sometimes to connect is it cheaper to buy each portion seperate?

[CupCrusher40]

I 'm pretty sure your allowed but will gate agent rebook if late?

[DancingDavidE]

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@CupCrusher40 wrote:

I 'm pretty sure your allowed but will gate agent rebook if late?

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It’s unofficially yes - as long as everything is on Southwest they will be able to see the prior flights. You may have to point it out to them though, the reservation won’t automatically pop up. 

It’s a little rare to see a big price drop on booking multicity vs a Southwest connection, but it is possible. 

[SoCalFlyer97]

@CupCrusher40, 

As @DancingDavidE mentioned, booking Multi-City (or two one way's) for a connection is typically more expensive but with a little bit of "flight shopping", one can still find some good deals for booking separate. Plus there are some advantages of this option that could add value to the overall trip as a trade off to the fare difference depending one's travel needs. A key item to keep in mind though if you're checking any bags under Multi-City or Two One-Ways and both legs occur on the same day, the stopover city will really be your "final" destination after the first leg and your bags will need to be claimed and re-checked for the second leg no earlier than four hours prior to the scheduled second flight. 

Last summer, I booked the Multi-City option for a trip from PDX to SAN. See my photo trip report. On my scheduled trip date, there was not a non-stop flight option but most of the resulting connecting flight options showed SJC as the layover airport.

Since I traveled carry-on only for that trip with a 50L Vancropak Carry-on Backpack as my luggage, I had the added flexibility of being able to leave the SJC layover airport without having to separately hand-carry or cart any luggage. Selecting Multi-City allowed me to 'extend' the SJC layover into a stopover destination with me taking an early morning flight from PDX and a later afternoon flight out of SJC to SAN. Thus, I was able to visit a destination in the Silicon Valley and reconnect with friend who lives there before continuing on to SAN. Multi-City also counted as two one-way flights toward A-List/Companion Pass. That for sure added value to the trip.

However, as I mentioned, I had to wear the Vancropak bag during my San Jose visit and I would assume many travelers would not want to haul their baggage around during a stopover city visit. Yes, there are third-party luggage storage services advertised; I have not used them yet as they don't appear to be fully established (I should check these out though).

Does booking multi-city or separately add value instead of booking a single flight with a connection? I would say "sometimes." 

[DancingDavidE]

I forget from an earlier thread did someone say they did successfully same day change their flight in order to have a long layover somewhere to visit a boyfriend or something?

In that case it was booked as a standard connection and then adjusted on the same day to extend the layover into a stop over.