| Answer | Crossword Clue |
|---|---|
| ROYKO | Chicago-based columnist |
| MIKEROYKO | Longtime Chicago columnist |
| ROYKO | Chicago columnist Mike |
| IRV | Chicago columnist Kupcinet |
| ROYKO | Long-time Chicago columnist |
| ROYKO | Chicago Tribune columnist Mike |
| ROEPER | Chicago Sun-Times columnist Richard |
| IRV | "Chicago Sun-Times" columnist Kupcinet |
| PAGE | Pulitzer-prize-winning Chicago columnist of 1989 |
