| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| Chicago got its first black mayor, Harold Washington, 4 years after its first woman mayor, her | Jane Byrne | $800 | DJ | WOMEN | 2000-05-18 | #3629 | |
| Mrs. Jay McMullen, she was mayor of Chicago from 1979-1983 | Jane Byrne DD | $1,300 | DJ | WOMEN | 1993-09-08 | #2068 | |
| She was the first woman mayor of Chicago | Jane Byrne | $600 | DJ | WOMEN | 1991-02-01 | #1485 |