| Chicago cable station | 21 |
| Chicago cagers | 14 |
| Chicago campus | 14 |
| Chicago cap letters | 19 |
| Chicago carriers | 16 |
| Chicago city council mem. | 25 |
| Chicago Classic restaurant chain | 32 |
| Chicago clock setting | 21 |
| Chicago clock setting: Abbr. | 28 |
| Chicago club | 12 |
| Chicago columnist Kupcinet | 26 |
| Chicago community | 17 |
| Chicago commuter carriers | 25 |
| Chicago commuter options | 24 |
| Chicago company | 15 |
| Chicago conveyance | 18 |
| Chicago cop Lieberman in Stuart M. Kaminsky novels | 50 |
| Chicago Cubs e.g. | 18 |
| Chicago Cubs spring training site | 33 |
| Chicago Cubs' field | 23 |
| Chicago Cubs' station | 25 |
| Chicago daily, briefly, with "the" | 44 |
| Chicago daily, familiarly | 25 |
| Chicago daily, for short | 24 |
| Chicago daily, with "the" | 35 |
| Chicago deep dish chain | 23 |
| Chicago description | 19 |
| Chicago destination | 19 |
| Chicago diamond cutter? | 23 |
| Chicago dinosaur | 16 |
| Chicago district | 16 |
| Chicago district (with ''the'') | 47 |
| Chicago district, with "the" | 38 |
| Chicago Eight defendant | 23 |
| Chicago Eight defendant Bobby | 29 |
| Chicago el feature | 18 |
| Chicago eleven | 14 |
| Chicago embrace? | 16 |
| Chicago entertainment district | 30 |
| Chicago event | 13 |
| 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 |