Well we always like to go early June- the discounts usually run through the 15th (we also have a PIN that goes through the 7th), a lot of schools are still in session, and maybe it's a degree or two cooler. Just found out SW has one nonstop from Omaha to MCO every Saturday. I'd like to book that if they continue that into the summer, so we are looking at a Saturday-Saturday trip. We'd normally pick the 4th-11th.
HOWEVER, DD14 really wants to go on the band/choir trip to Memphis & New Orleans and that is 6/4-6/9! Which pushes us back to 6/11-6/18 if we let her go. I guess if a public discount runs through the 15th as it has in the past we might still be able to get a partial discount. I would like to go earlier, but would feel bad about telling her she can't take that trip just because we don't want to push ours back a week. Gotta decide on the choir trip by 12/1. SW releases our dates on 12/8, and the early June discount will probably come out around the first of the year.