When to buy flights

[katieclooney]

We will be headed to WDW Labor day week (sept 2-6).
When is the best time to buy flights?
We are coming out of Chicago, but could easily fly out of Milwaukee.
Currently finding flights around $360 round trip on AA.

Thanks!

 

[Disneydreamer23]

I'm from Chicago to i fly mid way, march they always have 99 dollar flights to Orlando through south west for aug through October

 

[katieclooney]

are they direct flights or am i gonna be wasting the day on a plane?