jmastron

Is this separate tickets? I didn't think there was a way to book Southwest (commonly referred to by their code WN) and any other airline together. If not, any misconnect will be treated by Southwest as a no-show. For example, if your HA flight is in the air just 30 minutes longer and you can't call WN to cancel by 10 minutes before that flight, you may have to just forfeit that ticket and buy a new one (which will be more expensive then). Even if on-time, by the time you get to the gate and off the plane (could be 10 minutes) and walk to the Southwest gate (5 minutes) they will be well into boarding regardless of what your position is, and within 15 minutes of the cutoff.

I wouldn't take the risk, but if you are okay taking the next (or later flight) and either have travel insurance that would cover this sort of replacement ticket if needed, or the savings is enough to self-insure and accept the gamble of a much higher cost if it doesn't work out (good prep for Vegas!), it could work.