Thirty years after his first column for the Chicago Tribune, two-time Pulitzer Prize winning columnist Clarence Page reflects on race, politics, and social change in his new book Culture Worrier.

Back in Chicago, South Side native and Politico’s chief political columnist Roger Simon talks shop and discuss his past life as a city beat reporter. 

Chicago Sun-Times columnist Stella Foster calls it quits after 43 years. She joins us on her last day on the job to talk about her life, legacy, and what's next.

Paul Krugman

In an exclusive interview with Chicago Tonight, Nobel Prize winning economist Paul Krugman weighs in on Chicago's new infrastructure trust, and gives his thoughts on tackling Illinois' fiscal crisis.

Mary Schmich

Chicago Tribune columnist Mary Schmich talks about the Pulitzer Prize for commentary she was awarded this week.

Dan Savage

We take another look at a conversation we had last year with provocative sex columnist and Chicago native, Dan Savage.