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The Chicago Way

WGN Plus
Chicago
Brandon Johnson
Donald Trump
Chicago Teachers Union
Nikki Haley
Kim Fox
WGN Radio
Crime
Florida's Voice
Corporate Media
President Joe Biden
Crime In Chicago
Politics
Democratic Party
Venezuela
The Snowflakes' Revolt
Englewood
Disinvestment
Vladimir Putin
Tucker Carlson

Mild mannered Chicago Tribune columnist John Kass and WGN Radio's Jeff Carlin explore the week in news, politics and other thngs done the Chicago Way in this WGN Plus podcast from WGN Radio in Chicago.

PublishesWeeklyEpisodes104Founded10 years ago
Number of ListenersCategory
News

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Artwork for The Chicago Way

Latest Episodes

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 Zohran Mamdani’s role as a leader of the modern De... more

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 if New York is ready for what it’s voting for?

Check... more

Chicago Way w/John Kass (10/20/25): RealClear Politics’ Tom Bevan is here with a post-op on what impact the “No Kings” rallies (Chicago’s rally featured one of Illinois’ top gamblers -Gov. JB Pritzker (D), for whom Tom has a some choice words) will h... more

Chicago Way w/John Kass (10/13/25): This week, Garry McCarthy – former Chicago Police Department (CPD) Superintendent and current Chief of Police for Willow Springs, IL- joins John Kass and Jeff Carlin to discuss a disturbing dispatch call involving ... more

Key Facts

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Find out how many people listen to this podcast per episode and each month.

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Recent Guests

Tom Bevan
Co-founder and president of RealClear Politics
RealClear Politics
Episode: Chicago Way w/John Kass: ‘No Kings’ rallies and Pritzker’s gambling habits
James R. Brown
Retired Cook County Circuit Court judge
Cook County Court
Episode: Chicago Way w/John Kass: A retired judge on how a bad apple can spoil the bunch
Ted Dabrowski
Republican candidate for Governor of Illinois and founder of wirepoints.org
wirepoints.org
Episode: Chicago Way w/John Kass: Illinois voters have a clear choice for their future
Robert Milan
Former Cook County prosecutor
Episode: Chicago Way w/John Kass: Over 50 shot this weekend, but we don’t need help
Joe Abram
A father sharing his story about the tragic death of his daughter
Episode: Chicago Way w/John Kass: When IL Dems play Russian roulette with our children
Brendan Reilly
Alderman of Chicago
City of Chicago
Episode: Chicago Way w/John Kass: Ald. Reilly leading the way for ‘closet moderates’ against Preckwinkle
Ray Lopez
Alderman of the 15th Ward of Chicago, known for his forthrightness in city politics
Episode: Chicago Way w/John Kass: Dead people voting, flooded basements, and The Nice Man
James Banakis
Chicago restaurateur and writer
johnkassnews.com
Episode: Chicago Way w/John Kass: Business as usual means someone else’s hand in you pocket
Salvatore Camarda
Second-generation butcher and co-owner of Joseph's Finest Meats
Joseph's Finest Meats
Episode: Chicago Way w/John Kass: Straight from the butcher’s mouth

Hosts

John Kass
Mild mannered columnist and editor known for his thought-provoking commentary on Chicago politics and culture.
Jeff Carlin
Executive producer with experience in radio production and a strong presence in Chicago media.

Reviews

4.7 out of 5 stars from 1.2k ratings
  • Go Chicago Way

    We need more podcast-you make in packed-for the clueless people!!!

    Apple Podcasts
    5
    Natural News
    United States2 months ago
  • Refreshing in today’s climate

    I stared with John Kass when he wrote for the Tribune. Truly great journalism that is sadly lost in today’s click bait, easy answers social media method of delivering news. I’m glad to still be able to catch his thought provoking content on this podcast. Keep it up John.

    Apple Podcasts
    5
    Fan419
    United States3 months ago
  • Old and washed up

    John Kass talks about nothing important.

    Apple Podcasts
    1
    Southsidewhitesoxfan
    United States7 months ago
  • The best!

    Jk knows where the bodies are still walking!

    Apple Podcasts
    5
    JAWtree
    United States9 months ago
  • Uhh you know

    John’s brother is so knowledgeable uhh you know every 10 seconds

    And umm uh you know

    Apple Podcasts
    4
    Fardelsbear
    United States9 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Feedback indicates that despite political differences, the podcast remains a valuable platform for diverse opinions and local engagement.
Listeners appreciate the thought-provoking nature of the content, praising John Kass for his journalistic integrity.
Many find the mix of personal stories with political commentary engaging and relatable.
There are mixed feelings about the direction of recent episodes, with some long-time fans noting a decline in focus on core political issues.

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Talking Points

Recent interactions between the hosts and their guests.

Chicago Way w/John Kass: Revolutionary times
Q: How will that affect the presidential race of 2028?
I think there are a couple different scenarios that play out.
Chicago Way w/John Kass: Revolutionary times
Q: Jeff, are we living in revolutionary times?
Yes, we are beyond the pale on that now; everything seems to be compressed more.
Chicago Way w/John Kass: Illinois voters have a clear choice for their future
Q: How do you deal with the Combine cheerleaders of the Chicago Tribune?
Dabrowski acknowledges that he won't convert certain media figures, but he sees an opportunity with more reasoned media engagement.
Chicago Way w/John Kass: Illinois voters have a clear choice for their future
Q: What's your instant reaction, you know, instant polling? What do you feel? Do you feel different?
Dabrowski reflects on the dissatisfaction of many Illinoisans and indicates that there is an opening for change in the state politics.
Chicago Way w/John Kass: Over 50 shot this weekend, but we don’t need help
Q: How have you seen violence interrupting programs affect the situation?
Some violence interrupters have impressive intentions but may have questionable backgrounds and connections.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About The Chicago Way

What is The Chicago Way about and what kind of topics does it cover?

In this series, listeners are presented with an insightful examination of contemporary news and politics, particularly centered around the unique challenges and cultural narratives of Chicago. The discussions often intertwine personal anecdotes with sharp political commentary, exploring critical issues such as crime, immigration policy, and the dynamics of local governance. With an emphasis on engaging guests from various sectors, the series highlights contrasting viewpoints on political events, offering a robust platform for debate and reflection on the complex political landscape. Notably, it captures the essence of Chicago's storied past and how that shapes its present, making it relevant for anyone interested in understanding urban poli... more

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Which podcasts are similar to The Chicago Way?

These podcasts share a similar audience with The Chicago Way:

1. Chicago's Morning Answer with Dan Proft
2. RealClearPolitics Podcast
3. The Victor Davis Hanson Show
4. The Megyn Kelly Show
5. Pod Force One

How many episodes of The Chicago Way are there?

The Chicago Way launched 10 years ago and published 104 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on The Chicago Way?

Recent guests on The Chicago Way include:

1. Tom Bevan
2. James R. Brown
3. Ted Dabrowski
4. Robert Milan
5. Joe Abram
6. Brendan Reilly
7. Ray Lopez
8. James Banakis

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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