3 Measly Points

Here's the situation.

I have 13 points as a member of the Southwest frequent flier program, and I need 3 more before 8/23 to get a free roundtrip ticket to any domestic location - that's 3 one-way flights.

A roundtrip ticket to NY costs an average of $275.

I want to go to NY sometime in the next year (which is how long the free ticket is valid for).

My choices:

Purchase tickets from Baltimore to Long Island, from Long Island to Baltimore, and finally, (you guessed it) from Baltimore to Long Island. The total cost for this trip, on 3 airplanes which will each have at least one empty seat during their respective flights, is $120.

Fly from LA to Phoenix to grab lunch with my buddy Steve, from Phoenix to Vegas to play some slots at the airport, and from Vegas to LA just in time for dinner. Total cost: $150 +/- whatever I lose/win on the slots.


Do I minimize the amount of money spent by going with the first option, or do I become a big spender so that I can say that I actually went somewhere this summer?


P.S. Summer school Blows.