Our Top 10 Valentine’s Day Chicago films

Valentine’s day is just around the corner and with the global pandemic, many couples are choosing to stream movies at home “and chill”.

There are many romantic movies filmed in the windy city and we’ve taken the time to compile a list of the top ten best romantic films set in Chicago that you can stream this weekend with your Valentine. 

10. My Best Friend’s Wedding isn’t your average romantic comedy. Julia Roberts plays Julianne Potter, who is determined to split her life-long best friend Michael (Dermot Mulrony) from his fiance Kimberly (Cameron Diaz) before they are wed.

Julianne had been desperately in love with Michael for decades, yet Kimberly, unaware of this fact, chose Julianne to be her maid of honor. Julianne is selfish and makes a ton of mistakes, but learns the true meaning of “love” when she realizes she must put her best friend’s happiness ahead of her own, no matter how much it hurts her.

Don’t despair, Julianne doesn’t stay heartbroken for long, love was right under her nose and she didn’t even know it! Every notable filming location is authentic from Chicago O’hare to Fourth Presbyterian Church, every scene was shot in Chicago. 

9. Stranger Than Fiction follows IRS auditor Harold Crick (Will Ferrell) as he comes to the realization that his life is being narrated by an author named Karen Eiffel (Emma Thompson). Romance sparks between Harold and an incredibly enchanting bakery owner named Ana Pascal (Maggie Gyllenhaal) when he is tasked to audit her business after she refused to pay a portion of her taxes.

Harold seeks aid from Professor Jules Hilbert (Dustin Hoffman) in his attempt to find the author who is narrating his life, in his own mind. In the meantime, he completely changes how he lives his life and becomes completely smitten with Ana. Having issues completing her book, Karen’s publisher sends Penny (Queen Latifa) to assist her in finding a way to kill off the main character, known to the audience as Harold. 

This quirky film doesn’t fit into the “rom-com” category per-se, but the sparks that fly between Harold and Ana are heartwarming, plus the film has an unexpected ending.

Keen eyes can definitely tell that Stranger Than Fiction was filmed on location in Chicago, including scenes in Professor Hilbert’s office within the lecture hall at the University of Illinois at Chicago. A perfect Valentine’s Day film.

8. The Big Sick is a true story loosely based on the lives of the husband and wife duo (Kumail Nanjiani, Emily V. Gordon) who wrote this screenplay together. Kumail Nanjiani took the starring role as Kumail who falls in love with Emily (Zoe Kazan) while they deal with being an interethnic couple who must adapt to each other’s cultural differences.

This romantic comedy takes a dramatic twist when Emily becomes sick from a mysterious illness. Kumail was then forced to reach out to her parents Beth (Holly Hunter) and Terry (Ray Romano). While this film is romantic and heartwarming, the comedy is on point.

There are several jokes that hit so well that you will laugh out loud. This film isn’t your run of the mill “rom-com,” it has more depth and sophistication that comes from an actual couple sharing true moments from their courtship, some of which are exceptionally funny.  Not only does The Big Sick take place in Chicago, it was also filmed in Chicago. 

7. My Big Fat Greek Wedding is set in “a normal middle class Chicago neighborhood”. This charming and wholesome Academy Award nominated movie, produced by Rita Wilson, Tom Hanks, and Gary Goetzman is based off of the one woman play, starring the endearing Nia Vardalos.

The movie stars Vardalos as the lead character Toula who is wooed by Ian Miller, played by John Corbett, who some might remember as the lovable small town DJ Chris on the popular TV show Northern Exposure.

Toula is disillusioned with her “role” in life, which was intended for her to marry a Greek man and have a ton of Greek babies and she instead finds herself falling in love with a non-Greek, who is totally willing to participate in all the celebrations and traditions associated with a traditional Greek wedding.

My Big Fat Greek Wedding takes place in a quiet Chicago neighborhood, and while some of the movie was filmed in Chicago, most of the movie was filmed in Toronto Canada. While the subject of weddings and marriage might be a little too serious for a Valentine’s Date Night, This film is funny, sweet and light. 

6. Love Jones is a 1990s time capsule where we are privy to witness the relationship between photographer Nina (Nia Long) and writer Darius (Larenz Tate) as they attempt to navigate their feelings for each other amidst obstacles like an ex-fiance, long distance (Chicago to New York), jealousy, and insecurity.

The two meet at a poetry slam and don’t get off on the right foot with each other, but after they bump into each other at a record store, the two become inseparable until Nina’s ex-fiance Marvin (Khalil Kain) swoops in and entices her to move to New York with him in order to attempt to reestablish their long term relationship.

Nina decides that wasn’t the right move for her, and moves back home to Chicago. We spend the rest of the movie in “will they or won’t they” suspense, hoping the two can find their way back to each other. Love Jones was filmed all over Grant Park as well as many other Chicago locations which gives the feeling that the city exists within its own starring role in the film. 

