American Airlines has round-trip flights from Austin (AUS) to Port of Spain or Curacao (POS/CUR) for $342 with a connection. Flights scattered between July and November. Departures mostly on Monday, Tuesday, Wednesday, and Thursday. Extended Weekends available.
Priceline has “Express Deals” for $325/$387. With “Express Deals” the airline and exact flight are hidden until after purchase and those purchases are final. There is no 24-hour free cancellation for “Express Deals”. The flight is guaranteed to be on a major airline. Be sure to select the deal with 0 to 1 stops and a layover less than 4-hours.
Change fees are waived and carry-on bag is allowed for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
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Click for more details and booking links Cheap Flights: Austin to Port of Spain, Trinidad $325-$342 or Curacao $387-$408 r/t [July-November] – American Airlines / Priceline Express