| Chicago's Michigan (abbr.) | 30 |
| Chicago's Merchandise ___ | 29 |
| Chicago's locale | 20 |
| Chicago's Little Village, e.g. | 34 |
| Chicago's Jane Byrne, once | 30 |
| Chicago's hub | 17 |
| Chicago's first mayor William | 33 |
| Chicago's Emanuel | 21 |
| Chicago's Dan ___ Expressway | 32 |
| Chicago's county | 20 |
| Chicago's central business district | 39 |
| Chicago's airport | 21 |
| Chicago's "sister city" in Japan | 46 |
| Chicago WNBA team | 17 |
| Chicago winter clock setting: Abbr. | 35 |
| Chicago White ___ | 17 |
| Chicago White __ | 16 |
| Chicago White -- | 16 |
| Chicago weather forecast | 24 |
| Chicago university founded in 1945 | 34 |
| Chicago university | 18 |
| Chicago transports | 18 |
| Chicago transportation | 22 |
| Chicago transit trains | 22 |
| Chicago trains | 14 |
| Chicago tower builder | 21 |
| Chicago touchdown site | 22 |
| Chicago to Washington, D.C. dir. | 32 |
| Chicago to Washington dir. | 26 |
| Chicago to Miami dir. | 21 |
| Chicago to Baltimore dir. | 25 |
| Chicago time: Abbr. | 19 |
| Chicago time zone | 17 |
| Chicago time inits. | 19 |
| Chicago time | 12 |
| Chicago terminus | 16 |
| Chicago terminal | 16 |
| Chicago team, on Spanish radio | 30 |
| Chicago team, in headlines | 26 |
| Chicago team, for short | 23 |
| Chicago team, briefly | 21 |
| Chicago team | 12 |
| Chicago Teachers Union president Lewis | 38 |
| Chicago Symphony director, 1969-91 | 34 |
| Chicago Symphony director | 25 |
| Chicago Symphony conductor Georg | 32 |
| Chicago Surface Lines transports | 32 |
| Chicago superstation | 20 |
| Chicago Sun-Times rival, briefly | 32 |
| Chicago Sun Times critic | 27 |
| Chicago suburb or NBA legend Baylor | 35 |
| Chicago suburb | 14 |
| Chicago strip (Greater North Michigan Avenue Association) | 57 |
| Chicago stopover locale | 23 |
| Chicago stopover | 16 |
| Chicago Sting's org. | 24 |
| Chicago Sting org. | 18 |
| Chicago square for fodder merchants? | 36 |
| Chicago squad | 13 |
| Chicago soccer team | 19 |
| Chicago slugger | 15 |
| Chicago skyline site, formerly | 30 |
| Chicago Sky's org. | 22 |
| Chicago site of many connections | 32 |
| Chicago sights | 14 |
| Chicago sightings | 17 |
| Chicago shopping district | 25 |
| Chicago Seven member | 20 |
| Chicago Seven first name | 24 |
| Chicago seven (plus maybe Jackson) | 34 |
| Chicago setting: Abbr. | 22 |
| Chicago setting (Abbr.) | 23 |
| Chicago sausage king Froman impersonated by Ferris Bueller | 58 |
| Chicago runners | 15 |
| Chicago reviewer | 16 |
| Chicago recruiter | 17 |
| Chicago recording studio | 24 |
| Chicago railways | 16 |
| Chicago rails | 13 |
| Chicago put-down? | 17 |
| Chicago public transportation, familiarly | 41 |
| Chicago pro | 11 |
| Chicago political name | 22 |
| Chicago political family | 24 |
| Chicago player | 14 |
| Chicago pit purchase | 20 |
| Chicago pie style | 17 |
| Chicago phenomenon | 18 |
| Chicago paper, to locals | 24 |
| Chicago paper, informally | 25 |
| Chicago paper, for short, with "the" | 46 |
| Chicago paper, for short | 24 |
| Chicago paper, familiarly, with "the" | 47 |
| Chicago paper, familiarly | 25 |
| Chicago paper, casually | 23 |
| Chicago paper, briefly | 22 |
| Chicago paper | 13 |
| Chicago Outfit leader of the 1930s | 34 |
| Chicago Outfit leader | 21 |
| Chicago Outfit bigwig | 21 |