What are the cheapest airlines to fly from Massachusetts to Caribbean one-way?

To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $95. Frontier flights start at $128 while deals on Air Canada start at $131 one-way.

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.

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).

How far in advance should I book a flight from Massachusetts to Caribbean?

Find a great deal and save up to 5% by booking at least 27 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Massachusetts to Caribbean within the next two weeks, with the cheapest ticket starting at $225.

What is the cheapest month to fly from Massachusetts to Caribbean?

September can be a great time to fly to Caribbean from Massachusetts with a flight ticket averaging about $280. Cheapflights users have found deals in the month of September for as cheap as $56. The most expensive prices can be found in the month of December.

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.

$95+ Cheap Flights from Massachusetts to Caribbean

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Cheap flight deals from Massachusetts to Caribbean

Round-trip from	$183 (Kiwi.com)
One-way from	$95 (FlightHub)
Popular in	December
Cheapest in	September
Average price	$303
Good round-trip deal	$272 or less
Good one-way deal	$136 or less

From Massachusetts to Caribbean

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One-way flight from Massachusetts to Caribbean

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Highest demand for flights based on searches. 2% potential increase in price ($7 potential increase over avg. RT price).

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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).

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Average for round-trip flights in August 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 August 14, 2025.

Sun 8/316:05 amBOS - SJU

1 stop15h 43mSpirit Airlines

Wed 9/176:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/12

$183

Sat 9/612:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Sat 9/136:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/14

$186

Wed 9/1712:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Sat 9/206:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/12

$187

Sat 8/303:25 pmBOS - SJU

1 stop17h 40mSpirit Airlines

Sat 9/66:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/12

$188

Tue 9/912:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Wed 9/176:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/12

$191

Sun 8/316:05 amBOS - SJU

1 stop15h 43mSpirit Airlines

Fri 9/1211:59 amSJU - BOS

1 stop11h 58mSpirit Airlines

Deal found 8/12

$196

Sun 8/316:05 amBOS - SJU

1 stop15h 43mSpirit Airlines

Sat 9/66:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/13

$199

Tue 8/263:37 pmBOS - SJU

1 stop8h 20mSpirit Airlines

Wed 12/32:59 amSJU - BOS

1 stop8h 09mSpirit Airlines

Deal found 8/12

$200

Tue 9/1612:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Fri 9/266:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/12

$201

Tue 9/23:37 pmBOS - SJU

1 stop8h 20mSpirit Airlines

Sat 9/66:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/13

$202

Sun 9/146:49 pmBOS - SJU

1 stop16h 15mSpirit Airlines

Sat 9/206:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/14

$203

Tue 9/1612:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Fri 9/1911:59 amSJU - BOS

1 stop11h 58mSpirit Airlines

Deal found 8/13

$205

Best flights from Massachusetts to Caribbean
Discover carefully curated flight deals from Massachusetts to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 14, 2025.

