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

$97 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 Frontier, with prices starting from $127 and $129, respectively.

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

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

What are the most popular routes from Boston to Caribbean Islands?

Most travelers choose Boston Logan Intl - San Juan Luis Munoz Marin Intl, Boston Logan Intl - Punta Cana or Boston Logan Intl - Oranjestad Reina Beatrix when deciding on the best route from Boston to Caribbean Islands.

What are the cheapest flights from Boston to Caribbean Islands?

On average you can expect to pay $373 for a flight from Boston to Caribbean Islands. The cheapest flight overall is $90 while the most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl) is currently priced at $188.

What are the most reliable airlines from Boston to Caribbean Islands?

The top 3 most reliable airlines when flying from Boston to Caribbean Islands are Delta (89%), Etihad Airways (84%) and EL AL (83%).

What are the most popular airlines that fly from Boston to Caribbean Islands?

The most popular airlines flying from Boston to Caribbean Islands are American Airlines, JetBlue and Delta. Something to consider prior to booking your flight.

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 28 days in advance, which can save you up to 12% on flights from Boston to Caribbean Islands compared to booking the week you need them. Waiting 28 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $210. For sooner than that we have options available in the next 3 days from $268.

What is the cheapest month to fly from Boston to Caribbean Islands?

September can be a great time to fly to Caribbean Islands from Boston with a flight ticket averaging about $268. Cheapflights users have found deals in the month of September for as cheap as $54. The most expensive prices can be found in the month of December.

What airport do you fly from for flights from Boston to Caribbean Islands?

Most people fly from Boston Logan Intl (BOS) if they book a flight from Boston to Caribbean Islands. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

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

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

How can I find direct flights from Boston to Caribbean Islands?

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

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

Yes. Cheapflights offers flight deals from Boston to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$97+ Flights from Boston to Caribbean Islands

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Cheap flight deals from Boston to Caribbean Islands

Round-trip from	$174 (Cheapflightsfares)
One-way from	$97 (FlightHub)
Popular in	December
Cheapest in	September
Average price	$283

From Boston Logan Intl to Caribbean Islands

Search Deals

One-way flight from Boston Logan Intl to Caribbean Islands

Search Deals

Highest demand for flights based on searches. 10% potential increase in price ($30 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in July 2025

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Find flight deals from Boston to Caribbean Islands

Cheapest flights from Boston to Caribbean Islands
Explore the most affordable flight options available from Boston to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on juillet 2, 2025.

dim. 8/310:03 amBOS - SJU

Nonstop4h 05mSpirit Airlines

mer. 8/63:50 pmSJU - BOS

1 stop7h 58mSpirit Airlines

Deal found 6/30

$174

ven. 8/299:20 amBOS - SJU

1 stop17h 30mMultiple Airlines

mar. 9/22:11 amSJU - BOS

1 stop7h 28mMultiple Airlines

Deal found 6/30

$212

mar. 8/268:00 amBOS - SJU

Nonstop4h 06mJetBlue

sam. 8/306:54 pmSJU - BOS

Nonstop4h 05mJetBlue

Deal found 6/30

$244

lun. 9/86:55 pmBOS - STT

1 stop14h 49mSpirit Airlines

jeu. 9/1110:49 amSTT - BOS

1 stop13h 06mSpirit Airlines

Deal found 7/1

$281

sam. 11/19:25 amBOS - STT

Nonstop3h 59mJetBlue

sam. 11/82:05 pmSTT - BOS

1 stop6h 17mJetBlue

Deal found 7/2

$302

mer. 10/158:00 amBOS - STT

1 stop7h 50mAmerican Airlines

mer. 10/225:15 pmSTT - BOS

1 stop7h 19mAmerican Airlines

Deal found 6/30

$311

lun. 8/255:35 amBOS - SXM

1 stop8h 10mDelta

sam. 9/63:21 pmSXM - BOS

1 stop10h 00mDelta

Deal found 6/30

$335

mar. 7/228:39 pmBOS - SXM

1 stop17h 21mSpirit Airlines

mer. 7/303:05 pmSXM - BOS

1 stop8h 43mSpirit Airlines

Deal found 6/30

$336

sam. 8/237:10 amBOS - SXM

1 stop7h 33mUnited Airlines

sam. 8/303:55 pmSXM - BOS

2 stops18h 01mUnited Airlines

Deal found 6/30

$340

ven. 7/119:40 amBOS - SXM

1 stop25h 48mMultiple Airlines

mer. 7/233:05 pmSXM - BOS

1 stop8h 43mMultiple Airlines

Deal found 7/1

$344

lun. 8/118:39 pmBOS - PUJ

1 stop17h 51mSpirit Airlines

jeu. 8/2112:40 pmPUJ - BOS

2 stops22h 38mSpirit Airlines

Deal found 7/1

$347

ven. 9/266:00 amBOS - PUJ

2 stops9h 25mAmerican Airlines

ven. 10/312:08 pmPUJ - BOS

1 stop8h 06mAmerican Airlines

Deal found 6/30

$349

Best flights from Boston to Caribbean Islands
Discover carefully curated flight deals from Boston to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated juillet 2, 2025.

