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Caribbean Islands

$105+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Nov 1 — Nov 81
Sat 11/1
Sat 11/8
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 October 2, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$187
(Kiwi.com)

One-way from

$105
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$224
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. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 2, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/1. 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 10/212:15 pmBOS - SJU
1 stop11h 29mSpirit Airlines
Tue 10/282:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Deal found 10/1$191
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 10/1812:31 pmBOS - SJU
1 stop22h 25mSpirit Airlines
Tue 10/212:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Deal found 10/1$196
This Priceline deal was found by Cheapflights users on 9/30. 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.
Sat 10/252:15 pmBOS - SJU
1 stop10h 39mMultiple Airlines
Sun 11/210:39 pmSJU - BOS
1 stop10h 49mMultiple Airlines
Deal found 9/30$202
This Priceline deal was found by Cheapflights users on 10/1. 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.
Wed 10/292:15 pmBOS - SJU
1 stop11h 29mMultiple Airlines
Wed 11/51:26 pmSJU - BOS
1 stop19h 05mMultiple Airlines
Deal found 10/1$208
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 12/811:13 amBOS - SJU
1 stop7h 08mSpirit Airlines
Wed 12/102:59 amSJU - BOS
1 stop8h 09mSpirit Airlines
Deal found 9/30$214
This SmartFares deal was found by Cheapflights users on 10/1. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2110:14 amBOS - SJU
1 stop6h 28mJetBlue
Tue 10/287:00 amSJU - BOS
1 stop8h 00mJetBlue
Deal found 10/1$217
This Trip.com deal was found by Cheapflights users on 10/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/208:00 amBOS - SJU
Nonstop4h 27mJetBlue
Sun 10/265:10 amSJU - BOS
Nonstop4h 09mJetBlue
Deal found 10/1$220
This Trip.com deal was found by Cheapflights users on 9/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/281:55 pmBOS - SJU
Nonstop4h 02mJetBlue
Tue 11/42:33 pmSJU - BOS
Nonstop4h 13mJetBlue
Deal found 9/30$223
This Trip.com deal was found by Cheapflights users on 10/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:55 pmBOS - SJU
Nonstop3h 59mJetBlue
Mon 11/38:10 pmSJU - BOS
Nonstop4h 06mJetBlue
Deal found 10/2$225
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 10/1812:31 pmBOS - SJU
1 stop22h 25mSpirit Airlines
Mon 10/202:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Deal found 10/1$226
This Mytrip deal was found by Cheapflights users on 9/30. 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.
Wed 10/156:17 amBOS - SJU
2 stops19h 27mSpirit Airlines
Tue 10/212:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Deal found 9/30$228
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 12/711:13 amBOS - SJU
1 stop7h 08mSpirit Airlines
Fri 12/1212:10 pmSJU - BOS
1 stop10h 58mSpirit Airlines
Deal found 9/30$230

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 October 2, 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 11/1

7:43 pm-11:43 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Wed 11/5

12:30 pm-7:51 pm

1 stop8h 21m

$248

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 11/8

7:36 pm-3:48 am

1 stop7h 12m

San Juan Luis Munoz Marin Intl

Thu 11/13

9:30 am-3:00 pm

1 stop6h 30m

$251

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 10/20

8:00 am-12:27 pm

Nonstop4h 27m

San Juan Luis Munoz Marin Intl

Fri 10/31

2:31 pm-11:48 pm

1 stop9h 17m

$252

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 11/4

1:55 pm-6:57 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Sat 11/15

8:05 am-4:37 pm

1 stop9h 32m

$257

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 10/31

8:15 am-12:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Tue 11/4

2:32 pm-5:45 pm

Nonstop4h 13m

$262

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 10/28

8:15 am-12:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Tue 11/4

2:32 pm-5:45 pm

Nonstop4h 13m

$262

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 10/20

8:15 am-12:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Sat 10/25

1:32 pm-5:45 pm

Nonstop4h 13m

$262

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 11/17

8:10 am-1:15 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Mon 12/15

2:20 pm-5:45 pm

Nonstop4h 25m

$262

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 12/11

8:10 am-1:10 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Mon 12/15

2:20 pm-5:45 pm

Nonstop4h 25m

$262

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 10/28

8:15 am-12:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Sat 11/8

2:32 pm-5:45 pm

Nonstop4h 13m

$262

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

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 June is currently the most expensive (average of $339). 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 October 2, 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.

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 October 2, 2025.
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
8.0
Very good
7,962 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

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
7,962 reviews
Delta
8.0
Very good
7,962 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

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
8,933 reviews
Delta
8.0
Very good
7,962 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

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!
American Airlines
7.2
Good
11,033 reviews
Delta
8.0
Very good
7,962 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

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!
JetBlue
7.2
Good
2,911 reviews
Delta
8.0
Very good
7,962 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

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!
Spirit Airlines
6.3
Okay
8,070 reviews
Delta
8.0
Very good
7,962 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

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.

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

    For as low as $248, JetBlue can have you in Caribbean Islands from Boston in 4h. 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?

    $114 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Delta and Copa Airlines, with prices starting from $114 and $115, 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 - Santo Domingo Las Americas 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 Delta (77%), Hawaiian Airlines (75%) and Icelandair (71%).

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

    On average you can expect to pay $609 for a flight from Boston to Caribbean Islands. The cheapest flight overall is $123 while the most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl) is currently priced at $176.

  • 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 June is currently the most expensive (average of $339). 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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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 October 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$83Average$406FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$99Average$379FlexibilityNo cancel feeOn-time65%
DeltaCheapest$143Average$482FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$165Average$537FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$188Average$622FlexibilityNo cancel feeOn-time67%
ArajetCheapest$192Average$362FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$192Average$387FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$194Average$527FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$288Average$592FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$560FlexibilityNo cancel feeOn-time71%

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