Cheapest flights to the Caribbean by island and destination

In order to keep things fairly simple and easy to understand we are listing only the cheapest price we’ve found in the past 7 days in March 2020 (for a future booking in 2020) from any of the 3 New York City-area airports. The prices below are for one person. Interestingly and perhaps a bit surprising, this is the cheapest starting point for many of the destinations listed below due to the size and competition within the flight market. If you are flying to many of the smaller islands you’ll usually have to change planes in Puerto Rico or at least south Florida.

Those coming from cities other than New York will generally have to pay at least a bit more to reach these destinations, although they’ll likely rank in more or less the same order. If you are starting in either Miami or Fort Lauderdale you can find cheaper flights into Nassau (Bahamas), San Juan (Puerto Rico), and the US Virgin Islands, but many destinations are actually more expensive. When traveling from Atlanta you’ll find that there are a few good deals, but again, most prices are actually higher in spite of the shorter distance (thanks, Delta!).

• $118 – San Juan, Puerto Rico
• $244 – Rincon, Puerto Rico
• $284 – St. Thomas, US Virgin Islands
• $291 – Antigua & Barbuda
• $301 – St. Croix, US Virgin Islands
• $313 – Turks & Caicos
• $316 – Grand Cayman, Cayman Islands
• $328 – Aruba
• $333 – Samana, Dominican Republic
• $334 – Bermuda
• $340 – Nassau, Bahamas
• $343 – Trinidad and Tobago
• $350 – Punta Cana, Dominican Republic
• $351 – Anguilla
• $359 – Montego Bay, Jamaica
• $363 – Puerto Plata, Dominican Republic
• $376 – Curacao
• $392 – St. Maarten/St. Martin
• $392 – Negril, Jamaica
• $408 – Grenada
• $417 – Ocho Rios, Jamaica
• $419 – Tortola, British Virgin Islands
• $471 – Barbados
• $557 – St. Kitts and Nevis
• $605 – St. Lucia
• $612 – Guadeloupe
• $629 – Grand Bahama, Bahamas
• $651 – La Romana, Dominican Republic
• $750 – Bonaire
• $780- Martinique
• $961 – St. Barths

For the budget traveler it works out pretty well that most of the cheapest islands to reach are also the ones loaded with the cheaper resorts, but this isn’t always the case. St. Lucia, for example, has many very affordable beach hotels and it’s one of the cheapest of all Caribbean islands to vacation on, but due to the longer distance the flights aren’t quite so cheap.

Nearly all of the bottom third of the list are smaller islands where you’ll have to change planes at least once if not twice to reach them.

Stay tuned for our full Caribbean coverage that will sort out costs at all 31 of these islands and destinations to help find the bargains as well as the best ones to rub elbows with celebrities and others in the 1%.

Photo courtesy of michael feagans on Flickr