It's been years since I've paid any attention to the Southwest Rapid Rewards program. The last time I actually flew them was probably more than 5 years ago. The main reason for this is the very limited (virtually non-existent) partnerships that Southwest has for redeeming on international flights.
However, the RR program has always been fairly lucrative and extremely simple, given that you earn one point for every flight (two points for every round-trip), and 16 points gets you a free round-trip award anywhere Southwest flies. This means you could fly eight round-trips on relatively short (and cheap) hops like SJC-LAX, and then redeem for a cross-country trip.
The new RR 2.0 program that started in March 2011 sort of turns this system on its head. Similar in idea to the Virgin America Elevate program, the value of RR points are now tied to the cost of a ticket and the fare class. The exact details can be found here, but generally, the best value for redemption is now with the lowest Wanna Get Away fares at 60 points per fare dollar. As you go up the fare classes all the way to business fares, the points/dollar needed rises to 120. So while the best values for the RR program has been watered down, you can still get some decent awards if you book the lowest fares at an early date.
Which brings me to the latest offer from the Chase Southwest Visa Signature card. This is probably the best promotion I've seen from Southwest so far, and is the first Southwest credit card application I've actually jumped at. They are offering 50,000 RR points upon your first purchase, which translates to more than $833 in Wanna Get Away fares for redemption. I would say this is one of the better promotions this year, arguably more valuable than the Chase Sapphire Preferred 50,000 points, the Alaska Airlines 40,000 miles, or the US Airways 40,000 miles offer. The offer page says 2 free flights, but that is based on 4 one-way Wanna Get Away fares valued at $208 each (a bit of an arbitrary designation, but whatever).
You earn 2 points per dollar spent on Southwest airlines flights as well as RR hotel and car rental partner purchases, and 1 point per dollar on everything else. You can also receive 1,500 tier qualifying points for every $10,000 in purchases, up to 15,000 tier qualifying points per year. On every cardmember anniversary you will also earn 6,000 RR points. There is a balance transfer option that can net you up to another 15,000 points, but again, the fees make that proposition a fairly expensive one.
The annual fee is $99, and is NOT waived for the first year. The card showed up on my online Chase account with the $99 already charged to it. So actually you are getting a $734 bonus for this application. If you decide to keep this card past the first anniversary, the 6,000 RR bonus effectively pays for the annual fee. This offer ends on August 7, 2011, so if you plan on applying, do so very soon!
(EDIT: This offer has long expired, but the link I've provided still seems to work. You can apply, but there is no guarantee that you will receive the 50,000 bonus points. Proceed at your own risk!)