[Update 2023.4] Pay Yourself Back has now been extended through June 30, and dining reimbursements are capped at $300. Not sure whether Chase added this restriction early because Aeroplan’s unlimited PYB was being used too heavily.
Chase Southwest co-branded credit cards, both personal and business versions, have added the Pay Yourself Back feature. The redemption rate is 1 cpp toward the annual fee and 0.8 cpp toward dining purchases. In other words, a $100 annual fee can be offset with 10,000 Southwest points, and $80 in dining purchases can be offset with 10,000 Southwest miles.
Unfortunately, Southwest points can only be transferred from Chase UR, so this is probably only worth considering if there is a 30%+ transfer bonus from UR. Also, Southwest points are already quite valuable on their own: redeeming for flights is worth about 1.4 cpp, and with the Companion Pass, the value can be as high as 2.8 cpp. So using points for dining or the annual fee does not make a whole lot of sense. Still, having another redemption option is nice. For example, if you have some small leftover Southwest points, this gives you a way to cash them out.
