Should not be a problem. You will need a seat in the back. I think its gratis outbound, but you pay US taxes inbound. One of our friendly DL ticket counter people should be able to help find the taxes for you and you should be able to pay before leaving the US (I think)
If possible I would bring a ZED fare as a backup just in case the gate agent down there doesn't understand the whole jumpseating phenomenon. I can't speak for DAL but at my airline they don't really deal with jumpseaters down there too much. The ZED will generally include all departure taxes and they are 100% refundable if you don't need to use it.
Bring a ZED fair for the return. I got stuck in Delhi, India a day because the American ticket agents did not know how to list me with a taxes only cabin only jumpseat. A ZED fair would have gotten me out that night. I ended up waiting till Continental had a flight the next day and they thankfully knew how to get me out. You can also try buying a TAXES ONLY eticket from your airline.
If the Delta gate agents don't know how to list you remember to try jumpseating on other legacy carriers. If it's a legacy carrier than press the case that you're allowed to jumpseat. If at all possible intercept he flight crew so they motivate the ticket agents.
But seeing how you fly for SWA and not a legacy carrier you may want to actually verify your jumpseat agreements with UAL, AMR and CAL. Good luck!
I did it on NWA... Agent was not too familiar, but they called MSP and figured it out for me. They were very nice about it down there (Cabo)... just make sure you get to the airport early so they can figure it out (took about 1 hour to get sorted out). I paid the taxes to the ticket agent. The Captain was a jerk about it... told me that J/S was for commuters and not for vacation... but he let me on...
Just make sure you have your exit tax paid and you are on the passenger list by 1 hour prior to departure. We had to leave a WN jumpseater in San Jose CR because security thought he was a crew member and didn't send him to the ticket counter to get listed. The gate agent couldn't do anything by the time we found out what was going on - she said the 1 hour requirement was a TSA thing, and the passenger list had already been sent. The poor guy had to wait around 6 hours for the next flight.....
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