Ok, he/they are originating in Pittsburgh, so big difference. I had to look up where you are since it's not on your SB profile, but you are 63 miles from Baltimore, while he/they are 249 miles from that airport. I could get better flights if I drove to Dallas myself but won't, especially because of the return trip. We drove to Abilene for cheaper flights last summer and that backfired!
Checking all possible airlines on Matrix and all airports within 250 miles of Pittsburgh, it seems he could drive to Toronto, ON for non-stop flights, but that's 317 driving miles. Non-stop from a nearby airport to Cancun would beat connecting flights to Cozumel usually, but not an option in this discussion. Working with his situation rather than yours, I don't see any good non-stops to Cancun. So why did you want to confuse the guy?
Again, good to check SWA separately since they don't play on the usual sites or co-op with other airlines, but they don't off
"check nearby airports" on their site either so you just have to know the airports or look them up, then ask SWA one by one if they have non-stop service. Since he whined about getting home at midnight, I doubt he'd want to drive far to catch a plane.
Ugh, who told you Cielo was nice. Hated that place.