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$71+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
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Cheap flight deals from Caribbean to Massachusetts

Discover tips and strategies to find the most affordable flight options for your journey from Caribbean (0CB) to Massachusetts (USMA). 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 January 30, 2025.

Round-trip from

$98
(Cheapflightsfares)

One-way from

$71
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$185

Good round-trip deal

$142 or less

Good one-way deal

$149 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. 11% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 30, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 1/29. 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.
Thu 2/65:35 amSJU - BOS
Nonstop4h 28mFrontier
Sun 2/910:03 amBOS - SJU
Nonstop4h 04mFrontier
Deal found 1/29$98
This eDestinos deal was found by Cheapflights users on 1/29. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/269:34 pmSJU - BOS
1 stop12h 39mSpirit Airlines
Wed 3/510:43 amBOS - SJU
Nonstop4h 01mSpirit Airlines
Deal found 1/29$105
This Cheapflightsfares deal was found by Cheapflights users on 1/29. 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.
Wed 2/52:50 pmSJU - BDL
Nonstop4h 19mFrontier
Mon 2/104:03 pmBDL - SJU
Nonstop3h 50mFrontier
Deal found 1/29$109
This OneTravel deal was found by Cheapflights users on 1/29. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/76:45 pmSJU - BDL
1 stop16h 56mMultiple Airlines
Tue 3/114:21 pmBDL - SJU
Nonstop3h 50mMultiple Airlines
Deal found 1/29$124
This Cheapflightsfares deal was found by Cheapflights users on 1/30. 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.
Thu 3/64:49 pmSJU - BOS
Nonstop4h 23mMultiple Airlines
Mon 3/1011:22 amBOS - SJU
Nonstop3h 52mMultiple Airlines
Deal found 1/30$127
This FlightHub deal was found by Cheapflights users on 1/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/39:34 pmSJU - BDL
1 stop13h 48mSpirit Airlines
Mon 3/1011:36 amBDL - SJU
1 stop28h 58mSpirit Airlines
Deal found 1/29$157
This United Airlines deal was found by Cheapflights users on 1/28. 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.
Thu 1/302:05 amSJU - BOS
1 stop7h 08mUnited Airlines
Mon 2/32:45 pmBOS - SJU
1 stop6h 37mUnited Airlines
Deal found 1/28$207
This JetBlue deal was found by Cheapflights users on 1/30. 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.
Wed 3/53:26 amSJU - BOS
Nonstop4h 09mJetBlue
Mon 3/107:30 pmBOS - SJU
Nonstop4h 03mJetBlue
Deal found 1/30$218
This Mytrip deal was found by Cheapflights users on 1/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/102:15 pmPUJ - BOS
1 stop10h 29mFrontier
Mon 3/2411:22 amBOS - PUJ
1 stop6h 15mFrontier
Deal found 1/30$219
This JetBlue deal was found by Cheapflights users on 1/28. 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.
Fri 4/42:39 amSJU - BDL
Nonstop4h 01mJetBlue
Mon 4/77:43 pmBDL - SJU
Nonstop3h 53mJetBlue
Deal found 1/28$228
This Delta deal was found by Cheapflights users on 1/30. 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.
Thu 2/67:30 amSJU - BDL
1 stop11h 13mDelta
Tue 2/112:23 pmBDL - SJU
1 stop8h 23mDelta
Deal found 1/30$237
This American Airlines deal was found by Cheapflights users on 1/29. 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.
Thu 2/68:05 amSJU - BDL
1 stop17h 43mAmerican Airlines
Sun 2/912:22 pmBDL - SJU
1 stop10h 36mAmerican Airlines
Deal found 1/29$243

Find flights from Caribbean to Massachusetts within your budget

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 January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Wed 2/12

7:00 am-10:18 am

Nonstop4h 18m

Boston Logan Intl

Wed 2/19

11:18 am-4:15 pm

Nonstop3h 57m

$98

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Wed 2/26

9:34 pm-9:13 am

1 stop12h 39m

Boston Logan Intl

Wed 3/5

10:43 am-3:44 pm

Nonstop4h 01m

$105

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Thu 3/27

4:22 pm-8:41 pm

Nonstop4h 19m

Hartford Bradley Intl

Tue 4/1

12:29 pm-1:50 am

1 stop13h 21m

$112

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Fri 3/7

6:45 pm-10:41 am

1 stop16h 56m

Hartford Bradley Intl

Tue 3/11

4:21 pm-8:11 pm

Nonstop3h 50m

$124

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 3/6

4:49 pm-8:12 pm

Nonstop4h 23m

Boston Logan Intl

Mon 3/10

11:22 am-3:14 pm

Nonstop3h 52m

$127

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Mon 3/3

9:34 pm-10:22 am

1 stop13h 48m

Hartford Bradley Intl

Mon 3/10

11:36 am-4:34 pm

1 stop28h 58m

$157

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Wed 3/5

3:26 am-6:35 am

Nonstop4h 09m

Boston Logan Intl

Mon 3/10

7:30 pm-11:33 pm

Nonstop4h 03m

$218

Punta CanaBoston

PUJ - BOS

PUJBOS

Punta Cana

Mon 3/10

2:15 pm-12:44 am

1 stop10h 29m

Boston Logan Intl

Mon 3/24

11:22 am-5:37 pm

1 stop6h 15m

$219

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 2/27

2:05 am-9:50 am

1 stop8h 45m

Boston Logan Intl

Mon 3/3

4:09 pm-12:36 am

1 stop7h 27m

$224

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Fri 4/4

2:39 am-6:40 am

Nonstop4h 01m

Hartford Bradley Intl

Mon 4/7

7:43 pm-11:36 pm

Nonstop3h 53m

$228

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

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.

Travel insights for flights from Caribbean to Massachusetts

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

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 January 30, 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 January 30, 2025.

The most flights from 0CB to USMA are scheduled on a Thursday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 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 January 30, 2025.
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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.

Southwest
8.1
Very good
4,585 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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.

Alaska Airlines
8.0
Very good
9,688 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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.

Delta
8.0
Very good
8,454 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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.

JetBlue
7.4
Good
3,156 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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.

United Airlines
7.4
Good
8,913 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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 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?

    $71 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 United Airlines, with prices starting from $72 and $104, 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 January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$70Average$139FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$84Average$295FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$121Average$459FlexibilityNo cancel feeOn-time62%
DeltaCheapest$130Average$401FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$204Average$522FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$207Average$408FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$215Average$463FlexibilityNo cancel feeOn-time69%
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