HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$91+ Cheap flights from Massachusetts to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/20. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
may. 6 — may. 131
mar. 5/6
mar. 5/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Massachusetts to Caribbean Islands

Keep the following information in mind while searching for Massachusetts to Caribbean Islands flight deals. Data was last updated mayo 1, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$151
(Cheapflightsfares)

One-way from

$91
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$254
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-San Juan flights.
Search Deals
From Massachusetts to Caribbean Islands
Search Deals
One-way flight from Massachusetts to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2025
Search Deals

Find flight deals from Massachusetts to Caribbean Islands

Cheapest flights from Massachusetts to Caribbean Islands
Explore the most affordable flight options available from Massachusetts to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on mayo 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/84:40 pmBOS - SJU
1 stop8h 31mSpirit Airlines
mié. 10/1512:55 pmSJU - BOS
1 stop10h 34mSpirit Airlines
Deal found 4/30$155
This eDestinos deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/1511:43 amBOS - SJU
Nonstop4h 01mFrontier
dom. 5/186:30 amSJU - BOS
Nonstop4h 13mFrontier
Deal found 4/30$179
This Cheapflightsfares deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/259:15 amBDL - SJU
1 stop7h 31mSpirit Airlines
jue. 7/315:41 pmSJU - BDL
1 stop14h 29mSpirit Airlines
Deal found 4/30$184
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/59:05 pmBOS - SJU
1 stop13h 27mMultiple Airlines
jue. 5/156:30 amSJU - BOS
Nonstop4h 13mMultiple Airlines
Deal found 4/30$194
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 6/812:27 pmBDL - SJU
1 stop6h 40mMultiple Airlines
dom. 6/156:20 amSJU - BDL
Nonstop4h 02mMultiple Airlines
Deal found 4/30$197
This Cheapflightsfares deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 6/111:38 amBDL - SJU
Nonstop3h 55mFrontier
vie. 6/66:36 amSJU - BDL
Nonstop4h 02mFrontier
Deal found 4/30$214
This American Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/111:23 amBOS - SJU
2 stops8h 47mAmerican Airlines
lun. 10/612:00 pmSJU - BOS
1 stop12h 19mAmerican Airlines
Deal found 4/30$223
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/138:10 amBOS - SJU
Nonstop4h 05mDelta
mié. 9/171:27 pmSJU - BOS
Nonstop4h 12mDelta
Deal found 4/30$224
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/215:30 amBOS - SJU
1 stop7h 04mUnited Airlines
lun. 9/291:05 amSJU - BOS
1 stop8h 04mUnited Airlines
Deal found 4/30$233
This JetBlue deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/710:15 pmBOS - SJU
Nonstop4h 02mJetBlue
jue. 11/137:00 pmSJU - BOS
Nonstop4h 18mJetBlue
Deal found 4/30$234
This Priceline deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/35:45 amBOS - STT
1 stop7h 51mSpirit Airlines
mar. 6/102:41 pmSTT - BOS
1 stop7h 09mSpirit Airlines
Deal found 4/30$263
This American Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 5/185:44 amBDL - SJU
1 stop8h 56mAmerican Airlines
vie. 5/237:15 amSJU - BDL
1 stop17h 37mAmerican Airlines
Deal found 4/30$265

Cheapflights Fare Finder

Customize your flight search to find flights from Massachusetts to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated mayo 1, 2025.
Use the filters below to find and compare flights from Massachusetts to Caribbean Islands that are best for you.

