20 Classic Movies to Help You Celebrate Chicagoland From Home

Want to explore all of the amazing things that Chicagoland has to offer, right from the comfort of your couch? Fire up a movie! 

From the city to the suburbs, the Chicago area has a rich connection with the silver screen. Some of Hollywood’s most legendary writers, directors, and actors have called Chicagoland home over the years, and our area has long been a popular shooting location for movies — from the earliest days of the silent film era all the way through to today. 

Many of the most beloved movies of all time shine the spotlight on unique locations across the Chicago area. From teen comedies, to pulse-pounding thrillers, to family-friendly favorites, here are 20 classic movies that showcase what makes Chicagoland special: 

  1. Baby’s Day Out. This wacky family comedy follows an infant on an unlikely adventure, including stops in the Lincoln Park Zoo and the Magnificent Mile.
  2. Ferris Bueller’s Day Off. A legendary teen comedy that’s entertaining for all ages, Ferris Bueller was filmed at locations around Chicagoland — including a modernist home in Highland Park, picturesque Glencoe Beach, the Art Institute of Chicago, and Wrigley Field.
  3. The Untouchables.This Oscar-winning crime epic tells the story of some of Chicago’s most famous Prohibition-era cops and robbers, and features stunning shots of Union Station among other local institutions.
  4. Sixteen Candles. Filmed around Skokie, Evanston, and Highland Park, this coming-of-age-story has been delighting audiences for generations. 
  5. Public Enemies. Based on true events, this immersive crime thriller recreates 1930s Chicagoland with style. Look out for the legendary Biograph Theater, and keep your eyes peeled for scenes shot in Aurora, Joliet, and other suburban locales.
  6. Southside With You. The Chicago Cultural Center, the Lakefront, and the Music Box Theatre all help stand in for Chicago in the ‘80s in this presidential love story. 
  7. The Blues Brothers.This soulful comedy features some of the most legendary performers of all time, from Jim Belushi to Aretha Franklin — as well as some iconic Chicagoland sights.
  8. North By Northwest. A thrilling and hilarious classic from master filmmaker Alfred Hitchcock, this jet-setting adventure hops from New York to South Dakota, with a particularly entertaining stop right here in Chicagoland. 
  9. Adventures in BabysittingFull of twists and turns, this 1987 comedy features a particularly thrilling sequence set on the Crain Communications Building, one of the highlights of the Chicago skyline. 
  10. The Dark Knight. Chicago stands in for fictional Gotham City in this dark and imaginative Batman film.
  11. The Fugitive. Wrongfully accused of a crime, Harrison Ford flees from the law — and the chase takes him through some famous Chicago-area locations, including the old Cook County Hospital building. 
  12. Home Alone. The stunning red brick Georgian home at the center of Home Alone still stands proudly in Winnetka, just north of Chicago. 
  13. High Fidelity. Adapted from a novel originally set in London, this movie made stars of John Cusack and Jack Black — as well as the city’s musically minded Wicker Park neighborhood. 
  14. The Company. The Joffrey Ballet is a Chicagoland institution, and this adult drama from director Robert Altman explores a day in the life of the world-famous dance troupe. 
  15. Stir of Echoes. In the mood for a chilling horror feature? This paranormal frightfest features Kevin Bacon and some of the city’s most intriguing architecture. 
  16. Barbershop.This hilarious ensemble comedy celebrates the community spirit that makes Chicago special, and features shooting locations from around the city. 
  17. My Best Friend’s Wedding. Looking for a romantic comedy? The Riverwalk, Comiskey Park, and Union Station all add a healthy dose of local color to this Julia Roberts classic.
  18. While You Were Sleeping. Some of the most important scenes of this romance are set at CTA stations around Chicagoland; many key scenes were also shot in suburban La Grange.
  19. Widows. This 2018 thriller features an all-star cast in a story about Chicago politics and the importance of family, with key scenes shot along Lake Shore Drive and in hotels, restaurants, and homes across the region. 
  20. When Harry Met Sally. While many of this rom-com’s most famous scenes take place in New York, Chicago is the movie’s heart and soul, with key scenes set at the University of Chicago in Hyde Park

Did we leave off any Chicago-set classics? What movies always make you think of Chicagoland? Are you an avid DVD collector, or more of a streaming fan? Be sure to let us know your thoughts on social media! 

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