch that'll make you appreciate your own family, quirks and all.

While You Were Sleeping (1995)

Now, let's talk about a classic romantic comedy set in the Chicago Transit Authority (CTA) system – While You Were Sleeping. Lucy (Sandra Bullock), a lonely CTA token booth clerk, saves a man from being hit by a train and finds herself falling for his brother, Jack (Bill Pullman), after a case of mistaken identity.

The movie features some iconic Chicago locations, such as the CTA's elevated train system, the Shedd Aquarium, and even a cozy Christmas scene at Navy Pier. It's a feel-good movie that'll leave you with all the warm fuzzies, just like a classic Christmas rom-com should.

Planes, Trains and Automobiles (1987)

No list of Chicago Christmas movies would be complete without mentioning the hilarious and heartwarming Planes, Trains and Automobiles. After missing his flight, Neal Page (Steve Martin) finds himself on a disastrous road trip with shower ring salesman Del Griffith (John Candy) as they try to get back to Chicago in time for Thanksgiving.

While the movie isn't strictly about Christmas, it's filled with enough holiday cheer and classic Chicago scenes to warrant a spot on our list. From the Sears Tower (now Willis Tower) to the Chicago Skyway, this movie is a love letter to the city and a must-watch for anyone looking for a laugh this holiday season.

The Polar Express (2004)

Last but not least, we have an animated classic that might not be set entirely in Chicago, but features the city prominently – The Polar Express. Based on the popular children's book, this movie tells the story of a young boy who embarks on a magical adventure to the North Pole on Christmas Eve after boarding a mysterious train, the Polar Express.

The movie features some stunning animations of Chicago landmarks, such as the Chicago skyline and the Chicago & North Western Railway station. It's a delightful tale that's sure to captivate both kids and adults alike, making it the perfect family movie to watch during the holidays.

Wrapping Up

And there you have it, folks! Our list of the best Chicago Christmas movies that'll have you feeling festive in no time. So, whether you're in the mood for a laugh, a heartwarming drama, or an animated adventure, there's something for everyone on this list. So grab your favorite blanket, put on your favorite Christmas playlist, and get ready to experience the magic of the holidays in the Windy City.

Happy watching, and merry Christmas!

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