Southwest Airlines Community

There are limits to how you can book. Multi-City trips involve only two destinations, not three. International flights often require a clear departure and return ticket. Southwest may wait until you are at the ticket counter to check when there is uncertainty. One-way'ing the non-international portion may work best. ... View more

@parpitt1 wrote: You can double check but I believe you clear customs in Costa Rica at the airport before boarding for return to the USA.  I don't think Costa Rica has it yet - Bermuda, Bahamas, and Aruba.    Southwest wouldn't sell this combination if they didn't think it would work most of the time.    The wildcard here is if you clear customs in MCO if they let you recheck luggage and have a dedicated access to security re-screening in the international area or if you have to go back to the main lobby in which case the lines can be long.   Maybe @bec102896  have you ever come back to the US with MCO as the gateway? How is the customs and re-screening?     ... View more