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$130+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
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 July 27, 2026.

This Super.com deal was found by Cheapflights users on 7/25. 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 10/157:20 pm
BOS
-
SJU
Nonstop4h 38m
JetBlue
Thu 10/2210:30 am
SJU
-
BOS
1 stop6h 29m
JetBlue
Deal found 7/25$290
This American Airlines deal was found by Cheapflights users on 7/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:15 pm
BOS
-
SJU
1 stop16h 45m
American Airlines
Tue 9/152:22 pm
SJU
-
BOS
1 stop7h 27m
American Airlines
Deal found 7/24$291
This Delta deal was found by Cheapflights users on 7/24. 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.
Wed 9/98:55 am
BOS
-
SJU
Nonstop4h 02m
Delta
Tue 9/157:30 am
SJU
-
BOS
1 stop7h 12m
Delta
Deal found 7/24$292
This American Airlines deal was found by Cheapflights users on 7/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:42 am
BOS
-
SJU
1 stop13h 05m
American Airlines
Sun 9/204:38 pm
SJU
-
BOS
1 stop17h 36m
American Airlines
Deal found 7/24$293
This Super.com deal was found by Cheapflights users on 7/23. 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.
Mon 10/267:25 pm
BOS
-
SJU
Nonstop4h 00m
JetBlue
Wed 10/286:00 am
SJU
-
BOS
Nonstop4h 09m
JetBlue
Deal found 7/23$294
This Cheapflightsfares deal was found by Cheapflights users on 7/23. 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.
Thu 10/16:20 pm
BOS
-
SJU
Nonstop4h 07m
JetBlue
Sat 10/36:00 am
SJU
-
BOS
Nonstop4h 03m
JetBlue
Deal found 7/23$295
This Delta deal was found by Cheapflights users on 7/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:40 am
BOS
-
SJU
1 stop7h 36m
Delta
Wed 9/305:59 pm
SJU
-
BOS
1 stop7h 18m
Delta
Deal found 7/26$296
This JetBlue deal was found by Cheapflights users on 7/22. 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.
Mon 10/1911:20 am
BOS
-
SJU
Nonstop4h 09m
JetBlue
Wed 10/216:12 am
SJU
-
BOS
Nonstop4h 03m
JetBlue
Deal found 7/22$297
This Cheapflightsfares deal was found by Cheapflights users on 7/26. 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.
Thu 10/2211:20 am
BOS
-
SJU
Nonstop4h 09m
JetBlue
Thu 10/227:35 pm
SJU
-
BOS
Nonstop4h 08m
JetBlue
Deal found 7/26$299
This American Airlines deal was found by Cheapflights users on 7/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:25 pm
BOS
-
SJU
1 stop17h 59m
American Airlines
Tue 9/224:38 pm
SJU
-
BOS
1 stop8h 21m
American Airlines
Deal found 7/26$302
This Cheapflightsfares deal was found by Cheapflights users on 7/22. 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 10/277:25 pm
BOS
-
SJU
Nonstop4h 00m
JetBlue
Wed 11/47:00 am
SJU
-
BOS
Nonstop4h 13m
JetBlue
Deal found 7/22$303
This Cheapflightsfares deal was found by Cheapflights users on 7/26. 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 8/259:00 am
BOS
-
STT
Nonstop4h 03m
JetBlue
Tue 9/11:53 pm
STT
-
BOS
1 stop5h 44m
JetBlue
Deal found 7/26$308

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 July 27, 2026.

Round-trip from

$290
(Super.com)

One-way from

$130
(Air Canada)

Popular in

July

Cheapest in

January

Average price

$454

Good round-trip deal

$321 or less

Good one-way deal

$154 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. 16% potential increase in price ($67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 27, 2026.
Use the filters below to find and compare flights from Boston to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 10/25

