American Airlines and United have round-trip flights from Houston (IAH) to Turks & Caicos Islands, Bahamas, Jamaica, or Costa Rica (PLS, NAS, MBJ, LIR) for $265-$336 with a connection. Flights April to May. Origin/Destination reversible.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.