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$45+ Cheap flights from Massachusetts to Caribbean

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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
1 adult, Economy
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Cheap flight deals from Massachusetts to Caribbean

Keep the following information in mind while searching for Massachusetts to Caribbean flight deals. Data was last updated febrero 20, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$115
(Kiwi.com)

One-way from

$45
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$303

Good round-trip deal

$186 or less

Good one-way deal

$103 or less
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-San Juan flights.
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From Massachusetts to Caribbean
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One-way flight from Massachusetts to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Massachusetts to Caribbean.
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Price to beat on a one-way flight from Massachusetts to Caribbean.
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Find flight deals from Massachusetts to Caribbean

Cheapest flights from Massachusetts to Caribbean
Explore the most affordable flight options available from Massachusetts to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on febrero 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
mar. 3/1110:43 amBOS - SJU
Nonstop4h 01mMultiple Airlines
mié. 3/269:30 pmSJU - BOS
1 stop11h 25mMultiple Airlines
Deal found 2/20$115
This Frontier deal was found by Cheapflights users on 2/20. 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.
mar. 4/16:00 amBOS - SJU
1 stop10h 46mFrontier
mié. 4/212:59 amSJU - BOS
1 stop7h 49mFrontier
Deal found 2/20$117
This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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. 3/184:21 pmBDL - SJU
Nonstop3h 50mFrontier
mar. 3/2511:02 amSJU - BDL
Nonstop4h 19mFrontier
Deal found 2/19$118
This Justfly.com deal was found by Cheapflights users on 2/20. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/311:17 amBDL - SJU
1 stop11h 08mMultiple Airlines
jue. 3/64:22 pmSJU - BDL
Nonstop4h 19mMultiple Airlines
Deal found 2/20$123
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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. 4/296:20 pmBOS - SJU
1 stop15h 05mSpirit Airlines
mar. 5/66:15 pmSJU - BOS
1 stop16h 15mSpirit Airlines
Deal found 2/20$123
This FlightHub deal was found by Cheapflights users on 2/20. 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. 3/311:17 amBDL - SJU
1 stop11h 08mSpirit Airlines
jue. 3/66:45 pmSJU - BDL
1 stop16h 56mSpirit Airlines
Deal found 2/20$144
This JetBlue deal was found by Cheapflights users on 2/20. 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.
dom. 3/27:35 pmBOS - SJU
Nonstop4h 07mJetBlue
mar. 3/43:26 amSJU - BOS
Nonstop4h 09mJetBlue
Deal found 2/20$198
This United Airlines deal was found by Cheapflights users on 2/20. 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. 3/25:09 pmBOS - SJU
1 stop12h 03mUnited Airlines
mar. 3/42:05 amSJU - BOS
1 stop7h 38mUnited Airlines
Deal found 2/20$207
This JetBlue deal was found by Cheapflights users on 2/20. 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.
lun. 3/247:32 pmBDL - SJU
Nonstop3h 48mJetBlue
jue. 4/32:39 amSJU - BDL
Nonstop4h 01mJetBlue
Deal found 2/20$218
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/512:20 pmBDL - SJU
1 stop11h 05mSouthwest
jue. 3/67:05 amSJU - BDL
1 stop9h 00mSouthwest
Deal found 2/20$222
This Delta deal was found by Cheapflights users on 2/20. 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.
lun. 3/246:00 amBDL - SJU
1 stop10h 06mDelta
vie. 4/43:34 pmSJU - BDL
1 stop8h 44mDelta
Deal found 2/20$227
This Booking.com deal was found by Cheapflights users on 2/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/48:32 pmBOS - MBJ
2 stops15h 30mSpirit Airlines
vie. 3/71:07 pmMBJ - BOS
1 stop8h 30mSpirit Airlines
Deal found 2/19$262

Find flights from Massachusetts to Caribbean within your budget

Customize your flight search to find flights from Massachusetts to Caribbean 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 febrero 20, 2025.

Fly from

Massachusetts

Fly to

Caribbean

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mar. 3/11

10:43 am-2:44 pm

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

mié. 3/26

9:30 pm-8:55 am

1 stop11h 25m

$115

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mar. 4/1

6:00 am-5:21 pm

1 stop11h 21m

San Juan Luis Munoz Marin Intl

mar. 4/8

12:59 am-9:52 am

1 stop8h 53m

$117

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

mié. 3/5

4:33 pm-9:23 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

sáb. 3/8

5:31 pm-8:50 pm

Nonstop4h 19m

$118

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mar. 4/29

6:20 pm-9:25 am

1 stop15h 05m

San Juan Luis Munoz Marin Intl

mar. 5/6

6:15 pm-10:30 am

1 stop16h 15m

$123

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

lun. 3/3

11:17 am-11:25 pm

1 stop11h 08m

San Juan Luis Munoz Marin Intl

jue. 3/6

4:22 pm-7:41 pm

Nonstop4h 19m

$123

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

lun. 3/3

11:17 am-11:25 pm

1 stop11h 08m

San Juan Luis Munoz Marin Intl

jue. 3/6

6:45 pm-10:41 am

1 stop16h 56m

$144

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

dom. 3/2

7:35 pm-12:42 am

Nonstop4h 07m

San Juan Luis Munoz Marin Intl

mar. 3/4

3:26 am-6:35 am

Nonstop4h 09m

$198

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

dom. 3/2

4:09 pm-12:36 am

1 stop7h 27m

San Juan Luis Munoz Marin Intl

mar. 3/4

2:05 am-2:23 pm

2 stops13h 18m

$207

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

lun. 3/3

7:58 pm-12:44 am

Nonstop3h 46m

San Juan Luis Munoz Marin Intl

lun. 3/3

4:24 am-7:34 am

Nonstop4h 10m

$213

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

mié. 3/5

12:20 pm-12:25 am

1 stop11h 05m

San Juan Luis Munoz Marin Intl

jue. 3/6

7:05 am-3:05 pm

1 stop9h 00m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 60 results
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Best time to book a flight from Massachusetts to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

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

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

Currently, September is the cheapest month in which you can book a flight from Massachusetts to Caribbean (average of $254). Flying from Massachusetts to Caribbean in March is currently the most expensive (average of $363). 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 CB?

Find hourly flight availability from Massachusetts to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated febrero 20, 2025.

When flying from Massachusetts to Caribbean, 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

Explore weekly flight availability from Massachusetts to Caribbean. 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 febrero 20, 2025.

The most flights from USMA to 0CB are scheduled on a Sunday (18 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated febrero 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Copa Airlines
7.6
Good
1,510 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Caribbean. 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 one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $45. Spirit Airlines flights start at $61 while deals on Delta start at $99 one-way.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Massachusetts to Caribbean 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?

    Currently, September is the cheapest month in which you can book a flight from Massachusetts to Caribbean (average of $254). Flying from Massachusetts to Caribbean in March is currently the most expensive (average of $363). 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

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Alternative routes for Massachusetts to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 10 airlines flying from Massachusetts to Caribbean

Discover the top 10 airlines that operate flights from Massachusetts to Caribbean. 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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$75Average$386FlexibilityNo cancel feeOn-time65%
FrontierCheapest$76Average$365FlexibilityNo cancel feeOn-time62%
DeltaCheapest$141Average$508FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$142Average$556FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$200Average$527FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$222Average$592FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$229Average$591FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$266Average$832FlexibilityNo cancel feeOn-time67%
AviancaCheapest$292Average$518FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$452Average$798FlexibilityNo cancel feeOn-time63%
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