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$101+ 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 8/3. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$195
(Expedia)

One-way from

$100
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$283

Good round-trip deal

$189 or less

Good one-way deal

$163 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. 20% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 31, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/1510:16 pmSJU - BOS
1 stop16h 14mSpirit Airlines
lun. 8/183:37 pmBOS - SJU
1 stop8h 20mSpirit Airlines
Deal found 7/29$195
This OneTravel deal was found by Cheapflights users on 7/31. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/306:55 pmSJU - BOS
1 stop15h 44mMultiple Airlines
sáb. 9/612:20 pmBOS - SJU
1 stop8h 36mMultiple Airlines
Deal found 7/31$209
This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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. 8/294:12 pmSJU - BDL
1 stop7h 11mSpirit Airlines
lun. 9/16:45 amBDL - SJU
1 stop7h 32mSpirit Airlines
Deal found 7/31$210
This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/88:25 amSJU - BOS
Nonstop4h 09mJetBlue
lun. 8/118:45 pmBOS - SJU
Nonstop4h 04mJetBlue
Deal found 7/30$228
This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/225:30 amSJU - BDL
1 stop9h 39mAmerican Airlines
vie. 10/314:26 pmBDL - SJU
1 stop7h 33mAmerican Airlines
Deal found 7/29$234
This Southwest deal was found by Cheapflights users on 7/31. 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.
vie. 10/35:50 amSJU - BDL
1 stop6h 20mSouthwest
dom. 10/512:35 pmBDL - SJU
1 stop11h 40mSouthwest
Deal found 7/31$235
This Orbitz deal was found by Cheapflights users on 7/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/156:00 amSJU - BDL
Nonstop4h 00mMultiple Airlines
lun. 8/1812:53 pmBDL - SJU
1 stop8h 55mMultiple Airlines
Deal found 7/30$238
This Delta deal was found by Cheapflights users on 7/31. 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.
vie. 10/102:05 pmSJU - BDL
1 stop9h 09mDelta
lun. 10/135:30 amBDL - SJU
1 stop7h 22mDelta
Deal found 7/31$245
This American Airlines deal was found by Cheapflights users on 7/30. 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. 10/155:30 amSJU - BOS
1 stop9h 51mAmerican Airlines
lun. 10/2011:05 amBOS - SJU
1 stop12h 54mAmerican Airlines
Deal found 7/30$253
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/147:15 amSJU - BDL
Nonstop4h 00mFrontier
lun. 8/1810:47 amBDL - SJU
Nonstop3h 55mFrontier
Deal found 7/30$254
This Delta deal was found by Cheapflights users on 7/31. 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.
mié. 10/151:32 pmSJU - BOS
Nonstop4h 13mDelta
sáb. 10/188:15 amBOS - SJU
Nonstop4h 06mDelta
Deal found 7/31$254
This JetBlue deal was found by Cheapflights users on 7/31. 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. 9/56:33 pmSJU - BDL
Nonstop3h 56mJetBlue
dom. 9/285:20 pmBDL - SJU
Nonstop3h 50mJetBlue
Deal found 7/31$280

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 julio 31, 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

vie. 8/15

10:16 pm-2:30 pm

1 stop16h 14m

Boston Logan Intl

lun. 8/18

3:37 pm-11:57 pm

1 stop8h 20m

$195

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

sáb. 8/30

6:55 pm-10:39 am

1 stop15h 44m

Boston Logan Intl

sáb. 9/6

12:20 pm-8:56 pm

1 stop8h 36m

$209

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

vie. 8/29

4:12 pm-11:23 pm

1 stop7h 11m

Hartford Bradley Intl

lun. 9/1

6:45 am-2:17 pm

1 stop7h 32m

$210

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

vie. 8/8

8:25 am-12:34 pm

Nonstop4h 09m

Boston Logan Intl

lun. 8/11

8:45 pm-12:49 am

Nonstop4h 04m

$228

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

mié. 10/22

5:30 am-3:09 pm

1 stop9h 39m

Hartford Bradley Intl

vie. 10/31

4:26 pm-11:59 pm

1 stop7h 33m

$234

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

vie. 10/3

5:50 am-12:10 pm

1 stop6h 20m

Hartford Bradley Intl

dom. 10/5

12:35 pm-12:15 am

1 stop11h 40m

$235

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

vie. 8/15

6:00 am-10:00 am

Nonstop4h 00m

Hartford Bradley Intl

lun. 8/18

12:53 pm-9:48 pm

1 stop8h 55m

$238

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

vie. 10/10

2:05 pm-11:14 pm

1 stop9h 09m

Hartford Bradley Intl

lun. 10/13

5:30 am-12:52 pm

1 stop7h 22m

$245

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

mié. 10/15

5:30 am-3:21 pm

1 stop9h 51m

Boston Logan Intl

lun. 10/20

11:05 am-11:59 pm

1 stop12h 54m

$253

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

jue. 8/14

7:15 am-11:15 am

Nonstop4h 00m

Hartford Bradley Intl

lun. 8/18

10:47 am-2:42 pm

Nonstop3h 55m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 $311). 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 julio 31, 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 julio 31, 2025.

The most flights from 0CB to USMA are scheduled on a Thursday (31 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).

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 julio 31, 2025.
Read through reviews of airlines operating flights from Caribbean to Massachusetts, such as Southwest, Delta, and Avelo Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Copa Airlines
7.5
Good
1,493 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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?

    $100 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 Southwest and Delta, with prices starting from $118 and $123, 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 $311). 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$252FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$86Average$295FlexibilityNo cancel feeOn-time65%
DeltaCheapest$129Average$414FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$133Average$461FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$207Average$384FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$319Average$490FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$338Average$489FlexibilityNo cancel feeOn-time71%

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