| Chicago's __ House | 22 |
| Chicago's WNBA team | 23 |
| Chicago's winter hrs. | 25 |
| Chicago's Velvet Fog | 24 |
| Chicago's time zone | 23 |
| Chicago's Sting is one | 26 |
| Chicago's soccer team | 25 |
| Chicago's Sandberg | 22 |
| Chicago's planetarium | 25 |
| Chicago's plane place | 25 |
| Chicago's Papa Bear | 23 |
| Chicago's often on it | 25 |
| Chicago's NFL team | 22 |
| Chicago's Michigan: Abbr. | 29 |
| Chicago's Merchandise ___ | 29 |
| Chicago weather forecast | 24 |
| Chicago transportation | 22 |
| Chicago transit trains | 22 |
| Chicago touchdown site | 22 |
| Chicago to Washington dir. | 26 |
| Chicago to Baltimore dir. | 25 |
| Chicago team, in headlines | 26 |
| Chicago team, for short | 23 |
| Chicago Symphony director | 25 |
| Chicago Sun Times critic | 27 |
| Chicago stopover locale | 23 |
| Chicago Sting's org. | 24 |
| Chicago Sky's org. | 22 |
| Chicago shopping district | 25 |
| Chicago Seven first name | 24 |
| Chicago setting: Abbr. | 22 |
| Chicago setting (Abbr.) | 23 |
| Chicago recording studio | 24 |
| Chicago political name | 22 |
| Chicago political family | 24 |
| Chicago paper, to locals | 24 |
| Chicago paper, informally | 25 |
| Chicago paper, for short | 24 |
| Chicago paper, familiarly | 25 |
| Chicago paper, casually | 23 |
| Chicago paper, briefly | 22 |
| Chicago or Boston, e.g. | 23 |
| Chicago newspaper, familiarly | 29 |
| Chicago mayor since 2011 | 24 |
| Chicago mayor before Emanuel | 28 |
| Chicago mayor -- Emanuel | 24 |
| Chicago Loop's __ Center | 28 |
| Chicago layover, often | 22 |
| Chicago lakefront attraction | 28 |
| Chicago journalist Mike | 23 |
| Chicago hub, on luggage tags | 28 |
| Chicago fire starter: 1871 | 26 |
| Chicago Fire cow owner | 22 |
| Chicago financial area | 22 |
| Chicago expressway with The | 28 |
| Chicago exchange, for short | 27 |
| Chicago Eight defendant Bobby | 29 |
| Chicago Eight defendant | 23 |
| Chicago diamond cutter? | 23 |
| Chicago deep dish chain | 23 |
| Chicago daily, for short | 24 |
| Chicago daily, familiarly | 25 |
| Chicago Cubs' station | 25 |
| Chicago Cubs' field | 23 |
| Chicago commuter options | 24 |
| Chicago commuter carriers | 25 |
| Chicago columnist Kupcinet | 26 |
| Chicago clock setting: Abbr. | 28 |
| Chicago city council mem. | 25 |
| Chicago business district | 25 |
| Chicago Blue Line terminus | 26 |
| Chicago Bears' field | 24 |
| Chicago Bears' coach | 24 |
| Chicago Bears star Devin | 24 |
| Chicago Bears founder George | 28 |
| Chicago Band The Walk-___ | 25 |
| Chicago ballpark eponym, once | 29 |
| Chicago baggage letters | 23 |
| Chicago architect Burnham | 25 |
| Chicago airport letters | 23 |
| Chicago 'L,' e.g. | 25 |
| Chicago from St. Louis | 23 |
| Chic, to Austin Powers | 22 |
| Chic's Broadway partner | 27 |
| Chic piece of jewelry? | 22 |
| CHIC ENG. PAL gets fruit | 24 |
| Chianti and Beaujolais | 22 |
| Chiang's overthrower | 24 |
| Chiang's headquarters | 25 |
| Chiang ___, Mao's widow | 27 |
| Chiang Mai citizen, often | 25 |
| Chiang Kai-shek's haven | 27 |
| Chiang Kai-shek's city | 26 |
| Chiang Kai-shek's capital | 29 |
| Chiang Ch'ing's mate | 28 |
| Chia Pets and Beanie Babies | 27 |
| Chi.-to-D.C. direction | 22 |
| Chi. setting in summer | 22 |
| Chi. Cub or NY Met, e.g. | 24 |
| Chi. Cub or Atl. Brave, e.g. | 28 |