$76 Find Cheap Flights from Massachusetts to Caribbean Islands

1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Useful Info

Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$76
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 28% 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 San Juan Luis Munoz Marin Intl Airport (SJU), with an average flight price of $182.

  • 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 $274. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $319 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 $285 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 $324.

  • 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 $157 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 $157.

  • 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 $465 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $833 and $656 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 59m, covering a distance of 1752 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 Oranjestad (18% of total searches to Caribbean Islands). The next most popular destinations are Punta Cana (16%) and Santo Domingo (10%). Searches for flights to Santiago de los Caballeros (9%), to Montego Bay (8%) and to Saint Thomas Island (5%) are also popular.

Book cheap flights from Massachusetts to Caribbean Islands

Recent round-trip flight deals

7/8Tue
1 stop
14h 58mBOS-SJU
7/24Thu
nonstop
4h 17mSJU-BOS
$162
7/12Sat
1 stopFrontier
16h 59mBOS-SJU
7/16Wed
1 stopFrontier
18h 09mSJU-BOS
$167
6/30Mon
1 stopSpirit Airlines
13h 04mBOS-SJU
7/10Thu
nonstopSpirit Airlines
4h 17mSJU-BOS
$185
7/27Sun
nonstopSpirit Airlines
4h 05mBOS-SJU
8/7Thu
nonstopSpirit Airlines
4h 17mSJU-BOS
$186
10/19Sun
nonstopJetBlue
3h 50mBDL-SJU
10/26Sun
nonstopJetBlue
4h 10mSJU-BDL
$280
8/18Mon
1 stopJetBlue
8h 04mBOS-SJU
8/22Fri
nonstopJetBlue
4h 07mSJU-BOS
$289
9/16Tue
2 stopsAmerican Airlines
9h 38mBDL-SJU
9/24Wed
2 stopsAmerican Airlines
17h 17mSJU-BDL
$289
10/17Fri
1 stopDelta
7h 22mBDL-SJU
10/24Fri
1 stopDelta
9h 21mSJU-BDL
$299
9/8Mon
1 stopAmerican Airlines
10h 13mBOS-STT
9/11Thu
1 stopAmerican Airlines
7h 34mSTT-BOS
$311
6/30Mon
1 stopDelta
6h 49mBOS-SJU
7/8Tue
nonstopDelta
4h 14mSJU-BOS
$319

Search by stops

Search by airline

Search by price

Recent one-way flight deals

7/17Thu
nonstopSpirit Airlines
4h 05mBOS-SJU
$76
7/13Sun
nonstopSpirit Airlines
4h 05mBOS-SJU
$78
7/8Tue
1 stopFrontier
14h 58mBOS-SJU
$84
7/12Sat
1 stopFrontier
16h 59mBOS-SJU
$87
7/16Wed
1 stop
11h 03mBOS-SJU
$131
8/17Sun
2 stopsAmerican Airlines
7h 33mBOS-NAS
$139
6/25Wed
1 stopSouthwest
8h 45mBDL-SJU
$143
7/25Fri
1 stopAmerican Airlines
14h 26mBOS-NAS
$144
8/19Tue
1 stopSouthwest
8h 15mBDL-SJU
$145
8/10Sun
1 stop
9h 15mBOS-SDQ
$158

Search by stops

Search by airline

Search by price

Last minute flights from Massachusetts to Caribbean Islands

Last minute flight, train and bus deals

6/19Thu
multi-stopFrontier
11h 49mBOS-SJU
6/25Wed
multi-stopFrontier
23h 52mSJU-BOS
$194
6/20Fri
multi-stopFrontier
9h 50mBOS-SJU
6/28Sat
multi-stopFrontier
23h 52mSJU-BOS
$201
6/20Fri
multi-stop
9h 50mBOS-SJU
6/26Thu
nonstop
4h 07mSJU-BOS
$223
6/21Sat
multi-stop
16h 17mBDL-SJU
6/25Wed
multi-stop
12h 50mSJU-BDL
$225
6/22Sun
nonstopSpirit Airlines
3h 54mBOS-SJU
6/26Thu
nonstopSpirit Airlines
4h 07mSJU-BOS
$238
6/20Fri
multi-stopSpirit Airlines
15h 12mBDL-SJU
6/23Mon
multi-stopSpirit Airlines
12h 50mSJU-BDL
$255
6/21Sat
multi-stopSouthwest
6h 35mBDL-SJU
7/9Wed
multi-stopSouthwest
8h 30mSJU-BDL
$349
6/21Sat
multi-stopAmerican Airlines
8h 59mBDL-SJU
6/24Tue
multi-stopAmerican Airlines
10h 36mSJU-BDL
$367
6/19Thu
multi-stopAmerican Airlines
16h 08mBDL-SJU
6/24Tue
multi-stopAmerican Airlines
10h 36mSJU-BDL
$376
6/20Fri
multi-stopSouthwest
13h 00mBOS-SJU
6/24Tue
multi-stopSouthwest
7h 05mSJU-BOS
$388

Search by stops

Search by airline

Search by price

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 $198
Business Class flights to Caribbean Islandsfrom $185
Prem Econ Class flights to Caribbean Islandsfrom $182
Economy Class flights to Caribbean Islandsfrom $37

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.