Work out what your Rapid Rewards points are worth on a given fare - a simpler calculation than most programs, because Southwest ties the points price directly to the cash price.
Rapid Rewards is close to a fixed-value currency: the points cost of a Southwest ticket moves in step with the cash cost, so the cents per point you get stays within a narrow range whatever you book. That makes Southwest points genuinely easy to plan around. There is no saver space to hunt for and no award chart to learn. If a seat is for sale, it can be bought with points, which is a real advantage over programs where availability is the binding constraint.
The single most valuable thing in the Southwest ecosystem is not a redemption rate, it is the Companion Pass, which lets a chosen person fly with you for taxes only on both cash and points bookings. Earn it and you have effectively halved the cost of every flight for the rest of that year and the following one. Anyone seriously optimizing Southwest is doing it around the Pass qualification window rather than around cents per point, and timing when you earn it matters enormously because of how the two-year validity is calculated.
Southwest points bookings can generally be cancelled with the points returned to your account, which makes speculative booking far less risky than it is elsewhere. Booking early at a good price and rebooking if the fare drops is a normal part of using the program well, and it is worth building into how you think about the value rather than treating it as a footnote.
Chase Ultimate Rewards transfer to Rapid Rewards at 1:1. Because Southwest points are near-fixed in value, that transfer usually returns less than sending the same points to a partner where the ceiling is higher. The exception is when you need a specific Southwest seat and are short, or when a transfer bonus is running - check our transfer bonus tracker. Note also that transferred points do not count toward Companion Pass qualification, which catches people out.