Originally Posted by dgordon
I am not familiar with Southwest Airlines and how thier program works. Do you have to get an award ticket - do the accumulated miles become an award ticket that needs to be used in a year???? With the other programs, the miles sit in an account, and don't expire until you get an award - so that is the model I am used to. Maybe other people familiar with their program would be better to advise you....or go to their thread and see what strategy people use. It's good that you are gathering information - -- Good luck.
I know on WN the rules are tighter: you have a year to accrue 16 points and then a year to redeem the award. I don't know if your 16th point automatically turns into 1 available free flight on the spot, or if you can wait until the anniversary date of the 1st credit, then turn your points into a free flight, and have another year.
Still, the OP has a good point...if he knows he is never going to use WN again, then using the free flight for BWI-MDW is better than letting it expire unused. (I know WN awards are easily moved on the black market for $300+ - I guess if the OP knows the mechanics of that process, he/she could do that and then buy the BWI-MDW ticket.)