| 100% | LOOP | 4 | Chicago locale, with "the" |
| 76% | ARUBA | 5 | Caribbean locale with the slogan "One Happy Island" |
| 74% | ATLANTA | 7 | "Gone With the Wind" locale |
| 74% | TARA | 4 | "Gone With the Wind" locale |
| 74% | GEORGIA | 7 | "Gone With the Wind" locale |
| 74% | TARA | 4 | ''Gone With the Wind'' locale |
| 72% | OLEARY | 6 | Name associated with the Great Chicago Fire |
| 71% | DITKA | 5 | Five-time Pro Bowler with the Chicago Bears |
| 69% | ILLINOIS | 8 | The US state with Chicago and Springfield |
| 68% | WNBA | 4 | League with the Seattle Storm and the Chicago Sky: Abbr. |
| 68% | PAPERLACE | 9 | Band with the 1974 #1 hit "The Night Chicago Died" |
| 68% | USFL | 4 | Defunct sports org. with the Denver Gold and Chicago Blitz |
| 67% | LOOP | 4 | Chicago area, with "the" |
| 67% | TRIB | 4 | Chicago daily, with "the" |
| 67% | LOOP | 4 | Chicago district, with "the" |
| 67% | MERC | 4 | Chicago market, with "the" |
| 67% | MERC | 4 | Chicago market, with “the” |
| 67% | FENS | 4 | Lincolnshire locale, with "The" |
| 67% | SEA | 3 | Vacation locale, with "the" |
| 67% | MALL | 4 | Washington locale, with "the" |
| 67% | COAST | 5 | Vacation locale, with "the" |
| 67% | HAGUE | 5 | Court locale, with "The" |
| 67% | PALATINE | 8 | Chicago suburb with the same name as one of Rome's seven hills |
| 67% | MLS | 3 | Sports organization with the Chicago Fire and the Portland Timbers (Abbr.) |
| 67% | MARIN | 5 | ___ Headlands, California locale with a view of the Golden Gate Bridge |
| 66% | ILOVELA | 7 | 1983 song with the lyric "Let's leave Chicago to the Eskimos" |
| 65% | ANGEL | 5 | LSU basketball star ___ Reese, whose WNBA debut was with the Chicago Sky |
| 65% | BLACKHAWKS | 10 | Chicago team with three Stanley Cup wins in the 2010s |
| 65% | HOUSEMUSIC | 10 | Genre with roots in the Chicago club scene |
| 65% | RIVIERA | 7 | "Tender Is the Night" locale, with "the" |