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
Public Pools Open Next Week. Plus, Chicago’s New Women’s Sports Bar
Most of the city’s 77 public pools, 200 water features, and Chicago’s only inland beach are all opening next Friday. Plus, we’ve got more...
Red Line Weekend Detour and Ultimate Summer Guide
Red Line trains will be rerouted to elevated tracks for the third straight weekend due to maintenance work in the Loop subway. Executive...
Who's Running For Mayor? Plus, Bears Pick Hammond?!
Chicago’s mayoral election is nine months away. Last week, Illinois Comptroller Susana Mendoza became the first major candidate to make t...
Why Chicago Libraries Got It All. Plus, Are The Bears Still Ours?
Chicago is opening its 82nd public library branch in June, and loaning out books is just the tip of the iceberg when it comes to what the...
How the City Is Helping Chicagoans Buy Houses and Read More Books
Mayor Brandon Johnson and the Department of Housing are launching a new $21 million housing program to provide down payment and closing a...
City Buying Greyhound Station. Plus, Chicago’s Lesbian Business Directory
For almost two years, there have been questions about the future of Chicago’s downtown bus terminal. Flix, the parent company of Greyhoun...
What Happened in Springfield? Plus, Dreaming of Summer Break
What did lawmakers get done in Springfield? A $56 billion budget, a cellphone ban in schools, relief for those who lost SNAP benefits, an...
Your Guide to June 2026 in Chicago
June is officially summertime Chi in our world, so we’re going to help you make the most of it. Host Jacoby Cochran is joined by contribu...
School Board Hopefuls, Traffic Court Confusion, and Murakami Homers Again … And Again
This year, for the first time, Chicago will fully elect the 21-person school board. Candidates had to get their petitions in this week wi...
A Chicago Mayor and Pope Walk Into a Schlitz Bar…
Mayor Brandon Johnson is in Vatican City this week to meet Chicago’s very own Pope Leo XIV for the first time. The two are expected to di...