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$88+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
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 April 15, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$139
(Cheapflightsfares)

One-way from

$88
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$298

Good round-trip deal

$220 or less

Good one-way deal

$147 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
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Highest demand for flights based on searches. 12% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($13 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 April 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/57:52 pmBOS - SJU
Nonstop4h 00mSpirit Airlines
Fri 5/91:39 pmSJU - BOS
1 stop9h 12mSpirit Airlines
Deal found 4/14$139
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/57:52 pmBOS - SJU
Nonstop4h 00mMultiple Airlines
Thu 5/86:30 amSJU - BOS
Nonstop4h 13mMultiple Airlines
Deal found 4/14$160
This Cheapflightsfares deal was found by Cheapflights users on 4/13. 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 5/111:43 amBOS - SJU
Nonstop4h 01mFrontier
Thu 5/86:30 amSJU - BOS
Nonstop4h 13mFrontier
Deal found 4/13$195
This Delta deal was found by Cheapflights users on 4/14. 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.
Sun 5/48:25 amBOS - SJU
Nonstop4h 00mDelta
Fri 5/91:39 pmSJU - BOS
Nonstop4h 18mDelta
Deal found 4/14$254
This JetBlue Airways deal was found by Cheapflights users on 4/14. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/108:55 pmBOS - SJU
Nonstop4h 00mJetBlue
Thu 5/158:00 amSJU - BOS
Nonstop4h 13mJetBlue
Deal found 4/14$259
This United Airlines deal was found by Cheapflights users on 4/14. 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.
Wed 4/309:30 amBOS - SJU
2 stops14h 24mUnited Airlines
Wed 5/71:25 pmSJU - BOS
1 stop9h 02mUnited Airlines
Deal found 4/14$263
This Mytrip deal was found by Cheapflights users on 4/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/146:00 amBOS - STT
3 stops27h 57mSpirit Airlines
Wed 5/212:41 pmSTT - BOS
2 stops32h 48mSpirit Airlines
Deal found 4/14$274
This Booking.com deal was found by Cheapflights users on 4/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/288:35 pmBOS - MBJ
1 stop15h 20mSpirit Airlines
Wed 4/3012:00 pmMBJ - BOS
1 stop8h 59mSpirit Airlines
Deal found 4/14$281
This American Airlines deal was found by Cheapflights users on 4/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/186:02 amBOS - SJU
2 stops10h 18mAmerican Airlines
Mon 9/2211:55 amSJU - BOS
1 stop10h 54mAmerican Airlines
Deal found 4/14$290
This American Airlines deal was found by Cheapflights users on 4/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/57:40 amBOS - STT
1 stop7h 08mAmerican Airlines
Mon 5/121:25 pmSTT - BOS
1 stop9h 24mAmerican Airlines
Deal found 4/14$291
This JetBlue deal was found by Cheapflights users on 4/14. 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.
Sat 10/48:35 amBOS - STT
Nonstop4h 04mJetBlue
Sat 10/111:45 pmSTT - BOS
1 stop6h 05mJetBlue
Deal found 4/14$310
This Delta deal was found by Cheapflights users on 4/14. 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.
Sat 9/67:00 amBOS - STT
1 stop7h 55mDelta
Wed 9/102:49 pmSTT - BOS
1 stop10h 11mDelta
Deal found 4/14$319

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 April 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

Mon 5/5

7:52 pm-11:52 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Fri 5/9

1:39 pm-10:51 pm

1 stop9h 12m

$139

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 5/5

7:52 pm-11:52 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Thu 5/8

6:30 am-10:43 am

Nonstop4h 13m

$160

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 5/1

11:43 am-3:44 pm

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

Thu 5/8

6:30 am-10:43 am

Nonstop4h 13m

$195

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 5/4

8:25 am-12:25 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Fri 5/9

1:39 pm-5:57 pm

Nonstop4h 18m

$254

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 5/10

8:55 pm-12:55 am

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Thu 5/15

6:00 am-10:08 am

Nonstop4h 08m

$259

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 4/30

9:30 am-11:54 pm

2 stops14h 24m

San Juan Luis Munoz Marin Intl

Wed 5/7

1:25 pm-10:27 pm

1 stop9h 02m

$263

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 5/14

6:00 am-9:57 am

3 stops27h 57m

Saint Thomas Island Cyril E King

Wed 5/21

2:41 pm-11:29 pm

2 stops32h 48m

$274

BostonMontego Bay

BOS - MBJ

BOSMBJ

Boston Logan Intl

Mon 4/28

8:35 pm-10:55 am

1 stop15h 20m

Montego Bay Sangster Intl

Wed 4/30

12:00 pm-9:59 pm

1 stop8h 59m

$281

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Mon 5/5

5:55 am-2:48 pm

2 stops8h 53m

Saint Thomas Island Cyril E King

Mon 5/12

1:25 pm-10:49 pm

1 stop9h 24m

$291

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sat 10/4

8:35 am-12:39 pm

Nonstop4h 04m

Saint Thomas Island Cyril E King

Sat 10/11

1:45 pm-7:50 pm

1 stop6h 05m

$310

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

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 April 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 April 15, 2025.

The most flights from BOS to 0CB are scheduled on a Monday (20 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (5 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 April 15, 2025.
Alaska Airlines
8.0
Very good
9,871 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,871 reviews
Alaska Airlines
8.0
Very good
9,871 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,278 reviews
Alaska Airlines
8.0
Very good
9,871 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,917 reviews
Alaska Airlines
8.0
Very good
9,871 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Copa Airlines
7.6
Good
1,408 reviews
Alaska Airlines
8.0
Very good
9,871 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,656 reviews
Alaska Airlines
8.0
Very good
9,871 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 $88. However, be on the lookout for offers from Frontier 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: TAP AIR PORTUGAL (77%), Japan Airlines (71%), Delta( 69%).

  • What are the cheapest flights from Boston to Caribbean?

    The cheapest flight price from Boston to Caribbean is $88. On average you can expect to pay $555. The most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $139.

  • 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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$363FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$86Average$456FlexibilityNo cancel feeOn-time65%
DeltaCheapest$141Average$497FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$142Average$532FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$204Average$547FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$266Average$804FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$282Average$599FlexibilityNo cancel feeOn-time71%
AviancaCheapest$292Average$529FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$364Average$520FlexibilityNo cancel feeOn-time70%
SouthwestCheapest$427Average$787FlexibilityNo cancel feeOn-time63%

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