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The Chicago Way

WGN Plus
Chicago
Brandon Johnson
Donald Trump
Democratic Party
Joe Biden
Illinois
Kamala Harris
Crime
Chicago Way
Chicago Teachers Union
Deep State
J.B. Pritzker
Ukraine
Cook County
Joseph's Finest Meats
Chicago Tribune
Democratic National Convention
Christmas
CIA
WGN Radio

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 (07/20/26): John Kass & Jeff Carlin take a look a the rise of “agenda journalism” in media, what happens when teachers focus on activism instead of education, and why California should be a cautionary take for Illinois. Plus, ... more

Chicago Way w/John Kass (07/13/26): John Kass & Jeff Carlin welcome retired Chief of Detectives for the Chicago Police Department, Gene Roy, to discuss how dishonorably the outgoing Supt. Larry Snelling was treated by Mayor Brandon Johnson, what it’s... more

Chicago Way w/John Kass (07/07/26): Happy Birthday America! Charles Lipson joins John Kass & Jeff Carlin for a look at who is pushing the narrative that the US is bad, why people can’t seem to agree on common sense anymore, and what is at risk if we ... more

Chicago Way w/John Kass (06/30/26): John Kass & Jeff Carlin are back this week to dive into what the current state of American culture means to the rest of the world, how failures that stack up when we elect/hire/listen to unqualified leaders, and a ... more

Key Facts

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Recent Guests

Molly Mustard
Driver, Wienermobile
Oscar Mayer Wienermobile
Episode: Chicago Way w/John Kass: Reissue – Episode #6 from February of 2016
Kelly Ketchup
Driver, Wienermobile
Oscar Mayer Wienermobile
Episode: Chicago Way w/John Kass: Reissue – Episode #6 from February of 2016
Ray Lopez
Alderman of the 15th Ward
City of Chicago
Episode: Chicago Way w/John Kass: Does Mayor Brandon Johnson even want to run again?
Nicholas S. Kass
Former chairman of the National Intelligence Council
U.S. government / intelligence community
Episode: Chicago Way w/John Kass: On the hunt for politicization in U.S. intelligence
Sal Carmada
Writer for John Kass News, contributor to discussions
John Kass News
Episode: Chicago Way w/John Kass: A time for reflection
James Jennings
Writer, involved in Letters column discussions
Letters column contributor
Episode: Chicago Way w/John Kass: A time for reflection
Rafael Mangual
Criminology and policy expert
City Journal, Manhattan Institute
Episode: Chicago Way w/John Kass: Alders warn us ‘wrong place, wrong time’ but they created this
Tom Morrison
Illinois conservative politician and former state representative
Hillsdale College alumnus, Candidate Master Class founder
Episode: Chicago Way w/John Kass: A blueprint for getting involved in the Republic
Judge James Brown
Former Cook County judge, subject of the discussion
Judge James Brown (former Cook County Judge)
Episode: Chicago Way w/John Kass: Authoritarianism cometh from Springfield

Hosts

John Kass
Host of The Chicago Way; columnist and editor-in-chief at John Kass News; long-time Chicago political journalist.
Jeff Carlin
Co-host and executive producer; responsible for production and on-air contributions; frequent collaborator with John Kass.

Reviews

4.7 out of 5 stars from 1.2k ratings
  • Bless his heart

    Great pod, but I do miss John’s squeaky chair

    Apple Podcasts
    5
    Southsidewhitesoxfan
    United States7 months ago
  • Go Chicago Way

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

    Apple Podcasts
    5
    Natural News
    United States10 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 Statesa year ago
  • Old and washed up

    John Kass talks about nothing important.

    Apple Podcasts
    1
    Southsidewhitesoxfan
    United Statesa year ago
  • The best!

    Jk knows where the bodies are still walking!

    Apple Podcasts
    5
    JAWtree
    United Statesa year ago

Listeners Say

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

Show provides strong, credible analysis with memorable storytelling and personal anecdotes.
Listeners appreciate the candid, no-nonsense viewpoint and in-depth local context.
Guests are varied and high-caliber, offering fresh takes on Chicago and national issues.

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Talking Points

Recent interactions between the hosts and their guests.

Chicago Way w/John Kass: Reissue – Episode #6 from February of 2016
Q: How long do the residents of Chicago plan on keeping their blinders on?
The speakers acknowledge skepticism about political reform and the city's governance, suggesting that real changes are slow and contingent on broader political shifts and accountability rather than one-off reforms.
Chicago Way w/John Kass: Don’t (bleep) with a pit bull’s reputation
Q: What's your take on the press coverage and the ethics investigations surrounding campaigns?
There's a perception of a concerted effort by certain law firms and media outlets that weaponize headlines and lawsuits to influence elections, and that the system is tilted toward those with deep-pocketed backers.
Chicago Way w/John Kass: Don’t (bleep) with a pit bull’s reputation
Q: What have you told him about running again in the future?
I've told him, if he ever runs, I'll be honest about it and we'll see how things unfold; I'm prepared to close ranks or run as a spoiler if needed.
Chicago Way w/John Kass: Authoritarianism cometh from Springfield
Q: What is the next step if the Illinois Supreme Court won't address the issue?
They explain filing a federal lawsuit for declaratory judgment and seeking preliminary injunctions to reappoint Judge Brown and to recover damages, arguing constitutional violations.
Chicago Way w/John Kass: Authoritarianism cometh from Springfield
Q: Question to the Council. Who can you subpoena in this case?
The hosts discuss whether officials of the Bar Associations or other parties could be subpoenaed, suggesting it may be necessary later to pursue broader discovery to understand the basis of the Supreme Court's actions.

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?

The show centers on Chicago politics, local governance, media dynamics, and national issues with sharp, sometimes provocative commentary. Regular hosts dissect power struggles, policy trade-offs, and cultural touchpoints through a Chicago lens, often featuring diverse guests from politics, journalism, law, and advocacy to illuminate how national events intersect with city life. Notable strengths include candid storytelling, strong editorial perspective, and a willingness to tackle sensitive topics like policing, free speech, and trust in media, all while weaving in personal anecdotes and local sponsorships that reinforce community ties. This mix can appeal to listeners who want principled, opinionated discourse grounded in real-world Chicag... 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. Pod Force One
4. Victor Davis Hanson: In His Own Words
5. Bill O’Reilly’s No Spin News and Analysis

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. Molly Mustard
2. Kelly Ketchup
3. Ray Lopez
4. Nicholas S. Kass
5. Sal Carmada
6. James Jennings
7. Rafael Mangual
8. Tom Morrison

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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