I was thinking of visiting Panamá this summer but I'm not really sure if that's the right time to go. Whenever I search, fares are nearly $800 and aren't one-stop (my options are from CLT, RDU, and GSO). I was originally thinking of doing a multi-stop through SJU (stay for a day to say hello to my family then continue) but I don't think I can look at that again XD.
When is the best/cheapest time to visit Panamá? I always go to SJU over the Christmas season and that's usually under $600 per person, but every time I check PTY it's always more expensive than that. Would flying SJU-PTY-SJU for a weekend be cheaper? Or would CLT/RDU/GSO-XYZ-PTY-XYZ-CLT/RDU/GSO during Halloween/Easter/other be cheaper?
(I have family in both SJU and PTY, so hotel prices aren't a problem)

Centroamerica is never cheap, and unlike the usual airline price model, the further you travel from US, the more expensive it is.

Travel within Centroamerica tends to be even worse pricewise, though I have no idea what it would be from SJU. I do know prices TO SJU tend to be rather cheap because of lots of competition.

Wait, you do mean SJU, not SJO, right, because SJO tends to run in $600 range, while SJU tends to be much cheaper.

Long, long time ago TACA used to have Christmas Day / New Year Day sale when you could pick up a ticket very, very cheap, but I doubt they do that anymore.

Yes. To the OP, are you talking about San Jose, Costa Rica (SJO) or San Juan, Puerto Rico (SJU)?

San Juan/SJU. I'm in Charlotte so CLT-SJU in the winter is usually a bit more expensive.

Using miles is a good option here, especially *A miles due to the regional network.

I recently redeemed a one-way from Panama City to Boston, and had a free weekend to kill so.......Instead of PTY-BOS, I booked PTY-MGA(24 hours)-GUA (24 hours)-PTY-BOS. Same 17.5k miles as the non-stop and only 50$ more in taxes.

It'd be very easy to do RDU-UA Hub-SJO (24 hours)-PTY for 17.5 miles in economy.

Of course, you'd have to have some knowledge of miles and how to obtain them and use them more economically than purchasing the plane ticket outright.

Ah yes, the hub penalty / premium

Been able to get some cheap fares to SJU from DFW on UA as it's not a hub, much, much cheaper than to SJO or PTY

Not sure who other than Copa flies SJU-PTY, but Copa's fares aren't normally cheap, so I'm not sure that would save you money.

MIA has a lot of competition, so fares will likely be less expensive from there @:-)

Had to ask. I've talked to so many travelers here in Costa Rica who've told me, "It's so nice here. We've never been to Puerto Rico before." (Got news for you: You still havent.)

I just checked on Copa's website: SJU-PTY round-trip would run you a minimum of $500. That isn't going to save you any money.

Hey, even pilots don't always get it right

"Welcome to San Juan, Costa Rica" was the announcement a few years ago on one of my many flights to SJO

Well Spirit is the ultra-low cost airline to Central America & Northern South America/Caribbean.