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Caribbean Islands

$91+ 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
May 9 — May 161
Fri 5/9
Fri 5/16
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 May 4, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$140
(Cheapflightsfares)

One-way from

$91
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$254
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 May 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 May 4, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 5/4. 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 6/126:15 amBOS - SJU
1 stop13h 04mSpirit Airlines
Thu 6/199:30 amSJU - BOS
Nonstop4h 07mSpirit Airlines
Deal found 5/4$140
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 5/1811:43 amBOS - SJU
Nonstop4h 01mMultiple Airlines
Sun 6/11:59 amSJU - BOS
1 stop7h 10mMultiple Airlines
Deal found 5/3$177
This Delta deal was found by Cheapflights users on 5/3. 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.
Thu 10/238:10 amBOS - SJU
Nonstop4h 12mDelta
Mon 10/271:32 pmSJU - BOS
Nonstop4h 17mDelta
Deal found 5/3$224
This United Airlines deal was found by Cheapflights users on 5/4. 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 9/206:00 amBOS - SJU
1 stop8h 44mUnited Airlines
Sat 9/274:55 pmSJU - BOS
1 stop7h 02mUnited Airlines
Deal found 5/4$233
This American Airlines deal was found by Cheapflights users on 5/3. 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 9/255:00 amBOS - SJU
1 stop15h 10mAmerican Airlines
Tue 9/301:55 pmSJU - BOS
2 stops10h 20mAmerican Airlines
Deal found 5/3$253
This Cheapflightsfares deal was found by Cheapflights users on 5/3. 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.
Fri 5/305:45 amBOS - STT
1 stop7h 51mSpirit Airlines
Wed 6/410:52 amSTT - BOS
1 stop12h 37mSpirit Airlines
Deal found 5/3$259
This Cheapflightsfares deal was found by Cheapflights users on 5/4. 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 5/811:43 amBOS - SJU
Nonstop4h 01mFrontier
Sun 5/116:30 amSJU - BOS
Nonstop4h 13mFrontier
Deal found 5/4$276
This JetBlue deal was found by Cheapflights users on 5/3. 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 11/56:00 pmBOS - SJU
Nonstop4h 00mJetBlue
Mon 11/105:10 pmSJU - BOS
1 stop7h 40mJetBlue
Deal found 5/3$284
This American Airlines deal was found by Cheapflights users on 5/3. 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.
Fri 9/126:02 amBOS - STT
2 stops9h 58mAmerican Airlines
Fri 9/194:50 pmSTT - BOS
2 stops15h 34mAmerican Airlines
Deal found 5/3$301
This JetBlue deal was found by Cheapflights users on 5/4. 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 9/208:35 amBOS - STT
Nonstop4h 04mJetBlue
Sat 9/271:45 pmSTT - BOS
1 stop6h 05mJetBlue
Deal found 5/4$302
This Delta deal was found by Cheapflights users on 5/4. 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 6/245:35 amBOS - STT
1 stop9h 16mDelta
Tue 7/221:27 pmSTT - BOS
1 stop12h 12mDelta
Deal found 5/4$315
This Cheapflightsfares deal was found by Cheapflights users on 5/3. 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.
Fri 6/65:42 pmBOS - MBJ
2 stops18h 20mSpirit Airlines
Tue 6/1012:07 pmMBJ - BOS
1 stop10h 22mSpirit Airlines
Deal found 5/3$330

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 May 4, 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

Sat 6/14

8:14 pm-10:39 am

1 stop14h 25m

San Juan Luis Munoz Marin Intl

Thu 6/19

9:30 am-1:37 pm

Nonstop4h 07m

$139

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 5/15

9:46 am-8:02 pm

1 stop10h 16m

San Juan Luis Munoz Marin Intl

Sun 5/18

6:30 am-10:43 am

Nonstop4h 13m

$219

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 5/28

7:20 pm-11:25 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Wed 6/4

6:00 am-10:08 am

Nonstop4h 08m

$224

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 9/20

6:00 am-2:44 pm

1 stop8h 44m

San Juan Luis Munoz Marin Intl

Sat 9/27

4:55 pm-11:57 pm

1 stop7h 02m

$233

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 9/3

8:10 am-12:17 pm

Nonstop4h 07m

San Juan Luis Munoz Marin Intl

Mon 9/29

2:15 pm-11:34 pm

1 stop9h 19m

$254

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 5/30

5:45 am-1:36 pm

1 stop7h 51m

Saint Thomas Island Cyril E King

Wed 6/4

10:52 am-11:29 pm

1 stop12h 37m

$259

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 5/15

6:00 am-1:29 pm

1 stop7h 29m

San Juan Luis Munoz Marin Intl

Sun 5/18

6:30 am-10:43 am

Nonstop4h 13m

$298

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 6/24

5:35 am-2:51 pm

1 stop9h 16m

Saint Thomas Island Cyril E King

Tue 7/22

1:27 pm-1:39 am

1 stop12h 12m

$315

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 5/16

6:00 am-4:20 pm

2 stops10h 20m

Saint Thomas Island Cyril E King

Tue 5/20

1:25 pm-10:49 pm

1 stop9h 24m

$320

BostonMontego Bay

BOS - MBJ

BOSMBJ

Boston Logan Intl

Fri 6/6

5:42 pm-11:02 am

2 stops18h 20m

Montego Bay Sangster Intl

Tue 6/10

12:07 pm-11:29 pm

1 stop10h 22m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

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 May 4, 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 May 4, 2025.

The most flights from BOS to zzEPX are scheduled on a Sunday (18 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 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 May 4, 2025.
To help decide which airline to fly from Boston to Caribbean Islands, see what other customers have to say about Delta, Alaska Airlines and Southwest. 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.
Delta
8.0
Very good
7,937 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

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
7,937 reviews
Delta
8.0
Very good
7,937 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

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!
Alaska Airlines
8.0
Very good
9,985 reviews
Delta
8.0
Very good
7,937 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

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!
Southwest
8.0
Very good
4,292 reviews
Delta
8.0
Very good
7,937 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

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!
Copa Airlines
7.5
Good
1,418 reviews
Delta
8.0
Very good
7,937 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

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!
United Airlines
7.4
Good
8,701 reviews
Delta
8.0
Very good
7,937 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

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 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?

    $91 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 United Airlines, with prices starting from $127 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 - Oranjestad Reina Beatrix or Boston Logan Intl - Punta Cana 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 Turkish Airlines (90%), Japan Airlines (81%) and Delta (81%).

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

    On average you can expect to pay $482 for a flight from Boston to Caribbean Islands. The cheapest flight overall is $94 while the most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl) is currently priced at $155.

  • 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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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 May 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$364FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$84Average$459FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$494FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$145Average$533FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$156Average$734FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$204Average$551FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$282Average$599FlexibilityNo 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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