Southwest has round-trip flights from Dallas (DAL) to San Jose del Cabo, San Jose Costa Rica, Providenciales, Turks & Caicos Islands (SJD, SJO, PLS) for $233-$291, with a connection. About $96-$164 each-way. Flights September to November. No Fridays. Origin/Destination reversible.
Note: Turks & Caicos has limited availability, mid-August to the end of August.
Carry-on and checked bag are allowed for free. Southwest doesn’t charge change fees.
Additional Savings: Sam’s Club is selling $500 Southwest gift cards for $449 [linked]. You can save an additional $50 on Southwest flights if you travel often enough or with a big enough group to burn through the gift card credit.
Use the fare calendar links to pull up the fares.