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$76+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Mar 31 — Apr 71
Mon 3/31
Mon 4/7
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 March 26, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$119
(Kiwi.com)

One-way from

$77
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$264

Good round-trip deal

$209 or less

Good one-way deal

$128 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 ($36 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 March 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 March 26, 2025.

This eDestinos deal was found by Cheapflights users on 3/23. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/157:52 pmBOS - SJU
Nonstop4h 00mSpirit Airlines
Wed 4/307:00 pmSJU - BOS
1 stop16h 20mSpirit Airlines
Deal found 3/23$126
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/287:52 pmBOS - SJU
Nonstop4h 00mMultiple Airlines
Tue 5/66:30 amSJU - BOS
Nonstop4h 13mMultiple Airlines
Deal found 3/25$129
This Frontier deal was found by Cheapflights users on 3/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1411:16 amBOS - SJU
Nonstop3h 56mFrontier
Fri 4/186:00 amSJU - BOS
Nonstop4h 16mFrontier
Deal found 3/24$134
This JetBlue deal was found by Cheapflights users on 3/25. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/77:55 pmBOS - SJU
Nonstop4h 02mJetBlue
Thu 5/157:15 pmSJU - BOS
Nonstop4h 10mJetBlue
Deal found 3/25$176
This Southwest deal was found by Cheapflights users on 3/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/35:50 amBOS - SJU
1 stop13h 00mSouthwest
Sat 5/106:20 amSJU - BOS
1 stop9h 40mSouthwest
Deal found 3/25$185
This United Airlines deal was found by Cheapflights users on 3/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/312:30 pmBOS - SJU
2 stops11h 27mUnited Airlines
Sat 5/107:45 amSJU - BOS
2 stops11h 47mUnited Airlines
Deal found 3/25$198
This Delta deal was found by Cheapflights users on 3/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/78:00 amBOS - SJU
1 stop11h 48mDelta
Thu 5/151:39 pmSJU - BOS
Nonstop4h 18mDelta
Deal found 3/25$235
This Mytrip deal was found by Cheapflights users on 3/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/62:10 pmBOS - STT
1 stop19h 56mSpirit Airlines
Thu 4/1011:05 amSTT - BOS
2 stops10h 23mSpirit Airlines
Deal found 3/25$275
This Cheapflightsfares deal was found by Cheapflights users on 3/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/86:10 amBOS - AUA
1 stop8h 30mSpirit Airlines
Thu 5/153:45 pmAUA - BOS
1 stop7h 44mSpirit Airlines
Deal found 3/25$276
This JetBlue deal was found by Cheapflights users on 3/25. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/812:01 pmBOS - NAS
Nonstop3h 33mJetBlue
Tue 4/156:25 pmNAS - BOS
Nonstop3h 24mJetBlue
Deal found 3/25$280
This Cheapflightsfares deal was found by Cheapflights users on 3/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/58:35 pmBOS - MBJ
1 stop15h 20mSpirit Airlines
Wed 5/1412:07 pmMBJ - BOS
1 stop10h 22mSpirit Airlines
Deal found 3/25$281
This Delta deal was found by Cheapflights users on 3/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/156:40 amBOS - NAS
1 stop9h 20mDelta
Fri 4/183:20 pmNAS - BOS
Nonstop3h 42mDelta
Deal found 3/25$285

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 March 26, 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

Tue 4/15

7:52 pm-11:52 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Wed 4/30

7:00 pm-11:20 am

1 stop16h 20m

$126

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 4/28

7:52 pm-11:52 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Tue 5/6

6:30 am-10:43 am

Nonstop4h 13m

$129

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 4/14

11:16 am-3:12 pm

Nonstop3h 56m

San Juan Luis Munoz Marin Intl

Fri 4/18

6:00 am-10:16 am

Nonstop4h 16m

$134

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 5/7

7:55 pm-11:57 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Thu 5/15

7:15 pm-11:25 pm

Nonstop4h 10m

$176

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 5/3

5:50 am-6:50 pm

1 stop13h 00m

San Juan Luis Munoz Marin Intl

Sat 5/10

6:20 am-4:00 pm

1 stop9h 40m

$185

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 5/3

12:30 pm-11:57 pm

2 stops11h 27m

San Juan Luis Munoz Marin Intl

Sat 5/10

7:45 am-7:32 pm

2 stops11h 47m

$198

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 5/7

8:00 am-7:48 pm

1 stop11h 48m

San Juan Luis Munoz Marin Intl

Thu 5/15

1:39 pm-5:57 pm

Nonstop4h 18m

$235

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 4/6

2:10 pm-10:06 am

1 stop19h 56m

Saint Thomas Island Cyril E King

Thu 4/10

11:05 am-9:28 pm

2 stops10h 23m

$275

BostonOranjestad

BOS - AUA

BOSAUA

Boston Logan Intl

Thu 5/8

6:10 am-2:40 pm

1 stop8h 30m

Oranjestad Reina Beatrix

Thu 5/15

3:45 pm-11:29 pm

1 stop7h 44m

$276

BostonNassau

BOS - NAS

BOSNAS

Boston Logan Intl

Tue 4/8

12:01 pm-3:34 pm

Nonstop3h 33m

Nassau Intl

Tue 4/15

6:25 pm-9:49 pm

Nonstop3h 24m

$280

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

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 March 26, 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 March 26, 2025.
Southwest
8.1
Very good
4,274 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Alaska Airlines
8.0
Very good
9,789 reviews
Southwest
8.1
Very good
4,274 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,891 reviews
Southwest
8.1
Very good
4,274 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Copa Airlines
7.6
Good
1,393 reviews
Southwest
8.1
Very good
4,274 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,608 reviews
Southwest
8.1
Very good
4,274 reviews

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $77. 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: Delta (71%), Hawaiian Airlines (68%), Spirit Airlines( 65%).

  • What are the cheapest flights from Boston to Caribbean?

    The cheapest flight price from Boston to Caribbean is $96. On average you can expect to pay $666. The most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $135.

  • 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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Hartford to Luis Munoz Marin Intl flights
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Boston to Madrid flights
Boston to Pearson Intl flights
Hartford to Tampa 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 March 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$364FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$88Average$434FlexibilityNo cancel feeOn-time65%
DeltaCheapest$140Average$492FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$142Average$522FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$204Average$545FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$228Average$589FlexibilityNo cancel feeOn-time71%
AviancaCheapest$262Average$518FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$266Average$792FlexibilityNo cancel feeOn-time67%
Copa AirlinesCheapest$364Average$527FlexibilityNo cancel feeOn-time70%
SouthwestCheapest$427Average$790FlexibilityNo cancel feeOn-time63%
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