Caribbean Islands

$45+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
ene. 13 — ene. 201
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Cheap flight deals from Massachusetts to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from Massachusetts (USMA) to Caribbean Islands (zzEPX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 8, 2025.

Round-trip from

$106
(Frontier)

One-way from

$46
(Kiwi.com)
From Massachusetts to Caribbean Islands
One-way flight from Massachusetts to Caribbean Islands

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 enero 8, 2025.

This Mytrip deal was found by Cheapflights users on 1/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 1/286:00 amBOS - SJU
1 stop9h 07mFrontier
jue. 2/137:00 amSJU - BOS
Nonstop4h 18mFrontier
Deal found 1/7$109
This Cheapflightsfares deal was found by Cheapflights users on 1/7. 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.
mar. 2/410:00 amBOS - SJU
1 stop8h 45mSpirit Airlines
mié. 2/124:03 pmSJU - BOS
Nonstop4h 34mSpirit Airlines
Deal found 1/7$111
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
vie. 1/318:29 pmBOS - SJU
1 stop13h 49mMultiple Airlines
vie. 2/75:35 amSJU - BOS
Nonstop4h 28mMultiple Airlines
Deal found 1/6$123
This Frontier deal was found by Cheapflights users on 1/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 1/157:46 pmBDL - SJU
Nonstop3h 58mFrontier
jue. 1/239:49 pmSJU - BDL
1 stop11h 29mFrontier
Deal found 1/6$135
This FlightHub deal was found by Cheapflights users on 1/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/36:00 pmBDL - SJU
1 stop14h 21mMultiple Airlines
lun. 2/106:00 amSJU - BDL
1 stop12h 08mMultiple Airlines
Deal found 1/6$141
This United Airlines deal was found by Cheapflights users on 1/7. 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.
mar. 1/286:00 amBOS - SJU
1 stop7h 40mUnited Airlines
mié. 2/122:05 amSJU - BOS
1 stop8h 45mUnited Airlines
Deal found 1/7$194
This United Airlines deal was found by Cheapflights users on 1/7. 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.
mar. 1/142:50 pmBDL - SJU
1 stop6h 32mUnited Airlines
mar. 1/142:05 amSJU - BDL
2 stops13h 02mUnited Airlines
Deal found 1/7$222
This FlightHub deal was found by Cheapflights users on 1/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 1/216:00 amBOS - STT
1 stop27h 46mSpirit Airlines
vie. 1/2411:51 amSTT - BOS
2 stops12h 31mSpirit Airlines
Deal found 1/7$228
This American Airlines deal was found by Cheapflights users on 1/7. 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.
mar. 1/146:00 amBOS - STT
1 stop6h 29mAmerican Airlines
mié. 1/226:31 pmSTT - BOS
2 stops14h 44mAmerican Airlines
Deal found 1/7$229
This American Airlines deal was found by Cheapflights users on 1/7. 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.
sáb. 1/2512:59 pmBOS - SJU
2 stops10h 05mAmerican Airlines
vie. 1/316:20 pmSJU - BOS
1 stop7h 34mAmerican Airlines
Deal found 1/7$233
This JetBlue deal was found by Cheapflights users on 1/7. 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.
sáb. 3/17:58 pmBDL - SJU
Nonstop3h 46mJetBlue
lun. 3/103:34 amSJU - BDL
Nonstop4h 10mJetBlue
Deal found 1/7$238
This JetBlue deal was found by Cheapflights users on 1/7. 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.
mar. 1/148:00 amBOS - STT
Nonstop4h 05mJetBlue
jue. 1/232:00 pmSTT - BOS
1 stop5h 59mJetBlue
Deal found 1/7$242

Find flights from Massachusetts to Caribbean Islands within your budget

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 enero 8, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mié. 2/5

6:00 am-7:34 pm

1 stop12h 34m

San Juan Luis Munoz Marin Intl

jue. 2/6

5:35 am-9:03 am

Nonstop4h 28m

$106

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

lun. 2/24

10:08 am-3:08 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

jue. 2/27

7:00 am-10:18 am

Nonstop4h 18m

$107

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mar. 2/4

10:00 am-7:45 pm

1 stop8h 45m

San Juan Luis Munoz Marin Intl

mié. 2/12

4:03 pm-7:37 pm

Nonstop4h 34m

$111

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

dom. 1/19

4:01 pm-8:51 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

sáb. 1/25

9:15 pm-9:55 am

1 stop13h 40m

$134

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

lun. 2/3

6:00 pm-9:21 am

1 stop14h 21m

San Juan Luis Munoz Marin Intl

mar. 2/11

8:40 pm-10:22 am

1 stop14h 42m

$141

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

dom. 1/19

6:00 pm-9:21 am

1 stop14h 21m

San Juan Luis Munoz Marin Intl

dom. 1/26

6:55 pm-10:40 am

1 stop16h 45m

$147

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

dom. 2/2

9:30 am-10:22 pm

2 stops11h 52m

San Juan Luis Munoz Marin Intl

mar. 2/4

2:05 am-8:13 am

1 stop7h 08m

$194

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

mar. 2/4

2:50 pm-10:22 pm

1 stop6h 32m

San Juan Luis Munoz Marin Intl

mar. 2/11

5:50 pm-11:49 pm

1 stop6h 59m

$227

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

mar. 1/21

6:00 am-10:46 am

1 stop27h 46m

Saint Thomas Island Cyril E King

vie. 1/24

11:51 am-11:22 pm

2 stops12h 31m

$228

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

lun. 3/3

7:28 pm-1:54 pm

1 stop17h 26m

Saint Thomas Island Cyril E King

mar. 3/11

5:25 pm-11:41 am

1 stop18h 16m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 60 results
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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.

Travel insights for flights from Massachusetts to Caribbean Islands

Get recent, data-driven insights about flights from Massachusetts to Caribbean Islands including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $380). 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 enero 8, 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 enero 8, 2025.

The most flights from USMA to zzEPX are scheduled on a Tuesday (15 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 enero 8, 2025.
See what other customers who have flown with American Airlines, United Airlines and Spirit Airlines 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.
8.1
Very good
4,652 reviews

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,652 reviews
8.1
Very good
4,652 reviews

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,503 reviews
8.1
Very good
4,652 reviews

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
9,627 reviews
8.1
Very good
4,652 reviews

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.7
Good
1,650 reviews
8.1
Very good
4,652 reviews

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.5
Good
1,846 reviews
8.1
Very good
4,652 reviews

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier ($46), Spirit Airlines ($67), and United Airlines ($99).

  • 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 March is currently the most expensive (average of $380). 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

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Alternative routes for Massachusetts to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.

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 enero 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$74Average$332FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$99Average$396FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$142Average$587FlexibilityNo cancel feeOn-time62%
DeltaCheapest$143Average$505FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$200Average$527FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$244Average$601FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$263Average$608FlexibilityNo cancel feeOn-time69%
AviancaCheapest$292Average$505FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$427Average$812FlexibilityNo cancel feeOn-time63%
Air CanadaCheapest$444Average$780FlexibilityNo cancel feeOn-time67%
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