tarjames

If I am booking a flight from STL to San Antonio with a layover in Dallas can I book the flight from STL to Dallas for a RR then the flight from Dallas to San Antonio for another RR. By doing this will I be causing myself any problems?

mritty

You can, but it comes with several caveats:
1) The fare for the two individual flights may be greater than the fare for the one longer one-stop flight. (or it may be less, actually)
2) It will take some extra finagling and a knowledgable counter agent to check your bags all the way through. Otherwise, you'll have to pick them up in Dallas, re check them, and go back through security.
3) If the flight from STL to Dallas is delayed to the point that you miss your connecting flight, Southwest is under no obligation to get you to San Antonio, as you're simply a no-show. If it's a short amount of time after the 2nd flight has left, you'll probably still qualify for standby on the next flight under the "flat tire" rule, but that is an unwritten rule and therefore subject to change.

tarjames

I will not be checking a bag and will make sure to leave plenty of time between flights. It seems worth a try on a round trip getting 4 credits rather than 2. Thanks

mritty

You're welcome. FWIW, this is exaclty what I did last month. I went to book ORF->BWI->ALB, and found that I had a 3.5 hour layover, and the cost of both segments individually was only like $5 more, so I booked them separately and got my extra credit.