| 100% | WHITESOX | 8 | Team with a stadium on Chicago's South Side |
| 47% | WOODLAWN | 8 | Neighborhood on Chicago's South Side [I found his nemesis!] |
| 44% | HARLEM | 6 | ___ Globetrotters (exhibition basketball team that was actually founded on Chicago's South Side) |
| 43% | OBAMA | 5 | His presidential library will be built on Chicago's South Side |
| 43% | OBAMA | 5 | His presidential center is being built on Chicago's South Side |
| 43% | RAVENS | 6 | Team with a big B on its helmets |
| 42% | ASTROS | 6 | First MLB team with a domed stadium |
| 41% | CWS | 3 | South Side MLB team, on scoreboards |
| 41% | ASTRIDE | 7 | With a leg on either side |
| 41% | ASTRIDE | 7 | With a leg on each side |
| 41% | DREIDEL | 7 | Spinning top with a Hebrew letter on each side |
| 41% | COLTS | 5 | Football team with a blue horseshoe on its helmet |
| 41% | ASTRIDE | 7 | With a leg on either side of |
| 41% | ASTRADDLE | 9 | With a leg on each side of |
| 40% | ASTRIDE | 7 | With a leg on each side of a horse |
| 40% | ASTRIDE | 7 | With a leg on each side of an animal |
| 39% | ATLANTA | 7 | With 34-Across, NFC South squad that is one of four NFL teams that plays their home games in a fixed-roof stadium |
| 39% | SKYWRITERS | 10 | Columnists who report on Chicago’s W.N.B.A. team? |
| 38% | DIME | 4 | US coin with a torch on the reverse side |
| 38% | EURO | 4 | Coin with a map on one side |
| 38% | DIE | 3 | Cube with a different number of pips on each side |
| 38% | DIME | 4 | Coin with a torch on its reverse side |
| 37% | MOBY | 4 | Electronic musician who teamed with Gwen Stefani on the song "South Side" |
| 37% | ARAISININTHESUN | 15 | Classic 1959 drama with characters from Chicago's South Side |
| 37% | ROCKHOPPER | 10 | Small penguin with a yellow crest on each side of its head |
| 37% | STOP | 4 | Word on a red sign with eight sides |
| 36% | COMBATIVE | 9 | With a CHIP on one's shoulder |
| 36% | HUFFILY | 7 | With a chip on one's shoulder |
| 36% | ASTRIDE | 7 | Sitting with a leg on each side, like on a horse |
| 36% | BHUTAN | 6 | South Asian nation with a dragon on its flag |