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:

1. Medium Cool (1969)
2. Cooley High (1975)
3. Stony Island (1978)
4. The Blues Brothers (1980)
5. Ferris Bueller's Day Off (1986)
6. The Fugitive (1993)
7. Return to Me (2000)
8. Chicago (2002)
9. Barbershop 2: Back in Business (2004)
10. The Weather Man (2005)
11. The Dark Knight (2008)
12. Widows (2018)

This episode originally aired on July 17, 2025.

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