| Chicago's county | 20 |
| Chicago's Dan ___ Expressway | 32 |
| Chicago's Emanuel | 21 |
| Chicago's first mayor William | 33 |
| Chicago's hub | 17 |
| Chicago's Jane Byrne, once | 30 |
| Chicago's Little Village, e.g. | 34 |
| Chicago's locale | 20 |
| Chicago's Merchandise ___ | 29 |
| Chicago's Michigan (abbr.) | 30 |
| Chicago's Michigan: Abbr. | 29 |
| Chicago's NFL team | 22 |
| Chicago's official flower, familiarly | 41 |
| Chicago's often on it | 25 |
| Chicago's Papa Bear | 23 |
| Chicago's Peter | 19 |
| Chicago's plane place | 25 |
| Chicago's planetarium | 25 |
| Chicago's Richard ___ Center | 32 |
| Chicago's Rumanian-born conductor | 37 |
| Chicago's Saint ___ University | 34 |
| Chicago's Sandberg | 22 |
| Chicago's Sears Tower, for one | 34 |
| Chicago's soccer team | 25 |
| Chicago's St. ___ University | 32 |
| Chicago's Sting is one | 26 |
| Chicago's time zone | 23 |
| Chicago's United Center e.g. | 33 |
| Chicago's Velvet Fog | 24 |
| Chicago's winter hrs. | 25 |
| Chicago's WNBA team | 23 |
| Chicago's __ House | 22 |
| Chicago's __ Planetarium | 28 |
| Chicago's ___ Aquarium | 26 |
| Chicago's ___ Center | 24 |
| Chicago's ___ Drive | 23 |
| Chicago's ___ Expressway | 28 |
| Chicago's ___ House | 23 |
| Chicago's ___ Planetarium | 29 |
| Chicago's ___ Tower | 23 |
| 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 |