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When you have flexibility in your holiday season and it is a top priorities to keep flights cheap, I would strongly recommend that you stay at home for Christmas and New Year's Eve and go to another season. Although you really want to go in wintry weather, late November/early December and January/February are usually some of the best times for flights.
Bearing all this in mind, if you are still planning to fly somewhere over the holiday season, here's how you should get close to looking for cheap flights for Christmas and New Year's Eve: Book when: Tariffs on most carriers are sold approximately 12 month after the date of travel. South West Airways, which only a few month later published air fares.)
The Christmas/NYE flights of the next year will be sold in the same way as the Christmas/NYE flights of this year. They do not want to delay the booking until the last moment (prices are prone to rise), but they also do not want to book too early because they might miss a possible fall in rates in the near term.
You should try to book 5-10 month before your trip. This is much sooner than most other flight bookers, so you have a better opportunity to get the cheap places. Not only book an old ticket in the month of February to July, but rather await a particularly good price during this time.
As Christmas/NYE approaches, especially within a few month, I wouldn't expect to get anything that resembles a "cheap" one. So if you haven't made your booking by September and really want to go somewhere over Christmas/NJA, I would just be hoping not to be chiseled out. Cheap flights at the last moment or stand-by flights are practically non-existent these days. What's more, they're no longer a problem.
I would be glad if you are living in a big town ( NYC, LA, etc.) to get ~$500 sightseeing vacation flights to Europe, maybe a shadow higher to Asia. So the more flexibility you have with an airport, the better your chance of getting a cheap one. As an example, the price of a return trip from Philadelphia to Amsterdam may be $1,000, but only $500 from New York to Amsterdam.
From NYC to Amsterdam, prices can be $1,000, but only $500 NYC to Brussels. Location flights are your boyfriend. As an example, to book a one-way trip from Pittsburgh to London will usually be about $1,000, and even more over Christmas/NJA. On the other side, flights from NYC to London usually come for 500 dollars, if not more cheap.
Normally you can find a $150 roundtrip flight from Pittsburgh - or just ride if you feel cheeky - and cut your $350 by splitting your journey into two routes rather than one. It' a little less comfortable, safe, but if you are looking for cheap Christmas/NYE flights, your choices are generally less than perfect.