How long is the flight from Boston to Caribbean Islands?

For as low as $251, Spirit Airlines can have you in Caribbean Islands from Boston in 7h 14m. The distance from Boston to Caribbean Islands is about 1678 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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 Air Canada and JetBlue, with prices starting from $121 and $123, 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 - Santo Domingo Las Americas 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 $586 for a flight from Boston to Caribbean Islands. The cheapest flight overall is $118 while the most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl) is currently priced at $166.

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 (90%), EL AL (83%) and TAP AIR PORTUGAL (81%).

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 27 days in advance, which can save you up to 5% on flights from Boston to Caribbean Islands compared to booking the week you need them. Waiting 27 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 $225. For sooner than that we have options available in the next 3 days from $264.

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 $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.

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+ Cheap Flights from Boston to Caribbean Islands

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Boston to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Boston to Caribbean Islands

Round-trip from	$187 (SmartFares)
One-way from	$97 (eDestinos)
Popular in	December
Cheapest in	September
Average price	$303

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. 2% potential increase in price ($7 potential increase over avg. RT price).

Search Deals

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

Search Deals

Average for round-trip flights in August 2025

Search Deals

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 August 18, 2025.

Wed 9/1712:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Sat 9/206:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/17

$189

Mon 9/82:53 pmBOS - SJU

1 stop10h 01mSpirit Airlines

Fri 9/1911:59 amSJU - BOS

1 stop11h 58mSpirit Airlines

Deal found 8/16

$194

Tue 9/1612:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Fri 9/2611:59 amSJU - BOS

1 stop11h 58mSpirit Airlines

Deal found 8/17

$196

Tue 9/1612:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Thu 9/182:38 pmSJU - BOS

1 stop8h 09mSpirit Airlines

Deal found 8/17

$197

Tue 9/1612:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Tue 9/236:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/17

$198

Wed 9/36:30 amBOS - SJU

1 stop16h 58mSpirit Airlines

Fri 9/1211:59 amSJU - BOS

1 stop11h 58mSpirit Airlines

Deal found 8/17

$200

Sun 8/316:05 amBOS - SJU

1 stop15h 43mSpirit Airlines

Sat 9/136:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/17

$201

Wed 9/1712:20 pmBOS - SJU

1 stop8h 36mMultiple Airlines

Sat 9/2012:28 amSJU - BOS

1 stop8h 15mMultiple Airlines

Deal found 8/17

$202

Sun 8/313:37 pmBOS - SJU

1 stop9h 19mSpirit Airlines

Sat 9/66:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/17

$206

Sat 8/3010:34 amBOS - SJU

1 stop13h 23mSpirit Airlines

Sat 9/66:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/17

$207

Tue 9/1612:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Wed 9/176:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/17

$211

Tue 9/912:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Thu 9/2511:59 amSJU - BOS

1 stop11h 58mSpirit Airlines

Deal found 8/17

$212

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 August 18, 2025.

Wed 10/812:31 pmBOS - SJU

1 stop13h 13mSpirit Airlines

Mon 10/132:49 amSJU - BOS

1 stop10h 55mSpirit Airlines

Deal found 8/16

$213

Tue 9/166:40 amBOS - SJU

1 stop7h 14mJetBlue

Tue 9/234:35 pmSJU - BOS

1 stop7h 24mJetBlue

Deal found 8/16

$251

Wed 10/295:30 amBOS - PLS

1 stop10h 30mUnited Airlines

Wed 12/35:06 pmPLS - BOS

1 stop6h 35mUnited Airlines

Deal found 8/17

$339

Sat 11/86:09 pmBOS - PLS

1 stop16h 14mAmerican Airlines

Tue 11/113:25 pmPLS - BOS

1 stop9h 21mAmerican Airlines

Deal found 8/17

$344

Wed 9/176:10 amBOS - SDQ

1 stop9h 50mMultiple Airlines

Thu 10/21:20 pmSDQ - BOS

2 stops18h 32mMultiple Airlines

Deal found 8/18

$349

Sat 9/205:05 pmBOS - STI

1 stop7h 29mDelta

Sat 9/278:40 pmSTI - BOS

1 stop10h 38mDelta

Deal found 8/16

$371

Tue 9/1612:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Sat 9/206:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/16

