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$77+ Cheap flights from Boston (BOS) 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Boston to Caribbean

Cheapest flights from Boston to Caribbean
Explore the most affordable flight options available from Boston to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This Priceline deal was found by Cheapflights users on 12/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/209:25 amBOS - SJU
Nonstop4h 04mMultiple Airlines
Wed 12/243:15 pmSJU - BOS
Nonstop4h 24mMultiple Airlines
Deal found 12/11$169
This Priceline deal was found by Cheapflights users on 12/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Tue 12/238:00 amSJU - BOS
Nonstop4h 23mMultiple Airlines
Deal found 12/11$174
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 12/317:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Sun 1/113:55 amSJU - BOS
1 stop7h 51mMultiple Airlines
Deal found 12/9$181
This JetBlue deal was found by Cheapflights users on 12/9. 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 12/246:50 pmBOS - SJU
Nonstop4h 06mJetBlue
Thu 1/152:00 pmSJU - BOS
Nonstop4h 13mJetBlue
Deal found 12/9$186
This Super.com deal was found by Cheapflights users on 12/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Mon 12/222:59 amSJU - BOS
1 stop8h 02mSpirit Airlines
Deal found 12/11$192
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 12/1410:22 amBOS - SJU
1 stop8h 46mFrontier
Sun 12/216:00 amSJU - BOS
Nonstop4h 23mFrontier
Deal found 12/11$194
This Frontier deal was found by Cheapflights users on 12/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1410:22 amBOS - SJU
1 stop8h 46mFrontier
Thu 12/188:00 amSJU - BOS
Nonstop4h 23mFrontier
Deal found 12/11$196
This CheapOair deal was found by Cheapflights users on 12/10. 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.
Thu 12/1812:18 pmBOS - SJU
Nonstop4h 04mFrontier
Tue 12/238:00 amSJU - BOS
Nonstop4h 23mFrontier
Deal found 12/10$197
This Trip.com deal was found by Cheapflights users on 12/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/147:22 pmBOS - SJU
Nonstop4h 00mMultiple Airlines
Sun 12/216:00 amSJU - BOS
Nonstop4h 23mMultiple Airlines
Deal found 12/11$200
This Super.com deal was found by Cheapflights users on 12/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1812:18 pmBOS - SJU
Nonstop4h 04mFrontier
Sun 12/216:00 amSJU - BOS
Nonstop4h 23mFrontier
Deal found 12/9$201
This JetBlue deal was found by Cheapflights users on 12/10. 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 12/315:01 amBOS - STT
1 stop7h 59mJetBlue
Wed 1/72:00 pmSTT - BOS
1 stop5h 49mJetBlue
Deal found 12/10$266
This Delta deal was found by Cheapflights users on 12/10. 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 12/308:20 amBOS - STT
Nonstop4h 04mDelta
Thu 1/82:32 pmSTT - BOS
Nonstop4h 21mDelta
Deal found 12/10$312

Find flight deals from Boston to Caribbean

Keep the following information in mind while searching for Boston to Caribbean flight deals. Data was last updated December 12, 2025.

Round-trip from

$149
(CheapOair)

One-way from

$77
(Super.com)

Popular in

December

Cheapest in

January

Average price

$388

Good round-trip deal

$260 or less

Good one-way deal

$136 or less
From Boston Logan Intl to Caribbean
Search Deals
One-way flight from Boston Logan Intl to Caribbean
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Caribbean.
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Caribbean.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston to Caribbean 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 December 12, 2025.
Use the filters below to find and compare flights from Boston to Caribbean that are best for you.

