| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| For all but 12 years from 1955 to 2011, Chicago had a mayor with this last name | Daley | $800 | DJ | WINDY CITY POLITICS | 2019-11-22 | #8100 | |
| Last name of Chicago's longest-serving & second-longest-serving mayors | Daley | $1,200 | DJ | POLITICIANS | 2017-01-09 | #7441 | |
| Last name of Chicago's mayor; his father served as the city's mayor for 21 years | Daley | $200 | DJ | GOVERNMENT & POLITICS | 1998-11-30 | #3276 |