| Windy City baseball/football teams | 34 |
| Windy City baseballers | 22 |
| Windy City border area | 22 |
| Windy City commuters' inits. | 32 |
| Windy City daily, with "the" | 38 |
| Windy City destination | 22 |
| Windy City gridders | 19 |
| Windy City hrs. | 15 |
| Windy City hub | 14 |
| Windy City landing site | 23 |
| Windy City maestro | 18 |
| Windy City mecca | 16 |
| Windy City newspaper | 20 |
| Windy City newspaper, with "The" | 42 |
| Windy City paper | 16 |
| Windy City paper (with "The") | 39 |
| Windy City paper, familiarly | 28 |
| Windy City paper, with "The" | 38 |
| Windy City people | 17 |
| Windy City player | 17 |
| Windy City politician | 21 |
| Windy City pro | 14 |
| Windy City rail agcy. | 21 |
| Windy City rail agcy. (in NECTAR) | 33 |
| Windy City rail and bus agcy. | 29 |
| Windy City rail and bus org. | 28 |
| Windy City rail inits. | 22 |
| Windy City rail letters | 23 |
| Windy City rail org. | 20 |
| Windy City rail system (abbr.) | 30 |
| Windy City rug? | 15 |
| Windy City sights | 17 |
| Windy City skaters | 18 |
| Windy City superstation | 23 |
| Windy City team | 15 |
| Windy City terminal code | 24 |
| Windy City time | 15 |
| Windy City touchdown site | 25 |
| Windy City tower | 16 |
| Windy City trains | 17 |
| Windy City transportation gp. | 29 |
| Windy City transportation inits. | 32 |
| Windy City transportation org. | 30 |
| Windy City transports | 21 |
| Windy City travel org. | 22 |
| Windy City winter hrs. | 22 |
| Windy City, breezily | 20 |
| Windy City, for short | 21 |
| Windy day features | 18 |
| Windy day misfortunes during a spa visit? | 41 |
| Windy day phenomenon near the shore | 35 |
| Windy day toy | 13 |
| Windy day weather report word | 29 |
| Windy Highlander? | 17 |
| Windy home | 10 |
| Windy locale? | 13 |
| Windy mo. | 9 |
| Windy narrative | 15 |
| Windy one | 9 |
| Windy quality | 13 |
| Windy Scot? | 11 |
| Windy sort | 10 |
| Windy spot in the water? | 24 |
| Windy spray | 11 |
| Windy track star? | 17 |
| Windy weather phenomenon in the Great Plains | 44 |
| Windy weather toy | 17 |
| Windy weekend forecast? | 23 |
| Windy West Coast city? | 22 |
| Windy, rainy season | 19 |
| Windy-day advice | 16 |
| Windy-day eye hazard | 20 |
| Windy-day flier | 15 |
| Windy-day fun | 13 |
| Windy-day toy | 13 |
| Windy-day toys | 14 |
| Windy-weather sights | 20 |
| Windy? | 6 |
| Wind______ | 10 |
| Wine | 4 |
| Wine + soda | 11 |
| Wine + soda water | 17 |
| Wine additive | 13 |
| Wine adjective | 14 |
| Wine aficionado's prefix | 28 |
| Wine agent | 10 |
| Wine and dine | 13 |
| Wine and dine lavishly | 22 |
| Wine and dine, perhaps | 22 |
| Wine and dine, say | 18 |
| Wine and fruit juice drink | 26 |
| Wine and song link | 18 |
| Wine and ___ | 12 |
| Wine aperitif | 13 |
| Wine area | 9 |
| Wine area in Italy | 18 |
| Wine area in the upper boot | 27 |
| Wine area near Turin | 20 |
| Wine area of Italy | 18 |
| Wine asset | 10 |