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$56+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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 January 28, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 1/26. 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.
Tue 2/103:18 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Sun 2/1511:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 1/26$142
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Tue 2/33:43 pm
BOS
-
SJU
1 stop6h 50m
Spirit Airlines
Tue 2/1010:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Deal found 1/27$143
This CheapOair deal was found by Cheapflights users on 1/27. 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 2/73:43 pm
BOS
-
SJU
1 stop6h 50m
Spirit Airlines
Sat 2/1411:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 1/27$144
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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 1/313:43 pm
BOS
-
SJU
1 stop6h 50m
Spirit Airlines
Wed 2/410:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Deal found 1/28$145
This Priceline deal was found by Cheapflights users on 1/27. 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 1/313:18 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Tue 2/310:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Deal found 1/27$146
This CheapOair deal was found by Cheapflights users on 1/27. 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 1/313:18 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Fri 2/610:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Deal found 1/27$147
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sat 3/78:01 pm
BOS
-
SJU
Nonstop4h 07m
Spirit Airlines
Wed 3/1810:00 am
SJU
-
BOS
Nonstop4h 18m
Spirit Airlines
Deal found 1/27$148
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/43:43 pm
BOS
-
SJU
1 stop6h 50m
Spirit Airlines
Thu 2/54:40 pm
SJU
-
BOS
1 stop8h 17m
Spirit Airlines
Deal found 1/27$149
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/235:27 am
BOS
-
SJU
1 stop9h 04m
Multiple Airlines
Thu 3/56:00 am
SJU
-
BOS
Nonstop4h 19m
Multiple Airlines
Deal found 1/27$150
This CheapOair deal was found by Cheapflights users on 1/26. 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 2/73:18 pm
BOS
-
SJU
Nonstop4h 06m
Multiple Airlines
Fri 2/276:00 am
SJU
-
BOS
Nonstop4h 19m
Multiple Airlines
Deal found 1/26$152
This CheapOair deal was found by Cheapflights users on 1/26. 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.
Mon 2/23:18 pm
BOS
-
SJU
Nonstop4h 06m
Multiple Airlines
Thu 2/57:15 pm
SJU
-
BOS
Nonstop4h 13m
Multiple Airlines
Deal found 1/26$153
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/195:27 am
BOS
-
STT
1 stop10h 07m
Spirit Airlines
Wed 2/255:40 pm
STT
-
BOS
1 stop7h 04m
Spirit Airlines
Deal found 1/27$219

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 January 28, 2026.

Round-trip from

$142
(Cheapflightsfares)

One-way from

$56
(FlightHub)

Popular in

December

Cheapest in

January

Average price

$254

Good round-trip deal

$203 or less

Good one-way deal

$101 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. 8% potential increase in price ($28 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 January 2026
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 January 28, 2026.
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

Mon 3/2

5:27 am-3:31 pm

1 stop9h 04m

San Juan Luis Munoz Marin Intl

Sat 3/7

3:30 pm-6:56 pm

Nonstop4h 26m

$201

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 5/10

10:40 pm-2:39 am

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Sun 5/31

12:30 pm-4:39 pm

Nonstop4h 09m

$203

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 5/13

8:20 am-12:28 pm

Nonstop4h 08m

San Juan Luis Munoz Marin Intl

Fri 5/15

1:30 pm-5:53 pm

Nonstop4h 23m

$203

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 4/23

6:10 pm-10:12 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Wed 4/29

11:25 pm-3:25 am

Nonstop4h 00m

$203

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 2/25

1:35 pm-11:58 pm

1 stop9h 23m

San Juan Luis Munoz Marin Intl

Thu 3/5

7:00 am-3:15 pm

1 stop9h 15m

$212

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 3/3

11:15 am-11:58 pm

1 stop11h 43m

San Juan Luis Munoz Marin Intl

Thu 3/5

7:00 am-3:15 pm

1 stop9h 15m

$212

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Thu 2/26

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Tue 3/3

2:32 pm-5:53 pm

Nonstop4h 21m

$245

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Thu 3/19

8:40 am-12:43 pm

Nonstop4h 03m

Saint Thomas Island Cyril E King

Thu 3/26

2:45 pm-7:04 pm

Nonstop4h 19m

$245

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 3/3

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Wed 3/11

2:45 pm-7:04 pm

Nonstop4h 19m

$245

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 2/27

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Tue 3/3

5:32 pm-10:48 pm

1 stop6h 16m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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 January 28, 2026.

It’s typically best to fly out from Boston to Caribbean in the afternoon. Doing so could potentially save you 23% on the flight price compared to flying at noon, 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 January 24, 2026.

Travelers seeking maximum savings on their Boston to Caribbean flight should consider departing on Wednesday 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 January 28, 2026.

The most flights from BOS to 0CB are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 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 January 28, 2026.
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
8,120 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Entertainment

7.8

Food

7.2

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
8,120 reviews
Delta
7.9
Good
8,120 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Entertainment

7.8

Food

7.2

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
11,199 reviews
Delta
7.9
Good
8,120 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Entertainment

7.8

Food

7.2

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
2,889 reviews
Delta
7.9
Good
8,120 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Entertainment

7.8

Food

7.2

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
8,385 reviews
Delta
7.9
Good
8,120 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Entertainment

7.8

Food

7.2

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
5.7
Fair
3,056 reviews
Delta
7.9
Good
8,120 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Entertainment

7.8

Food

7.2

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 3h 59m. Spirit Airlines provides one of the quickest options available for as low as $203. 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 - Punta Cana.

  • 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: Delta (77%), Spirit Airlines (62%), EL AL( 62%).

  • What are the cheapest flights from Boston to Caribbean?

    The cheapest flight price from Boston to Caribbean is $63. On average you can expect to pay $554. The most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $89.

  • 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.

See more FAQs

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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 Reagan-National flights
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Hartford to Tampa flights
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Boston to Charlotte 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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$402FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$79Average$341FlexibilityNo cancel feeOn-time65%
Air CanadaCheapest$129Average$586FlexibilityNo cancel feeOn-time67%
DeltaCheapest$136Average$460FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$140Average$509FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$177Average$474FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$179Average$366FlexibilityNo cancel feeOn-time70%
ArajetCheapest$181Average$389FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$242Average$606FlexibilityNo cancel feeOn-time71%
AviancaCheapest$249Average$684FlexibilityNo cancel feeOn-time71%

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