Since you're going in October, and SW has already posted their schedules for October there's not a big chance that low cost airlines will reduce their fares much. Normally, I've seen a pattern that alot of the non-major airlines (i.e. ATA, AirTran, Spirit, America West, etc.) wait to see what SW is doing. There is a chance, however, with these new "Ding" fares that SW might come up with something for your time period.
It's hard to give an opinion because I know how difficult it is to just "bite the bullet" and grab the tickets. Last year I got burned on ATA. The tickets went down about $25 per about a month and a half after I bought them. I probably should have done something about it, but with the impending pull out of ATA from Midway to Orlando, I didn't see a need to because we probably wouldn't be flying with them to any other destination but Orlando.
We are thinking AirTran as well for this December simply because I can't bare to become a part of the SW Cattle Call, but if the prices are substantially better, I don't see an alternative. I'd hate to think of having to get up an hour earlier to get to O'Hare.
All I can off you is Good Luck and have a great trip!!
Brian