Southwest "Multi-City" Fare Pricing
 

Just made a curious discovery that I had never seen before, maybe somebody else has?

I was booking a ticket from OAK-DEN in February but prices were a bit high...so as usual I tried seeing if buying two separate segments using the "Return to" option to Denver instead of back to Oakland would be cheaper. So I searched for an OAK-BUR-DEN fare and while the individual segments were $110 and $101 each, the total ticket priced out to $175.

Saved me about $45 from buying a ticket from OAK-DEN (even with the connection) and the BUR fare I found wasn't offered as a choice when booking OAK-DEN.

I just found that odd because I'd never seen the Southwest site lower the price of the combined two segments. Maybe it was a hidden fare from OAK-DEN that just wasn't displaying originally?

I just tried the same thing on an upcoming connecting flight as multi city legs...both legs priced out to $899 but when I clicked continue it adjusted the price down to $649...which is the available price for the connecting flight at AT fare.

Suspect your "reduced" price is somewhere in the system for the OAK-DEN route.

The range of February fares displayed via the lowfare calendar is mostly $69 to $99, with a pair of $119 days, and a pair of $150-ish days. Your $175 fare is higher than any of those. It sounds like your plans are flexible, so you should try finding something via the low fare calendar.

I know...unfortunately I have to be back in Denver before 6pm and I'm not willing to get up at the ungodly hour for a 5:30am departure out of Oakland. Everything else was over $175 on their website. So in the end I was happy with how it worked out, and I don't have to connect in LAX :D

What we call custom connection bookings or A-B-C bookings sometimes offer exceptional value. Usually they cost more than the default fares from A to C. There is no user-friendly rule to determine when you will save money. You just have to hunt for possible connections (one flight number on each leg, plus a legal connecting time) and try them.

Most Southwest customers fly nonstop trips, for which an advanced technique like this is of no use. Unless you want to be even more advanced and book a connection with low on-time performance and hope for a big delay plus success standing by for the nonstop.