$217

Thu 10/162:53 pmBOS - SJU

1 stop10h 51mSpirit Airlines

Thu 10/2311:51 amSJU - BOS

1 stop12h 08mSpirit Airlines

Deal found 8/18

$217

Wed 9/178:00 amBOS - SJU

Nonstop4h 17mJetBlue

Sat 9/274:40 pmSJU - BOS

1 stop7h 19mJetBlue

Deal found 8/17

$262

Wed 9/178:00 amBOS - SJU

Nonstop4h 17mJetBlue

Sat 9/204:40 pmSJU - BOS

1 stop7h 19mJetBlue

Deal found 8/17

$262

Wed 11/56:15 amBOS - STT

1 stop7h 56mSpirit Airlines

Tue 11/184:06 pmSTT - BOS

1 stop7h 02mSpirit Airlines

Deal found 8/16

$256

Fri 8/2912:00 pmBOS - SJU

Nonstop4h 04mJetBlue

Wed 9/34:35 pmSJU - BOS

1 stop7h 24mJetBlue

Deal found 8/16

$262

Last-minute flights from Boston to Caribbean Islands
Discover last-minute flight deals from Boston to Caribbean Islands. Data last updated August 18, 2025 and is based on user searches.

Sat 8/3010:34 amBOS - SJU

1 stop13h 23mSpirit Airlines

Sat 9/66:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/17

$207

Sun 8/316:05 amBOS - SJU

1 stop15h 43mSpirit Airlines

Sat 9/136:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/17

$201

Sun 8/313:37 pmBOS - SJU

1 stop9h 19mSpirit Airlines

Sat 9/66:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/17

$206

Wed 9/36:30 amBOS - SJU

1 stop16h 58mSpirit Airlines

Fri 9/1211:59 amSJU - BOS

1 stop11h 58mSpirit Airlines

Deal found 8/17

$200

Mon 9/82:53 pmBOS - SJU

1 stop10h 01mSpirit Airlines

Fri 9/1911:59 amSJU - BOS

1 stop11h 58mSpirit Airlines

Deal found 8/16

$194

Tue 9/912:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Thu 9/116:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/17

$212

Tue 9/1612:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Fri 9/2611:59 amSJU - BOS

1 stop11h 58mSpirit Airlines

Deal found 8/17

$196

Tue 9/1612:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Thu 9/182:38 pmSJU - BOS

1 stop8h 09mSpirit Airlines

Deal found 8/17

$197

Tue 9/1612:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Tue 9/236:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/17

$198

Tue 9/1612:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Wed 9/176:44 amSJU - BOS

1 stop7h 04mSpirit Airlines

Deal found 8/17

$211

Wed 9/1712:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Thu 9/1811:59 amSJU - BOS

1 stop11h 58mSpirit Airlines

Deal found 8/17

$189

Wed 9/1712:20 pmBOS - SJU

1 stop8h 36mMultiple Airlines

Sat 9/2012:28 amSJU - BOS

1 stop8h 15mMultiple Airlines

Deal found 8/17

$202

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 August 18, 2025.

