I was able to get a southwest charge reimbursed the other day. My fare was $229.96 and I paid it this way:
91.99 - travel funds from a prior reservation
40.00 - purchased a WN GC using my Hilton card while not signed into my account. This was not reimbursed
97.97 - charged on my AMEX Hilton card. Purchased the flight on July 3, The $97.97 was reimbursed on July 6.