Certainly, you'll have no issues. Just remember to get the tag for it before boarding time, and note that SWA is one of the few airlines that will have you sign a damage claim waiver in order to check (either at gate or regular baggage) a stroller.
No only is it FREE to check in - but you can take it directly to the gate with you and check it at the airplane and when you arrive - it should magically appear right outside the plane when you walk off! Sometimes, even opened and ready to go!
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Let Dreams Unlimited Travel take care of all the details, so you can sit back, relax, and enjoy a stress-free vacation.