If you go last-minute, then no one will convince you to not use the award. That's the beauty about the WN awards - if you want to fly on non-blackout days, you can just drive to the airport and hop on a flight. (I assume you know what the blackout days are and are avoiding them.)

But if your plans firm up anytime soon, check again for fares before burning the award. Doing a simple WAS-CHI search in Orbitz using their Flexible Date tool, I see nonstops on every weekend for $184 R/T (which is $179 R/T plus bonus miles booked directly). Obviously that isn't WN, but I'm guessing those fares are available on one or two of the other airlines that you like. Just a little advice, because we FT'ers are programmed to think this way: Friends Don't Let Friends Use Their Awards When $179 Tickets Are Available.