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Caribbean Islands

$45+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
feb. 15 — feb. 221
sáb. 2/15
sáb. 2/22
1 adult, Economy
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Cheap flight deals from Boston to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Caribbean Islands (zzEPX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated febrero 10, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$116
(Kiwi.com)

One-way from

$45
(Frontier)

Popular in

December

Cheapest in

September

Average price

$303
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. 10% potential increase in price ($30 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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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 febrero 10, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
lun. 2/2410:18 amBOS - SJU
Nonstop3h 57mMultiple Airlines
mar. 3/41:30 amSJU - BOS
1 stop6h 55mMultiple Airlines
Deal found 2/10$116
This Priceline deal was found by Cheapflights users on 2/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 3/16:00 amBOS - SJU
1 stop17h 59mFrontier
mié. 3/57:00 amSJU - BOS
Nonstop4h 18mFrontier
Deal found 2/10$118
This Cheapflightsfares deal was found by Cheapflights users on 2/10. 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.
lun. 3/34:20 pmBOS - SJU
1 stop6h 22mSpirit Airlines
jue. 3/64:38 amSJU - BOS
1 stop9h 23mSpirit Airlines
Deal found 2/10$136
This CheapOair deal was found by Cheapflights users on 2/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/61:56 pmBOS - STT
1 stop20h 05mSpirit Airlines
dom. 3/911:11 amSTT - BOS
2 stops20h 14mSpirit Airlines
Deal found 2/9$236
This JetBlue deal was found by Cheapflights users on 2/8. 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.
mié. 4/27:00 amBOS - SJU
Nonstop4h 01mJetBlue
mié. 4/29:35 pmSJU - BOS
Nonstop4h 03mJetBlue
Deal found 2/8$249
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/96:34 amBOS - STT
2 stops9h 56mAmerican Airlines
dom. 9/145:20 pmSTT - BOS
2 stops18h 41mAmerican Airlines
Deal found 2/10$249
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/265:40 amBOS - MBJ
1 stop8h 03mSpirit Airlines
mié. 3/51:07 pmMBJ - BOS
1 stop27h 25mSpirit Airlines
Deal found 2/10$258
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
lun. 5/126:00 amBOS - MBJ
1 stop8h 01mMultiple Airlines
dom. 5/182:21 pmMBJ - BOS
1 stop20h 27mMultiple Airlines
Deal found 2/10$278
This FlightHub deal was found by Cheapflights users on 2/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/55:29 pmBOS - AUA
1 stop21h 16mSpirit Airlines
mar. 3/113:50 pmAUA - BOS
1 stop18h 09mSpirit Airlines
Deal found 2/10$293
This United Airlines deal was found by Cheapflights users on 2/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/285:30 amBOS - STT
2 stops10h 13mUnited Airlines
jue. 5/82:10 pmSTT - BOS
1 stop8h 17mUnited Airlines
Deal found 2/9$307
This Delta deal was found by Cheapflights users on 2/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/2610:00 amBOS - NAS
Nonstop3h 44mDelta
sáb. 3/293:15 pmNAS - BOS
Nonstop3h 46mDelta
Deal found 2/10$330
This JetBlue deal was found by Cheapflights users on 2/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/299:53 amBOS - STT
Nonstop4h 02mJetBlue
mar. 5/64:45 pmSTT - BOS
1 stop6h 40mJetBlue
Deal found 2/10$338

Find flights from Boston to Caribbean Islands within your budget

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 febrero 10, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

lun. 2/24

10:18 am-3:15 pm

Nonstop3h 57m

San Juan Luis Munoz Marin Intl

mar. 3/4

1:30 am-7:25 am

1 stop6h 55m

$116

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

lun. 2/24

12:54 pm-9:16 pm

1 stop7h 22m

San Juan Luis Munoz Marin Intl

jue. 2/27

10:31 pm-8:07 am

1 stop10h 36m

$117

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

jue. 3/6

10:43 am-3:44 pm

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

mar. 3/11

3:49 pm-8:12 pm

Nonstop4h 23m

$133

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

jue. 3/6

1:56 pm-11:01 am

1 stop20h 05m

Saint Thomas Island Cyril E King

dom. 3/9

11:11 am-7:25 am

2 stops20h 14m

$236

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mié. 4/2

7:00 am-11:01 am

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

mié. 4/2

9:35 pm-1:38 am

Nonstop4h 03m

$249

BostonMontego Bay

BOS - MBJ

BOSMBJ

Boston Logan Intl

mié. 2/26

5:40 am-1:43 pm

1 stop8h 03m

Montego Bay Sangster Intl

mié. 3/5

1:07 pm-4:32 pm

1 stop27h 25m

$258

BostonMontego Bay

BOS - MBJ

BOSMBJ

Boston Logan Intl

lun. 5/12

6:00 am-1:01 pm

1 stop8h 01m

Montego Bay Sangster Intl

dom. 5/18

2:21 pm-11:48 am

1 stop20h 27m

$278

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

mar. 4/1

5:20 am-4:31 pm

1 stop11h 11m

Saint Thomas Island Cyril E King

dom. 4/13

5:50 pm-10:23 am

1 stop16h 33m

$289

BostonOranjestad

BOS - AUA

BOSAUA

Boston Logan Intl

mié. 3/5

5:29 pm-3:45 pm

1 stop21h 16m

Oranjestad Reina Beatrix

mar. 3/11

3:50 pm-9:59 am

1 stop18h 09m

$293

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

lun. 4/28

8:30 am-3:43 pm

1 stop7h 13m

Saint Thomas Island Cyril E King

jue. 5/8

2:10 pm-10:27 pm

1 stop8h 17m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

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.

Travel insights for flights from Boston to Caribbean Islands

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

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 March is currently the most expensive (average of $370). 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 febrero 10, 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 febrero 10, 2025.

The most flights from BOS to zzEPX are scheduled on a Tuesday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 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 febrero 10, 2025.
To help decide which airline to fly from Boston to Caribbean Islands, see what other customers have to say about Southwest, Delta and Alaska Airlines. 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.
Southwest
8.1
Very good
4,509 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Southwest
8.1
Very good
4,509 reviews
Southwest
8.1
Very good
4,509 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Delta
8.0
Very good
8,351 reviews
Southwest
8.1
Very good
4,509 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Alaska Airlines
8.0
Very good
9,691 reviews
Southwest
8.1
Very good
4,509 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Copa Airlines
7.7
Good
1,563 reviews
Southwest
8.1
Very good
4,509 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Aeromexico
7.5
Good
1,795 reviews
Southwest
8.1
Very good
4,509 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

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?

    $45 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and Delta, with prices starting from $58 and $114, 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 Delta (59%), Spirit Airlines (59%) and EL AL (58%).

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

    On average you can expect to pay $484 for a flight from Boston to Caribbean Islands. The cheapest flight overall is $53 while the most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl) is currently priced at $99.

  • 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 March is currently the most expensive (average of $370). 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 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 febrero 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$362FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$95Average$387FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$509FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$142Average$522FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$200Average$527FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$222Average$596FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$229Average$586FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$266Average$889FlexibilityNo cancel feeOn-time67%
AviancaCheapest$292Average$518FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$452Average$804FlexibilityNo cancel feeOn-time63%
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