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Caribbean Islands

$74+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Dec 19 — Dec 261
Fri 12/19
Fri 12/26
1 adult, Economy
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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 November 19, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$191
(Delta)

One-way from

$74
(Delta)

Popular in

December

Cheapest in

January

Average price

$318
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
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From Boston Logan Intl to Caribbean Islands
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One-way flight from Boston Logan Intl to Caribbean Islands
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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. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 19, 2025.

This Delta deal was found by Cheapflights users on 11/19. 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.
Tue 12/96:45 amBOS - SJU
1 stop9h 43mDelta
Tue 12/234:48 pmSJU - BOS
1 stop8h 09mDelta
Deal found 11/19$195
This Cheapflightsfares deal was found by Cheapflights users on 11/18. 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 12/1010:56 amBOS - SJU
1 stop12h 20mSpirit Airlines
Fri 12/194:10 amSJU - BOS
1 stop7h 40mSpirit Airlines
Deal found 11/18$196
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/245:45 pmBOS - SJU
1 stop16h 04mSpirit Airlines
Fri 12/56:14 pmSJU - BOS
1 stop6h 42mSpirit Airlines
Deal found 11/18$198
This CheapOair deal was found by Cheapflights users on 11/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/138:11 pmBOS - SJU
1 stop13h 22mSpirit Airlines
Tue 12/233:15 pmSJU - BOS
Nonstop4h 24mSpirit Airlines
Deal found 11/18$199
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/245:45 pmBOS - SJU
1 stop16h 04mSpirit Airlines
Mon 12/84:10 amSJU - BOS
2 stops30h 51mSpirit Airlines
Deal found 11/18$201
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:08 amBOS - SJU
1 stop12h 08mSpirit Airlines
Mon 12/84:10 amSJU - BOS
2 stops30h 51mSpirit Airlines
Deal found 11/17$202
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/245:45 pmBOS - SJU
1 stop16h 04mSpirit Airlines
Thu 12/1111:38 amSJU - BOS
1 stop8h 28mSpirit Airlines
Deal found 11/18$204
This Cheapflightsfares deal was found by Cheapflights users on 11/17. 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.
Sat 12/68:11 pmBOS - SJU
1 stop13h 22mSpirit Airlines
Mon 12/156:14 pmSJU - BOS
1 stop6h 42mSpirit Airlines
Deal found 11/17$205
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/811:08 amBOS - SJU
1 stop12h 08mSpirit Airlines
Fri 12/192:59 amSJU - BOS
1 stop8h 02mSpirit Airlines
Deal found 11/18$206
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/78:11 pmBOS - SJU
1 stop13h 22mSpirit Airlines
Thu 12/1111:38 amSJU - BOS
1 stop8h 28mSpirit Airlines
Deal found 11/18$207
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1412:57 pmBOS - SJU
1 stop12h 53mFrontier
Thu 12/188:00 amSJU - BOS
Nonstop4h 23mFrontier
Deal found 11/18$208
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1010:56 amBOS - SJU
1 stop12h 20mSpirit Airlines
Fri 12/126:14 pmSJU - BOS
1 stop6h 42mSpirit Airlines
Deal found 11/18$209

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston to Caribbean Islands 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 November 19, 2025.
Use the filters below to find and compare flights from Boston to Caribbean Islands that are best for you.

Fly from

Boston

Fly to

Caribbean Islands

Route

Depart

Return

Price

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 2/1

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Sat 2/7

5:55 pm-10:53 pm

1 stop5h 58m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 1/18

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Fri 1/23

2:00 pm-6:59 pm

1 stop5h 59m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sat 1/3

9:40 am-2:40 pm

Nonstop4h 00m

Saint Thomas Island Cyril E King

Sat 1/10

3:45 pm-8:44 pm

1 stop5h 59m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 2/22

8:00 am-1:06 pm

Nonstop4h 06m

Saint Thomas Island Cyril E King

Tue 3/3

2:01 pm-6:54 pm

1 stop5h 53m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 1/23

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Sat 1/31

5:55 pm-10:53 pm

1 stop5h 58m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 2/22

8:00 am-1:06 pm

Nonstop4h 06m

Saint Thomas Island Cyril E King

Sat 2/28

4:50 pm-9:39 pm

1 stop5h 49m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 1/30

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Sat 2/7

5:55 pm-10:53 pm

1 stop5h 58m

$234

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 12/8

8:10 am-1:10 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Thu 12/11

3:32 pm-1:27 am

1 stop10h 55m

$248

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 11/25

11:06 pm-4:03 am

Nonstop3h 57m

San Juan Luis Munoz Marin Intl

Fri 12/5

1:41 pm-4:54 pm

Nonstop4h 13m

$264

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 12/30

8:20 am-1:24 pm

Nonstop4h 04m

Saint Thomas Island Cyril E King

Thu 1/8

2:32 pm-5:53 pm

Nonstop4h 21m

$266

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Showing 1-10 of 60 results
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2
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6

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, January is the cheapest month in which you can book a flight from Boston to Caribbean Islands (average of $88). Flying from Boston to Caribbean Islands in September is currently the most expensive (average of $147). 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?

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 November 19, 2025.

A simple way to save on the total cost of your ticket is to fly from Boston to Caribbean Islands at noon. If you’re flexible enough to do this you can expect to save up to 15% on your trip compared to booking a flight in the morning.

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

Use this chart to determine the cheapest time to fly round-trip from Boston to Caribbean Islands. Price data was last updated on November 2, 2025.

Travelers seeking maximum savings on their Boston to Caribbean Islands flight should consider departing on Friday afternoons when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Boston to Caribbean Islands

Explore weekly flight availability from Boston to Caribbean Islands. 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 November 19, 2025.

The most flights from BOS to zzEPX are scheduled on a Tuesday (6 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (1 on average).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Caribbean Islands. Reviews last updated November 19, 2025.
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
7.9
Good
8,004 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Overall

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,004 reviews
Delta
7.9
Good
8,004 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Overall

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,025 reviews
Delta
7.9
Good
8,004 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Overall

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,046 reviews
Delta
7.9
Good
8,004 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Overall

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,903 reviews
Delta
7.9
Good
8,004 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Overall

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,154 reviews
Delta
7.9
Good
8,004 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Overall

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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?

    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 $248, JetBlue can have you in Caribbean Islands from Boston in 4h. 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?

    $74 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on JetBlue and American Airlines, with prices starting from $122 and $127, 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 Hawaiian Airlines (79%), Icelandair (69%) and TAP AIR PORTUGAL (66%).

  • What are the cheapest flights from Boston to Caribbean Islands?

    On average you can expect to pay $500 for a flight from Boston to Caribbean Islands. The cheapest flight overall is $125 while the most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl) is currently priced at $146.

  • 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, January is the cheapest month in which you can book a flight from Boston to Caribbean Islands (average of $88). Flying from Boston to Caribbean Islands in September is currently the most expensive (average of $147). 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.

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Top 10 airlines flying from Boston to Caribbean Islands

Discover the top 10 airlines that operate flights from Boston to Caribbean Islands. 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 November 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$86Average$397FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$100Average$378FlexibilityNo cancel feeOn-time65%
Air CanadaCheapest$141Average$623FlexibilityNo cancel feeOn-time67%
DeltaCheapest$144Average$476FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$172Average$535FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$190Average$514FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$192Average$345FlexibilityNo cancel feeOn-time70%
ArajetCheapest$230Average$423FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$288Average$589FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$578FlexibilityNo cancel feeOn-time71%

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