| Chicago's ___Planetarium | 28 |
| Chicago, band-wise | 18 |
| Chicago, e.g. | 13 |
| Chicago, for one | 16 |
| Chicago, in a song | 18 |
| Chicago, the -- City | 20 |
| Chicago, with "the" | 29 |
| Chicago-area institution home to the world's most powerful particle accelerator | 83 |
| Chicago-based cable superstation | 32 |
| Chicago-based critic | 20 |
| Chicago-based daytime host | 26 |
| Chicago-based film critic | 25 |
| Chicago-based film reviewer | 27 |
| Chicago-based food giant | 24 |
| Chicago-based insurance company that sponsors Manchester United's uniforms | 78 |
| Chicago-based magazine with one-million-plus circulation | 56 |
| Chicago-based monthly since 1945 | 32 |
| Chicago-based professional org. | 31 |
| Chicago-based station | 21 |
| Chicago-based Superstation | 26 |
| Chicago-based TV show | 21 |
| Chicago-based TV talk show | 26 |
| Chicago-born actress | 20 |
| Chicago-D.C. dir. | 17 |
| Chicago-fire name | 17 |
| Chicago-skyline site | 20 |
| Chicago-St. Louis dir. | 22 |
| Chicago-style deep dish chain | 29 |
| Chicago-style hot dog options | 29 |
| Chicago-style, as pizza | 23 |
| Chicago-time initials | 21 |
| Chicago-to-Atlanta dir. | 23 |
| Chicago-to-Atlanta direction | 28 |
| Chicago-to-Baltimore dir. | 25 |
| Chicago-to-D.C. dir. | 20 |
| Chicago-to-Detroit dir. | 23 |
| Chicago-to-Indianapolis dir. | 28 |
| Chicago-to-Knoxville dir. | 25 |
| Chicago-to-Louisville dir. | 26 |
| Chicago-to-Memphis dir. | 23 |
| Chicago-to-Miami dir. | 21 |
| Chicago-to-Nashville dir. | 25 |
| Chicago-to-Pittsburgh dir. | 26 |
| Chicago-to-St. Louis dir. | 25 |
| Chicago-to-Tampa dir. | 21 |
| Chicago/L.A. rock band famous for viral videos | 46 |
| Chicagoan | 9 |
| Chicagoan Catherine with a famous barn | 38 |
| Chicagoan in 1871 news | 22 |
| ChicagoÂ’s ___ Tower | 23 |
| Chicago–New Orleans product | 34 |
| Chicana | 7 |
| Chicaneries | 11 |
| Chicanery | 9 |
| Chicano | 7 |
| Chicano bears? | 14 |
| Chicano cubs | 12 |
| Chichén Itzá attraction | 29 |
| Chichén Itzá builder | 26 |
| Chichén Itzá constructor | 30 |
| Chichén Itzá natives | 26 |
| Chichén __ | 13 |
| Chichén __ (Mayan tourist site) | 34 |
| Chichén __: Mayan ruins | 26 |
| Chichén ___ | 14 |
| Chichén ___ (Mayan city) | 27 |
| Chichén ___ (Mayan ruins) | 28 |
| Chichén ___ (Mayan site) | 27 |
| Chichén Itzá builder | 34 |
| Chichén Itzá resident | 35 |
| Chichen Itza boy | 16 |
| Chichen Itza resident | 21 |
| Chichen Itza residents | 22 |
| Chichen ___ (famed Mayan ruins) | 31 |
| Chichen ___ (pre-Columbian city) | 32 |
| Chichester chap | 15 |
| Chichester chum | 15 |
| Chichewa and English are its two official languages | 51 |
| Chichi | 6 |
| Chichi chopped liver, essentially | 33 |
| Chichi getaway | 14 |
| Chichi salad green | 18 |
| Chichi shopping area in Tokyo | 29 |
| Chichi ___, Japan | 17 |
| Chichi-___ (largest of Japan's Bonin Islands) | 49 |
| Chick | 5 |
| Chick and fire | 14 |
| Chick at the piano | 18 |
| Chick chaser | 12 |
| Chick chaser's cry | 22 |
| Chick chaser? | 13 |
| Chick chat | 10 |
| Chick chatter | 13 |
| Chick chitchat | 14 |
| Chick comment | 13 |
| Chick Corea and Miles Davis | 27 |
| Chick ender | 11 |
| Chick ending | 12 |
| Chick flick subject | 19 |
| Chick follower | 14 |