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$92+ Cheap flights from Caribbean to Massachusetts

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 6/19. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
may. 6 — may. 131
mar. 5/6
mar. 5/13
1 adult, Economy
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Cheap flight deals from Caribbean to Massachusetts

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

Round-trip from

$176
(Mytrip)

One-way from

$92
(Cheapflightsfares)

Popular in

June

Cheapest in

September

Average price

$235

Good round-trip deal

$198 or less

Good one-way deal

$147 or less
From Caribbean to Massachusetts
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One-way flight from Caribbean to Massachusetts
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Highest demand for flights based on searches. 12% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Price to beat on a round-trip flight from Caribbean to Massachusetts.
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Price to beat on a one-way flight from Caribbean to Massachusetts.
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Find flight deals from Caribbean to Massachusetts

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

This Mytrip deal was found by Cheapflights users on 5/1. 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.
mié. 5/281:59 amSJU - BOS
1 stop7h 10mSpirit Airlines
lun. 6/27:47 pmBOS - SJU
1 stop25h 30mSpirit Airlines
Deal found 5/1$176
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.
jue. 7/175:41 pmSJU - BDL
1 stop14h 29mSpirit Airlines
lun. 7/289:15 amBDL - SJU
1 stop7h 31mSpirit 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.
jue. 6/56:36 amSJU - BDL
Nonstop4h 02mMultiple Airlines
dom. 6/812:27 pmBDL - SJU
1 stop6h 40mMultiple Airlines
Deal found 4/30$200
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. 5/236:36 amSJU - BDL
Nonstop4h 04mFrontier
lun. 5/2611:38 amBDL - SJU
Nonstop3h 54mFrontier
Deal found 4/30$212
This Mytrip deal was found by Cheapflights users on 4/29. 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.
mié. 6/412:07 pmMBJ - BOS
1 stop10h 22mSpirit Airlines
mié. 6/116:10 amBOS - MBJ
1 stop5h 52mSpirit Airlines
Deal found 4/29$220
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.
dom. 5/186:30 amSJU - BOS
Nonstop4h 13mMultiple Airlines
lun. 5/266:10 amBOS - SJU
1 stop12h 57mMultiple Airlines
Deal found 4/30$221
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.
jue. 9/253:55 pmSJU - BOS
1 stop8h 40mAmerican Airlines
mar. 9/307:43 amBOS - SJU
1 stop7h 04mAmerican 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.
jue. 9/251:27 pmSJU - BOS
Nonstop4h 12mDelta
mar. 9/308:10 amBOS - SJU
Nonstop4h 05mDelta
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.
mié. 9/101:05 amSJU - BOS
2 stops9h 30mUnited Airlines
dom. 9/146:00 amBOS - SJU
1 stop7h 45mUnited Airlines
Deal found 4/30$233
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. 5/1810:53 amMBJ - BDL
Nonstop4h 02mAvelo Airlines
dom. 6/16:45 amBDL - MBJ
Nonstop4h 08mAvelo Airlines
Deal found 4/30$255
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.
jue. 5/86:30 amSJU - BOS
Nonstop4h 13mFrontier
dom. 5/1111:43 amBOS - SJU
Nonstop4h 01mFrontier
Deal found 4/30$255
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.
jue. 5/151:30 pmSJU - BDL
2 stops10h 23mAmerican Airlines
dom. 5/185:44 amBDL - SJU
1 stop8h 56mAmerican Airlines
Deal found 4/30$265

Cheapflights Fare Finder

Customize your flight search to find flights from Caribbean to Massachusetts 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 Caribbean to Massachusetts that are best for you.

Fly from

Caribbean

Fly to

Massachusetts

Route

Depart

Return

Price

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

mié. 5/28

1:59 am-9:09 am

1 stop7h 10m

Boston Logan Intl

lun. 6/2

7:47 pm-9:17 pm

1 stop25h 30m

$176

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

jue. 7/17

5:41 pm-8:10 am

1 stop14h 29m

Hartford Bradley Intl

lun. 7/28

9:15 am-4:46 pm

1 stop7h 31m

$184

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

jue. 6/5

6:36 am-10:38 am

Nonstop4h 02m

Hartford Bradley Intl

dom. 6/8

12:27 pm-7:07 pm

1 stop6h 40m

$200

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

jue. 5/29

5:25 am-2:15 pm

2 stops8h 50m

Boston Logan Intl

jue. 5/29

4:19 pm-10:30 pm

1 stop6h 11m

$210

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

vie. 5/23

6:36 am-10:40 am

Nonstop4h 04m

Hartford Bradley Intl

lun. 5/26

11:38 am-3:32 pm

Nonstop3h 54m

$212

Montego BayBoston

MBJ - BOS

MBJBOS

Montego Bay Sangster Intl

mié. 6/4

12:07 pm-11:29 pm

1 stop10h 22m

Boston Logan Intl

mié. 6/11

6:10 am-11:02 am

1 stop5h 52m

$220

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

dom. 5/18

6:30 am-10:43 am

Nonstop4h 13m

Boston Logan Intl

lun. 5/26

6:10 am-7:07 pm

1 stop12h 57m

$221

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

jue. 9/25

1:27 pm-5:39 pm

Nonstop4h 12m

Boston Logan Intl

mar. 9/30

8:10 am-12:15 pm

Nonstop4h 05m

$224

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

mié. 9/10

1:05 am-10:35 am

2 stops9h 30m

Boston Logan Intl

dom. 9/14

6:00 am-1:45 pm

1 stop7h 45m

$233

Montego BayHartford

MBJ - BDL

MBJBDL

Montego Bay Sangster Intl

dom. 5/18

10:53 am-3:55 pm

Nonstop4h 02m

Hartford Bradley Intl

dom. 6/1

6:45 am-9:53 am

Nonstop4h 08m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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

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

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

Currently, January is the cheapest month in which you can book a flight from Caribbean to Massachusetts (average of $218). Flying from Caribbean to Massachusetts in July is currently the most expensive (average of $310). 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 CB to MA?

Find hourly flight availability from Caribbean to Massachusetts. 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 Caribbean to Massachusetts, 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 Caribbean to Massachusetts

Explore weekly flight availability from Caribbean to Massachusetts. 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 0CB to USMA are scheduled on a Wednesday (24 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Massachusetts by month

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

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

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

If weather is an important factor for your trip to Massachusetts, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated mayo 1, 2025.
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Alaska Airlines
8.0
Very good
9,968 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Southwest
8.0
Very good
4,294 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Copa Airlines
7.5
Good
1,414 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
LATAM Airlines
7.5
Good
1,767 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

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

    $92 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and JetBlue, with prices starting from $97 and $143, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean to Massachusetts 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 Caribbean to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Caribbean to Massachusetts (average of $218). Flying from Caribbean to Massachusetts in July is currently the most expensive (average of $310). 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 Caribbean to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Caribbean to Massachusetts

Discover the top 7 airlines that operate flights from Caribbean to Massachusetts. 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
Spirit AirlinesCheapest$64Average$329FlexibilityNo cancel feeOn-time65%
FrontierCheapest$69Average$247FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$132Average$483FlexibilityNo cancel feeOn-time62%
DeltaCheapest$134Average$433FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$207Average$397FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$317Average$471FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$337Average$507FlexibilityNo cancel feeOn-time71%

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