dim. 8/310:03 amBOS - SJU

Nonstop4h 05mSpirit Airlines

mar. 8/51:21 amSJU - BOS

1 stop7h 16mSpirit Airlines

Deal found 6/30

$174

ven. 8/299:20 amBOS - SJU

1 stop17h 30mMultiple Airlines

mar. 9/22:11 amSJU - BOS

1 stop7h 28mMultiple Airlines

Deal found 6/30

$212

mar. 8/268:00 amBOS - SJU

Nonstop4h 06mJetBlue

sam. 8/306:54 pmSJU - BOS

Nonstop4h 05mJetBlue

Deal found 6/30

$244

lun. 9/86:00 amBOS - STT

2 stops10h 00mAmerican Airlines

jeu. 9/111:40 pmSTT - BOS

2 stops17h 34mAmerican Airlines

Deal found 6/30

$311

lun. 8/255:35 amBOS - SXM

1 stop8h 10mDelta

sam. 9/63:21 pmSXM - BOS

1 stop10h 00mDelta

Deal found 6/30

$335

sam. 8/237:10 amBOS - SXM

1 stop7h 33mUnited Airlines

sam. 8/303:55 pmSXM - BOS

2 stops18h 01mUnited Airlines

Deal found 6/30

$340

dim. 9/1410:20 amBOS - NAS

2 stops31h 10mAir Canada

mer. 9/246:30 pmNAS - BOS

2 stops15h 00mAir Canada

Deal found 7/1

$385

lun. 9/86:55 pmBOS - STT

1 stop14h 49mSpirit Airlines

jeu. 9/1110:49 amSTT - BOS

1 stop13h 06mSpirit Airlines

Deal found 7/1

$281

ven. 7/119:40 amBOS - SXM

1 stop25h 48mMultiple Airlines

mer. 7/233:05 pmSXM - BOS

1 stop8h 43mMultiple Airlines

Deal found 7/1

$344

ven. 9/266:00 amBOS - PUJ

2 stops9h 25mAmerican Airlines

ven. 10/312:08 pmPUJ - BOS

1 stop8h 06mAmerican Airlines

Deal found 6/30

$349

mar. 7/297:19 amBOS - PUJ

Nonstop4h 01mJetBlue

sam. 8/24:17 pmPUJ - BOS

Nonstop4h 15mJetBlue

Deal found 6/30

$350

ven. 9/266:05 amBOS - MBJ

1 stop6h 20mDelta

lun. 9/294:59 pmMBJ - BOS

1 stop7h 19mDelta

Deal found 6/29

$361

Last-minute flights from Boston to Caribbean Islands
Discover last-minute flight deals from Boston to Caribbean Islands. Data last updated juillet 2, 2025 and is based on user searches.

