I'm assuming you'll be flying to WDW. I lived in California (Central Coast) for 16 years. Traveled a lot to East Coast frequently for family and WDW over the years. We are DVC Members so we start planning 12 months out and booking window opens at 11 months. So, I start trolling airline sights as soon as 12 months out. I my experience, at the 12 month and 11 month mark, airfare is extremely expensive. It will go down....it will go up. Constantly changing. It's good to have an idea of the cost now so when you think you found a better price, you'll know for sure and not second guess yourself. You didn't mention when you were traveling, but as you probably already know, anytime time it's a holiday or when school is out, it's going to be more expensive. As I mentioned, I lived on the Central Coast. So we usually flew out of a small airport with connections either at SFO or Phoenix. It wasn't cost effective for us to fly out of SFO because of all the other costs like hotel and parking. Hopefully you're flying out of a larger airport. As far as Southwest goes, again my experience, it wasn't a money saver and not just because of being in SFO for us. In most cases, United beat Southwest prices. I did try one year (we were traveling to WDW for Easter) to get those great deals on Southwest when the window was opening for holiday airfare for Easter. I stayed up all night because you never know when it will go live. I couldn't even get to the site or get them on the phone. Sold out sooooo quickly. In that case, the airfare was really low and would of been worth flying out of SFO. But I think most importantly know your budget and what you're willing to spend so when that fare comes up in your price range, get it and don't second guess yourself.