| 100% | WINDY | 5 | "The ___ City" (Chicago nickname) |
| 100% | WINDY | 5 | The ___ City (Chicago nickname) |
| 93% | WINDY | 5 | "The ___ City," nickname of Chicago |
| 83% | LOU | 3 | The __ (arch city nickname) |
| 81% | WINDY | 5 | Chicago, the — City |
| 78% | CHITOWN | 7 | Nickname for the Windy City |
| 77% | APPLE | 5 | The Big ___ (New York City nickname) |
| 77% | WINNIPEG | 8 | City nicknamed Gateway to the West |
| 77% | DRESDEN | 7 | City nicknamed "Florence on the Elbe" |
| 77% | AMSTERDAM | 9 | City nicknamed Venice of the North |
| 76% | ELM | 3 | The ___ City (tree-based nickname for New Haven, Connecticut) |
| 75% | STLOUIS | 7 | City nicknamed "The Gateway to the West" |
| 75% | BELFAST | 7 | City nicknamed the "Athens of Northern Ireland" |
| 75% | AKRONOHIO | 9 | City nicknamed "Rubber Capital of the World" |
| 75% | SALEM | 5 | Capital nicknamed the Cherry City |
| 74% | BEAN | 4 | The ___, nickname for Chicago's Cloud Gate sculpture |
| 74% | NEONGREEN | 9 | Nickname for the garishly colored Chicago-style relish |
| 74% | ATL | 3 | City nicknamed the "Hollywood of the South": Abbr. |
| 74% | TULSA | 5 | City once nicknamed "Oil Capital of the World" |
| 74% | CHITOWN | 7 | Alternate nickname for the Windy City |
| 74% | TAMPA | 5 | Florida city nicknamed the "Big Guava" |
| 73% | BIGAPPLE | 8 | The ___ (fruity nickname for New York City): 2 wds. |
| 72% | GENOA | 5 | Italian city with the nickname “La Superba” |
| 72% | COLUMBUS | 8 | State capital with the nickname "Arch City" |
| 72% | ELS | 3 | What the Chicago trains have been nicknamed |
| 72% | TAMPA | 5 | U.S. city nicknamed the Big Guava |
| 72% | VENICE | 6 | Italian city nicknamed Bride of the Sea |
| 72% | HELENA | 6 | Capital nicknamed "Queen City of the Rockies" |
| 72% | GENEVA | 6 | Swiss city, nicknamed the Peace Capital |
| 72% | BAYOU | 5 | "The __ City": Houston nickname |