Are These the Best Chicago Movies of All Time?
Holidays are a great time to catch up on movies, from summer blockbusters to nostalgic classics. Earlier this year, the City Cast Chicago team set a lofty goal: To put together a list of the best Chicago movies of all time. Host Jacoby Cochran, executive producer Simone Alicea, Hey Chicago newsletter editor Emmi Mack, and social media manager Rick Homuth came up with 12 films deserving of this honor.
The List:
- Medium Cool (1969)
- Cooley High (1975)
- Stony Island (1978)
- The Blues Brothers (1980)
- Ferris Bueller's Day Off (1986)
- The Fugitive (1993)
- Return to Me (2000)
- Chicago (2002)
- Barbershop 2: Back in Business (2004)
- The Weather Man (2005)
- The Dark Knight (2008)
- Widows (2018)
This episode originally aired on July 17, 2025.
Good News: Lincoln Park Zoo lights, Brookfield Holiday Magic, Botanic Gardens Lightscape, Light of Christmas Drive thru at Sox Park
Want some more City Cast Chicago news? Then make sure to sign up for our Hey Chicago newsletter.
Follow us @citycastchicago
You can also text us or leave a voicemail at: 773 780-0246
Learn more about the sponsors of this Dec. 30 episode:
Become a member of City Cast Chicago.
Interested in advertising with City Cast? Find more info HERE
Subscribe To Our Newsletter
Stay connected to City Cast Chicago and get ready to join the local conversation.
Latest Episodes
Are Illinois’ County Jails in Crisis? Plus, Big Changes at MSI
Following a historic number of deaths in 2023, growing concerns over standards violations, and an investigation into ongoing unreporting,...
Where Are the Flock Cameras? Plus, Circus on the River
Today we’re talking about the rise of Flock automatic license plate reading cameras on college campuses, including at the University of I...
More Chicagoans Can’t Afford Food. Plus, Fall Storefront Theater
This year, Chicagoans have seen more grocery stores close on the South and West Sides, SNAP benefits stripped from tens of thousands of h...
Who Owns the Word 'Dope'? Plus, Chicago's Divviest Summer Ever
Today we’re talking about a local historian’s fascinating copyright battle, the rise of microcinemas and film clubs, and the ‘Divvyficati...
Who’s Building Guerrilla Bus Benches in Ukrainian Village? Plus, Fall in the Air
A neighborhood group is building bus benches in Ukrainian Village. But will the city remove the unauthorized infrastructure? Executive pr...
Who’s All Running For Mayor? Plus, Live From Printers Row
Mayor Brandon Johnson has officially announced his campaign for a second term in office. He enters alongside more than a dozen challenger...
City Expands Free Narcan. Plus, Best of Open House Chicago
Chicago’s Department of Public Health has worked diligently in recent years to expand access to free Naloxone/Narcan, the opioid overdose...
Could White Sox Really Leave Bridgeport? Plus, Mexican Independence Celebrations
Over the weekend, White Sox minority owner Justin Ishbia released stadium renderings that confirmed the team is considering a move to the...
Big Marsh Celebrates 10 Years. The Oprah Winfrey Show Celebrates 40.
As Big Marsh Park prepares to officially celebrate ten years on the South East side, the park has cut the ribbon on new bike features on...
Loop Restaurants Resurging, Chicago’s Climate Resilience, And Meet Us At Lit Fest
A 2026 study has ranked Chicago as the ‘World’s Most Climate Resilient’ major city. After a summer of torrential storms, tornado warnings...