Southwest has an insane deal to Costa with all bags included. While they do charge an extra $75 for a surfboard bag — that is a lot less than Delta charging $150 PER BOARD, or United who charges $150 per board bag.

Not to mention both of those airlines charge $35 for the first checked bag and $40 for the second. You easily cover your surfboard bag fee just with what you save on the other checked bags (which are free).

Boston to Costa Rica generally runs $450+ — these cheap surf flights save 35% and get you there with One Stop on Southwest Airlines.

While these flights tie / equal the cheapest price I have ever seen to Costa Rica from Boston, the biggest deal here is the free bag fees — THAT we have not seen before. Free bags saves at least $100 extra, probably more like $150 depending on how you pack (and $250ish vs a discount airline like Spirit etc).

These fly into San Jose as opposed to Liberia, so depending on where your final destination is that could be more (or less) of a drive. In years past I have flown into San Jose and then made the drive out to Guanacaste — just because I couldn't get a flight below $650 into Liberia (never got one anywhere near this cheap with bags).

Do-able for sure and 100% worth it to go surf someplace warm this January.

Cheap Costa Rica Flight Availability

Most of the cheapest flights go down in January and February — but there are some options starting as soon as November, or alternately as late as March — both options run another $20-$30 or so.

  • November from $314
  • December from $330+
  • January from $289
  • February from $289
  • March from $330+

How to Book Southwest

Since southwest doesn't allow direct links to specific dates, the best way to go about this is to hit the Southwest Low Fare Calendar. From there enter the airport you want to fly from (BOS to SJO) and then select January (alternately February):

That should land you on the right calendar. You are looking for the flights that are $127 on the way out there, and $164 on the way back. Generally the sale covers October through December.

Once you select a date you want to hit continue at which point you are looking for the One-Stop 'Wanna Get Away' flights.

That should land you with a total of $289 or $290 that ideally looks like this: