American Airlines and Delta have round-trip flights from Austin (AUS) to Kingston Jamaica or Grand Cayman (KIN/GCM) for $318-$359 with a connection. Flights October to November. Very few weekends available. Origin/Destination reversible.
Note: Most flights to Grand Cayman have a long connection for this deal.
Note: Carry-on bag is allowed for free on Delta or American Airlines. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
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