nwflyboy
Contributor
I have Alaska Airlines mileage, and usually never have issues finding a flight that will work. I leave for Cozumel out of Toledo in January via Cancun. My home airport is usually Fairbanks, but since I'm in the lower 48 for the holidays I'll leave out of Toledo this time. This is my 7th trip to either Cozumel or Roatan in 7 years, and each time has been with miles. This will be my second time doing the bag drag as I usually fly into Cozumel, but this time it was going to be either that or staying 6 hours in a connecting airports lobby.
Alaska has the best loyalty program of all the US airlines. I agree that their program is amongst the easiest to use, and it's straightforward, with few sneaky hidden little gotchas. I'm a fan of their program (it's my home-town airline, too, which is nice). Southwest's program is also quite good (although, it's mostly limited to where Southwest goes - not much of a help if you wanna get away to say, Tokyo or Rome - Alaska has partners that cover many international destinations).
That's two of you who said that is generally easy. I wonder if I did it wrong? I checked again, just one-way from Cancun to Lubbock, no restrictions on number of stops or anything - and they show two dates that could work for me in late August, but those include overnights in Houston, or worse. From Cozumel to Lubbock, nothing from August 11 to September 22. View attachment 439409
I never said any of this would be "easy". Some are just worse than others. Right away I see two major issues in your case:
1) Lubbock. Not exactly a major hub. How many United flights a day are there? You need to keep in mind that "award seats" are very, very limited (maybe 1 or 2 per flight at best). If you have just 1 or 2 flights a day to/from a city, that makes it nearly impossible. So if you want to include a leg to/from a smaller city like Lubbock, that limits you tremendously. Try searching from a larger city nearby with more flight options, eg Dallas, maybe even OK City, or Albuquerque.
2) You're late to the game. You're searching for flights roughly 9 months out. For United, they load their inventory 330 days out (~11 months ahead). Flights on popular routes - or on routes with limited availability (see above) get snapped up quickly, sometimes within minutes of loading into the system. If you really want to fly in/out of a small city like Lubbock, you need to book ~300 days out or more. I know some people scoff at planning that far ahead, it's just the way it works.
Hope the above is helpful.