| 100% | ROYKO | 5 | Pulitzer-winning Chicago journalist Mike |
| 71% | ROYKO | 5 | Chicago journalist Mike |
| 60% | ANNE | 4 | 2004 Pulitzer winning journalist and author Applebaum |
| 54% | ROYKO | 5 | Pulitzer-winning columnist Mike |
| 54% | HERSH | 5 | Pulitzer-winning journalist Seymour |
| 54% | GENE | 4 | Pulitzer-winning journalist Weingarten |
| 54% | RESTON | 6 | Pulitzer-winning journalist James |
| 54% | ANNA | 4 | Pulitzer-winning journalist Quindlen |
| 54% | ISABEL | 6 | Pulitzer-winning journalist Wilkerson |
| 52% | RESTON | 6 | James, journalist who won the Pulitzer in 1945 and 1957 |
| 51% | ERNIEPYLE | 9 | Pulitzer-winning W.W. II journalist |
| 51% | ANNE | 4 | Pulitzer-winning historian and journalist Applebaum |
| 51% | ANNA | 4 | Pulitzer-winning journalist and novelist Quindlen |
| 51% | ERNIEPYLE | 9 | 1944 Pulitzer-winning journalist |
| 50% | RESTON | 6 | Two-time Pulitzer-winning journalist |
| 49% | DOWD | 4 | Pulitzer-winning journalist for her Clinton-Lewinsky columns |
| 47% | LOISLANE | 8 | Fictional Pulitzer-winning journalist in a 2006 film |
| 47% | PYLE | 4 | Ernie ___, Pulitzer-winning journalist of W.W. II |
| 46% | GENE | 4 | Author and Pulitzer-winning WaPo journalist Weingarten |
| 45% | DITKA | 5 | Chicago Bears coaching legend Mike |
| 45% | ROGEREBERT | 10 | Noted Chicago journalist |
| 43% | ROREM | 5 | 1976 Pulitzer winning composer, Ned ___ |
| 43% | DITKA | 5 | Longtime Chicago Bears coach Mike |
| 43% | DITKA | 5 | Former Chicago Bears coach Mike |
| 43% | HERSH | 5 | Pulitzer journalist Seymour |
| 42% | FAGIN | 5 | Dan, award-winning journalist and 2014 General Nonfiction Pulitzer recipient |
| 41% | LESS | 4 | Andrew Greer's 2017 Pulitzer winning novel |
| 41% | VARGAS | 6 | Pulitzer-winning journalist Jose Antonio who wrote the memoir "Dear America: Notes of an Undocumented Citizen" |
| 41% | LEE | 3 | Pulitzer Prize winning author Harper |
| 41% | AGEE | 4 | Pulitzer Prize winning novelist James ___ |