5 Classic Movies That Make Us Want to Hop on a Flight to the Windy City
We never really need an excuse to take a trip to the Windy City. Just the thought of a deep dish slice from Giordano’s or a few hours of shoe shopping in Ikram is well worth the price of airfare alone. But there are a handful of classic films that capture the city's spirit so perfectly, we’re practically digging out our weekend bags by the time the credits roll.
From Ferris Bueller's epic parade performance on Dearborn Street to My Best Friend’s Wedding’s tearjerker boat scene on the Chicago River, we’re looking back on some of our all-time favorite films that are unofficial love letters to the best of the Midwest. Because really, who hasn’t secretly wanted to run through O’Hare Airport like the McCallisters in Home Alone?
My Best Friend’s Wedding (1997)
This romcom is full of Windy City love, as Julianne (Julia Roberts) tries to sabotage the impending nuptials of her BFF Michael (Dermot Mulroney) and his fiancé Kimmy (Cameron Diaz), a student at the University of Chicago. Many of the movie’s most memorable moments span the city, like the White Sox game with the boys at the old Comiskey Park and the car chase to Union Station terminal where Julianne finds a heartbroken Michael. Our fave? The heartbreaking boat scene on the Chicago River that showcases some of the city’s most magical views.
Ferris Bueller’s Day Off (1986)
How should a mischievous high schooler (Matthew Broderick) spend a day playing hookie? Running around one of the best cities in the world, of course, which makes sense since writer and director John Hughes lived most of his life in the Windy City. On Bueller’s hit list: the Art Institute of Chicago, Sears Tower, and Wrigley Field, among others. And who could forget his rousing rendition of “Danke Schoen” in the street parade.
The Oscar-winning film, led by Catherine Zeta-Jones, Renee Zellweger, and Richard Gere, brought the famed Broadway musical to the masses, but with a renewed razzle dazzle. Basking in the glow of the city’s glamorous 1920s nightlife, the movie serves up sex, corruption, murder, and pretty much the best jazz hands we've ever seen.
Home Alone (1990)
This family fave gives us the warm fuzzies even when it’s not Christmas time. Set in the suburbs of Chi-Town, Home Alone captures Midwestern charm at its best—picturesque houses, snowy front yards, and general stores with clerks named Herb and Jimmy. And even if there is a slight burglary problem, you always know that your neighbor has your back.
Wicker Park (2004)
The actual Wicker Park, which sits in Chicago’s West Side District, is paramount to the plot of this twisty thriller that stars Josh Hartnett as a city slicker searching for his missing lover (Diane Kruger). Rose Byrne steals the show with her turn as the deranged former neighbor with a bit of a stalking problem, but we re-watch it for the cinematic shots of the cast walking around the park in the snow.