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Caribbean Islands

$90+ Cheap flights from Boston (BOS) to Caribbean Islands

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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Apr 30 — May 71
Wed 4/30
Wed 5/7
1 adult, Economy
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Cheap flight deals from Boston to Caribbean Islands

Keep the following information in mind while searching for Boston to Caribbean Islands flight deals. Data was last updated April 25, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$151
(Cheapflightsfares)

One-way from

$90
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$299
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 Islands
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One-way flight from Boston Logan Intl to Caribbean Islands
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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 April 2025
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Find flight deals from Boston to Caribbean Islands

Cheapest flights from Boston to Caribbean Islands
Explore the most affordable flight options available from Boston to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 25, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/25. 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 6/122:42 pmBOS - SJU
Nonstop3h 54mSpirit Airlines
Thu 6/199:30 amSJU - BOS
Nonstop4h 07mSpirit Airlines
Deal found 4/25$151
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/37:52 pmBOS - SJU
Nonstop4h 00mMultiple Airlines
Thu 5/86:30 amSJU - BOS
Nonstop4h 13mMultiple Airlines
Deal found 4/24$184
This Cheapflightsfares deal was found by Cheapflights users on 4/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1111:43 amBOS - SJU
Nonstop4h 01mFrontier
Thu 5/156:30 amSJU - BOS
Nonstop4h 13mFrontier
Deal found 4/24$192
This Delta deal was found by Cheapflights users on 4/25. 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 10/228:10 amBOS - SJU
Nonstop4h 12mDelta
Fri 10/311:32 pmSJU - BOS
Nonstop4h 17mDelta
Deal found 4/25$214
This American Airlines deal was found by Cheapflights users on 4/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/85:00 amBOS - SJU
1 stop10h 00mAmerican Airlines
Tue 5/133:35 pmSJU - BOS
1 stop8h 44mAmerican Airlines
Deal found 4/24$273
This Cheapflightsfares deal was found by Cheapflights users on 4/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/295:45 amBOS - STT
1 stop6h 41mSpirit Airlines
Sat 6/71:21 pmSTT - BOS
1 stop10h 26mSpirit Airlines
Deal found 4/24$282
This JetBlue deal was found by Cheapflights users on 4/24. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1711:05 amBOS - SJU
1 stop9h 03mJetBlue
Mon 9/297:00 pmSJU - BOS
Nonstop4h 04mJetBlue
Deal found 4/24$289
This American Airlines deal was found by Cheapflights users on 4/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/27:50 pmBOS - STT
1 stop16h 54mAmerican Airlines
Thu 6/54:00 pmSTT - BOS
2 stops15h 20mAmerican Airlines
Deal found 4/24$291
This United Airlines deal was found by Cheapflights users on 4/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2812:29 pmBOS - SJU
2 stops11h 28mUnited Airlines
Sat 5/311:25 pmSJU - BOS
1 stop8h 40mUnited Airlines
Deal found 4/24$293
This Delta deal was found by Cheapflights users on 4/25. 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.
Fri 5/96:55 amBOS - STT
1 stop8h 15mDelta
Wed 5/142:51 pmSTT - BOS
1 stop9h 42mDelta
Deal found 4/25$296
This Cheapflightsfares deal was found by Cheapflights users on 4/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/266:10 amBOS - MBJ
1 stop5h 52mSpirit Airlines
Fri 5/3012:07 pmMBJ - BOS
1 stop10h 22mSpirit Airlines
Deal found 4/24$310
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/116:00 amBOS - PUJ
1 stop29h 47mMultiple Airlines
Sat 5/243:22 pmPUJ - BOS
1 stop8h 07mMultiple Airlines
Deal found 4/24$339

Cheapflights Fare Finder

Customize your flight search to find flights from Boston to Caribbean Islands 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 25, 2025.
Use the filters below to find and compare flights from Boston to Caribbean Islands that are best for you.

