Bob Chiarito

Bob Chiarito is a lifelong Chicago-area resident and has been called “an-old fashioned shoe-leather reporter and one of the best in town” by Tony Fitzpatrick and “One of the most prolific and talented freelance writers in town” by Rick Kogan. 



Bob freelances for a number of publications. He reports on local stories for Block Club Chicago, Chicago Magazine, The Chicago Reporter and The Chicago Ambassador and nationally for the New York Times, Reuters and Agence France-Presse (AFP). He also writes for England’s New Music Express (NME); Gateway Journalism Review and just started something new — doing radio stories for Wisconsin Public Radio.

Bob started at the legendary City News Bureau of Chicago and also worked for the Chicago Daily Law Bulletin. 

Over the last couple years, he’s been at the forefront of some of the biggest stories in the country, including the Jason Van Dyke trial, the Aurora, IL mass shooting, the federal trial of Brendt Christensen — who killed Chinese grad student YingYing Yang at U of I; the historic Chicago Mayoral election; Jussie Smollett, R. Kelly and more.

Most recently, he’s written several stories about two women who say they were betrayed by Cook County State’s Attorney’s Kim Foxx’s office and the ongoing case against the man who assaulted them – James Mather — while continuing to cover other stories for the plethora of outlets he reports for.

The hardest questions he’s often asked is what do you like to cover most? and what is your favorite story? To that, he says He likes to cover everything and tries to approach each story with an equal amount of vigor — and for his favorite story — he’ll say it’s his next story.

While some in the industry ultimate move on to public relations or move up to being an editor, Bob’s always wanted to remain a reporter. And while he ideally would opt for a staff job — he understands the reality of the industry and is able to survive in the freelance world by staying hungry and constantly hustling. 

“I may not be the best writer, I may not be the best reporter, but I’d wager my passion for reporting is equal than or greater than anyones.” – Bob Chiarito



(847) 878-3724

When the biggest stories break, the news outlets I work for usually call me first. I currently work for The New York Times,  Chicago Sun-Times, Thomson Reuters, Chicago Magazine, Block Club Chicago, Agence France-Presse (AFP), New Music Express (NME), Wisconsin Public Radio, Chicago Tribune, Gateway Journalism Review, VICE News, The Daily Herald and a few others. In addition, I run an online publication called The Chicago Ambassador which has won awards for excellence in journalism




2017– Present THE NEW YORK TIMES, New York, NY 

Freelance Reporter

• Cover breaking news as assigned from Chicago

• Stories included the Jussie Smollett investigation and indictment and the R. Kelly indictments and related stories



Freelance Reporter

• Cover breaking news as assigned

• Pitched and wrote numerous stories



Freelance Reporter

• Pitched and wrote numerous stories

• Covered breaking news as assigned

• Most active freelancer in Block Club Chicago’s stable


2015 – Present THOMSON REUTERS, Chicago, IL

Freelance Reporter

• Cover breaking news as assigned

• Stories included the 2018/2019 trial of Chicago Police officer Jason Van Dyke; the Federal trial of Brendt Christensen; the February 2019 mass shooting in Aurora, IL; the 2016 Presidential election; the  indictment of former House speaker Dennis Hastert, the eleven tornadoes which struck northern Illinois, forming a supercell thunderstorm, in 04/2015; many protests and more

• Most active freelancer in Reuters’ stable

2014 – Present THE CHICAGO AMBASSADOR Chicago, IL

Founder and Managing Editor, 

• May 2018 – Won Peter Lisagor Award for Best Independent Continuing Blog. The Lisagor Awards are given by The Chicago Headline Club, the Chicago chapter of The Society of Professional Journalists, for exemplary journalism.

• Founded to report content relevant to Chicagoans, specifically stories which do not have a voice in mainstream media

• Publish weekly Chicago feature and news stories, ranging from entertainment to economics, as well as periodic columnists

• Determine all editorial content and drive brand development

• Manage 10-person staff; three reporters and seven contributing photographers and copy editors


2013 – 2016 & October 2019 – Present, THE CHICAGO TRIBUNE Chicago, IL

Freelance Reporter

• Cover local governments, school boards, and police stories




• Generated story ideas and covered daily news and features stories for legal-focused newspaper.  Content focused on ongoing patent/intellectual property, corporate, and trial cases.

• Wrote weekly column on suburban law issues, specifically, industry trends, industry profiles, and emerging practice areas 



• Investigated and reported on police beat, Mayor’s office, and a variety of daily news stories for one of the first wire services in the US

• Staffed as editor and rewrite and broadcast writer on rotating weekend schedule



• Bachelor of Arts

• Major:  Journalism


Wednesday Journal – Interned for this weekly newspaper in Oak Park, IL

Robert Novak – Interned for this award winning syndicated columnist in Washington, D.C.

CBS2 Chicago – Interned for Pulitzer-prize winning investigative reporter Pam Zekman


• November 2019 – Featured on WGN Radio 720 (Andrea Darlas and the Reporters) talking about my career

• August 2019 – Featured on WGN Radio 720 (After Hours with Rick Kogan) for a news story I wrote on mental hazards of crime reporting for Gateway Journalism Review

• August 2019 – Interviewed live on South African radio about my coverage of the R. Kelly case for The New York Times

• July 2019 – Elected secretary of the Chicago Headline Club Foundation Board

May 2018 – Won Peter Lisagor Award for Best Independent Continuing Blog. The Lisagor Awards are given by The Chicago Headline Club, the Chicago chapter of The Society of Professional Journalists, for exemplary journalism.

• 2018: Spoke on a panel of writers, actors and other professions about Storytelling at Columbia College Chicago

• 2018: Spoke at the Illinois College Press Association annual conference on “Story development in the freelance world”

• 2017-Present: Member of the Chicago Headline Club’s Foundation Board (Local chapter, Society of Professional Journalists)

 2017 – One of twenty journalists from across the U.S. selected by Lakeland University’s Office of the Advancement of Free Enterprise Education to attend a two-day seminar at the Federal Reserve Bank of Chicago

• 2017: Illinois College Press Association awards judge

• 2016: Featured twice on WGN-Radio 720 for news stories that I wrote

2015:  Speaker at Chicago Headline Club luncheon regarding the state of the journalism industry


Several times in 2020 and 2021. 

Bob Chiarito on “Andrea Darlas & The Reporters” WGN AM 720, November 11, 2019

Voyage Chicago interview of Bob Chiarito (September 2018)

Bob Chiarito on “After Hours with Rick Kogan” WGN AM 720, August 18, 2019 (skip to the 43:48 mark)

Bob Chiarito on “After Hours with Rick Kogan” WGN AM 720, June 20, 2019

Bob Chiarito on “The Max & Tony Show” podcast 6/15/2018

Bob Chiarito on WGN AM 720 on 10/6/15 to talk about his Stephen Martin interview, Ivy Davis story and Naked Raygun. Skip to the 1:11 mark to listen!

Bob Chiarito being interviewed live on WGN AM 720 in March 2015 about The Chicago Ambassador!

Bob Chiarito interviewed on Rivet Radio in June 2015  about his story on a 11-year-old American girl being kept in Ghana against the wishes of her mother and the orders of a Cook County Judge

Listen to Bob Chiarito talking about The Chicago Ambassador on the Lisa D Show (April 2017)

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