Not much money in TA work from what I understand.
You'll know when 330 days is since Cheryl, Nancy, Janice and I will all be talking about it I'm sure. However, it will also depend on when you plan on flying down. Also, I don't think you can get the fly back date until it is 330 days from then. If MW (Airtran doesn't put theirs up at 330 days) sells the one way at 1/2 the cost, then I may pick up our outbound right away and book the return a week later when it comes available.
Doing a quick calculation, if you wait until the return is available, you'd be looking at December 5th of this year (or maybe it's the 6th, but if you try on the 5th and it's not there, no big loss - as opposed to going on, on the 6th to find out it was the 5th

).
We plan on going on Friday, October 23rd, so 330 days should be November 27th for the outbound. If all else fails, we'll fly in/out of Tampa (actually like that because it is less of a hassle) or wait until AT's fairs come out.
If you fly out of Chicago again, you'll have less of a fight for tickets.