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Caribbean Islands

$71+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
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 January 12, 2026.

Round-trip from

$140
(Cheapflightsfares)

One-way from

$71
(CheapOair)

Popular in

December

Cheapest in

January

Average price

$253
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. 8% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 12, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 1/12. 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 2/53:43 pm
BOS
-
SJU
1 stop17h 04m
Spirit Airlines
Tue 2/1010:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Deal found 1/12$140
This Cheapflightsfares deal was found by Cheapflights users on 1/12. 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 1/255:34 am
BOS
-
SJU
1 stop9h 01m
Spirit Airlines
Sat 1/3110:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Deal found 1/12$141
This Booking.com deal was found by Cheapflights users on 1/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/265:34 am
BOS
-
SJU
1 stop9h 01m
Spirit Airlines
Wed 2/46:00 am
SJU
-
BOS
1 stop9h 38m
Spirit Airlines
Deal found 1/12$142
This Priceline deal was found by Cheapflights users on 1/10. 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.
Mon 1/263:18 pm
BOS
-
SJU
Nonstop4h 06m
Multiple Airlines
Thu 1/294:22 pm
SJU
-
BOS
1 stop9h 51m
Multiple Airlines
Deal found 1/10$143
This Kiwi.com deal was found by Cheapflights users on 1/12. 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 1/243:18 pm
BOS
-
SJU
Nonstop4h 06m
Multiple Airlines
Sat 1/316:11 pm
SJU
-
BOS
1 stop8h 02m
Multiple Airlines
Deal found 1/12$144
This Kiwi.com deal was found by Cheapflights users on 1/10. 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.
Fri 2/278:01 pm
BOS
-
SJU
Nonstop4h 07m
Spirit Airlines
Wed 3/1110:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 1/10$145
This Kiwi.com deal was found by Cheapflights users on 1/12. 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.
Fri 1/233:18 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Tue 2/310:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Deal found 1/12$146
This Kiwi.com deal was found by Cheapflights users on 1/10. 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.
Sun 1/183:18 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Sat 1/3110:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Deal found 1/10$147
This Kiwi.com deal was found by Cheapflights users on 1/10. 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.
Thu 1/223:18 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Thu 1/294:40 pm
SJU
-
BOS
1 stop8h 17m
Spirit Airlines
Deal found 1/10$148
This Mytrip deal was found by Cheapflights users on 1/12. 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.
Mon 1/265:34 am
BOS
-
SJU
1 stop9h 01m
Spirit Airlines
Thu 1/294:40 pm
SJU
-
BOS
1 stop8h 17m
Spirit Airlines
Deal found 1/12$149
This Kiwi.com deal was found by Cheapflights users on 1/12. 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 1/213:43 pm
BOS
-
SJU
1 stop6h 50m
Spirit Airlines
Sat 1/3110:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Deal found 1/12$150
This Expedia deal was found by Cheapflights users on 1/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/18:00 am
BOS
-
STT
Nonstop4h 05m
JetBlue
Thu 2/52:00 pm
STT
-
BOS
1 stop5h 49m
JetBlue
Deal found 1/11$185

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 January 12, 2026.
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

Wed 4/1

9:30 pm-1:29 am

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Thu 4/30

11:25 pm-3:25 am

Nonstop4h 00m

$203

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 3/3

7:55 pm-12:58 am

Nonstop4h 03m

San Juan Luis Munoz Marin Intl

Sun 3/15

11:45 am-3:59 pm

Nonstop4h 14m

$203

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 3/2

7:05 am-2:40 pm

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Mon 3/2

2:05 am-2:29 pm

2 stops13h 24m

$207

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 2/3

5:35 am-2:31 pm

1 stop7h 56m

San Juan Luis Munoz Marin Intl

Tue 2/10

7:00 am-3:53 pm

1 stop9h 53m

$212

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 1/26

2:20 pm-10:22 pm

1 stop7h 02m

San Juan Luis Munoz Marin Intl

Thu 1/29

2:05 am-2:29 pm

2 stops13h 24m

$212

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 1/24

1:00 pm-11:57 pm

1 stop9h 57m

San Juan Luis Munoz Marin Intl

Wed 1/28

6:27 pm-1:04 am

1 stop7h 37m

$212

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 1/25

5:45 am-1:17 pm

1 stop6h 32m

San Juan Luis Munoz Marin Intl

Wed 2/11

2:05 am-9:15 am

1 stop8h 10m

$212

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 1/21

12:08 pm-10:22 pm

2 stops9h 14m

San Juan Luis Munoz Marin Intl

Wed 1/28

8:35 am-6:32 pm

2 stops10h 57m

$212

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 2/3

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Sat 2/7

2:42 pm-7:41 pm

1 stop5h 59m

$225

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Mon 2/2

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Wed 2/11

2:32 pm-5:53 pm

Nonstop4h 21m

$225

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/9

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.

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, January is the cheapest month in which you can book a flight from Boston to Caribbean Islands (average of $86). Flying from Boston to Caribbean Islands in November is currently the most expensive (average of $177). 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 January 12, 2026.

A simple way to save on the total cost of your ticket is to fly from Boston to Caribbean Islands in the afternoon. If you’re flexible enough to do this you can expect to save up to 27% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Boston to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Boston to Caribbean Islands. Price data was last updated on January 3, 2026.

Travelers seeking maximum savings on their Boston to Caribbean Islands flight should consider departing on Sunday at noon when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 January 12, 2026.

The most flights from BOS to zzEPX are scheduled on a Monday (12 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (4 on average).

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 January 12, 2026.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Boston to Caribbean Islands. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,039 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Food

7.2

Comfort

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,039 reviews
Delta
7.9
Good
8,039 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Food

7.2

Comfort

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,149 reviews
Delta
7.9
Good
8,039 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Food

7.2

Comfort

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,114 reviews
Delta
7.9
Good
8,039 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Food

7.2

Comfort

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,884 reviews
Delta
7.9
Good
8,039 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Food

7.2

Comfort

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,303 reviews
Delta
7.9
Good
8,039 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Food

7.2

Comfort

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.

  • How long is the flight from Boston to Caribbean Islands?

    For as low as $203, JetBlue can have you in Caribbean Islands from Boston in 3h 59m. The distance from Boston to Caribbean Islands is about 1678 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    $44 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Delta and Spirit Airlines, with prices starting from $54 and $59, 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 (66%), TAP AIR PORTUGAL (63%) and Etihad Airways (63%).

  • 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 $66 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, January is the cheapest month in which you can book a flight from Boston to Caribbean Islands (average of $86). Flying from Boston to Caribbean Islands in November is currently the most expensive (average of $177). 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 January 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$81Average$403FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$102Average$366FlexibilityNo cancel feeOn-time65%
Air CanadaCheapest$141Average$604FlexibilityNo cancel feeOn-time67%
DeltaCheapest$152Average$467FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$176Average$523FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$179Average$397FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$194Average$495FlexibilityNo cancel feeOn-time69%
ArajetCheapest$206Average$432FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$242Average$621FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$804FlexibilityNo cancel feeOn-time71%

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