Wed 9/36:55 pmBOS - STT

1 stop14h 49mSpirit Airlines

Sat 9/610:49 amSTT - BOS

1 stop13h 08mSpirit Airlines

Deal found 8/12

$205

Sun 8/246:15 pmBDL - SJU

1 stop6h 41mMultiple Airlines

Wed 8/2711:17 amSJU - BDL

Nonstop4h 00mMultiple Airlines

Deal found 8/14

$262

Sun 8/178:45 pmBOS - SJU

Nonstop4h 04mJetBlue

Thu 8/2112:45 pmSJU - BOS

Nonstop4h 08mJetBlue

Deal found 8/12

$264

Fri 9/195:35 amBOS - SXM

1 stop8h 15mDelta

Fri 9/263:20 pmSXM - BOS

1 stop9h 58mDelta

Deal found 8/13

$335

Fri 9/126:00 amBOS - SDQ

1 stop8h 10mUnited Airlines

Sun 9/215:45 amSDQ - BOS

1 stop7h 39mUnited Airlines

Deal found 8/13

$355

Tue 2/35:30 amBOS - NAS

1 stop7h 00mAir Canada

Tue 2/101:35 pmNAS - BOS

1 stop19h 57mAir Canada

Deal found 8/14

$360

Sun 8/316:15 pmBDL - SJU

1 stop6h 41mSpirit Airlines

Thu 9/43:19 pmSJU - BDL

2 stops19h 16mSpirit Airlines

Deal found 8/14

$252

Tue 9/3010:00 amBOS - SJU

1 stop10h 20mJetBlue

Sat 10/44:32 pmSJU - BOS

1 stop7h 27mJetBlue

Deal found 8/12

$267

Thu 8/219:09 pmBDL - SJU

Nonstop3h 55mMultiple Airlines

Wed 8/272:11 amSJU - BDL

1 stop9h 10mMultiple Airlines

Deal found 8/12

$274

Fri 9/511:30 amBDL - SJU

2 stops33h 26mSpirit Airlines

Thu 9/113:19 pmSJU - BDL

2 stops19h 16mSpirit Airlines

Deal found 8/13

$259

Sat 9/278:31 amBOS - SJU

Nonstop4h 19mJetBlue

Wed 10/14:35 pmSJU - BOS

1 stop7h 24mJetBlue

Deal found 8/12

$268

Wed 9/36:55 pmBOS - STT

1 stop14h 49mSpirit Airlines

Tue 9/910:49 amSTT - BOS

1 stop24h 24mSpirit Airlines

Deal found 8/13

$259

Last-minute flights from Massachusetts to Caribbean
Discover last-minute flight deals from Massachusetts to Caribbean. Data last updated August 14, 2025 and is based on user searches.

Thu 8/216:15 pmBDL - SJU

1 stop6h 41mSpirit Airlines

Sat 8/302:11 amSJU - BDL

1 stop9h 10mSpirit Airlines

Deal found 8/13

$253

Thu 8/219:09 pmBDL - SJU

Nonstop3h 55mFrontier

Sat 8/304:24 pmSJU - BDL

Nonstop4h 00mFrontier

Deal found 8/12

$254

Fri 8/229:20 amBOS - SJU

1 stop9h 48mMultiple Airlines

Fri 8/2910:16 pmSJU - BOS

1 stop16h 14mMultiple Airlines

Deal found 8/13

$246

Sat 8/234:38 pmBOS - SJU

1 stop7h 19mSpirit Airlines

Sat 9/66:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/12

$188

Sat 8/232:45 pmBDL - SJU

1 stop9h 12mSpirit Airlines

Sat 8/302:11 amSJU - BDL

1 stop9h 10mSpirit Airlines

Deal found 8/12

$224

Sat 8/234:38 pmBOS - SJU

1 stop7h 19mMultiple Airlines

Wed 8/2712:59 amSJU - BOS

1 stop7h 43mMultiple Airlines

Deal found 8/13

$226

Sat 8/234:38 pmBOS - SJU

1 stop7h 19mSpirit Airlines

Thu 9/42:38 pmSJU - BOS

1 stop8h 09mSpirit Airlines

Deal found 8/12

$227

Sat 8/232:45 pmBDL - SJU

1 stop9h 12mMultiple Airlines

Thu 8/284:24 pmSJU - BDL

Nonstop4h 00mMultiple Airlines

Deal found 8/13

$233

Sat 8/232:45 pmBDL - SJU

1 stop9h 12mMultiple Airlines

Sat 8/304:24 pmSJU - BDL

Nonstop4h 00mMultiple Airlines

Deal found 8/12

$235

Sat 8/232:45 pmBDL - SJU

1 stop9h 12mMultiple Airlines

Fri 8/299:00 amSJU - BDL

1 stop25h 25mMultiple Airlines

Deal found 8/13

$241

Sat 8/239:09 pmBDL - SJU

Nonstop3h 55mFrontier

Sat 8/304:24 pmSJU - BDL

Nonstop4h 00mFrontier

Deal found 8/12

$249

Sun 8/246:05 amBOS - SJU

1 stop15h 43mSpirit Airlines

Thu 9/42:38 pmSJU - BOS

1 stop8h 09mSpirit Airlines

Deal found 8/13

$240

One-way flights from Massachusetts to Caribbean
Search for one-way flight options from Massachusetts to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 14, 2025.

Tue 9/1612:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Deal found 8/11

$95

Tue 8/266:05 amBOS - MBJ

1 stop6h 09mSpirit Airlines

Deal found 8/12

$98

Wed 9/36:30 amBOS - SJU

1 stop16h 58mSpirit Airlines

Deal found 8/14

$98

Wed 9/36:05 amBOS - MBJ

1 stop6h 09mSpirit Airlines

Deal found 8/14

$99

Sun 8/316:30 amBOS - SJU

1 stop7h 47mSpirit Airlines

Deal found 8/12

$101

Sat 9/136:10 amBOS - AUA

1 stop8h 30mSpirit Airlines

Deal found 8/13

$102

Sun 10/262:53 pmBOS - SJU

1 stop10h 51mSpirit Airlines

Deal found 8/14

$102

Sun 8/246:05 amBOS - SJU

1 stop15h 43mSpirit Airlines

Deal found 8/12

$103

Tue 9/96:10 amBOS - MBJ

1 stop5h 55mSpirit Airlines

Deal found 8/13

$105

Sat 8/306:55 pmBOS - SJU

1 stop26h 53mSpirit Airlines

Deal found 8/11

$106

Tue 9/210:34 amBOS - SJU

1 stop13h 23mSpirit Airlines

Deal found 8/12

$107

Mon 9/292:53 pmBOS - SJU

1 stop10h 01mSpirit Airlines

Deal found 8/12

$108

Cheapflights Fare Finder

Use the filters below to find and compare flights from Massachusetts to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 9/3

