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$93+ Cheap flights from Caribbean to Boston (BOS)

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 12/20. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Jan 6 — Jan 131
Tue 1/6
Tue 1/13
1 adult, Economy
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Cheap flight deals from Caribbean to Boston

Cheapest flights from Caribbean to Boston
Explore the most affordable flight options available from Caribbean to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 7, 2025.

This Priceline deal was found by Cheapflights users on 12/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/238:00 amSJU - BOS
Nonstop4h 23mMultiple Airlines
Sat 1/35:45 amBOS - SJU
1 stop15h 20mMultiple Airlines
Deal found 12/4$132
This Kiwi.com deal was found by Cheapflights users on 12/6. 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.
Tue 12/238:00 amSJU - BOS
Nonstop4h 23mMultiple Airlines
Wed 1/711:55 amBOS - SJU
1 stop9h 10mMultiple Airlines
Deal found 12/6$133
This CheapOair deal was found by Cheapflights users on 12/7. 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.
Tue 12/238:00 amSJU - BOS
Nonstop4h 23mFrontier
Mon 1/58:08 amBOS - SJU
1 stop16h 16mFrontier
Deal found 12/7$134
This Cheapflightsfares deal was found by Cheapflights users on 12/5. 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.
Wed 12/243:15 pmSJU - BOS
Nonstop4h 24mSpirit Airlines
Mon 1/57:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Deal found 12/5$135
This Mytrip deal was found by Cheapflights users on 12/5. 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.
Thu 12/258:00 amSJU - BOS
Nonstop4h 23mMultiple Airlines
Tue 1/611:55 amBOS - SJU
1 stop9h 10mMultiple Airlines
Deal found 12/5$137
This Mytrip deal was found by Cheapflights users on 12/5. 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.
Tue 12/238:00 amSJU - BOS
Nonstop4h 23mMultiple Airlines
Mon 1/511:55 amBOS - SJU
1 stop9h 10mMultiple Airlines
Deal found 12/5$138
This Kiwi.com deal was found by Cheapflights users on 12/5. 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 12/257:00 amSJU - BOS
1 stop19h 19mFrontier
Tue 1/612:31 pmBOS - SJU
Nonstop3h 59mFrontier
Deal found 12/5$146
This eDestinos deal was found by Cheapflights users on 12/7. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/193:15 pmSJU - BOS
Nonstop4h 24mSpirit Airlines
Sun 1/47:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Deal found 12/7$154
This Cheapflightsfares deal was found by Cheapflights users on 12/5. 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.
Wed 12/242:59 amSJU - BOS
1 stop9h 35mSpirit Airlines
Thu 1/17:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Deal found 12/5$156
This Kiwi.com deal was found by Cheapflights users on 12/6. 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 12/243:39 pmPUJ - BOS
1 stop20h 44mFrontier
Sun 1/1112:31 pmBOS - PUJ
1 stop23h 56mFrontier
Deal found 12/6$239
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2410:41 amSDQ - BOS
1 stop25h 42mFrontier
Tue 1/612:31 pmBOS - SDQ
1 stop21h 41mFrontier
Deal found 12/4$245
This Kiwi.com deal was found by Cheapflights users on 12/6. 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 12/1710:26 amSDQ - BOS
1 stop25h 57mMultiple Airlines
Sun 1/1112:31 pmBOS - SDQ
1 stop26h 58mMultiple Airlines
Deal found 12/6$246

Find flight deals from Caribbean to Boston

Keep the following information in mind while searching for Caribbean to Boston flight deals. Data was last updated December 7, 2025.

Round-trip from

$124
(Cheapflightsfares)

One-way from

$93
(Delta)

Popular in

July

Cheapest in

February

Average price

$234

Good round-trip deal

$137 or less

Good one-way deal

$147 or less
From Caribbean to Boston Logan Intl
Search Deals
One-way flight from Caribbean to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Caribbean to Boston Logan Intl.
Search Deals
Price to beat on a one-way flight from Caribbean to Boston Logan Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean to Boston 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 December 7, 2025.
Use the filters below to find and compare flights from Caribbean to Boston that are best for you.

