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$45+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Feb 24 — Mar 31
Mon 2/24
Mon 3/3
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 February 19, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$115
(eDestinos)

One-way from

$45
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$303

Good round-trip deal

$186 or less

Good one-way deal

$103 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. 10% potential increase in price ($31 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 February 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 February 19, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Wed 2/2611:18 amBOS - SJU
Nonstop3h 57mFrontier
Wed 3/58:30 pmSJU - BOS
1 stop13h 25mFrontier
Deal found 2/19$115
This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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.
Tue 3/44:47 pmBOS - SJU
1 stop6h 40mMultiple Airlines
Wed 3/57:00 amSJU - BOS
Nonstop4h 18mMultiple Airlines
Deal found 2/19$116
This Priceline deal was found by Cheapflights users on 2/18. 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.
Tue 3/44:47 pmBOS - SJU
1 stop6h 40mSpirit Airlines
Tue 3/113:49 pmSJU - BOS
Nonstop4h 23mSpirit Airlines
Deal found 2/18$121
This JetBlue deal was found by Cheapflights users on 2/19. 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 3/17:35 pmBOS - SJU
Nonstop4h 07mJetBlue
Wed 3/53:26 amSJU - BOS
Nonstop4h 09mJetBlue
Deal found 2/19$198
This United Airlines deal was found by Cheapflights users on 2/19. 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 2/269:20 amBOS - SJU
2 stops12h 02mUnited Airlines
Sat 3/12:05 amSJU - BOS
1 stop7h 38mUnited Airlines
Deal found 2/19$233
This CheapOair deal was found by Cheapflights users on 2/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/302:59 pmBOS - STT
2 stops19h 07mSpirit Airlines
Sat 4/512:43 pmSTT - BOS
2 stops18h 12mSpirit Airlines
Deal found 2/17$248
This American Airlines deal was found by Cheapflights users on 2/18. 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 2/275:25 amBOS - STT
1 stop11h 16mAmerican Airlines
Thu 3/62:00 pmSTT - BOS
1 stop10h 11mAmerican Airlines
Deal found 2/18$249
This FlightHub deal was found by Cheapflights users on 2/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/711:14 amBOS - MBJ
1 stop24h 48mSpirit Airlines
Wed 4/1612:00 pmMBJ - BOS
1 stop8h 53mSpirit Airlines
Deal found 2/18$278
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1911:14 amBOS - AUA
1 stop27h 31mSpirit Airlines
Tue 3/253:50 pmAUA - BOS
1 stop18h 09mSpirit Airlines
Deal found 2/19$293
This JetBlue deal was found by Cheapflights users on 2/18. 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 2/266:00 amBOS - STT
1 stop8h 41mJetBlue
Tue 3/44:36 pmSTT - BOS
1 stop8h 42mJetBlue
Deal found 2/18$295
This JetBlue deal was found by Cheapflights users on 2/19. 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.
Mon 3/310:11 amBOS - NAS
Nonstop3h 38mJetBlue
Wed 3/53:09 pmNAS - BOS
Nonstop3h 34mJetBlue
Deal found 2/19$300
This Delta deal was found by Cheapflights users on 2/18. 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 2/256:55 amBOS - NAS
1 stop6h 46mDelta
Wed 3/53:57 pmNAS - BOS
Nonstop3h 33mDelta
Deal found 2/18$305

Find flights from Boston to Caribbean within your budget

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 February 19, 2025.

Fly from

Boston

Fly to

Caribbean

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 2/26

11:18 am-4:15 pm

Nonstop3h 57m

San Juan Luis Munoz Marin Intl

Wed 3/5

8:30 pm-8:55 am

1 stop13h 25m

$115

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 3/4

4:47 pm-12:27 am

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Wed 3/5

7:00 am-10:18 am

Nonstop4h 18m

$116

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 3/4

4:47 pm-12:27 am

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Tue 3/11

3:49 pm-8:12 pm

Nonstop4h 23m

$121

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 3/1

7:35 pm-12:42 am

Nonstop4h 07m

San Juan Luis Munoz Marin Intl

Mon 3/10

12:59 am-5:04 am

Nonstop4h 05m

$198

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 2/26

9:20 am-10:22 pm

2 stops12h 02m

San Juan Luis Munoz Marin Intl

Sat 3/1

2:05 am-8:43 am

1 stop7h 38m

$233

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 3/30

2:59 pm-10:06 am

2 stops19h 07m

Saint Thomas Island Cyril E King

Sat 4/5

12:43 pm-6:55 am

2 stops18h 12m

$248

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 5/7

6:00 am-4:12 pm

2 stops10h 12m

Saint Thomas Island Cyril E King

Sat 5/17

5:05 pm-10:44 am

1 stop17h 39m

$249

BostonMontego Bay

BOS - MBJ

BOSMBJ

Boston Logan Intl

Mon 4/7

11:14 am-11:02 am

1 stop24h 48m

Montego Bay Sangster Intl

Wed 4/16

12:00 pm-9:53 pm

1 stop8h 53m

$278

BostonOranjestad

BOS - AUA

BOSAUA

Boston Logan Intl

Wed 3/19

11:14 am-2:45 pm

1 stop27h 31m

Oranjestad Reina Beatrix

Tue 3/25

3:50 pm-9:59 am

1 stop18h 09m

$293

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Mon 3/3

8:00 am-3:41 pm

1 stop6h 41m

Saint Thomas Island Cyril E King

Tue 3/11

4:36 pm-12:44 am

1 stop8h 08m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

Travel insights for flights from Boston to Caribbean

Get recent, data-driven insights about flights from Boston to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $363). 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 February 19, 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 February 19, 2025.

The most flights from BOS to 0CB are scheduled on a Monday (18 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (9 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 February 19, 2025.
Southwest
8.1
Very good
4,413 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,413 reviews
Southwest
8.1
Very good
4,413 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,236 reviews
Southwest
8.1
Very good
4,413 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,691 reviews
Southwest
8.1
Very good
4,413 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Copa Airlines
7.6
Good
1,514 reviews
Southwest
8.1
Very good
4,413 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,771 reviews
Southwest
8.1
Very good
4,413 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $45. 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: Spirit Airlines (80%), Delta (68%), Hawaiian Airlines( 60%).

  • What are the cheapest flights from Boston to Caribbean?

    The cheapest flight price from Boston to Caribbean is $58. On average you can expect to pay $483. The most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $101.

  • 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 March is currently the most expensive (average of $363). 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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Boston to George Bush Intcntl flights
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Boston to Charleston flights
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Boston to Baltimore flights
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Boston to Newark flights
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Boston to London City flights
Boston to Nashville flights
Boston to New Orleans flights
Hartford to Fort Lauderdale flights
Boston to Oranjestad flights
Boston to Savannah flights
Boston to Atlanta flights
Boston to Amsterdam flights
Boston to Jacksonville 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 February 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$75Average$386FlexibilityNo cancel feeOn-time65%
FrontierCheapest$76Average$365FlexibilityNo cancel feeOn-time62%
DeltaCheapest$141Average$508FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$142Average$522FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$200Average$527FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$222Average$592FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$229Average$591FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$266Average$832FlexibilityNo cancel feeOn-time67%
AviancaCheapest$292Average$518FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$452Average$798FlexibilityNo cancel feeOn-time63%
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