Fly from

Massachusetts

Fly to

Caribbean Islands

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

jue. 5/29

9:46 am-8:02 pm

1 stop10h 16m

San Juan Luis Munoz Marin Intl

mar. 6/3

1:59 am-9:09 am

1 stop7h 10m

$170

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

jue. 5/15

11:43 am-3:44 pm

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

dom. 5/18

6:30 am-10:43 am

Nonstop4h 13m

$179

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

vie. 7/25

9:15 am-4:46 pm

1 stop7h 31m

San Juan Luis Munoz Marin Intl

jue. 7/31

5:41 pm-8:10 am

1 stop14h 29m

$184

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

lun. 5/5

9:05 pm-10:32 am

1 stop13h 27m

San Juan Luis Munoz Marin Intl

jue. 5/15

6:30 am-10:43 am

Nonstop4h 13m

$194

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

dom. 6/8

12:27 pm-7:07 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

dom. 6/15

6:20 am-10:22 am

Nonstop4h 02m

$197

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

dom. 6/1

11:38 am-3:33 pm

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

dom. 6/8

6:36 am-10:38 am

Nonstop4h 02m

$214

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

mar. 6/3

5:45 am-1:36 pm

1 stop7h 51m

Saint Thomas Island Cyril E King

mar. 6/10

2:41 pm-9:50 pm

1 stop7h 09m

$263

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

dom. 5/18

5:44 am-2:40 pm

1 stop8h 56m

San Juan Luis Munoz Marin Intl

vie. 5/23

7:15 am-12:52 am

1 stop17h 37m

$265

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

dom. 6/1

8:03 pm-11:56 pm

Nonstop3h 53m

San Juan Luis Munoz Marin Intl

mié. 6/4

4:00 pm-8:06 pm

Nonstop4h 06m

$266

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

jue. 5/15

6:00 am-4:20 pm

2 stops10h 20m

Saint Thomas Island Cyril E King

mar. 5/20

1:25 pm-10:49 pm

1 stop9h 24m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Massachusetts to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Massachusetts with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Massachusetts to Caribbean Islands

What is the cheapest month to book a flight from Massachusetts to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Massachusetts to Caribbean Islands (average of $254). Flying from Massachusetts to Caribbean Islands in December is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MA to EPX?

Find hourly flight availability from Massachusetts to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated mayo 1, 2025.

When flying from Massachusetts to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Massachusetts to Caribbean Islands

Explore weekly flight availability from Massachusetts to Caribbean Islands. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated mayo 1, 2025.

The most flights from USMA to zzEPX are scheduled on a Thursday (18 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated mayo 1, 2025.
See what other customers who have flown with Delta, Alaska Airlines and Southwest from Massachusetts to Caribbean Islands have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Alaska Airlines
8.0
Very good
9,972 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Southwest
8.0
Very good
4,294 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Copa Airlines
7.5
Good
1,415 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Massachusetts to Caribbean Islands one-way?

    The cheapest airlines for a one-way flight from Massachusetts to Caribbean Islands are Spirit Airlines ($91), Frontier ($97), and JetBlue ($134).

  • Can I find deals for flights from Massachusetts to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Caribbean Islands.

  • Can I find deals for business class flights from Massachusetts to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Massachusetts to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Massachusetts to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Massachusetts to Caribbean Islands (average of $254). Flying from Massachusetts to Caribbean Islands in December is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Massachusetts to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to John F Kennedy Intl flights
LaGuardia to Fort Lauderdale flights
John F Kennedy Intl to Los Angeles flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to Miami flights
Dallas/Fort Worth to LaGuardia flights
LaGuardia to Miami flights
Newark to Miami flights
Newark to Las Vegas flights
Los Angeles to Seattle flights
LaGuardia to Dallas/Fort Worth flights
LaGuardia to O'Hare Intl flights
San Francisco to John F Kennedy Intl flights
Newark to Orlando flights
Dallas/Fort Worth to Seattle flights
Los Angeles to Newark flights
Newark to Cancún flights
Dallas/Fort Worth to Los Angeles flights
Dallas/Fort Worth to O'Hare Intl flights
Dallas/Fort Worth to John F Kennedy Intl flights
O'Hare Intl to Dallas/Fort Worth flights
John F Kennedy Intl to Seattle flights
O'Hare Intl to LaGuardia flights
Seattle to Los Angeles flights
George Bush Intcntl to Cancún flights
Los Angeles to Dallas/Fort Worth flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to Cancún flights
Newark to Dallas/Fort Worth flights
John F Kennedy Intl to Cancún flights
John F Kennedy Intl to Fort Lauderdale flights
Newark to Seattle flights
Dallas/Fort Worth to Newark flights
John F Kennedy Intl to Orlando flights
O'Hare Intl to Cancún flights
Newark to San Francisco flights
LaGuardia to Atlanta flights
Newark to Los Angeles flights
Los Angeles to LaGuardia flights
LaGuardia to Orlando flights
Newark to O'Hare Intl flights
San Francisco to Newark flights
John F Kennedy Intl to Hobby flights
LaGuardia to Los Angeles flights
John F Kennedy Intl to Dallas/Fort Worth flights
Seattle to John F Kennedy Intl flights
John F Kennedy Intl to San Francisco flights
San Jose to Los Angeles flights
John F Kennedy Intl to West Palm Beach flights

Top 10 airlines flying from Massachusetts to Caribbean Islands

Discover the top 10 airlines that operate flights from Massachusetts to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated mayo 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$364FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$84Average$459FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$494FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$145Average$550FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$156Average$734FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$204Average$551FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$282Average$599FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$529FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$364Average$520FlexibilityNo cancel feeOn-time70%
SouthwestCheapest$402Average$787FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.