The winter season tends to be a busy and lucrative period for airlines offering routes connecting the US to popular holiday destinations, typically in the Latin American and Caribbean markets. Major US airlines, including American Airlines, United, JetBlue, Delta Air Lines, and Southwest, all offer extensive winter schedules to the Caribbean.
Winter island escapes can be expensive, but you can book holidays to five handpicked and popular Caribbean destinations using earned points and miles. This guide highlights five Caribbean islands that travelers can visit by redeeming points and miles from major US airline loyalty programs.
1 St. Lucia
Airline: American Airlines
American Airlines has long been a major player in the Caribbean market. In May 2024, the airline unveiled its winter schedule, adding eight new Caribbean routes from its hubs across the US. Most of America’s flights to the Caribbean operate from its hub in Miami (MIA).
Photo: Anand Balaji | Shutterstock
However, the airline opted to expand its route network across different bases. One of these routes, opening on December 7, 2024, connects New York (JFK) with St. Lucia’s Hewanorra International Airport (UVF). This will be a Saturday-only flight, utilizing the carrier’s Boeing 737s. According to the airline’s website, a round-trip ticket between JFK and UVF would cost 16,000 AAdvantage points in the main cabin and 40,000 points in business class.
Photo: American Airlines
It is worth noting that JetBlue is the only competitor operating nonstop scheduled flights on this route.
The airline announced eight new routes today.
2 Dominica
Airline: United Airlines
Dominica is seen as an ideal winter holiday destination, and 
The Star Alliance carrier will operate once-weekly flights between the two cities using its fleet of Boeing 737-700 aircraft. It is worth noting that passengers can use the United Airlines MileagePlus points. The round-trip economy ticket between EWR and DOM would cost approximately 50,000 MileagePlus points.
Photo: United Airlines
Notably, United Airlines is the sole carrier offering service between EWR and DOM. However, it is worth mentioning that other US airlines also serve DOM airport, though from different airports and with varying frequencies.
The new route will launch in February 2025, and will be operated by the Boeing 737.
3 St. Martin
Airline: Delta Air Lines
St. Martin is not only a good winter getaway but also a planespotters’ paradise. Many airlines, from European to US carriers, serve this destination. The island is best known for its beaches, which offer close-up views of planes landing just overhead.
Photo: Mayskyphoto | Shutterstock
According to the aviation analytics company Cirium, Delta Air Lines is among five US airlines offering services to St. Martin (SXM). The Atlanta-based airline has three routes connecting SXM airport:
Atlanta (ATL) to SXM New York (JFK) to SXM Minneapolis (MSP) to SXM
Delta’s most frequently operated route is from ATL to SXM, with 28 monthly flights in November 2024, according to Cirium data. Delta runs the SkyMiles loyalty program, meaning that passengers with approximately 66,000 SkyMiles points can afford the round-trip between the two destinations.
Photo: Delta Air Lines
4 Curaçao
Airline: JetBlue Airways
JetBlueoffers a strong route network throughout the Caribbean. The airline has been expanding its services by adding new routes and increasing flight frequencies from its primary base at New York John F. Kennedy International Airport (JFK).
Photo: Markus Mainka | Shutterstock
In 2023, JetBlue increased the number of flights from New York’s JFK Airport to Curaçao International Airport (CUR) from three to five times a week. According to Flightradar24.com data, the carrier currently operates daily flights connecting JFK and CUR. Notably, the airline utilizes its fleet of Airbus A320 aircraft on approximately four-hour flights.
JetBlue runs the TrueBlue loyalty program. The round-trip ticket between the two destinations would cost passengers approximately 24,000 TrueBlue miles.
Photo: JetBlue
It’s important to note that JetBlue is the only airline operating the route from JFK to CUR. While American Airlines also flies to CUR, it only operates from its Miami (MIA) base. Delta offers nonstop service from its ATL base, while United flies to CUR from Newark (EWR).
5 San Juan, Puerto Rico
Airline: Southwest Airlines
San Juan, Puerto Rico, is a highly popular island destination for American travelers, especially during the winter season. 
Austin (AUS) Baltimore/Washington (BWI) Chicago (MDW) Fort Lauderdale (FLL) Houston (HOU) Nashville (BNA) Orlando (MCO) St. Louis (STL) Tampa (TPA)
Photo: Austin Deppe | Shutterstock
It is worth noting that one of the most popular routes includes nonstop flights from Orlando International Airport (MCO) to San Juan Airport (SJU) in Puerto Rico. A round-trip ticket between Orlando (MCO) and San Juan (SJU) costs around $350.
Travelers can also book the flight using miles and points through Southwest’s Rapid Rewards loyalty program. According to the airline’s website, the cheapest round-trip ticket would cost approximately 36,000 Rapid Rewards points.
Photo: Southwest Airlines
Southwest also offers flights to destinations in the Caribbean, such as Nassau, Aruba, Punta Cana, Grand Cayman, Montego Bay, Turks and Caicos, and Havana.
The big three US legacy carriers undoubtedly made the list.
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Publish date : 2024-10-11 17:02:00
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