Caribbean

$93+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
mai 20 — mai 271
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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 mai 15, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$150
(Kiwi.com)

One-way from

$93
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$264

Good round-trip deal

$278 or less

Good one-way deal

$143 or less
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
Provider most trusted by Cheapflights users for Boston Logan Intl-San Juan flights.
From Boston Logan Intl to Caribbean
One-way flight from Boston Logan Intl to Caribbean
Highest demand for flights based on searches. 10% potential increase in price ($31 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Average for round-trip flights in May 2025
Price to beat on a round-trip flight from Boston Logan Intl to Caribbean.
Price to beat on a one-way flight from Boston Logan Intl to Caribbean.

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 mai 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 5/15. 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.
mer. 10/84:40 pmBOS - SJU
1 stop8h 31mSpirit Airlines
mer. 10/1512:55 pmSJU - BOS
1 stop10h 34mSpirit Airlines
Deal found 5/15$144
This JetBlue deal was found by Cheapflights users on 5/15. 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.
mer. 7/169:30 pmBOS - SJU
Nonstop4h 01mJetBlue
mer. 7/306:05 amSJU - BOS
Nonstop4h 07mJetBlue
Deal found 5/15$198
This United Airlines deal was found by Cheapflights users on 5/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 9/176:10 amBOS - SJU
1 stop8h 34mUnited Airlines
lun. 9/221:05 amSJU - BOS
1 stop8h 42mUnited Airlines
Deal found 5/14$207
This American Airlines deal was found by Cheapflights users on 5/15. 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.
lun. 9/85:29 amBOS - SJU
1 stop7h 16mAmerican Airlines
ven. 9/193:55 pmSJU - BOS
1 stop6h 37mAmerican Airlines
Deal found 5/15$212
This Delta deal was found by Cheapflights users on 5/15. 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.
mar. 6/178:15 amBOS - SJU
Nonstop4h 08mDelta
mer. 6/251:33 pmSJU - BOS
Nonstop4h 11mDelta
Deal found 5/15$236
This Mytrip deal was found by Cheapflights users on 5/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 6/75:45 amBOS - STT
2 stops28h 12mSpirit Airlines
sam. 6/1410:47 amSTT - BOS
1 stop12h 09mSpirit Airlines
Deal found 5/15$256
This JetBlue deal was found by Cheapflights users on 5/14. 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.
sam. 6/79:30 amBOS - STT
Nonstop4h 02mJetBlue
sam. 6/141:35 pmSTT - BOS
1 stop5h 49mJetBlue
Deal found 5/14$276
This American Airlines deal was found by Cheapflights users on 5/15. 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.
sam. 9/66:46 pmBOS - STT
2 stops18h 04mAmerican Airlines
mer. 9/101:50 pmSTT - BOS
2 stops18h 34mAmerican Airlines
Deal found 5/15$285
This Cheapflightsfares deal was found by Cheapflights users on 5/15. 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.
jeu. 6/122:42 pmBOS - SJU
Nonstop3h 54mMultiple Airlines
lun. 6/1612:59 amSJU - BOS
1 stop7h 07mMultiple Airlines
Deal found 5/15$288
This Delta deal was found by Cheapflights users on 5/14. 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.
dim. 6/86:05 amBOS - STT
1 stop6h 09mDelta
lun. 6/94:01 pmSTT - BOS
1 stop6h 39mDelta
Deal found 5/14$298
This Mytrip deal was found by Cheapflights users on 5/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 6/612:53 pmBOS - STT
3 stops45h 04mMultiple Airlines
mar. 6/102:41 pmSTT - BOS
2 stops32h 48mMultiple Airlines
Deal found 5/15$306
This American Airlines deal was found by Cheapflights users on 5/15. 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.
lun. 6/1612:15 pmBOS - NAS
2 stops9h 11mAmerican Airlines
jeu. 6/193:05 pmNAS - BOS
1 stop7h 38mAmerican Airlines
Deal found 5/15$347

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 mai 15, 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

mar. 6/10

5:42 pm-12:54 am

1 stop7h 12m

San Juan Luis Munoz Marin Intl

dim. 6/15

9:30 am-1:37 pm

Nonstop4h 07m

$150

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mer. 7/16

9:30 pm-1:31 am

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

mer. 7/30

6:05 am-10:12 am

Nonstop4h 07m

$198

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

jeu. 5/29

12:29 pm-11:57 pm

2 stops11h 28m

San Juan Luis Munoz Marin Intl

mer. 6/4

1:05 am-8:55 am

1 stop7h 50m

$207

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mar. 6/17

8:15 am-12:23 pm

Nonstop4h 08m

San Juan Luis Munoz Marin Intl

mer. 6/25

1:33 pm-5:44 pm

Nonstop4h 11m

$236

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

sam. 6/7

5:45 am-9:57 am

2 stops28h 12m

Saint Thomas Island Cyril E King

mer. 6/11

10:52 am-11:29 pm

1 stop12h 37m

$258

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

sam. 6/7

9:30 am-1:32 pm

Nonstop4h 02m

Saint Thomas Island Cyril E King

sam. 6/14

1:35 pm-7:24 pm

1 stop5h 49m

$276

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mer. 5/21

5:55 am-12:45 pm

1 stop6h 50m

San Juan Luis Munoz Marin Intl

mer. 5/28

5:25 am-7:24 pm

1 stop13h 59m

$285

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

dim. 7/20

6:05 am-12:17 pm

1 stop6h 12m

Saint Thomas Island Cyril E King

jeu. 7/31

4:10 pm-10:51 pm

1 stop6h 41m

$285

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

jeu. 6/12

2:42 pm-6:36 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

lun. 6/16

12:59 am-8:06 am

1 stop7h 07m

$288

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

jeu. 5/29

6:05 am-4:20 pm

1 stop10h 15m

Saint Thomas Island Cyril E King

jeu. 6/5

5:00 pm-7:20 am

2 stops14h 20m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/15

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 mai 15, 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.

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 mai 15, 2025.

The most flights from BOS to 0CB are scheduled on a Thursday (17 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (12 on average).

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 mai 15, 2025.
8.0
Very good

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good
8.0
Very good

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 Spirit Airlines, with whom users have recently found tickets for as low as $93. However, be on the lookout for offers from Delta 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?

  • 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: Turkish Airlines (90%), Japan Airlines (81%), Delta( 81%).

  • What are the cheapest flights from Boston to Caribbean?

    The cheapest flight price from Boston to Caribbean is $98. On average you can expect to pay $462. The most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $140.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Boston to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.

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 mai 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$364FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$92Average$463FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$495FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$147Average$532FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$156Average$724FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$204Average$544FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$282Average$601FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$518FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$364Average$520FlexibilityNo cancel feeOn-time70%
SouthwestCheapest$427Average$783FlexibilityNo cancel feeOn-time63%

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