Fly from

Boston

Fly to

Caribbean Islands

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 6/12

2:42 pm-6:36 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Thu 6/19

9:30 am-1:37 pm

Nonstop4h 07m

$151

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 5/3

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

$184

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 5/11

11:43 am-3:44 pm

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

Thu 5/15

6:30 am-10:43 am

Nonstop4h 13m

$192

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 5/7

1:59 pm-6:05 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Tue 5/13

6:00 am-10:08 am

Nonstop4h 08m

$264

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 5/25

8:20 am-12:21 pm

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

Mon 6/2

1:39 pm-5:57 pm

Nonstop4h 18m

$269

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 5/8

5:00 am-3:00 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Tue 5/13

3:35 pm-12:19 am

1 stop8h 44m

$273

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Thu 5/29

5:45 am-3:30 pm

1 stop9h 45m

Saint Thomas Island Cyril E King

Thu 6/12

3:03 pm-11:47 pm

1 stop8h 44m

$282

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Mon 6/2

7:50 pm-12:44 pm

1 stop16h 54m

Saint Thomas Island Cyril E King

Thu 6/5

4:00 pm-7:20 am

2 stops15h 20m

$291

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 5/10

12:00 pm-11:54 pm

2 stops11h 54m

San Juan Luis Munoz Marin Intl

Fri 5/16

1:05 am-8:56 am

1 stop7h 51m

$295

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 5/9

6:55 am-3:10 pm

1 stop8h 15m

Saint Thomas Island Cyril E King

Wed 5/14

2:51 pm-12:33 am

1 stop9h 42m

$296

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/25

Showing 1-10 of 60 results
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Best time to book a flight from Boston to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

What is the cheapest month to book a flight from Boston to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Boston to Caribbean Islands (average of $254). Flying from Boston to Caribbean Islands 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 EPX?

Find hourly flight availability from Boston to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 25, 2025.

When flying from Boston to Caribbean Islands, 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 Islands

Explore weekly flight availability from Boston to Caribbean Islands. 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 25, 2025.

The most flights from BOS to zzEPX are scheduled on a Thursday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated April 25, 2025.
To help decide which airline to fly from Boston to Caribbean Islands, see what other customers have to say about Alaska Airlines, Southwest and Delta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,927 reviews

Entertainment

7.1

Boarding

8.2

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.9

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
9,927 reviews
Alaska Airlines
8.0
Very good
9,927 reviews

Entertainment

7.1

Boarding

8.2

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.9

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
4,289 reviews
Alaska Airlines
8.0
Very good
9,927 reviews

Entertainment

7.1

Boarding

8.2

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.9

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
7,920 reviews
Alaska Airlines
8.0
Very good
9,927 reviews

Entertainment

7.1

Boarding

8.2

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.9

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
1,411 reviews
Alaska Airlines
8.0
Very good
9,927 reviews

Entertainment

7.1

Boarding

8.2

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.9

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
8,685 reviews
Alaska Airlines
8.0
Very good
9,927 reviews

Entertainment

7.1

Boarding

8.2

Food

7.1

Crew

8.5

Overall

8.0

Comfort

7.9

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 Islands. 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 Islands?

    Most people fly from Boston Logan Intl (BOS) if they book a flight from Boston to Caribbean Islands. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

  • What are the cheapest airlines to fly from Boston to Caribbean Islands one-way?

    $90 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and Delta, with prices starting from $96 and $137, respectively.

  • What are the most popular routes from Boston to Caribbean Islands?

    Most travelers choose Boston Logan Intl - San Juan Luis Munoz Marin Intl, Boston Logan Intl - Punta Cana or Boston Logan Intl - Oranjestad Reina Beatrix when deciding on the best route from Boston to Caribbean Islands.

  • What are the most reliable airlines from Boston to Caribbean Islands?

    The top 3 most reliable airlines when flying from Boston to Caribbean Islands are Aer Lingus (78%), Japan Airlines (75%) and TAP AIR PORTUGAL (74%).

  • What are the cheapest flights from Boston to Caribbean Islands?

    On average you can expect to pay $566 for a flight from Boston to Caribbean Islands. The cheapest flight overall is $88 while the most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl) is currently priced at $151.

  • Can I find deals for flights from Boston to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Boston to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Caribbean Islands.

  • Can I find deals for business class flights from Boston to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Boston to Caribbean Islands 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 Islands?

    Currently, September is the cheapest month in which you can book a flight from Boston to Caribbean Islands (average of $254). Flying from Boston to Caribbean Islands 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.

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Alternative routes for Boston to Caribbean Islands

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Top 10 airlines flying from Boston to Caribbean Islands

Discover the top 10 airlines that operate flights from Boston to Caribbean Islands. 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 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$364FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$84Average$456FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$496FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$143Average$532FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$204Average$549FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$266Average$790FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$282Average$603FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$529FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$364Average$520FlexibilityNo cancel feeOn-time70%
SouthwestCheapest$402Average$787FlexibilityNo cancel feeOn-time63%

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