Mon 9/152:53 pmBOS - SJU

1 stop10h 01mSpirit Airlines

Deal found 8/17

$97

Tue 9/166:10 amBOS - MBJ

1 stop5h 55mSpirit Airlines

Deal found 8/17

$98

Tue 9/96:10 amBOS - PUJ

1 stop8h 04mSpirit Airlines

Deal found 8/17

$102

Sat 9/203:00 pmBOS - SJU

2 stops23h 17mSpirit Airlines

Deal found 8/16

$102

Sat 9/133:00 pmBOS - SJU

2 stops23h 17mSpirit Airlines

Deal found 8/18

$105

Sat 9/63:00 pmBOS - SJU

1 stop20h 04mSpirit Airlines

Deal found 8/18

$106

Fri 11/76:00 amBOS - SJU

1 stop9h 23mSpirit Airlines

Deal found 8/18

$108

Sun 9/145:50 amBOS - SJU

1 stop7h 53mSpirit Airlines

Deal found 8/18

$109

Wed 9/2412:20 pmBOS - SJU

1 stop8h 36mSpirit Airlines

Deal found 8/18

$110

Tue 9/166:10 amBOS - PUJ

1 stop8h 04mSpirit Airlines

Deal found 8/16

$112

Sun 9/76:10 amBOS - MBJ

1 stop5h 55mSpirit Airlines

Deal found 8/18

$115

Sat 9/206:10 amBOS - PUJ

1 stop8h 04mSpirit Airlines

Deal found 8/17

$115

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

Wed 10/8

12:31 pm-1:44 am

1 stop13h 13m

San Juan Luis Munoz Marin Intl

Mon 10/13

2:49 am-1:44 pm

1 stop10h 55m

$213

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 9/16

12:20 pm-8:56 pm

1 stop8h 36m

San Juan Luis Munoz Marin Intl

Sat 9/20

6:44 am-1:48 pm

1 stop7h 04m

$217

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 10/16

2:53 pm-1:44 am

1 stop10h 51m

San Juan Luis Munoz Marin Intl

Thu 10/23

11:51 am-11:59 pm

1 stop12h 08m

$217

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 9/16

6:40 am-1:54 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Tue 9/23

4:35 pm-11:59 pm

1 stop7h 24m

$251

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 11/5

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

$256

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 9/17

8:00 am-12:17 pm

Nonstop4h 17m

San Juan Luis Munoz Marin Intl

Sat 9/27

4:40 pm-11:59 pm

1 stop7h 19m

$262

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 9/17

8:00 am-12:17 pm

Nonstop4h 17m

San Juan Luis Munoz Marin Intl

Sat 9/20

4:40 pm-11:59 pm

1 stop7h 19m

$262

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 8/29

12:00 pm-4:04 pm

Nonstop4h 04m

San Juan Luis Munoz Marin Intl

Wed 9/3

4:35 pm-11:59 pm

1 stop7h 24m

$262

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 10/24

12:00 pm-4:05 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Wed 10/29

4:05 am-12:11 pm

1 stop8h 06m

$262

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 10/21

6:48 am-1:45 pm

1 stop6h 57m

San Juan Luis Munoz Marin Intl

Tue 10/28

7:10 am-11:23 am

Nonstop4h 13m

$262

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

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 Sunday (20 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (14 on average).

Reviews of airlines servicing Caribbean Islands

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

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Delta

8.0

Very good

7,981 reviews

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

United Airlines

7.4

Good

8,925 reviews

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

JetBlue

7.2

Good

2,915 reviews

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Spirit Airlines

6.3

Okay

8,038 reviews

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.
How long is the flight from Boston to Caribbean Islands?
For as low as $251, Spirit Airlines can have you in Caribbean Islands from Boston in 7h 14m. The distance from Boston to Caribbean Islands is about 1678 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.
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 Air Canada and JetBlue, with prices starting from $121 and $123, 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 - Santo Domingo Las Americas 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 (90%), EL AL (83%) and TAP AIR PORTUGAL (81%).
What are the cheapest flights from Boston to Caribbean Islands?
On average you can expect to pay $586 for a flight from Boston to Caribbean Islands. The cheapest flight overall is $118 while the most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl) is currently priced at $166.
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$80	Average$376	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$99	Average$386	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$140	Average$480	FlexibilityNo cancel fee	On-timeN/A
JetBlue	Cheapest$153	Average$538	FlexibilityNo cancel fee	On-time62%
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%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$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 9/14. 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

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

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 August 18, 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 August 18, 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 August 18, 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 August 18, 2025.

Weekly flight availability from Boston to Caribbean Islands

Reviews of airlines servicing Caribbean Islands

Read reviews from past customers who have flown Delta, United Airlines, and American 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?

How long is the flight 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

100% Free

Book with Flexibility

Travel Smart

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 August 18, 2025.