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$90+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
may. 4 — may. 111
dom. 5/4
dom. 5/11
1 adult, Economy
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Cheap flight deals from Boston to Caribbean

Keep the following information in mind while searching for Boston to Caribbean flight deals. Data was last updated abril 29, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$139
(Cheapflightsfares)

One-way from

$90
(eDestinos)

Popular in

December

Cheapest in

September

Average price

$300

Good round-trip deal

$244 or less

Good one-way deal

$137 or less
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-San Juan flights.
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From Boston Logan Intl to Caribbean
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One-way flight from Boston Logan Intl to Caribbean
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Boston Logan Intl to Caribbean.
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Price to beat on a one-way flight from Boston Logan Intl to Caribbean.
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Find 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 abril 29, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
dom. 6/152:42 pmBOS - SJU
Nonstop3h 54mSpirit Airlines
jue. 6/199:30 amSJU - BOS
Nonstop4h 07mSpirit Airlines
Deal found 4/29$151
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
jue. 5/1511:43 amBOS - SJU
Nonstop4h 01mFrontier
dom. 5/186:30 amSJU - BOS
Nonstop4h 13mFrontier
Deal found 4/29$194
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
vie. 5/166:10 amBOS - SJU
1 stop12h 57mMultiple Airlines
dom. 5/186:30 amSJU - BOS
Nonstop4h 13mMultiple Airlines
Deal found 4/29$198
This American Airlines deal was found by Cheapflights users on 4/29. 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.
sáb. 9/207:43 amBOS - SJU
1 stop12h 27mAmerican Airlines
mié. 9/243:58 pmSJU - BOS
1 stop8h 29mAmerican Airlines
Deal found 4/29$223
This Delta deal was found by Cheapflights users on 4/29. 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.
jue. 10/168:10 amBOS - SJU
Nonstop4h 12mDelta
mar. 10/211:32 pmSJU - BOS
Nonstop4h 17mDelta
Deal found 4/29$224
This JetBlue deal was found by Cheapflights users on 4/29. 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.
mié. 9/2411:05 amBOS - SJU
1 stop9h 03mJetBlue
lun. 9/297:00 pmSJU - BOS
Nonstop4h 04mJetBlue
Deal found 4/29$268
This Priceline deal was found by Cheapflights users on 4/29. 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.
mar. 5/205:45 amBOS - STT
1 stop7h 51mSpirit Airlines
vie. 5/302:41 pmSTT - BOS
1 stop9h 06mSpirit Airlines
Deal found 4/29$268
This American Airlines deal was found by Cheapflights users on 4/29. 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.
vie. 5/166:00 amBOS - STT
2 stops10h 20mAmerican Airlines
mié. 5/215:10 pmSTT - BOS
1 stop7h 09mAmerican Airlines
Deal found 4/29$291
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/155:40 amBOS - STT
1 stop9h 30mDelta
mar. 5/202:51 pmSTT - BOS
1 stop7h 24mDelta
Deal found 4/28$296
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
lun. 5/265:42 pmBOS - MBJ
2 stops18h 20mSpirit Airlines
vie. 5/3012:07 pmMBJ - BOS
1 stop10h 22mSpirit Airlines
Deal found 4/29$328
This JetBlue deal was found by Cheapflights users on 4/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/68:35 amBOS - STT
Nonstop4h 04mJetBlue
mié. 9/103:00 pmSTT - BOS
1 stop8h 04mJetBlue
Deal found 4/28$332
This Frontier deal was found by Cheapflights users on 4/29. 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.
sáb. 6/146:00 amBOS - PUJ
1 stop7h 55mFrontier
sáb. 6/213:00 pmPUJ - BOS
1 stop9h 44mFrontier
Deal found 4/29$339

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 abril 29, 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

dom. 6/15

2:42 pm-6:36 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

jue. 6/19

9:30 am-1:37 pm

Nonstop4h 07m

$151

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

jue. 5/15

11:43 am-3:44 pm

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

dom. 5/18

6:30 am-10:43 am

Nonstop4h 13m

$194

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

vie. 5/16

6:10 am-7:07 pm

1 stop12h 57m

San Juan Luis Munoz Marin Intl

dom. 5/18

6:30 am-10:43 am

Nonstop4h 13m

$198

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

mar. 5/20

5:45 am-1:36 pm

1 stop7h 51m

Saint Thomas Island Cyril E King

vie. 5/30

2:41 pm-11:47 pm

1 stop9h 06m

$268

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

vie. 5/16

6:05 am-4:20 pm

1 stop10h 15m

Saint Thomas Island Cyril E King

mié. 5/21

5:10 pm-12:19 am

1 stop7h 09m

$291

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

jue. 5/15

5:40 am-3:10 pm

1 stop9h 30m

Saint Thomas Island Cyril E King

mar. 5/20

2:51 pm-10:15 pm

1 stop7h 24m

$296

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mié. 5/28

1:30 pm-5:30 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

mié. 6/4

6:00 am-10:08 am

Nonstop4h 08m

$304

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mar. 5/27

8:20 am-12:21 pm

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

sáb. 5/31

1:39 pm-5:57 pm

Nonstop4h 18m

$314

BostonMontego Bay

BOS - MBJ

BOSMBJ

Boston Logan Intl

lun. 5/26

5:42 pm-11:02 am

2 stops18h 20m

Montego Bay Sangster Intl

vie. 5/30

12:07 pm-11:29 pm

1 stop10h 22m

$328

BostonPunta Cana

BOS - PUJ

BOSPUJ

Boston Logan Intl

sáb. 6/14

6:00 am-1:55 pm

1 stop7h 55m

Punta Cana

sáb. 6/21

3:00 pm-12:44 am

1 stop9h 44m

$339

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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, September is the cheapest month in which you can book a flight from Boston to Caribbean (average of $254). Flying from Boston to Caribbean in December is currently the most expensive (average of $336). 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 abril 29, 2025.

When flying from Boston to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, 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).

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 abril 29, 2025.
Delta
8.0
Very good
7,936 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,936 reviews
Delta
8.0
Very good
7,936 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Alaska Airlines
8.0
Very good
9,968 reviews
Delta
8.0
Very good
7,936 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Southwest
8.0
Very good
4,295 reviews
Delta
8.0
Very good
7,936 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Copa Airlines
7.5
Good
1,411 reviews
Delta
8.0
Very good
7,936 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
SWISS
7.5
Good
1,588 reviews
Delta
8.0
Very good
7,936 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

  • 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 $90. However, be on the lookout for offers from Spirit Airlines and Delta, 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: Aer Lingus (78%), Japan Airlines (75%), TAP AIR PORTUGAL( 74%).

  • What are the cheapest flights from Boston to Caribbean?

    The cheapest flight price from Boston to Caribbean is $94. On average you can expect to pay $482. The most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $151.

  • 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, September is the cheapest month in which you can book a flight from Boston to Caribbean (average of $254). Flying from Boston to Caribbean in December is currently the most expensive (average of $336). 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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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 abril 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$364FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$84Average$459FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$494FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$145Average$533FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$156Average$734FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$204Average$551FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$282Average$599FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$529FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$364Average$520FlexibilityNo cancel feeOn-time70%
SouthwestCheapest$402Average$787FlexibilityNo cancel feeOn-time63%

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