6:00 am-12:15 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

Thu 10/29

7:05 am-5:27 pm

2 stops10h 22m

$296

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 8/25

9:00 am-1:03 pm

Nonstop4h 03m

Saint Thomas Island Cyril E King

Fri 8/28

2:49 pm-8:32 pm

1 stop5h 43m

$308

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sat 8/29

5:45 am-12:58 pm

1 stop7h 13m

Saint Thomas Island Cyril E King

Sat 9/5

4:45 pm-11:59 pm

1 stop7h 14m

$310

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 9/6

5:45 am-12:54 pm

1 stop7h 09m

San Juan Luis Munoz Marin Intl

Wed 9/9

1:25 pm-9:59 pm

1 stop8h 34m

$315

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 10/7

5:05 pm-11:56 pm

1 stop6h 51m

San Juan Luis Munoz Marin Intl

Sun 10/11

2:06 pm-6:11 pm

Nonstop4h 05m

$325

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 9/18

8:55 am-12:57 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Tue 9/22

1:16 pm-11:10 pm

1 stop9h 54m

$325
Quickest round-trip

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 8/29

8:50 am-12:57 pm

Nonstop4h 07m

San Juan Luis Munoz Marin Intl

Tue 9/1

2:10 pm-6:21 pm

Nonstop4h 11m

$335

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 9/4

5:05 pm-11:52 pm

1 stop6h 47m

San Juan Luis Munoz Marin Intl

Tue 9/15

1:16 pm-11:10 pm

1 stop9h 54m

$335

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 10/1

2:35 pm-12:20 am

2 stops9h 45m

San Juan Luis Munoz Marin Intl

Tue 10/6

5:05 am-2:55 pm

2 stops9h 50m

$354

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 8/21

1:34 pm-11:52 pm

1 stop10h 18m

San Juan Luis Munoz Marin Intl

Mon 8/31

2:10 pm-6:21 pm

Nonstop4h 11m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
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6

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 $427). Flying from Boston to Caribbean in December is currently the most expensive (average of $597). 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 July 27, 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.

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 July 27, 2026.

The most flights from BOS to 0CB are scheduled on a Monday (13 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

How far ahead should I book a flight from Boston to Caribbean?

The best time to book flights from Boston to Caribbean is 46 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 July 18, 2026.

Travelers seeking maximum savings on their Boston to Caribbean flight should consider departing on Wednesday evenings 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.

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 July 27, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican Airlines 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
7.8
Good
8,484 reviews

Overall

7.8

Entertainment

7.8

Boarding

8.1

Crew

8.5

Comfort

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

Cidalia,Aug 2023

BOS - MIA

I like Delta overall but the delays lately without justification are not leaving a good impression. Both flights were delayed for over 2 hours
Delta
7.8
Good
8,484 reviews
Delta
7.8
Good
8,484 reviews

Overall

7.8

Entertainment

7.8

Boarding

8.1

Crew

8.5

Comfort

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

Cidalia,Aug 2023

BOS - MIA

I like Delta overall but the delays lately without justification are not leaving a good impression. Both flights were delayed for over 2 hours
United Airlines
7.4
Good
10,042 reviews
Delta
7.8
Good
8,484 reviews

Overall

7.8

Entertainment

7.8

Boarding

8.1

Crew

8.5

Comfort

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

Cidalia,Aug 2023

BOS - MIA

I like Delta overall but the delays lately without justification are not leaving a good impression. Both flights were delayed for over 2 hours
American Airlines
7.1
Good
11,842 reviews
Delta
7.8
Good
8,484 reviews

Overall

7.8

Entertainment

7.8

Boarding

8.1

Crew

8.5

Comfort

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

Cidalia,Aug 2023

BOS - MIA

I like Delta overall but the delays lately without justification are not leaving a good impression. Both flights were delayed for over 2 hours
JetBlue
7.1
Good
3,026 reviews
Delta
7.8
Good
8,484 reviews

Overall

7.8

Entertainment

7.8

Boarding

8.1

Crew

8.5

Comfort

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

Cidalia,Aug 2023

BOS - MIA

I like Delta overall but the delays lately without justification are not leaving a good impression. Both flights were delayed for over 2 hours

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 03m. United Airlines provides one of the quickest options available for as low as $308. Boston and Caribbean are separated by a distance of 1697 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 Delta, with whom users have recently found tickets for as low as $54. However, be on the lookout for offers from Frontier and JetBlue, 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: EL AL (83%), Delta (82%), TAP AIR PORTUGAL( 73%).

  • What are the cheapest flights from Boston to Caribbean?

    The cheapest flight price from Boston to Caribbean is $164. On average you can expect to pay $360. The most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $282.

  • 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 $427). Flying from Boston to Caribbean in December is currently the most expensive (average of $597). 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 West Palm Beach flights
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Hartford to O'Hare Intl flights
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Boston to Minneapolis flights
Boston to Love Field flights
Boston to Pearson Intl 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 July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$456FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$130Average$487FlexibilityNo cancel feeOn-time67%
DeltaCheapest$148Average$472FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$164Average$527FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$166Average$460FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$177Average$345FlexibilityNo cancel feeOn-time70%
ArajetCheapest$183Average$397FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$242Average$566FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$313Average$570FlexibilityNo cancel feeOn-time63%
Hahn AirCheapest$317Average$576FlexibilityNo cancel feeOn-timeN/A

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