I've been planning WDW trips for myself (Chicago) and family that live in Indy and San Fran and this is the highest I've ever seen it. We usually go early November or early December but chose October to coincide with some school fall breaks. SW seems to have less flights which coupled with fall breaks becoming more common, maybe that is pushing up fares. I looked at the afternoon SW non-stop MCO-IND for the Sunday home for my family and the day the schedule opened at 5am when i got up it was $249. I pretty much balked at that and checked again when I got to work....$299. Next day it sat at $329....then a week later only Anytime Fares remained. Now 3 months out and it's sold out. We were somewhat limited with times as we want to have a little park time that Sunday but want to have the kinds in bed at a reasonable time. We ended up settling on non-stop SFB-Louisville on Allegiant for an okay price when you factor in bag/seat fees. But we are giving up a little peace of mind by booking operationally challenged Allegiant vs Southwest or Delta.
I think current airline pricing models are keeping prices higher, longer and discounting even closer to departure than in the past. That makes it much riskier to wait on flights. If they discount flights a month out it might drop a lot. But if you hold out and the flights are selling well, you could be paying much higher, close-in fares that are more targeted at price-insensitive business people. I do think October flights will come down...but who knows. I use Google flights to track my flights. They don't do SW flights, but do all the others. They watch your flights and send emails when a flight you are tracking drops/increases. It's a great tool to help grab a lower fare when they drop.