| Chicago exchange, for short | 27 |
| Chicago exchange, informally, with "the" | 50 |
| Chicago expressway | 18 |
| Chicago expressway with The | 28 |
| Chicago feature | 15 |
| Chicago field | 13 |
| Chicago film critic | 19 |
| Chicago film reviewer | 21 |
| Chicago financial area | 22 |
| Chicago Fire cow owner | 22 |
| Chicago fire figure | 19 |
| Chicago Fire Mrs. | 17 |
| Chicago fire name | 17 |
| Chicago fire starter: 1871 | 26 |
| Chicago Fire's sports org. | 30 |
| Chicago five | 12 |
| Chicago football team | 21 |
| Chicago footballer | 18 |
| Chicago franchise, with "the" | 39 |
| Chicago futures exchange, for short | 35 |
| Chicago gangster | 16 |
| Chicago gridder | 15 |
| Chicago gridders | 16 |
| Chicago GSB degree | 18 |
| Chicago has a big one | 21 |
| Chicago hrs. | 12 |
| Chicago hub | 11 |
| Chicago hub, on luggage tags | 28 |
| Chicago indie rock band, The ___ | 32 |
| Chicago journalist Mike | 23 |
| Chicago keyboardist Robert who wrote many of the band's early hits | 70 |
| Chicago L, for one | 18 |
| Chicago lakefront attraction | 28 |
| Chicago landing place | 21 |
| Chicago landing site | 20 |
| Chicago landmark | 16 |
| Chicago layover, often | 22 |
| Chicago lines | 13 |
| Chicago loc. | 12 |
| Chicago locale, with "the" | 36 |
| Chicago Loop carriers | 21 |
| Chicago Loop feature | 20 |
| Chicago Loop group | 18 |
| Chicago Loop loopers | 20 |
| Chicago Loop trains | 19 |
| Chicago Loop's __ Center | 28 |
| Chicago major-leaguer | 21 |
| Chicago Manual of Style alternative | 35 |
| Chicago market, with "the" | 36 |
| Chicago mayor | 13 |
| Chicago mayor (working at Arby's) | 37 |
| Chicago mayor -- Emanuel | 24 |
| Chicago mayor before Emanuel | 28 |
| Chicago mayor Emanuel | 21 |
| Chicago mayor Rahm | 18 |
| Chicago mayor Rahm __ | 21 |
| Chicago mayor since 2011 | 24 |
| Chicago Mrs. | 12 |
| Chicago Museum of Science and ___ | 33 |
| Chicago N.B.A. team | 19 |
| Chicago N.F.L. team | 19 |
| Chicago name | 12 |
| Chicago neighborhood | 20 |
| Chicago news group? | 19 |
| Chicago newspaper | 17 |
| Chicago newspaper, familiarly | 29 |
| Chicago nine | 12 |
| Chicago or Boston, e.g. | 23 |
| Chicago or Erie | 15 |
| Chicago or Miami | 16 |
| Chicago Outfit bigwig | 21 |
| Chicago Outfit leader | 21 |
| Chicago Outfit leader of the 1930s | 34 |
| Chicago paper | 13 |
| Chicago paper, briefly | 22 |
| Chicago paper, casually | 23 |
| Chicago paper, familiarly | 25 |
| Chicago paper, familiarly, with "the" | 47 |
| Chicago paper, for short | 24 |
| Chicago paper, for short, with "the" | 46 |
| Chicago paper, informally | 25 |
| Chicago paper, to locals | 24 |
| Chicago phenomenon | 18 |
| Chicago pie style | 17 |
| Chicago pit purchase | 20 |
| Chicago player | 14 |
| Chicago political family | 24 |
| Chicago political name | 22 |
| Chicago pro | 11 |
| Chicago public transportation, familiarly | 41 |
| Chicago put-down? | 17 |
| Chicago rails | 13 |
| Chicago railways | 16 |
| Chicago recording studio | 24 |
| Chicago recruiter | 17 |
| Chicago reviewer | 16 |
| Chicago runners | 15 |
| Chicago sausage king Froman impersonated by Ferris Bueller | 58 |
| Chicago setting (Abbr.) | 23 |
| Chicago setting: Abbr. | 22 |