I'm sorry if this has been discussed before, but I haven't seen it.

By definition it has always been possible to use a RR to get anywhere in southewest's system one-way, including airports not normally sold on one PNR. For instance, although ISP-PHL isn't a route served by southwest it can be ticketed as a point to point ticket using a rapid reward. The method by which to do this on WN's website is to use the first column in booking as the originating city, followed by the middle column as the connection city and the last column as the arrival city.

IE a common routing for PHL to ISP would be

1st column PHL
2nd column MDW
3rd column ISP

with both departing and arrival dates being the same.

Interstingly enough the connecting seems to be able to be nearly any city served by WN. Also although forcing a layover usually can only be limited to I think 3 hours in situations such as the one listed above the three hour limit doesn't apply.

This results in an interesting use of a RR, I have a good friend who goes to school in PHL who's mother lives in MCO and who's father has an office in ISP, for him it is possible for him to visit his mother in MCO for approx 12 hours or so on the way to his father's office in ISP, using only half a RR.

This back door is only really useful in most cases where two airports are relatively close together for instance WAS and BWI can, I believe it was trickier to ticket, use this method to take one day trips to places on half an RR.

The question I have is since

"For one roundtrip Award, you can make roundtrip reservations for travel to destinations in the continental U.S., including New York's LaGuardia Airport, Washington D.C.'s Reagan National Airport, and Dallas/Ft. Worth International Airport. And, for two roundtrip Awards,"

it would stand to reason that for half a round trip award you should be able to fly one way between ISP and LGA possibly with the connecting city anywhere you wanted, as is the case with other cities that service isn't scheduled between. Could one not use this as a cheaper way for one day meetings etc? It would seem that this is more ideal than any other airport combinations because there is easy relatively cheap access to both ISP and LGA via public transit. (The problem with using the phl isp example or most airports is that you would have a concern as to how to get to and from the aiport considering you couldn't leave your car at one because you would be arriving to another etc. I know LIRR out in the morning would be possible returning on amtrak at night but this would defeat the purpose i think)

Sorry for making this post so long, but I think the part about what was possible was complicated and not discussed enough to be well known before going into the question about the new ATA rewards.

The problem/concern is that I haven't been able to get a flight to "price out" using the website to go from LGA to ISP as one half a RR, perhaps a phone call is needed? What are thoughts and ideas about this whole concept?

Thanks!