I've done it again, purchased yet ANOTHER plane ticket. I don't think I have had a credit card cycle all year in which I haven't purchased at least one round-trip ticket. I've already earned one Jet Blue round trip ticket and am well on my way to another. JFK is my home airport, so Jet Blue is my airline of choice, and while they tend to be the cheapest, I will still pay for their service and in-flight TV for up to $20 more than the next-cheapest airline if they are not the best deal. I consider this to be the price of entertainment value, as well as an investment towards free flights via my Jet Blue points.
My usual style of purchasing tickets is that I A) develop an urge to go somewhere or B) have a real reason to go somewhere (i.e. wedding, event), I find the best flight, and I try to grab it before prices go up. My favorite travel search engine is Kayak.com- it's simple and you can change all kinds of parameters to compare only the flights you want. (I've become picky about travel times and layovers since my weekends are short) Sometimes I watch fares for a while, but I'm of the camp that believes in "first price is the best price." Not always the case- flight prices do tend to fluctuate. My experience with Jet Blue is that if the price drops by more than $20 after you purchase the flight, they will award you the difference in flight credit to use for future flights. Given the current state of airline penny-pinching, I don't know how willing they are to do this anymore, but it's happened for me twice in the past.
In regards to the ticket I just bought, it involved some cost/time/convenience analysis.
I used a Jet Blue reward voucher to book a ticket to San Francisco the Thursday night before a Friday night wedding. (You can now split Jet Blue rewards into two one-way tickets) I know a lot of people in the Bay area, so I decided that rather than leave on Saturday, I would like to leave on Sunday so that I can visit some people and maybe go out on Saturday night. Having taken half a dozen red-eyes back to NYC from the west coast this year already, I decided early that I did not want to fly out Sunday night. Unfortunately, the only flight leaving the Bay area for which I could use my other one-way Jet Blue reward (OK I love Jet Blue but I hate how difficult they have made it to redeem rewards lately!) was a Sunday morning flight out of San Jose with a connection in Long Beach that would add about 2.5 hours to my travel time. San Jose is not convenient to either of the possible locations I would be staying (either with a friend in Oakland or in SF), nor could I get there using BART, and I like to be self-reliant rather than make a friend drive all the way out there super early in the morning. I found a flight on Virgin America (love airlines with in-flight entertainment) for $220 that left SFO slightly earlier in the morning, which means I could get back to NYC with some time to unwind, and get myself to the airport if necessary. I tracked the VA flight for a couple of weeks and watched it go up to $270, so when it came back down to $220, I felt the need to decide quickly.
Summary of options:
Free flight, inconvenient airport (might cost me $50 in cab fare to get there if no one can take me), extra 2.5 hours with layover
$220 flight, convenient airport, direct with an early-ish return to NYC.
Conclusion: I chose the $220 flight. I can save the voucher for another time, even if the flight value may not be as high as this cross-country one, but any added expense of getting to an inconvenient airport probably compensates for this fact.
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