I can tell this to you in one line:
If you want to fly for free on Delta or Northwest or Continental airlines or any other Skyteam alliance airlines, it is very very hard to do so.
This post specifically targets Skyteam after my 6-8 day marathon in an attempt to book free tickets using my 31000 flying blue miles. The miles were up for expiry at the end of August, so I was calling around Air France at the end of July to try to book a ticket to the Caribbean or to Latin America (which cost 30000 miles and is a good deal). Of course since Air France is based in France, they do not offer an online booking option for booking on other airlines. This is standard industry practice so I don't blame them.
But the difficult part was trying to find booking on Continental or Delta or Northwest. I searched for several dates in March and in May, and the cheap 30000 miles economy class was not available on either the outward or inward legs for several day pairs that I tried. A word here about looking for award seat availability. Delta's website was by far the easiest which showed availabilty for 14 days before and after your requested date. So at a simple glance at the month you could easily figure out what dates were good. But often, the answer was none. Northwest's website was the worst to deal with. Continental was in between, in terms of searching for award seat availability.
I could not find any availability to (gasp) Puerto Rico (SJU), US Virgin Islands (STT), Santo Domingo (SDU), Caracas (CCS), San Jose Costa Rica (SJO), Honduras (TGP?). The only place with some easier availability was Panama City (PTY) but I was not too keen on Panama, especially compared to Costa Rica. So why do I have an issue with Skyteam: well while I was looking for flights on skyteam airlines, I was also checking on American Airlines, on which there was tons and tons of off peak availability in March and May - the times I was looking for a Spring break or early summer travel. The other reason apart from mile expiry for me was that Delta/Northwest fly out of my little town, but not American.
However, that incentive was removed once I called Air France - they ruled out award tickets from my obscure town's airport and also mentioned that come Jan 09 there wont be any skyteam flights out of here anyway. I spent 3-4 phone sessions lasting 20+ minutes each (burning valuable daytime minutes) looking for tix to Latin america, Hawaii (very hard even normally), or Alaska or even New Mexico or Arizona from the east coast.
At this point I was envisioning conspiracy theories that airline computers are programmed to reduce availability on returns within a week or two of outgoing flights to PR/latin america etc so I started searching in a different browser for awards from Latin America to US to check my theory. Fortunately in that search there was no availability from Latin America to US on my "originally planned return dates". So I felt a ray of hope that there was no evil programming against me. Also, in the past I have tried booking tickets on Jet Airways or Kingfisher airlines only to be quoted outrageous fuel surcharges of $105 per trip so I decided against doing those trips. I should add though that I have flown award tix on United twice without any hassle or major difficulty in finding seats.
So now after 3 phone sessions which did not lead anywhere, I did an aggressive search on Continental.com and finally found availabily in a nice 1 week window in May from JFK to Puerto Rico. That's it, I dropped everything and called Air France, reeled off the exact dates and times to the AF rep and bingo, the agent was happy to find me seats. Of course, little did she know that I knew exactly what was open. Then I had to pay up fuel surcharges and taxes to reserve my ticket so I ended up spending $78 immediately for a ticket next May to a Caribbean island. At least, I would not need to carry a passport on that trip, whew!
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