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$97+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
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 septiembre 11, 2025.

Round-trip from

$176
(CheapOair)

One-way from

$97
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$205

Good round-trip deal

$246 or less

Good one-way deal

$136 or less
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. 3% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
mié. 10/112:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
lun. 10/62:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Deal found 9/9$181
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
mié. 9/2412:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
mié. 10/16:44 amSJU - BOS
1 stop7h 04mSpirit Airlines
Deal found 9/9$190
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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. 9/256:49 pmBOS - SJU
1 stop16h 15mSpirit Airlines
mar. 9/306:44 amSJU - BOS
1 stop7h 04mSpirit Airlines
Deal found 9/10$193
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
mié. 12/36:15 amBOS - SJU
1 stop16h 04mSpirit Airlines
mar. 2/35:27 pmSJU - BOS
Nonstop4h 07mSpirit Airlines
Deal found 9/10$195
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
sáb. 9/2712:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
mié. 10/16:44 amSJU - BOS
1 stop7h 04mSpirit Airlines
Deal found 9/9$200
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
mar. 9/2312:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
sáb. 9/276:44 amSJU - BOS
1 stop7h 04mSpirit Airlines
Deal found 9/9$207
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
sáb. 9/2712:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
sáb. 10/46:44 amSJU - BOS
1 stop7h 04mSpirit Airlines
Deal found 9/10$209
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
mié. 9/2412:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
mar. 9/306:44 amSJU - BOS
1 stop7h 04mSpirit Airlines
Deal found 9/11$211
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
sáb. 9/2012:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
mié. 9/246:44 amSJU - BOS
1 stop7h 04mSpirit Airlines
Deal found 9/9$212
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
mar. 11/116:15 amBOS - SJU
1 stop12h 06mSpirit Airlines
sáb. 11/156:00 amSJU - BOS
1 stop18h 25mSpirit Airlines
Deal found 9/11$213
This Mytrip deal was found by Cheapflights users on 9/11. 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.
jue. 10/26:49 pmBOS - STT
1 stop14h 55mSpirit Airlines
mar. 10/711:01 amSTT - BOS
1 stop12h 58mSpirit Airlines
Deal found 9/11$237
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
mar. 10/73:00 pmBOS - STT
1 stop18h 56mSpirit Airlines
mar. 10/1411:01 amSTT - BOS
1 stop24h 25mSpirit Airlines
Deal found 9/10$246

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 septiembre 11, 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. 11/4

2:15 pm-10:04 pm

1 stop6h 49m

San Juan Luis Munoz Marin Intl

jue. 11/13

8:10 pm-11:16 pm

Nonstop4h 06m

$270

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

lun. 1/5

8:00 am-1:05 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

jue. 1/29

2:23 pm-5:51 pm

Nonstop4h 28m

$282

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mar. 11/4

8:15 am-1:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

jue. 11/13

2:27 pm-5:50 pm

Nonstop4h 23m

$282

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

dom. 11/16

6:55 pm-11:54 pm

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

lun. 11/24

9:25 pm-12:30 am

Nonstop4h 05m

$282

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

dom. 9/28

6:05 am-12:13 pm

1 stop6h 08m

San Juan Luis Munoz Marin Intl

mié. 10/15

1:32 pm-5:45 pm

Nonstop4h 13m

$287

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

dom. 11/16

9:59 am-5:20 pm

1 stop6h 21m

San Juan Luis Munoz Marin Intl

jue. 11/20

2:27 pm-5:50 pm

Nonstop4h 23m

$287

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

dom. 1/18

8:10 am-1:18 pm

Nonstop4h 08m

San Juan Luis Munoz Marin Intl

sáb. 1/24

7:30 am-5:47 pm

1 stop11h 17m

$287

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

dom. 11/16

6:00 am-2:40 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

mié. 11/19

2:05 am-9:14 am

1 stop8h 09m

$291

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

dom. 11/9

1:55 pm-6:57 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

vie. 11/14

3:34 pm-11:48 pm

1 stop9h 14m

$291

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

dom. 3/1

2:00 pm-10:04 pm

1 stop7h 04m

San Juan Luis Munoz Marin Intl

mar. 3/10

8:10 pm-12:21 am

Nonstop4h 11m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

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 June is currently the most expensive (average of $339). 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 septiembre 11, 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 septiembre 11, 2025.

The most flights from BOS to 0CB are scheduled on a Thursday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

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 septiembre 11, 2025.
Get a feel of what it's like to fly with Delta, American Airlines, and JetBlue 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
8.0
Very good
7,960 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

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!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

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!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

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!
JetBlue
7.2
Good
2,913 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

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!
Spirit Airlines
6.3
Okay
8,023 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

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!
Frontier
5.8
Fair
3,177 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

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.

  • How long is the flight from Boston to Caribbean?

    A quick flight from Boston to Caribbean can take about 4h 05m. JetBlue provides one of the quickest options available for as low as $282. Boston and Caribbean are separated by a distance of 1678 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 Spirit Airlines, with whom users have recently found tickets for as low as $107. However, be on the lookout for offers from JetBlue and Air Canada, 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 (92%), EL AL (79%), TAP AIR PORTUGAL( 76%).

  • What are the cheapest flights from Boston to Caribbean?

    The cheapest flight price from Boston to Caribbean is $123. On average you can expect to pay $615. The most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $176.

  • 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 June is currently the most expensive (average of $339). 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.
Boston to Orlando flights
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Boston to Lisbon flights
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Boston to London City flights
Boston to Pearson Intl flights
Hartford to Luis Munoz Marin Intl flights
Boston to Pittsburgh flights
Boston to Columbus 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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$80Average$379FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$99Average$379FlexibilityNo cancel feeOn-time65%
DeltaCheapest$141Average$481FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$159Average$538FlexibilityNo cancel feeOn-time62%
ArajetCheapest$187Average$357FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$188Average$613FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$194Average$534FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$195Average$412FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$288Average$592FlexibilityNo cancel feeOn-time71%
AviancaCheapest$361Average$560FlexibilityNo cancel feeOn-time71%

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