mar. 7/85:45 amBOS - STT

1 stop8h 13mSpirit Airlines

mar. 7/2210:43 amSTT - BOS

1 stop8h 51mSpirit Airlines

Deal found 7/1

$296

mar. 7/86:00 amBOS - STT

2 stops9h 55mAmerican Airlines

mar. 7/2211:34 amSTT - BOS

1 stop12h 00mAmerican Airlines

Deal found 6/30

$330

mar. 7/85:55 amBOS - PUJ

1 stop6h 29mAmerican Airlines

mar. 7/1511:29 amPUJ - BOS

1 stop12h 05mAmerican Airlines

Deal found 7/1

$394

mer. 7/96:10 amBOS - MBJ

1 stop7h 35mMultiple Airlines

mer. 7/1612:10 pmMBJ - BOS

1 stop10h 38mMultiple Airlines

Deal found 7/1

$389

jeu. 7/1010:03 amBOS - SJU

Nonstop4h 05mSpirit Airlines

mar. 7/151:21 amSJU - BOS

1 stop7h 16mSpirit Airlines

Deal found 6/30

$198

jeu. 7/109:01 amBOS - SJU

1 stop14h 58mMultiple Airlines

mar. 7/151:21 amSJU - BOS

1 stop7h 16mMultiple Airlines

Deal found 6/30

$228

ven. 7/116:00 amBOS - SJU

1 stop10h 00mFrontier

mer. 7/161:43 pmSJU - BOS

1 stop18h 09mFrontier

Deal found 6/29

$222

ven. 7/119:40 amBOS - SXM

1 stop25h 48mMultiple Airlines

mer. 7/233:05 pmSXM - BOS

1 stop8h 43mMultiple Airlines

Deal found 7/1

$344

sam. 7/126:10 amBOS - PUJ

1 stop9h 45mSpirit Airlines

sam. 7/193:25 pmPUJ - BOS

1 stop8h 23mSpirit Airlines

Deal found 7/1

$348

sam. 7/127:26 pmBOS - PUJ

1 stop13h 28mMultiple Airlines

mer. 7/163:25 pmPUJ - BOS

1 stop8h 23mMultiple Airlines

Deal found 6/30

$355

sam. 7/128:39 pmBOS - MBJ

1 stop14h 14mSpirit Airlines

ven. 7/1812:10 pmMBJ - BOS

1 stop6h 24mSpirit Airlines

Deal found 7/2

$363

sam. 7/128:39 pmBOS - AUA

1 stop18h 01mSpirit Airlines

sam. 7/193:45 pmAUA - BOS

1 stop8h 03mSpirit Airlines

Deal found 7/1

$393

One-way flights from Boston to Caribbean Islands
Search for one-way flight options from Boston to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated juillet 2, 2025.

dim. 8/316:05 amBOS - SJU

1 stop15h 43mSpirit Airlines

Deal found 6/30

$97

sam. 8/166:05 amBOS - MBJ

1 stop6h 09mSpirit Airlines

Deal found 7/2

$115

mar. 8/56:10 amBOS - PUJ

1 stop8h 20mSpirit Airlines

Deal found 7/2

$117

mar. 9/25:40 amBOS - SJU

1 stop7h 05mSouthwest

Deal found 6/30

$127

jeu. 7/316:00 amBOS - SJU

1 stop9h 52mFrontier

Deal found 6/30

$129

dim. 8/318:00 amBOS - SJU

Nonstop4h 06mDelta

Deal found 6/30

$132

sam. 8/27:40 amBOS - NAS

Nonstop3h 22mJetBlue

Deal found 6/30

$134

mer. 7/166:00 amBOS - SJU

1 stop11h 03mMultiple Airlines

Deal found 6/29

$135

mer. 7/305:35 amBOS - SXM

1 stop8h 21mDelta

Deal found 6/30

$137

mar. 9/306:00 amBOS - SJU

2 stops12h 14mAmerican Airlines

Deal found 6/29

$137

lun. 7/218:35 pmBOS - STT

1 stop15h 55mSpirit Airlines

Deal found 7/1

$137

lun. 7/286:05 amBOS - NAS

1 stop5h 28mDelta

Deal found 7/2

$139

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

dim. 8/3

10:03 am-2:08 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

mar. 8/5

1:21 am-8:37 am

1 stop7h 16m

$174

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

ven. 8/29

9:20 am-2:50 am

1 stop17h 30m

San Juan Luis Munoz Marin Intl

mar. 9/2

2:11 am-9:39 am

1 stop7h 28m

$212

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mar. 8/26

8:00 am-12:06 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

sam. 8/30

6:54 pm-10:59 pm

Nonstop4h 05m

$244

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

lun. 9/8

6:55 pm-9:44 am

1 stop14h 49m

Saint Thomas Island Cyril E King

jeu. 9/11

10:49 am-11:55 pm

1 stop13h 06m

$281

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

lun. 9/8

6:00 am-4:00 pm

2 stops10h 00m

Saint Thomas Island Cyril E King

jeu. 9/11

1:40 pm-7:14 am

2 stops17h 34m

$311

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

lun. 8/25

5:35 am-1:45 pm

1 stop8h 10m

Simpson Bay Princess Juliana

sam. 9/6

3:21 pm-1:21 am

1 stop10h 00m

$335

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

mar. 7/22

8:39 pm-2:00 pm

1 stop17h 21m

Simpson Bay Princess Juliana

mer. 7/30

3:05 pm-11:48 pm

1 stop8h 43m

$336

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

sam. 8/23

7:10 am-2:43 pm

1 stop7h 33m

Simpson Bay Princess Juliana

sam. 8/30

3:55 pm-9:56 am

2 stops18h 01m

$340

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

ven. 7/11

9:40 am-11:28 am

1 stop25h 48m

Simpson Bay Princess Juliana

mer. 7/23

3:05 pm-11:48 pm

1 stop8h 43m

$344

BostonPunta Cana

BOS - PUJ

BOSPUJ

Boston Logan Intl

lun. 8/11

8:39 pm-2:30 pm

1 stop17h 51m

Punta Cana

jeu. 8/21

12:40 pm-11:18 am

2 stops22h 38m

$347

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 60 results

...

Best time to book a flight from Boston to Caribbean Islands

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

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

Currently, September is the cheapest month in which you can book a flight from Boston to Caribbean Islands (average of $254). Flying from Boston to Caribbean Islands 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 BOS to EPX?

