| Chicago Bears star Devin | 24 |
| Chicago Bears head coach Smith | 30 |
| Chicago Bears founder George | 28 |
| Chicago Bears coaching legend Mike | 34 |
| Chicago Bears coaching legend George | 36 |
| Chicago bearers? | 16 |
| Chicago basketball team sold to the Vatican? | 44 |
| Chicago baseballer | 18 |
| Chicago band whose one-take 2005 video was choreographed and filmed in their backyard | 85 |
| Chicago band who make one-take viral videos | 43 |
| Chicago Band The Walk-___ | 25 |
| Chicago ballplayer's interviewer? | 37 |
| Chicago ballpark eponym, once | 29 |
| Chicago balloonists' needs? | 31 |
| Chicago baggage letters | 23 |
| Chicago attraction | 18 |
| Chicago athlete | 15 |
| Chicago area, with "the" | 34 |
| Chicago area | 12 |
| Chicago architect Burnham | 25 |
| Chicago animal | 14 |
| Chicago and Boston | 18 |
| Chicago alternative to O'Hare | 33 |
| Chicago airport letters | 23 |
| Chicago airport control center | 30 |
| Chicago airport code | 20 |
| Chicago airport | 15 |
| Chicago air hub | 15 |
| Chicago adjective | 17 |
| Chicago 11 | 10 |
| Chicago "You're ___ Alone" | 40 |
| Chicago "What Kind of Man Would ___?" | 47 |
| Chicago "Hard ___ to Break" | 37 |
| Chicago "Baby, What a Big ___" | 40 |
| Chicago 'L,' e.g. | 25 |
| Chicago in a song | 18 |
| Chicago from St. Louis | 23 |
| Chicago | 7 |
| Chica or Raton | 14 |
| Chic, to Austin Powers | 22 |
| Chic, in the 1960s | 18 |
| Chic, in the '60s | 21 |
| Chic, in a 1960s way | 20 |
| Chic, for short | 15 |
| Chic, and then some | 19 |
| Chic, 1960s-style | 17 |
| Chic, 1960s style | 17 |
| Chic, '60s-style | 20 |
| Chic's Broadway partner | 27 |
| Chic Young's dimwit character | 33 |
| Chic Young strip | 16 |
| Chic Young creation to a treehugger | 36 |
| Chic Young creation | 19 |
| Chic Young comic strip wife, nee Boopadoop | 42 |
| Chic style? | 11 |
| Chic shop | 9 |
| Chic scientists love these Day-Glo accessories for Special Forces troops... | 75 |
| Chic scavenger? | 15 |
| Chic resort | 11 |
| Chic piece of jewelry? | 22 |
| Chic or tony | 12 |
| Chic or cheeky | 14 |
| Chic no more | 12 |
| Chic no longer | 14 |
| Chic monogram | 13 |
| Chic modifier | 13 |
| Chic Johnson's vaudeville partner | 37 |
| Chic in the Sixties | 19 |
| Chic in the 1960s | 17 |
| Chic group | 10 |
| Chic getaways | 13 |
| Chic getaway | 12 |
| Chic genre | 10 |
| Chic French magazine | 20 |
| CHIC ENG. PAL gets fruit | 24 |
| Chic end of London | 18 |
| Chic clique | 11 |
| Chic Chanel | 11 |
| Chic beach resort | 17 |
| Chic and jaunty | 15 |
| Chic again | 10 |
| Chic "Bye" | 20 |
| Chic | 4 |
| Chibchan Indian | 15 |
| Chibchan | 8 |
| Chiba ___ Marines (Japanese team managed by Bobby Valentine) | 60 |
| Chiba sash | 10 |
| Chiba coin | 10 |
| Chiapas people | 14 |
| Chiapas chum | 12 |
| Chiapas child | 13 |
| Chiapas cheer | 13 |
| Chiapas chaperon | 16 |
| Chiapas chap | 12 |
| Chiantis, e.g. | 14 |
| Chianti, per esempio | 20 |
| Chianti, in Chianti | 19 |
| Chianti, for one | 16 |
| Chianti, e.g. | 13 |
| Chianti's region | 20 |