If you are a citizen of earth you’ve probably noticed how many movies are set in Chicago. Or, if you’re like me you don’t fully realize it until you live here and start noticing location after location that has you feeling like you live in a straight up rom-com or action flick. And silly me thought New York was the mega star of the big screen. Technically it is but Chicago is close at numero très following Los Angeles, which isn’t too shabby.
So, if your curiosity has been peaked by this cinematic city, then let’s dive deeper into some of its top moments on the big screen!
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While You Were Sleeping– The adorable Christmas romantic comedy starring Sandra Bullock, Bill Pullman, and that guy from Center Stage with the great eyebrows (note to self: Google eyebrow guy’s name). The trains are front and center in this one, specifically Randolph-Wabash El Station where Sandra’s character, Lucy, works and falls for the classy businessman (eyebrow guy) and eventually saves his life. Later, Lake Point Tower and Lady of Mount Carmel Church are featured as well as Emmanuel Episcopal Church. This movie highlights the warmth and familial beauty of Chicago that aren’t readily seen by an initial glance. Who said big cities can’t be homey?
My Best Friend’s Wedding– A more classic Julia Robert’s tale there was not…okay except Pretty Woman. But Pretty Woman lacks Chicago which is the heart of this film as its beautiful backdrop for love and love lost. O’Hare Airport is the memorable moment of Michael and Jules’ classic movie airport reunion.
From there, Fourth Presbyterian Church on E Chestnut St is where the rehearsal and the wedding were filmed. The Chicago Hilton is seen in the film as well as the Drake Hotel. The Chicago Union Station is in my opinion the most memorable as Jules chases after Michael, trying to undo the damage she’s done. Julia may not have gotten the guy in this one but Chicago sure had its moment of glory.
The Vow– This is an emotional romantic drama based on a true story of a woman who lost her memory and a husband who woos her for a second time into loving him. The wife played by Rachel McAdams is an artist…or she was before she lost her memory. It’s neat to see the artsy side of Chicago for those who may not march to that beat. The film shoots at Southlake Regional Healthcare, the iconic Millennium Park, The Roastery Coffee House, and Casa Loma. The tear-jerking moments are made worth it by the great Chicago sights and happy ending of course!
Divergent– To see Chicago in a post-apocalyptic, dystopian future is haunting yet still beautiful. Divergent is full of thrills and plenty of action with the trains of Chicago, Navy Pier’s Centennial Wheel, Pioneer Court, and the old Chicago Defender building still making their mark. Even if covered in a little rust and overgrown vines, they still fit the iconic bill. The Dauntless faction must jump from the trains as part of their fearless way of life. The grinding of metal cars against the steel rails is an unmistakable sound that follows you throughout the movie and, in real life, plays like the city’s very own soundtrack.
Never Been Kissed- Drew Barrymore fans know by heart that Josie Grossy’s place of work is Chicago…and no, she’s not Josie Grossy anymore! In this timeless comedy, we have Chicago Avenue on the Brown Line CTA stop featured. Also, Josie’s office interior and job scenes were filmed in Chicago. If you need some love maybe Chicago’s where it’s at? Or at least in the ever-loveable Never Been Kissed.
The Fugitive- Countless spots all over Chicago are featured in this iconic Harrison Ford film where he’s wrongly accused of murdering his wife. He must find the real killer as he’s being hunt down by an expert U.S. Marshall. No biggie for Harrison. The Chicago Hilton is featured at the end of the movie and, apparently, has also hosted four of the U.S. Presidents since opening. That’s hot.
Adventures in Babysitting- One of my personal childhood favorites of babysitting gone oh so very wrong as Elizabeth Shue, Chris Parker, takes a group of kids downtown to rescue a runaway friend with car-jacking rings, singing the blues, and skyscraper danger in between. The Michigan Avenue Tower is where the parents’ work party is held and superimposed into several shots.
The Dan Ryan Expressway is where the tire of the old station wagon blows, specifically between Monroe and Madison. The bus station exterior 20 E. Randolph Street is where they (spoiler) at last pick up Brenda in the end. The interior for the Silver Dollar Room/Fitzgerald’s Night Club is on Roosevelt Road where they can’t leave without singing the blues. This late 80’s flick shines as it warns of Chicago crime in, like, the most entertaining way ever.
Home Alone & Home Alone 2 Lost in New York– For the all-time most famous Chicago movie ever (I mean there’s no contest, right?) we have the Home Alone 90’s masterpieces. Winnetka, the suburb of Chicago, 671 Lincoln Avenue to be exact, is the address of the picturesque McCallister home. I don’t know about you, but this was the fanciest house my seven-year-old eyes had ever seen! And the fictional McCallister home—looking unchanged from the exterior—is still a hugely popular tourist attraction to this day.
Evidently, Covid lockdowns added to its tourist numbers as bored city dwellers flocked to Kevin’s abode (to the neighboring residents’ chagrin). This house bears a forever warm place in our hearts as the home Kevin so brilliantly defended and if nothing else, Chicago will remain on the map because of it.
And last but not least, the McCallister’s reunion in the enormous hotel room at the end of Home Alone 2 was actually filmed at the Conrad Hilton Suite in Chicago.
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And there we have just a drop in the bucket of some of Chicago’s most iconic movie set magic. Check out these links for some awesome Chicago Film Tours and make some movie magic of your own!