The 10 Cheapest Flights from Boston to the Caribbean

Want to escape Boston's notorious weather? A look at the 10 cheapest flights from Boston to the Caribbean should do the trick.

Hopper Editors - Oct. 26, 2017

For Boston locals all too familiar with the shivering colds of the New England winter and the windswept Atlantic beaches of Cape Cod, the Caribbean — with its glittering sands, sultry year-round temperatures and tepid tropical shore waters — can be a gift straight from heaven. What's more, with oodles of direct and indirect air connections now departing out of the Logan International Airport for the sunny climes of the south, there are some serious bargains to be had on flights. That's why Hopper's expert team has focused the full force of their big data statistics engine on the region — to discover the ten cheapest flights from Boston to the Caribbean, on average.

Also take a look at the 10 cheapest flights from Boston to Europe, according to Hopper's research team

10. Fly from Boston to Saint Croix, US Virgin Islands, for as low as $399 round trip

Our first pick from the beautiful US Virgin Islands, and the most expensive least-expensive destination on Logan's line-up of top 10 bargain departures, comes in the form of Christiansted; a glittering wisp of a town that clusters between the aquamarine waters of the Caribbean Sea and the rising foothills of central Saint Croix island. Tickets on the route will set travelers back just under $400, and all flights fly indirect to the Henry E Rohlsen Airport.

9. Fly from Boston to Montego Bay, Jamaica, for as low as $391 round trip

Nothing says "welcome to the Caribbean" like a plate of Jamaican jerk chicken and the mellifluous tunes of Bob Marley floating through the air, which is why we love these bargain flight connections between Boston's Logan International and Montego Bay — the gateway to the pristine beaches of Negril and Ocho Rios along the island's northern shore. Tickets on the route are currently averaging at around just $391 round trip, with JetBlue's direct flight coming in as the cheapest!

8. Fly from Boston to George Town, Cayman Islands, for as low as $371 round trip

Granting travelers access to the tropical wonders of Grand Cayman, these bargain flights from Boston to George Town can cost as little as $371 return. And while the cheapest seats on the route are with American Airlines going indirect, passengers can opt to pay just a little bit more to fly nonstop with JetBlue, hitting the strips of the Seven Mile Beach after just four hours in the air and saving some cash on checked baggage fees in the process.

7. Fly from Boston to Port-au-Prince, Haiti, for as low as $363 round trip

Ticking over to the earthy tunes of African folk music and the off-beats of Caribbean jazz alike, Haiti has risen like a phoenix from the destruction of the 2010 earthquake and now represents one of the region's most enthralling of destinations, for sure. Yes there are beaches and bustling all-inclusive hotels, but there are also the crumbling walls of old French colonialism to explore and the sobering remnants of the slave trade. All flights to the Toussaint Louverture International Airport from Boston are indirect and will cost passengers around just $363 round trip.

6. Fly from Boston to Oranjestad, Aruba, for as low as $357 round trip

If you've been put off booking a third-quarter holiday to the Caribbean for fear of those tropical storms and cyclones, then this bargain connection from Boston to the Aruban capital of Oranjestad may just be the perfect option. Of course, the island still touts all the usual pristine beaches, fascinating snorkeling spots and luxurious seaside hotels, but also lies far outside the Atlantic Hurricane belt, which keeps it relatively dry for most of the year. What's more, average round trip tickets cost just $357, and perhaps even less on United's indirect route into town.

5. Fly from Boston to Aguadilla, Puerto Rico, for as low as $355 round trip

Midway down our list of the cheapest air connections between Boston and the Caribbean comes pretty, Puerto Rican Aguadilla, which can be found nestled between the rolling left and right surf breaks of the island's western shore, amidst seas of luxury golf resorts and some of the most celebrated beaches the region has to offer. If that sounds like you, then expect to pay around $355 for a round trip ticket into town, and be sure to check out United Airlines' offering, whose indirect route has the cheapest average price tag overall.

4. Fly from Boston to Providenciales, Turks and Caicos, for as low as $351 round trip

Forget ageing colonial homes and hotels set in 16th century mansions, because Providenciales is a land of high, modern, unadulterated luxury — well primed for the honeymoon traveler in search of Caribbean beaches and all the creature comforts of home. Flights to the international airport here from Boston are currently ebbing at a nice low of $351 round trip, with February offering some excellent bargains and direct connections with either US Airways or American coming in as the cheapest.

3. Fly from Boston to Nassau, The Bahamas, for as low as $355 round trip

With Spring Break rearing its hedonistic head once again and all the college-goers of Boston looking for the next big thing, we think these super cheap flights to the throbbing nightlife hub of the Bahamas is going to be big. At an average of just $355 round trip, they actually come in at an exquisitely affordable joint second on this list, leaving oodles of doubloons for the Senor Frogs and the Watling rum bars. The only drawback: Indirect connections are the cheapest, with United, US and American all coming up trumps.

2. Fly from Boston to San Juan, Puerto Rico, for as low as $335 round trip

For travelers looking to immerse themselves in the long history of the Caribbean, San Juan is the perfect place. Around the painted Spanish mansions, narrow flagstone lanes and bustling European plazas of its charming colonial centre lie some of the oldest architectural relics in the New World, from the El Morro citadel to the UNESCO-attested frontispieces of La Fortaleza on the hill. What's more, with average round trip flight prices from Boston sitting at just $355, there should be plenty of cash left in the budget to splash on the museums!

1. Fly from Boston to Saint Thomas, US Virgin Islands, for as low as $294 round trip

And the prize for the single cheapest Caribbean destination for fliers out of Boston's Logan International goes to…Charlotte Amalie on Saint Thomas of the USVI; which is great news for anyone eager to case out this bubbling capital town of boutique jeweler shops and quirky rum joints without having to make the usual cruise ship journey to its shores! Average flight tickets are currently sitting at an amazingly wallet-friendly $294 round trip, although it seems the cheapest connections are indirect, flying with Delta Air Lines, or American via Charlotte, North Carolina.

Learn more ways to find the best deals on airfare by taking a look at our when to fly and buy reports at

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