| Chicago paper, informally | 25 |
| Chicago paper, to locals | 24 |
| Chicago political family | 24 |
| Chicago political name | 22 |
| Chicago recording studio | 24 |
| Chicago setting (Abbr.) | 23 |
| Chicago setting: Abbr. | 22 |
| Chicago Seven first name | 24 |
| Chicago shopping district | 25 |
| Chicago Sky's org. | 22 |
| Chicago Sting's org. | 24 |
| Chicago stopover locale | 23 |
| Chicago Sun Times critic | 27 |
| Chicago Symphony director | 25 |
| Chicago team, for short | 23 |
| Chicago team, in headlines | 26 |
| Chicago to Baltimore dir. | 25 |
| Chicago to Washington dir. | 26 |
| Chicago touchdown site | 22 |
| Chicago transit trains | 22 |
| Chicago transportation | 22 |
| Chicago weather forecast | 24 |
| Chicago's Merchandise ___ | 29 |
| Chicago's Michigan: Abbr. | 29 |
| Chicago's NFL team | 22 |
| Chicago's often on it | 25 |
| Chicago's Papa Bear | 23 |
| Chicago's plane place | 25 |
| Chicago's planetarium | 25 |
| Chicago's Sandberg | 22 |
| Chicago's soccer team | 25 |
| Chicago's Sting is one | 26 |
| Chicago's time zone | 23 |
| 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, with "the" | 29 |
| Chicago-based daytime host | 26 |
| Chicago-based film critic | 25 |
| Chicago-based film reviewer | 27 |
| Chicago-based food giant | 24 |
| Chicago-based Superstation | 26 |
| Chicago-based TV talk show | 26 |
| Chicago-St. Louis dir. | 22 |
| Chicago-style deep dish chain | 29 |
| Chicago-style hot dog options | 29 |
| Chicago-style, as pizza | 23 |
| Chicago-to-Atlanta dir. | 23 |
| Chicago-to-Atlanta direction | 28 |
| Chicago-to-Baltimore dir. | 25 |
| 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-Nashville dir. | 25 |
| Chicago-to-Pittsburgh dir. | 26 |
| Chicago-to-St. Louis dir. | 25 |
| Chicagoan in 1871 news | 22 |
| ChicagoÂ’s ___ Tower | 23 |
| Chichén Itzá attraction | 29 |
| Chichén Itzá builder | 26 |
| Chichén Itzá natives | 26 |
| Chichén __: Mayan ruins | 26 |
| Chichén ___ (Mayan city) | 27 |
| Chichén ___ (Mayan ruins) | 28 |
| Chichén ___ (Mayan site) | 27 |
| Chichen Itza residents | 22 |
| Chichi shopping area in Tokyo | 29 |
| Chick chaser's cry | 22 |
| Chick Corea and Miles Davis | 27 |
| Chick lit book #1 (1992) | 24 |
| Chick lit book #3 (1965) | 24 |
| Chick lit book #4 (1974) | 24 |
| Chick lit book #5 (1960) | 24 |
| Chick lit book #6 (1930) | 24 |
| Chick lit book #7 (1985) | 24 |
| Chick lit book #8 (1967) | 24 |
| Chick that gives a hoot | 23 |
| Chick's expression | 22 |
| Chick's first course? | 25 |
| Chick's pronouncement | 25 |
| Chick's slang mate | 22 |
| Chick, Clifton, Jack, and Jim | 29 |
| Chick-fil-A spokescritter | 25 |
| Chick-___-A (fast food chain) | 29 |
| Chick-___-A (mall eatery) | 25 |
| Chickadee's chirps | 22 |
| Chickadee's cousin | 22 |
| Chickadee's perch. | 22 |