| Windy City baseball/football teams | 34 |
| Windy City commuters' inits. | 32 |
| Windy City daily, with "the" | 38 |
| Windy City newspaper, with "The" | 42 |
| Windy City paper (with "The") | 39 |
| Windy City paper, with "The" | 38 |
| Windy City rail agcy. (in NECTAR) | 33 |
| Windy City transportation inits. | 32 |
| Windy day misfortunes during a spa visit? | 41 |
| Windy day phenomenon near the shore | 35 |
| Windy weather phenomenon in the Great Plains | 44 |
| Wine bluntly turned down in "Sideways" | 48 |
| Wine community in Sonoma County, CA | 35 |
| Wine connoisseur's consideration | 36 |
| Wine designation, or a cologne brand | 36 |
| Wine disparaged in "Sideways" | 39 |
| Wine enthusiast's list of killer reds? | 42 |
| Wine enthusiast's philosophy? | 33 |
| Wine featured in "Sideways" | 37 |
| Wine flavored by pine resin-sealed barrels | 42 |
| Wine made from the Garganega grape | 34 |
| Wine made from the moscato bianco grape | 39 |
| Wine made from the Moscato grape | 32 |
| Wine mentioned in Hungary's national anthem | 47 |
| Wine popularized by "Sideways" | 40 |
| Wine quality denoted by the word "sec" | 48 |
| Wine refused in "Sideways" | 36 |
| Wine region of the Gironde département | 41 |
| Wine region south of the Matterhorn | 35 |
| Wine region where Riesling is made | 34 |
| Wine sometimes blended with Cabernet Sauvignon | 46 |
| Wine that causes incoherent talk? | 33 |
| Wine type named after a river in western German | 47 |
| Wine whose name means "fragrant" | 42 |
| Wine whose name means "young blackbird" | 49 |
| Wine, hot water, sugar, nutmeg and lemon mix | 44 |
| Wine-drinking, egg-eating rituals | 33 |
| Wine-growing county in California | 33 |
| Wine-producing area of SE France | 32 |
| Wine-serving twin of a fictional mouse? | 39 |
| Winehouse "Tears ___ on Their Own" | 44 |
| Winehouse "You ___ Me Flying" | 39 |
| Winemaker's aboveground storage | 35 |
| Winemaking village east of Verona | 33 |
| Winery owner's autobiography? | 33 |
| Wines revived by new fermentation | 33 |
| Winfrey's production company | 32 |
| Winfrey's quasi-eponymous studio | 36 |
| Wing of a bird and arm of a man, e.g. | 37 |
| Wing that won't aid in flying | 33 |
| Winged assistants of private eyes? | 34 |
| Winged figure of Greek mythology | 32 |
| Winged forms of ants, aphids, etc. | 34 |
| Winged god who's a symbol of romance | 40 |
| Winged goddess of Greek mythology | 33 |
| Winged insect with letter marking | 33 |
| Winged monster who fought Godzilla | 34 |
| Winged thing + winged thing = English club | 42 |
| Winged University of Miami mascot | 33 |
| Winger "___ for a Heartbreak" | 39 |
| Winger in "Black Widow" | 33 |
| Winger of "An Officer and a Gentleman" | 48 |
| Winger of "Black Widow" | 33 |
| Winger of "Shadowlands" | 33 |
| Winger of "Terms of Endearment" | 41 |
| Winger of "Urban Cowboy" | 34 |
| Winger/Whitesnake guitarist Beach | 33 |
| Wings "___ People Never Know" | 39 |
| Wings' "--- Wheels" | 33 |
| Wingtip-to-wingtip dimension for an airplane | 44 |
| Winkler of "Happy Days" | 33 |
| Winkler role, with "the" | 34 |
| Winnebago enthusiast, in the lingo | 34 |
| Winnemac, in Sinclair Lewis novels | 34 |
| Winner at Madison Square Garden: Sept. 1977 | 43 |
| Winner at the Battle of Cold Harbor | 35 |
| Winner at the inaugural Latin Grammy Awards | 43 |
| Winner at the second battle of Bull Run | 39 |
| Winner between two Pats Super Bowls | 35 |
| Winner in a famous 1948 headline | 32 |
| Winner in a landmark 1973 Supreme Court case | 44 |
| Winner in an hors d'oeuvres cook-off? | 41 |
| Winner in Mailer's "The Fight" | 44 |
| Winner of '82 PGA Anheuser-Busch classic | 44 |
| Winner of "Survivor: Cook Islands" | 44 |
| Winner of "The Thrilla in Manila" | 43 |
| Winner of 10 tennis Grand Slam singles titles | 45 |
| Winner of 100 NCAA team championships | 37 |
| Winner of 101 Pulitzer Prizes: Abbr. | 36 |
| Winner of 11 Grand Slam tournament titles | 41 |
| Winner of 12 NCAA basketball championships | 42 |
| Winner of 14 tennis majors in the 1990s | 39 |
| Winner of 159 electoral votes in 1996 | 37 |
| Winner of 2.7% of the 2000 presidential vote | 44 |
| Winner of 81 P.G.A. Tour victories | 34 |
| Winner of 82 PGA Tour tournaments | 33 |
| Winner of a career Grand Slam in tennis | 39 |
| Winner of a Fox talent show beginning in 2002 | 45 |
| Winner of a landmark 1966 Supreme Court decision | 48 |
| Winner of a noted 1978 Supreme Court case | 41 |