When flying from Boston to Caribbean Islands, 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 Boston to Caribbean Islands

The most flights from BOS to zzEPX are scheduled on a Wednesday (17 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (5 on average).

Reviews of airlines servicing Caribbean Islands

Read reviews from past customers who have flown Southwest, Delta, and Copa Airlines from Boston to Caribbean Islands. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,272 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Southwest

8.0

Very good

4,272 reviews

Southwest

8.0

Very good

4,272 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Delta

8.0

Very good

7,975 reviews

Southwest

8.0

Very good

4,272 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Copa Airlines

7.5

Good

1,465 reviews

Southwest

8.0

Very good

4,272 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

United Airlines

7.4

Good

8,861 reviews

Southwest

8.0

Very good

4,272 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

JetBlue

7.3

Good

2,918 reviews

Southwest

8.0

Very good

4,272 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

What airport do you fly from for flights from Boston to Caribbean Islands?
Most people fly from Boston Logan Intl (BOS) if they book a flight from Boston to Caribbean Islands. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.
What are the cheapest airlines to fly from Boston to Caribbean Islands one-way?
$97 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 Frontier, with prices starting from $127 and $129, respectively.
What are the most popular routes from Boston to Caribbean Islands?
Most travelers choose Boston Logan Intl - San Juan Luis Munoz Marin Intl, Boston Logan Intl - Punta Cana or Boston Logan Intl - Oranjestad Reina Beatrix when deciding on the best route from Boston to Caribbean Islands.
What are the most reliable airlines from Boston to Caribbean Islands?
The top 3 most reliable airlines when flying from Boston to Caribbean Islands are Delta (89%), Etihad Airways (84%) and EL AL (83%).
What are the cheapest flights from Boston to Caribbean Islands?
On average you can expect to pay $373 for a flight from Boston to Caribbean Islands. The cheapest flight overall is $90 while the most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl) is currently priced at $188.
Can I find deals for flights from Boston to Caribbean Islands that include hotel bookings?
Yes. In addition to deals on Boston to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Boston to Caribbean Islands?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Caribbean Islands.
Can I find deals for business class flights from Boston to Caribbean Islands?
Yes. Cheapflights offers flight deals from Boston to Caribbean Islands 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 Boston to Caribbean Islands?
Currently, September is the cheapest month in which you can book a flight from Boston to Caribbean Islands (average of $254). Flying from Boston to Caribbean Islands 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 Boston to Caribbean Islands

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$76	Average$369	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$95	Average$404	FlexibilityNo cancel fee	On-time65%
Arajet	Cheapest$122	Average$343	FlexibilityNo cancel fee	On-timeN/A
Delta	Cheapest$141	Average$501	FlexibilityNo cancel fee	On-timeN/A
JetBlue	Cheapest$149	Average$531	FlexibilityNo cancel fee	On-time62%
Air Canada	Cheapest$188	Average$678	FlexibilityNo cancel fee	On-time67%
United Airlines	Cheapest$204	Average$547	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$288	Average$592	FlexibilityNo cancel fee	On-time71%
Avianca	Cheapest$292	Average$518	FlexibilityNo cancel fee	On-time71%
Copa Airlines	Cheapest$353	Average$520	FlexibilityNo cancel fee	On-time70%

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$97+ Cheap flights from Boston (BOS) to Caribbean Islands

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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Boston to Caribbean Islands with Cheapflights

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Cheap flight deals from Boston to Caribbean Islands

Keep the following information in mind while searching for Boston to Caribbean Islands flight deals. Data was last updated juillet 2, 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Boston to Caribbean Islands

Cheapest flights from Boston to Caribbean IslandsExplore the most affordable flight options available from Boston to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on juillet 2, 2025.

Explore the most affordable flight options available from Boston to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on juillet 2, 2025.

Cheapflights Fare Finder

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

Best time to book a flight from Boston to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Boston with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Boston to Caribbean Islands

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

What is the cheapest time of day to fly from BOS to EPX?

Find hourly flight availability from Boston to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated juillet 2, 2025.

Weekly flight availability from Boston to Caribbean Islands

Reviews of airlines servicing Caribbean Islands

Read reviews from past customers who have flown Southwest, Delta, and Copa Airlines from Boston to Caribbean Islands. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Boston to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly from for flights from Boston to Caribbean Islands?

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

What are the most popular routes from Boston to Caribbean Islands?

What are the most reliable airlines from Boston to Caribbean Islands?

What are the cheapest flights from Boston to Caribbean Islands?

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

How can I find direct flights from Boston to Caribbean Islands?

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

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

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 Boston to Caribbean Islands

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

Top 10 airlines flying from Boston to Caribbean Islands

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Cheapest flights from Boston to Caribbean Islands
Explore the most affordable flight options available from Boston to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on juillet 2, 2025.