| 100% | WINDYCITY | 9 | Chicago, with "the" |
| 99% | OLEARY | 6 | Name associated with the Great Chicago Fire |
| 97% | DITKA | 5 | Five-time Pro Bowler with the Chicago Bears |
| 97% | LOOP | 4 | Historical center of Chicago, with The |
| 95% | ILLINOIS | 8 | The US state with Chicago and Springfield |
| 94% | WNBA | 4 | League with the Seattle Storm and the Chicago Sky: Abbr. |
| 94% | PAPERLACE | 9 | Band with the 1974 #1 hit "The Night Chicago Died" |
| 94% | USFL | 4 | Defunct sports org. with the Denver Gold and Chicago Blitz |
| 94% | BLACKHAWKS | 10 | Chicago team with three Stanley Cup wins in the 2010s |
| 92% | MLS | 3 | Sports organization with the Chicago Fire and the Portland Timbers (Abbr.) |
| 90% | ILOVELA | 7 | 1983 song with the lyric "Let's leave Chicago to the Eskimos" |
| 90% | ANGEL | 5 | LSU basketball star ___ Reese, whose WNBA debut was with the Chicago Sky |
| 89% | HOUSEMUSIC | 10 | Genre with roots in the Chicago club scene |
| 89% | LOOP | 4 | Heart of Chicago, with "the" |
| 86% | YESWECAN | 8 | Campaign slogan associated with a Chicago politician of the 2000s |
| 85% | THELASTDANCE | 12 | 2020 ESPN docuseries about Michael Jordan's final season with the Chicago Bulls (3 wds.) |
| 85% | LOOP | 4 | Chicago area, with "the" |
| 85% | TRIB | 4 | Chicago daily, with "the" |
| 85% | LOOP | 4 | Chicago district, with "the" |
| 85% | MERC | 4 | Chicago market, with "the" |
| 85% | LOOP | 4 | Chicago locale, with "the" |
| 85% | MERC | 4 | Chicago market, with “the” |
| 85% | PALATINE | 8 | Chicago suburb with the same name as one of Rome's seven hills |
| 81% | OLDDAYS | 7 | Chicago song with the lyric "Take me back / To the world gone away" (2 wds.) |
| 81% | OLDDAYS | 7 | Chicago song with the lyrics "Take me back / To the world gone away" (2 wds.) |
| 81% | OLDDAYS | 7 | Chicago song with the lyrics "Take me back / To a world gone away" (2 wds.) |
| 81% | TRIB | 4 | Chicago paper, familiarly, with "the" |
| 81% | TRIB | 4 | Chicago daily, briefly, with "the" |
| 81% | TRIB | 4 | Chicago paper, briefly, with "the" |
| 81% | MERC | 4 | Chicago exchange, briefly, with "the" |