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If I book two one ways does my Southwest count that as a round trip flight so that I can meet the qualifications for keeping A-list the rest of the year?
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Southwest requires 25 one way flights to qualify for A-List status. If you book a trip as a roundtrip that would count as 2 flights for the purpose of A-List qualification. Booking as one-way versus roundtrip does not affect your qualification count.
The one exception would be if you booked a flight to go from A to B that had a layover in Q. If you booked the flights separately as A to Q and Q to B that would count as 2 trips for A-List. This is usually more expensive than just booking A to B and could lead to problems if the A to Q flight was delayed or if you were planning on checking baggage.
Hope that helps clear things up,
--TheMiddleSeat