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
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...
Mayor Johnson Answers Your Toughest Questions
As Mayor Brandon Johnson prepares to make a big announcement about his “political future” on Sunday, Sept. 13, we visited City Hall for a...
Former Loretto Exec Finally In Court. Plus, Does Chicago Have an Alderman Problem?
Former Loretto Hospital COO Anosh Ahmed was finally in federal court this week, where he pleaded not guilty to defrauding the safety-net...
Washington Park Mass Shooting, Ye & North in Chicago, and Printers Row Lit Quiz
Today we are joined by contributors Jill Hopkins and Leigh Giangreco to discuss the tragic mass shooting in Washington Park over the week...
Why Are Chicago Judges Deporting More Kids? Plus, Sox Parking Scam
An immigration judge in Chicago ordered 6 children to be deported. We break down what children are facing in Chicago immigration courtroo...
Your Guide to September 2026 in Chicago
September in Chicago is going to see us outside, come storms or heatwaves. Between Mexican Independence Day celebrations, Fall Theater Se...
What’s In Mayor’s Latest Exec Order? Plus, Fall Exhibitions and Flavors
Last week, Mayor Brandon Johnson signed an executive order barring companies with a recent history of workplace discrimination from recei...