6:55 pm-9:44 am

1 stop14h 49m

Saint Thomas Island Cyril E King

Sat 9/6

10:49 am-11:57 pm

1 stop13h 08m

$205

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sun 8/31

6:15 pm-12:56 am

1 stop6h 41m

San Juan Luis Munoz Marin Intl

Thu 9/4

3:19 pm-10:35 am

2 stops19h 16m

$252

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Fri 9/5

11:30 am-8:56 pm

2 stops33h 26m

San Juan Luis Munoz Marin Intl

Thu 9/11

3:19 pm-10:35 am

2 stops19h 16m

$259

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 9/3

6:55 pm-9:44 am

1 stop14h 49m

Saint Thomas Island Cyril E King

Tue 9/9

10:49 am-11:13 am

1 stop24h 24m

$259

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sun 8/24

6:15 pm-12:56 am

1 stop6h 41m

San Juan Luis Munoz Marin Intl

Wed 8/27

11:17 am-3:17 pm

Nonstop4h 00m

$262

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 11/12

6:15 am-3:11 pm

1 stop7h 56m

Saint Thomas Island Cyril E King

Tue 11/18

4:06 pm-10:08 pm

1 stop7h 02m

$262

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 11/12

6:15 am-3:11 pm

1 stop7h 56m

Saint Thomas Island Cyril E King

Wed 11/19

4:06 pm-10:08 pm

1 stop7h 02m

$263

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 8/17

8:45 pm-12:49 am

Nonstop4h 04m

San Juan Luis Munoz Marin Intl

Thu 8/21

12:45 pm-4:53 pm

Nonstop4h 08m

$264

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 11/11

6:15 am-3:11 pm

1 stop7h 56m

Saint Thomas Island Cyril E King

Wed 11/19

4:06 pm-10:08 pm

1 stop7h 02m

$266

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 11/11

6:15 am-3:11 pm

1 stop7h 56m

Saint Thomas Island Cyril E King

Tue 11/18

4:06 pm-10:08 pm

1 stop7h 02m

$266

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 60 results

...

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.

Cheapflights Insights

Everything you need to know about your flight from Massachusetts to Caribbean

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 June is currently the most expensive (average of $339). 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?

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

The most flights from USMA to 0CB are scheduled on a Thursday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

Related info for your journey

What are the cheapest airlines to fly from Massachusetts to Caribbean one-way?
To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $95. Frontier flights start at $128 while deals on Air Canada start at $131 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 June is currently the most expensive (average of $339). 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

Top 10 airlines flying from Massachusetts to Caribbean

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$80	Average$376	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$99	Average$386	FlexibilityNo cancel fee	On-time65%
JetBlue	Cheapest$136	Average$555	FlexibilityNo cancel fee	On-time62%
Delta	Cheapest$140	Average$480	FlexibilityNo cancel fee	On-timeN/A
Arajet	Cheapest$187	Average$345	FlexibilityNo cancel fee	On-timeN/A
Air Canada	Cheapest$188	Average$660	FlexibilityNo cancel fee	On-time67%
Copa Airlines	Cheapest$192	Average$387	FlexibilityNo cancel fee	On-time70%
United Airlines	Cheapest$204	Average$542	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$288	Average$591	FlexibilityNo cancel fee	On-time71%
Avianca	Cheapest$356	Average$549	FlexibilityNo cancel fee	On-time71%

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$95+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Massachusetts to Caribbean with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

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 August 14, 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Massachusetts to Caribbean

Cheapest flights from Massachusetts to CaribbeanExplore 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 August 14, 2025.

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 August 14, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Massachusetts to Caribbean that are best for you.

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.

Cheapflights Insights

Everything you need to know about your flight from Massachusetts to Caribbean

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

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 August 14, 2025.

Weekly flight availability from Massachusetts to Caribbean

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?

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

How can I find direct flights from Massachusetts to Caribbean?

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Massachusetts to Caribbean

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

Top 10 airlines flying from Massachusetts to Caribbean

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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 August 14, 2025.