Given airfare trends, I think it makes sense to book holiday travel as soon as possible (if you haven’t already). If that happens, I won’t have saved any points but I’ll save myself a phone call to Southwest to see if they could split the PNR to remove me and re-add me. The other half of the reason why I booked my seat separately is because my wife may earn a companion pass this year, in which case it would be easier to cancel my seat and re-add me as her companion if I were on a separate reservation from the beginning.
I should caution though that separating your family onto different PNRs could cause a headache in the event of irregular operations, which is always a threat at peak travel periods (particularly when you mix in winter weather). That’s only a savings of 1500 points, but I’ll take a small win here and there. However, by booking my seat first and separately, we paid 9,990 points for my seat and 34,500 points for the other 3 passengers. When I input 4 passengers for my family of 4, Southwest displayed a price of about 11,500 points per passenger (about 46,000 points for my family of 4). For example, on one flight I booked, there was 1 seat left at 9,990 points. Note that if you’re booking multiple passengers, you may be able to save some points by splitting up your booking. Southwest Airlines has extended its booking calendar to January 4, 2023.I just booked my holiday trips and in the five minutes between looking at dates and discussing times, some of the flights we wanted increased in price. If you were looking to book flights around the December holidays, you probably want to do that sooner rather than later given the trends on domestic airfares. Southwest has today extended its booking calendar into early 2023.