For me a vacation doesn't become set in stone until the flight is booked. Room reservations, ADRs and tours are all easily cancelled. Just a simple phone call and it's all wiped away. Nothing lost.
As I'm not able to buy expensive, refundable flights, booking a flight has the air of permanence. Sure I could change my flight later on, but even that comes with a $100 fee. Flights are not easily or cheaply changed. Once I've booked my flight, my vacation become so much more real. Until then, for me they are just whispers of what might come to be.
Im lucky enough to have three airports fairly close I can travel from, although leaving from NYC got crossed off the list fairly quickly. My family flat out refuses to drive to the major airports, so that would leave me the option of either driving and parking for the week or taking the shuttle service from CT. I've done both before. Driving there got crossed off the list right off the bat. The one time I did this, I arrived to find the long-term lot at LaGuardia full and had to pay to park in the short-term lot. Luckily the trip was only for a long weekend. Cost me a fortune. The CT limo shuttle costs $130 roundtrip.

I don't think so.
That leaves flying from Hartford, CT or White Plains, NY. White Plains may be slightly closer to my house, but not enough to really factor into the decision. The love and kindness of my family does however, as White Plains is a tiny airport with virtually no parking. It's smack dab in the middle of a ritzy area and the residents have no desire to see the airport grow. As a result, the airport has one tiny garage. It's $2.90 per half hour to park there. $24 per day. Ouch!

That will add up fast. It's an easy drive from my town though, and if you have someone to drop you off it's wonderful.
Hartford is bigger, and if I need to drive and leave my car it's the best option. Lots of lots where you can reserve a spot ahead of time and pay $5-$7 a day to park. It's also close enough, and easy enough to deal with that family doesn't mind dropping me off. (Free - even better).
So basically it comes down to airlines, times and price. Southwest or Delta out of Hartford. AirTran or JetBlue out of White Plains. I've been keeping my eye out on prices for awhile. Delta and AirTran have had their flights listed for awhile and JetBlue just extended through December last Friday. I also tend to be a bit particular when I fly. Especially when I fly to Orlando. I like to leave early enough so that once I arrive I still have enough time to enjoy a good portion of the day in a park. On the way home I'm a little less picky, but prefer to leave late afternoon if possible. I don't do the parks my last day, but I like to take it easy and not have to rush. (Especially with how early ME pickup times are). Later afternoon flights allow me that, and still get me in at a decent time if someone is picking me up. I also like to pick out my seat ahead of time. I hate sitting in the middle seat. Aisle or window is fine, but I hate getting stuck between two strangers for a couple of hours. If possible I prefer non-stop flights as well. It's such a short flight that I hate seeing it drag out with stops.
Delta had a nice early non-stop flight out on Saturday the 5th, and an equally as nice non-stop late afternoon flight home. Not so nice - the price. $365. That doesn't include $30 in baggage fees. AirTran has been my airline of choice for my past few trips to both Orlando. They always had early non-stop flights and decent prices. Not any longer. The only non-stop flight they are offering for the flight down was at 2pm, which would cause me to lose an entire Disney day. In the morning when there used to be a non-stop flight, there is now a flight with one stop. Which would get me into Orlando about 1ish. For the way home there was only one non-stop flight out at about 1:30pm or so. Flights were about $80 each way, but once you add in the luggage and seat selection fees it bounced up to $100 each way.
I got the e-mail on Friday morning that JetBlue's tickets had gone on sale. With what I had seen from Delta and AirTran I wasn't expecting much. Needless to say I was happily surprised to find multiple flights priced decently for both the trip down and the return flight. The flight down was a bit earlier than I would have liked, but wasn't horrible, and there there were a lot of choices for the flights home. Best though - all non-stop flights, first checked bag included, no charge to select a seat and decent prices. I was a bit torn. Should I book now, or wait to see what Southwest's prices are when they eventually release their times, and if I waited would JetBlue's go up too much. Sigh. I wish the airlines would just all release their flights at the same time. It would make life so much easier.
After much thought, I decided that since I was satisfied with JetBlue's fares, and liked everything else about the flights I'd book. Maybe Ill be missing out on a good Southwest deal, but Im happy with what I got. It seems it was the right decision too, as when I took a peak on JetBlues website today the flight to Orlando that I paid $99 for on Friday is already up to $144 and there was only about 2 seats left at that price. The flight home had only gone up about $10.

Woo Hoo!!!

I'm going on vacation. Flights are booked!
Im really going to owe my dad after this. My flight on the way down leaves at 6:40 am. Horribly, horribly early, but luckily hes a morning person. Best though is that Ill be in Orlando by 9:30 am. Ill have pretty much the whole day in the parks. My flight home is at 4:30, so at least thats being a bit kinder when he picks me up.
No backing out now!