February 21, 2026 Boston to Trinidad for only $280 roundtrip Cheap flights from Boston to Trinidad for only $280 roundtrip with Copa Airlines.
February 20, 2026 New York to the US Virgin Islands for only $226 roundtrip Cheap flights from New York to the US Virgin Islands for only $226 roundtrip with Delta Air Lines.
February 20, 2026 Dallas, Texas to the Cayman Islands for only $278 roundtrip Cheap flights from Dallas, Texas to the Cayman Islands for only $278 roundtrip with JetBlue.
February 20, 2026 Non-stop from Manchester or Birmingham, UK to Montego Bay, Jamaica from only £329 roundtrip Non-stop flights from Manchester or Birmingham, UK to Montego Bay, Jamaica from only £329 roundtrip.
February 19, 2026 Amsterdam, Netherlands to San Juan, Puerto Rico for only €397 roundtrip Cheap flights from Amsterdam, Netherlands to San Juan, Puerto Rico for only €397 roundtrip with JetBlue.
February 17, 2026 Ottawa, Canada to Turks and Caicos for only $385 CAD roundtrip Cheap flights from Ottawa, Canada to Turks and Caicos for only $385 CAD roundtrip with United Airlines.
February 17, 2026 London or Manchester, UK to Barbados from only £420 roundtrip Cheap flights from London or Manchester, UK to Barbados from only £420 roundtrip with KLM.
February 15, 2026 Glasgow, Scotland to Barbados for only £450 roundtrip Cheap flights from Glasgow, Scotland to Barbados for only £450 roundtrip with KLM.
February 12, 2026 Non-stop from Fort Lauderdale to Montego Bay, Jamaica for only $275 roundtrip Non-stop flights from Fort Lauderdale to Montego Bay, Jamaica for only $275 roundtrip with JetBlue.