$77 Find Cheap Flights from Massachusetts to Caribbean Islands

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Useful Info
Useful Info

Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$77
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 29% increase in price.
Flight from Boston to San Juan Airport

FAQs for booking flights from Massachusetts to Caribbean Islands

  • How does KAYAK find such low prices on flights from Massachusetts to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Massachusetts to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Massachusetts to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Massachusetts to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Massachusetts to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Massachusetts to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Massachusetts to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Massachusetts to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which is the cheapest airport to fly into in Caribbean Islands?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Caribbean Islands is Castries Hewanorra Airport (UVF), with an average flight price of $158.

  • What is the cheapest day to fly to Caribbean Islands?

    Based on KAYAK data, the cheapest day to fly to Caribbean Islands is Tuesday where round-trip tickets can be as cheap as $260. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $308 on average.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the evening, when round-trip flights cost $280 on average. Morning departures are around 1% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $299.

  • What is the cheapest flight to Caribbean Islands?

    The cheapest ticket to Caribbean Islands from Massachusetts found in the last 72 hours was to San Juan Luis Munoz Marin Intl Airport, at $134 round-trip. The most popular route is Boston (BOS) to San Juan Luis Munoz Marin Intl Airport (SJU) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $134.

  • What is the cheapest month to fly from Massachusetts to Caribbean Islands?

    The cheapest month for flights from Massachusetts to Caribbean Islands is September, when tickets cost $478 (return) on average. On the other hand, the most expensive months are December and February, when the average cost of round-trip tickets is $844 and $661 respectively.

  • How far in advance should I book a flight from Massachusetts to Caribbean Islands?

    To get a below average price on the flight from Massachusetts to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

  • How long is the flight to Caribbean Islands?

    An average nonstop flight from Massachusetts to Caribbean Islands takes 6h 14m, covering a distance of 1725 miles. The shortest route is Boston (BOS) to Nassau (NAS) with an average flight time of 3h 19m.

  • What are the most popular destinations in Caribbean Islands?

    Based on KAYAK flight searches, the most popular destination is Oranjestad (18% of total searches to Caribbean Islands). The next most popular destinations are Santo Domingo (14%) and Punta Cana (13%). Searches for flights to Montego Bay (7%), to Santiago de los Caballeros (7%) and to Providenciales (5%) are also popular.

Book cheap flights from Massachusetts to Caribbean Islands

Recent round-trip flight deals

6/15Sun
nonstopSpirit Airlines
3h 54mBOS-SJU
6/19Thu
nonstopSpirit Airlines
4h 07mSJU-BOS
$151
5/29Thu
1 stopSpirit Airlines
12h 57mBOS-SJU
6/4Wed
1 stopSpirit Airlines
9h 17mSJU-BOS
$152
5/15Thu
nonstopFrontier
4h 01mBOS-SJU
5/18Sun
nonstopFrontier
4h 13mSJU-BOS
$193
5/15Thu
nonstopFrontier
4h 01mBOS-SJU
5/18Sun
nonstopFrontier
4h 13mSJU-BOS
$194
5/15Thu
nonstop
4h 01mBOS-SJU
5/29Thu
1 stop
9h 12mSJU-BOS
$197
5/16Fri
1 stop
12h 57mBOS-SJU
5/18Sun
nonstop
4h 13mSJU-BOS
$198
9/20Sat
1 stopAmerican Airlines
14h 41mBOS-SJU
9/24Wed
2 stopsAmerican Airlines
8h 33mSJU-BOS
$223
10/16Thu
nonstopDelta
4h 12mBOS-SJU
10/22Wed
nonstopDelta
4h 17mSJU-BOS
$224
8/31Sun
nonstopDelta
4h 07mBOS-SJU
9/6Sat
nonstopDelta
4h 20mSJU-BOS
$269
5/13Tue
2 stopsAmerican Airlines
10h 25mBOS-STT
5/20Tue
1 stopAmerican Airlines
9h 24mSTT-BOS
$291

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Recent one-way flight deals

6/21Sat
1 stopSpirit Airlines
14h 25mBOS-SJU
$77
6/21Sat
1 stopSpirit Airlines
14h 25mBOS-SJU
$81
5/15Thu
nonstopFrontier
4h 01mBOS-SJU
$90
5/15Thu
nonstopFrontier
4h 01mBOS-SJU
$96
5/13Tue
1 stopSouthwest
6h 45mBDL-SJU
$138
5/31Sat
nonstopJetBlue
3h 53mBDL-SJU
$140
5/20Tue
1 stop
21h 06mBOS-SJU
$140
5/24Sat
nonstopJetBlue
3h 53mBDL-SJU
$160
5/29Thu
2 stops
31h 50mBOS-STI
$160
5/6Tue
1 stopSouthwest
10h 25mBDL-SJU
$180

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Last minute flights from Massachusetts to Caribbean Islands

Last minute flight, train and bus deals

5/3Sat
multi-stopSpirit Airlines
12h 27mBOS-SJU
6/6Fri
multi-stopSpirit Airlines
9h 12mSJU-BOS
$192
5/3Sat
multi-stopSpirit Airlines
12h 27mBOS-SJU
6/5Thu
multi-stopSpirit Airlines
7h 10mSJU-BOS
$199
5/4Sun
nonstop
4h 00mBOS-SJU
5/18Sun
nonstop
4h 13mSJU-BOS
$206
5/3Sat
multi-stop
12h 27mBOS-SJU
5/8Thu
nonstop
4h 13mSJU-BOS
$213
5/3Sat
multi-stopFrontier
14h 25mBDL-SJU
5/18Sun
nonstopFrontier
4h 04mSJU-BDL
$284
5/1Thu
nonstopFrontier
3h 54mBDL-SJU
5/15Thu
nonstopFrontier
4h 04mSJU-BDL
$304
5/5Mon
multi-stopAmerican Airlines
14h 16mBDL-SJU
5/12Mon
multi-stopAmerican Airlines
17h 25mSJU-BDL
$339
5/5Mon
multi-stopAmerican Airlines
10h 25mBOS-STT
5/31Sat
multi-stopAmerican Airlines
17h 39mSTT-BOS
$340
5/3Sat
nonstopJetBlue
3h 45mBDL-SJU
5/18Sun
nonstopJetBlue
3h 56mSJU-BDL
$343
5/3Sat
nonstopJetBlue
3h 45mBDL-SJU
5/17Sat
nonstopJetBlue
3h 57mSJU-BDL
$353

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Everything you need to know for your flight to Caribbean Islands

Cabin class types available on flights to Massachusetts

Cabin classes available on flights to Massachusetts. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Caribbean Islandsfrom $162
Business Class flights to Caribbean Islandsfrom $288
Prem Econ Class flights to Caribbean Islandsfrom $182
Economy Class flights to Caribbean Islandsfrom $42

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