Fly from

Caribbean

Fly to

Boston

Route

Depart

Return

Price

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 1/2

5:18 pm-8:32 pm

Nonstop4h 14m

Boston Logan Intl

Sat 1/10

7:30 am-12:33 pm

Nonstop4h 03m

$186

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 3/26

5:10 am-9:22 am

Nonstop4h 12m

Boston Logan Intl

Sun 3/29

8:55 pm-12:55 am

Nonstop4h 00m

$202

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Sun 1/18

10:52 am-2:12 pm

Nonstop4h 20m

Boston Logan Intl

Thu 1/22

3:43 pm-11:33 pm

1 stop6h 50m

$222

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 12/25

2:15 pm-10:48 pm

1 stop9h 33m

Boston Logan Intl

Wed 12/31

6:45 am-2:40 pm

1 stop6h 55m

$233

Saint Thomas IslandBoston

STT - BOS

STTBOS

Saint Thomas Island Cyril E King

Fri 1/30

2:32 pm-5:53 pm

Nonstop4h 21m

Boston Logan Intl

Wed 2/4

8:55 am-2:00 pm

Nonstop4h 05m

$234

Saint Thomas IslandBoston

STT - BOS

STTBOS

Saint Thomas Island Cyril E King

Fri 2/6

2:00 pm-6:59 pm

1 stop5h 59m

Boston Logan Intl

Sun 2/8

8:00 am-1:05 pm

Nonstop4h 05m

$234

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Tue 2/10

8:15 am-5:13 pm

1 stop9h 58m

Boston Logan Intl

Tue 2/17

8:50 pm-1:50 am

Nonstop4h 00m

$234

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 12/26

6:01 am-2:12 pm

1 stop9h 11m

Boston Logan Intl

Tue 12/30

6:50 pm-11:56 pm

Nonstop4h 06m

$242

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Sat 12/27

1:59 am-7:41 am

1 stop6h 42m

Boston Logan Intl

Mon 1/5

8:00 pm-1:05 am

Nonstop4h 05m

$242

Saint Thomas IslandBoston

STT - BOS

STTBOS

Saint Thomas Island Cyril E King

Fri 1/30

6:39 pm-10:00 am

1 stop16h 21m

Boston Logan Intl

Wed 2/4

6:00 am-5:05 pm

2 stops10h 05m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

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

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

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

Currently, February is the cheapest month in which you can book a flight from Caribbean to Boston (average of $56). Flying from Caribbean to Boston in October is currently the most expensive (average of $138). 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 CB to BOS?

Find hourly flight availability from Caribbean to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 7, 2025.

It’s typically best to fly out from Caribbean to Boston at noon. Doing so could potentially save you 25% on the flight price compared to flying in the evening, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Caribbean to Boston. Price data was last updated on December 6, 2025.

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

Weekly flight availability from Caribbean to Boston

Explore weekly flight availability from Caribbean to Boston. 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 December 7, 2025.

The most flights from 0CB to BOS are scheduled on a Saturday (22 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (9 on average).

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated December 7, 2025.
See what other customers who have flown with Delta, American Airlines, and JetBlue from Caribbean to Boston have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,013 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Boarding

8.1

Food

7.3

Entertainment

7.9

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
8,013 reviews
Delta
7.9
Good
8,013 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Boarding

8.1

Food

7.3

Entertainment

7.9

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
11,046 reviews
Delta
7.9
Good
8,013 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Boarding

8.1

Food

7.3

Entertainment

7.9

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
2,897 reviews
Delta
7.9
Good
8,013 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Boarding

8.1

Food

7.3

Entertainment

7.9

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
8,167 reviews
Delta
7.9
Good
8,013 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Boarding

8.1

Food

7.3

Entertainment

7.9

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.
Frontier
5.8
Fair
3,090 reviews
Delta
7.9
Good
8,013 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Boarding

8.1

Food

7.3

Entertainment

7.9

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 Caribbean to Boston. 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 into for flights to Boston from Caribbean?

    Located just 2.6 mi from the city center, Boston Logan Intl (BOS) is the airport most travelers will use when flying to Boston from Caribbean.

  • How long is the flight from Caribbean to Boston?

    A quick flight from Caribbean to Boston can take about 4h 14m. JetBlue provides one of the quickest options available for as low as $186. Airlines will cover a distance of 1678 mi. All flights are typically nonstop.

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

    One-way options have recently been found by users for as low as $57 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $70 and JetBlue from $114 one-way.

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

    When deciding which route to take from Caribbean to Boston consider Santo Domingo Las Americas - Boston Logan Intl, San Juan Luis Munoz Marin Intl - Boston Logan Intl or Santiago de los Caballeros - Boston Logan Intl as they are the most popular.

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

    The top 3 most reliable airlines when flying from Caribbean to Boston are Etihad Airways (95%), WestJet (86%) and Japan Airlines (85%).

  • What are the cheapest flights from Caribbean to Boston?

    On average you can expect to pay $206 for a flight from Caribbean to Boston. The cheapest flight overall is $88 while the most popular route, (Santo Domingo Las Americas - Boston Logan Intl) is currently priced at $231.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Caribbean to Boston (average of $56). Flying from Caribbean to Boston in October is currently the most expensive (average of $138). 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

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Hampton Beach
Watertown
Seabrook
Seekonk
Cranston
Lincoln
Lowell
Smithfield
Peabody
Brockton
Quincy
York Beach
Warwick
Londonderry
Swansea
Old Orchard Beach
Waltham
Chelsea

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Top 8 airlines flying from Caribbean to Boston

Discover the top 8 airlines that operate flights from Caribbean to Boston. 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 December 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$301FlexibilityNo cancel feeOn-time65%
FrontierCheapest$90Average$269FlexibilityNo cancel feeOn-time62%
DeltaCheapest$134Average$423FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$178Average$542FlexibilityNo cancel feeOn-time62%
ArajetCheapest$178Average$417FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$192Average$233FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$208Average$500FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$338Average$495FlexibilityNo cancel feeOn-time71%

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