| 1966 Grammy winner for "If He Walked Into My Life |
| Emmy winner as Gotti |
| Grammy winner Blige |
| 2000 Best Song Oscar winner |
| Actor who won comedy and drama Emmys for the same role |
| Australian winner of 11 Grand Slam tournaments |
| A pageant winner's title |
| Five-time Kentucky Derby winner |
| Academy Award winner with notable eyebrows |
| 'Arthur' Oscar winner John |
| Peter ___ (Chicago singer and bassist) |
| Chicago university |
| Chicago N.F.L. team |
| Chicago's Little Village, e.g. |
| 'Blue Sky' Oscar winner Jessica |
| Chicago's locale |
| Chicago ballplayer |
| Les Misérables" Oscar winner Hathaway |
| Chicago's United Center e.g. |
| Actor Jannings, winner of the first Best Actor Oscar |
| Chicago's ___ Center |
| Actor Richard of "Unfaithful" and "Chicago |
| Setting for Chicago's Summerfest: Abbr. |
| Oscar-winner Witherspoon |
| Golden Globe winner Sedgwick |
| A Fish Called Wanda" Oscar winner |
| 1977 Cy Young Award winner Sparky |
| Winner of tennis's Grand Slam in 1962 and 1969 |
| Chicago's Peter |
| Academy Award winner Jared who's playing another Joker soon, because lord knows there haven't been enough of those |