Not exactly.

If you transfer to SWA the exchange from UR points to RR points is 1:1. When you buy a ticket with RR points the points are usually valued in the 1.2-1.5 c/point range. For example, a couple fares I'm tracking for upcoming travel include a $129 fare that is 8500pts + $5.60 (which works out to 1.45c/point) and another $224 fare that is 17000points + $5.60 (1.28c/point). (You could also argue that these c/p values are slightly too high because they don't account for the couple hundred new RR points and status credits I'd get from flying on a paid ticket, or you could argue that the full refundability of the RR reward tickets makes them more valuable. But you get the idea.)

If you book through the Chase portal, you're getting 1.25 (CSP) or 1.5 (CSR) per point, and getting the equivalent of a cash ticket that earns new points and status credits.

Change/refund flexibility is the other big consideration (all of this assumes you're buying the cheapest fares, not Business Select or whatever):

• Tickets booked with RR are fully refundable, period. If you cancel, you get your points back.
• Tickets booked on southwest.com with cash, if canceled, currently give you a credit that can be used toward one or more future tickets. .
  • At the moment those credits never expire. But soon (I think starting 5/27/25, so just another week or two) Southwest will add expiration dates of 6-12months depending on the specific fare..
• Tickets booked through the Chase portal (whether you pay with cash or UR points or a mix), if canceled, give you a credit that can only be used toward one future flight. If you use it to book a new flight that is cheaper than your original flight, you forfeit the excess.
  • Currently those credits are good for 12 months from the original booking. I assume they'll add the 6 month expiration for applicable fares once those fares exist.