Delta has round-trip flights from Houston (IAH/HOU) to San Juan, Saint Thomas, Saint Croix, Aruba, Grand Cayman, Coxen Hole, Costa Rica, Nassau, Belize, Antigua, Montego Bay, Bermuda, Providenciales, Saint Kitts, and more (STX, STT, SJU, AUA, GCM, RTB, LIR, SJO, PUJ, BZE, ANU, MBJ, BDA, PLS, SKB, more..) for $157-$319 with a connection. Flights April to March. Some weekends available.
The cheapest destinations are: San Juan, Saint Thomas, and Saint Croix.
COVID rules and restrictions vary depending on destination. You’ll need to research what rules apply for your trip.