Fly from

Boston

Fly to

Caribbean

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 2/14

6:00 am-11:05 am

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Fri 2/20

8:20 pm-11:32 pm

Nonstop4h 12m

$202

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 1/6

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Wed 1/14

2:32 pm-5:53 pm

Nonstop4h 21m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 1/9

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Mon 1/12

2:32 pm-5:53 pm

Nonstop4h 21m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 1/25

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Sat 1/31

5:50 pm-10:38 pm

1 stop5h 48m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 1/23

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Sun 2/1

2:32 pm-5:53 pm

Nonstop4h 21m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 2/3

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Tue 2/10

2:00 pm-6:59 pm

1 stop5h 59m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 1/13

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Sun 1/18

2:32 pm-5:53 pm

Nonstop4h 21m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 1/9

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Tue 1/13

2:00 pm-6:49 pm

1 stop5h 49m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 1/23

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Sun 1/25

2:32 pm-5:53 pm

Nonstop4h 21m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 3/18

9:45 am-1:46 pm

Nonstop4h 01m

Saint Thomas Island Cyril E King

Tue 3/31

3:00 pm-8:46 pm

1 stop5h 46m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 60 results
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Best time to book a flight from Boston to Caribbean

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

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

Currently, January is the cheapest month in which you can book a flight from Boston to Caribbean (average of $88). Flying from Boston to Caribbean in November is currently the most expensive (average of $177). 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 CB?

Find hourly flight availability from Boston 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 December 12, 2025.

It’s typically best to fly out from Boston to Caribbean at noon. Doing so could potentially save you 16% on the flight price compared to flying in the morning, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Boston to Caribbean. Price data was last updated on December 6, 2025.

Travelers seeking maximum savings on their Boston to Caribbean 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

Explore weekly flight availability from Boston to Caribbean. 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 December 12, 2025.

The most flights from BOS to 0CB are scheduled on a Thursday (12 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated December 12, 2025.
Get a feel of what it's like to fly with Delta, American Airlines, and JetBlue from Boston to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.1

Overall

7.9

Food

7.3

Comfort

7.9

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
8,008 reviews
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.1

Overall

7.9

Food

7.3

Comfort

7.9

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
11,050 reviews
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.1

Overall

7.9

Food

7.3

Comfort

7.9

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
2,899 reviews
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.1

Overall

7.9

Food

7.3

Comfort

7.9

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
8,179 reviews
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.1

Overall

7.9

Food

7.3

Comfort

7.9

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.
Frontier
5.8
Fair
3,084 reviews
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.1

Overall

7.9

Food

7.3

Comfort

7.9

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. 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?

    Boston Logan Intl (BOS), located 2.6 mi from the city center, is the airport you fly out of when you book flights from Boston to Caribbean.

  • How long is the flight from Boston to Caribbean?

    A quick flight from Boston to Caribbean can take about 4h 05m. JetBlue provides one of the quickest options available for as low as $202. Boston and Caribbean are separated by a distance of 1678 mi. This flight may include one or multiple stops.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $44. However, be on the lookout for offers from Delta and Spirit Airlines, as they are both options that can get you from Boston to Caribbean for a low price.

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

    The most popular flight routes from Boston to Caribbean are Boston Logan Intl - San Juan Luis Munoz Marin Intl, Boston Logan Intl - Oranjestad Reina Beatrix and Boston Logan Intl - Santo Domingo Las Americas.

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

    Before booking your flight to Caribbean from Boston, check out the most reliable airlines to get you to your destination on time: Hawaiian Airlines (79%), TAP AIR PORTUGAL (78%), Delta( 77%).

  • What are the cheapest flights from Boston to Caribbean?

    The cheapest flight price from Boston to Caribbean is $93. On average you can expect to pay $514. The most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $107.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Boston 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 Boston to Caribbean?

    Currently, January is the cheapest month in which you can book a flight from Boston to Caribbean (average of $88). Flying from Boston to Caribbean in November is currently the most expensive (average of $177). 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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Alternative routes for Boston to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Boston to Charlotte flights
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Hartford to Fort Lauderdale flights
Boston to Nashville flights
Boston to Cozumel flights

Top 10 airlines flying from Boston to Caribbean

Discover the top 10 airlines that operate flights from Boston to Caribbean. 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$87Average$415FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$99Average$372FlexibilityNo cancel feeOn-time65%
Air CanadaCheapest$141Average$605FlexibilityNo cancel feeOn-time67%
DeltaCheapest$149Average$473FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$176Average$529FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$180Average$389FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$190Average$489FlexibilityNo cancel feeOn-time69%
ArajetCheapest$208Average$434FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$288Average$594FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$593FlexibilityNo cancel feeOn-time71%

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