$71 Find Cheap Flights from Massachusetts to Caribbean Islands

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Useful Info

Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$71
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 28% increase in price.
Flight from Hartford 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 Providenciales Airport (PLS), with an average flight price of $179.

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

    Based on KAYAK data, the cheapest day to fly to Caribbean Islands is Monday where round-trip tickets can be as cheap as $282. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $320 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 morning, when round-trip flights cost $289 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. The most expensive time of day to fly to Caribbean Islands is generally at night, which is peak travel time and where the average cost of a ticket is $330.

  • 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 $179 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 $179.

  • 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 $464 (return) on average. On the other hand, the most expensive months are December and February, when the average cost of round-trip tickets is $833 and $655 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 4 weeks before departure.

  • How long is the flight to Caribbean Islands?

    An average nonstop flight from Massachusetts to Caribbean Islands takes 5h 46m, covering a distance of 1699 miles. The shortest route is Boston (BOS) to Nassau (NAS) with an average flight time of 3h 22m.

  • What are the most popular destinations in Caribbean Islands?

    Based on KAYAK flight searches, the most popular destination is Punta Cana (17% of total searches to Caribbean Islands). The next most popular destinations are Oranjestad (14%) and Santo Domingo (12%). Searches for flights to Montego Bay (9%), to Santiago de los Caballeros (8%) and to Simpson Bay (5%) are also popular.

Book cheap flights from Massachusetts to Caribbean Islands

Recent round-trip flight deals

8/3Sun
nonstopSpirit Airlines
4h 05mBOS-SJU
8/6Wed
1 stopSpirit Airlines
9h 56mSJU-BOS
$175
8/3Sun
nonstopSpirit Airlines
4h 05mBOS-SJU
8/4Mon
1 stopSpirit Airlines
7h 16mSJU-BOS
$177
8/24Sun
1 stopFrontier
15h 45mBDL-SJU
8/30Sat
nonstopFrontier
4h 00mSJU-BDL
$185
8/21Thu
1 stop
15h 45mBDL-SJU
8/27Wed
1 stop
9h 10mSJU-BDL
$186
8/24Sun
nonstopFrontier
3h 55mBDL-SJU
8/28Thu
nonstopFrontier
4h 00mSJU-BDL
$198
8/24Sun
nonstop
3h 55mBDL-SJU
8/27Wed
1 stop
9h 10mSJU-BDL
$203
11/26Wed
nonstopArajet
4h 15mBOS-SDQ
11/30Sun
nonstopArajet
4h 15mSDQ-BOS
$228
11/27Thu
nonstopArajet
4h 15mBOS-SDQ
11/30Sun
nonstopArajet
4h 15mSDQ-BOS
$238
8/26Tue
nonstopJetBlue
4h 04mBOS-SJU
9/3Wed
nonstopJetBlue
4h 04mSJU-BOS
$244
11/1Sat
nonstopJetBlue
3h 59mBOS-STT
11/8Sat
1 stopJetBlue
6h 17mSTT-BOS
$302

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Recent one-way flight deals

8/31Sun
1 stopFrontier
15h 45mBDL-SJU
$71
7/12Sat
1 stopFrontier
10h 49mBOS-SJU
$75
8/3Sun
nonstopSpirit Airlines
4h 05mBOS-SJU
$76
8/10Sun
nonstopSpirit Airlines
4h 05mBOS-SJU
$78
9/1Mon
1 stopSouthwest
7h 05mBOS-SJU
$127
9/2Tue
nonstopDelta
4h 08mBOS-SJU
$132
8/2Sat
nonstopJetBlue
3h 22mBOS-NAS
$134
7/30Wed
1 stopDelta
8h 21mBOS-SXM
$137
10/1Wed
1 stopSouthwest
11h 50mBDL-SJU
$145
10/3Fri
nonstopJetBlue
3h 50mBDL-SJU
$150

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Last minute flights from Massachusetts to Caribbean Islands

Last minute flight, train and bus deals

7/7Mon
multi-stopFrontier
21h 19mBDL-SJU
7/11Fri
nonstopFrontier
4h 00mSJU-BDL
$222
7/7Mon
multi-stopFrontier
21h 19mBDL-SJU
7/27Sun
nonstopFrontier
4h 00mSJU-BDL
$238
7/8Tue
multi-stop
14h 58mBOS-SJU
7/12Sat
multi-stop
11h 10mSJU-BOS
$243
7/8Tue
multi-stop
14h 58mBOS-SJU
7/17Thu
nonstop
4h 17mSJU-BOS
$244
7/6Sun
nonstopSpirit Airlines
3h 54mBOS-SJU
7/12Sat
multi-stopSpirit Airlines
11h 10mSJU-BOS
$276
7/6Sun
nonstopSpirit Airlines
3h 54mBOS-SJU
7/10Thu
nonstopSpirit Airlines
4h 17mSJU-BOS
$278
7/8Tue
nonstopJetBlue
3h 50mBDL-SJU
7/17Thu
multi-stopJetBlue
9h 56mSJU-BDL
$322
7/8Tue
multi-stopAmerican Airlines
9h 55mBOS-STT
7/22Tue
multi-stopAmerican Airlines
12h 00mSTT-BOS
$330
7/4Fri
nonstopJetBlue
3h 57mBDL-SJU
7/16Wed
nonstopJetBlue
3h 53mSJU-BDL
$360
7/8Tue
multi-stopAmerican Airlines
6h 29mBOS-PUJ
7/15Tue
multi-stopAmerican Airlines
12h 05mPUJ-BOS
$394

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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 $236
Business Class flights to Caribbean Islandsfrom $185
Prem Econ Class flights to Caribbean Islandsfrom $182
Economy Class flights to Caribbean Islandsfrom $39

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