The Chicago Way Podcast
1) Chicago Way w/John Kass: O Holy Night
Chicago Way w/John Kass (12/24/25): Merry Christmas, Kyrie Elaison. John Kass reads ‘O Holy Night,’ his annual Christmas column. Blessings to all! Check out more from Kass at JohnKass...Show More
2) Chicago Way w/John Kass: A Christmas soup debate
Chicago Way w/John Kass (12/19/25): Greetings, good tidings, and cheer from John Kass & Jeff Carlin at The Chicago Way podcast. In this last collab before the traditional Christmas column reading...Show More
3) Chicago Way w/John Kass: A funeral for a friend and the city’s finances
Chicago Way w/John Kass (12/15/25): Austin Berg, Executive Director of the Chicago Policy Center at the Illinois Policy Institute, join John Kass & Jeff Carlin with a look at just how badly Mayor...Show More
4) Chicago Way w/John Kass: Why Pastor Brooks has zero confidence in Johnson
Chicago Way w/John Kass (12/08/25): Pastor Corey Brooks joins John Kass & Jeff Carlin to discuss how his fundraising effort to walk across the entire United States in a year is going, why he has ...Show More
5) Chicago Way w/John Kass: Retired police chief talks SAFE-T Act reforms, Reed case
Chicago Way w/John Kass (12/01/25): This week, retired Police Chief, Tom Weitzel (Riverside), joins John Kass & Jeff Carlin to talk about who is to blame for the release of veteran convict Lawren...Show More
6) Chicago Way w/John Kass: A Thanksgiving need for a warm cup of Midwestern common sense
Chicago Way w/John Kass (11/24/25): Thanksgiving is upon us, but senseless violence continues to plague the city, and John Kass wonders if the judges who let career violent criminals back on the stree...Show More
7) Chicago Way w/John Kass: Who can heal the basket case city?
Chicago Way w/John Kass (11/17/25): Paul Vallas is here to talk about his latest column- “Chicago’s Killing Fields”, Mayor Brandon Johnson’s awful policies, and the time he played th...Show More
8) Chicago Way w/John Kass: A recipe for compromise
Chicago Way w/John Kass (11/11/25): Chicago Ald. Ray Lopez (15th) is here to explain his amnesty plan to John Kass & Jeff Carlin and discuss why he’s not surprised Chuy Garcia used old-scho...Show More
9) Chicago Way w/John Kass: A smile to bring down a city
Chicago Way w/John Kass (11/03/25): Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, joins John Kass and Jeff Carlin this week to discuss what ...Show More
10) Chicago Way w/John Kass: Revolutionary times
Chicago Way w/John Kass (10/28/25): This week, John Kass & Jeff Carlin wax philosophically about how the U.S. found itself in revolutionary times and where do we go from here. Plus, Kasso wonders...Show More