5. Southside With You follows the first date between future President Barack Obama (Parker Sawers) and future First Lady, Michelle Robinson (Tika Sumpter) in 1989 Chicago. While the film stars Sawers and Sumpter, the city of Chicago shares the spotlight with the two as it is featured as the beautiful backdrop to the very sweet, blossoming romance between Barack and Michelle.

If you fell in love with them during his presidency, you will fall in love with them all over again when you watch an interpretation of their earliest interactions. While the film’s pace is a little slow, it is well worth a watch and a perfect first date movie to watch on Valentine’s Day.

Throughout the film Michelle insists that it is “not a date” as Barack attempts to “wear her down” into admitting their obvious chemistry. Not only is this film a Valentine’s Day letter to the romance between Barack and Michelle, it is also a love letter to the city of Chicago, itself. 

4. Drinking Buddies showcases the Chicago “local beer scene” and filmmaker Joe Swanberg was intent to make sure viewers were well aware that not only does the film take place in Chicago, it was also filmed entirely within that very specific Chicago local beer scene.

Kate (Olivia Wilde) and Luke (Jake Johnson) work together at Chicago craft Brewery Revolution Brewing, and while they have undeniable chemistry, they each have their own significant others with Kate dating Cris (Ron Livingston) and Luke dates Jill (Anna Kendrick). Olivia Wilde is absolutely bewitching and the entire cast is delightful in their roles.

While the thought of people stepping out on their significant others (or vice versa) might not seem like the optimal Valentine’s Day date night movie, you will absolutely find yourself rooting for Luke and Kate to give in to their attractions and pursue a romance with each other.

This movie is almost the “anti-date” date night movie, as we watch for over an hour to find out if the two will succumb to their mutual affection or remain platonic Drinking Buddies.

Grab your hunny or your own drinking buddy, and a six-pack of one of Chicago’s myriad of available craft beers to choose from, and enjoy this witty and well written film! 

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3. While You Were Sleeping took the #3 spot in Our Top 10 Chicago Christmas films list and it’s such a great romantic comedy that we’re bringing it back for this list! Sandra Bullock plays the Chicago Transit Authority token collector, Lucy, who believes she has fallen in love with handsome commuter, Peter (Peter Gallagher), who is pushed off the platform and rescued by Lucy.

She accidentally sets off a comedic misunderstanding, which includes Peter’s entire family, when she mutters to herself, “I was gonna marry him”, which was overheard by a nurse. Of course, the real romance develops between Lucy and Peter’s brother Jack (Bill Pullman).

The city of Chicago is highlighted as a lead character of the film and the film was almost exclusively shot in Chicago.

The Chicago Transit Authority even awarded the movie special permission to shut down both Randolph and Wabash stations for daytime filming for four weekends, as well as The Sedgewick station for one day to film the scene where Lucy jumps down to the tracks to save Peter’s life. 

2. The Lake House was based on the South Korean film Il Mare and stars Keanu Reeves as Alex Wyler and Sandra Bullock as Kate. The two inhabit the same lake house on Maple Lake, located within the Maple lake Forest Preserve in Willow Springs, a suburb of Chicago, but 2 years apart. Due to some unexplained time paradox, the two are able to communicate with each other by writing letters to each other and leaving them in the same mailbox.

This movie is ridiculously romantic and we spend the entire movie desperately hoping there is some way for the two of them to find each other in the same time period. This is definitely one of the all time most Valentine’s Day movies and it was set in the Chicago area. 

1. Return to Me is one of the most romantic movies ever made. Amazing for Valentine’s Day. We’ve all heard the stories about relatives and loved ones of organ donors meeting up with their recipients, but in this film, it becomes a love story.

Bonnie Hunt directed this heartwarming tearjerker that follows heartbroken widower Bob Rueland (David Duchovny) who lost his beloved and beautiful wife in a tragic car accident who’s heart is donated to Grace Briggs (Minnie Driver) who was near death without the donated heart.

The two cross paths when Bob attempts to begin dating again and goes out on a blind date at Grace’s family’s restaurant. While the date didn’t go very well, he feels a connection to the waitress, who unbeknownst to him, now has the heart of his wife.

The two embark on an unusual romance. 2000 was a big year for making films in Chicago and this was one of them, of course the scenes in Rome, Italy were filmed in Italy. 

And a Bonus.

She’s Having A Baby Written and directed by the late John Hughes, this film is based loosely on Hughes’ life. Jake (Kevin Bacon) and Kristy Briggs (Elizabeth McGovern) have made the leap from high school sweethearts to newlyweds, but married life is not what Jake expected. While he fantasizes about a dream girl and envies the lifestyle of his single best friend (Alec Baldwin), Kristy is ready to have a baby. Sending Jake into panic mode until. You will laugh and cry. (There is one unforgettable emotional scene that made me realize long ago, what a truly gifted actor Kevin Bacon is.) Enjoy!

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Let us know in the comments, what’s your favorite Valentine’s Day movie set in Chicago? 


Joia DaVida reports on the entertainment business in both Chicago and Los Angeles.