| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| A career was born in 1955 when Esther Lederer took over the Ann Landers column of this city's Sun-Times | Chicago | $400 | J | NEWSPAPERS | 2012-04-18 | #6358 | |
| From its Sun-Times:"Former Blagojevich fund-raiser gets 37 months in prison" | Chicago | $400 | J | 2009 HEADLINES IN THE CITY'S NEWSPAPER | 2009-12-23 | #5818 | |
| When Field Enterprises closed down this city's Daily News in 1978, it owned the Sun-Times | Chicago | $400 | DJ | NEWSPAPERS | 1991-04-24 | #1543 |