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$123+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Oct 25 — Nov 11
Sat 10/25
Sat 11/1
1 adult, Economy
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Cheap flight deals from Caribbean to Boston

Keep the following information in mind while searching for Caribbean to Boston flight deals. Data was last updated September 25, 2025.

Round-trip from

$176
(Expedia)

One-way from

$123
(Cheapflightsfares)

Popular in

July

Cheapest in

January

Average price

$224

Good round-trip deal

$198 or less

Good one-way deal

$161 or less
From Caribbean to Boston Logan Intl
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One-way flight from Caribbean to Boston Logan Intl
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Highest demand for flights based on searches. 21% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Caribbean to Boston Logan Intl.
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Price to beat on a one-way flight from Caribbean to Boston Logan Intl.
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Find 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 September 25, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 10/311:59 amSJU - BOS
1 stop11h 58mSpirit Airlines
Tue 10/72:15 pmBOS - SJU
1 stop11h 29mSpirit Airlines
Deal found 9/23$201
This American Airlines deal was found by Cheapflights users on 9/24. 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.
Tue 10/211:35 pmSJU - BOS
1 stop7h 18mAmerican Airlines
Wed 10/226:00 amBOS - SJU
2 stops9h 54mAmerican Airlines
Deal found 9/24$205
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 10/212:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Tue 10/282:15 pmBOS - SJU
1 stop11h 29mSpirit Airlines
Deal found 9/23$214
This SmartFares deal was found by Cheapflights users on 9/22. 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.
Fri 10/38:22 pmSJU - BOS
Nonstop4h 02mJetBlue
Mon 10/68:00 amBOS - SJU
Nonstop4h 27mJetBlue
Deal found 9/22$216
This Trip.com deal was found by Cheapflights users on 9/24. 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.
Fri 10/108:22 pmSJU - BOS
Nonstop4h 02mJetBlue
Wed 10/297:40 amBOS - SJU
Nonstop4h 04mJetBlue
Deal found 9/24$221
This Trip.com deal was found by Cheapflights users on 9/23. 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.
Fri 10/38:22 pmSJU - BOS
Nonstop4h 02mJetBlue
Sun 10/58:00 amBOS - SJU
Nonstop4h 07mJetBlue
Deal found 9/23$222
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 10/239:06 pmSJU - BOS
1 stop18h 50mMultiple Airlines
Mon 10/276:16 amBOS - SJU
1 stop9h 00mMultiple Airlines
Deal found 9/24$229
This JetBlue deal was found by Cheapflights users on 9/24. 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.
Mon 10/68:22 pmSJU - BOS
Nonstop4h 02mJetBlue
Tue 10/712:00 pmBOS - SJU
Nonstop4h 05mJetBlue
Deal found 9/24$233
This SmartFares deal was found by Cheapflights users on 9/23. 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.
Fri 11/75:15 amSJU - BOS
1 stop7h 56mJetBlue
Sun 11/97:00 pmBOS - SJU
Nonstop3h 59mJetBlue
Deal found 9/23$236
This Delta deal was found by Cheapflights users on 9/25. 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.
Fri 10/31:25 pmSJU - BOS
Nonstop4h 05mDelta
Tue 10/78:15 amBOS - SJU
Nonstop4h 06mDelta
Deal found 9/25$238
This Priceline deal was found by Cheapflights users on 9/23. 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 10/72:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Tue 10/282:15 pmBOS - SJU
1 stop11h 29mSpirit Airlines
Deal found 9/23$239
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 10/812:09 pmMBJ - BOS
1 stop10h 50mSpirit Airlines
Tue 10/146:16 amBOS - MBJ
1 stop5h 44mSpirit Airlines
Deal found 9/23$241

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 September 25, 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

Thu 10/16

8:22 pm-12:24 am

Nonstop4h 02m

Boston Logan Intl

Mon 10/20

8:00 am-12:27 pm

Nonstop4h 27m

$238

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 11/6

2:32 pm-5:45 pm

Nonstop4h 13m

Boston Logan Intl

Mon 11/10

8:10 am-1:17 pm

Nonstop4h 07m

$238

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 10/23

1:32 pm-5:45 pm

Nonstop4h 13m

Boston Logan Intl

Mon 10/27

8:15 am-12:21 pm

Nonstop4h 06m

$238

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 10/31

5:10 am-9:19 am

Nonstop4h 09m

Boston Logan Intl

Sun 11/2

7:40 am-12:44 pm

Nonstop4h 04m

$238

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 10/30

5:10 am-9:19 am

Nonstop4h 09m

Boston Logan Intl

Mon 11/3

1:55 pm-6:57 pm

Nonstop4h 02m

$238

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 10/23

1:32 pm-5:45 pm

Nonstop4h 13m

Boston Logan Intl

Sun 10/26

8:15 am-12:21 pm

Nonstop4h 06m

$238

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 10/17

8:22 pm-12:24 am

Nonstop4h 02m

Boston Logan Intl

Mon 10/20

8:00 am-12:27 pm

Nonstop4h 27m

$238

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Wed 10/22

1:32 pm-5:45 pm

Nonstop4h 13m

Boston Logan Intl

Tue 10/28

8:15 am-12:21 pm

Nonstop4h 06m

$238

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 11/7

2:33 pm-5:46 pm

Nonstop4h 13m

Boston Logan Intl

Sun 11/9

7:00 pm-11:59 pm

Nonstop3h 59m

$238

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Sun 10/26

5:10 am-9:19 am

Nonstop4h 09m

Boston Logan Intl

Wed 10/29

7:40 am-11:44 am

Nonstop4h 04m

$238

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/24

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, January is the cheapest month in which you can book a flight from Caribbean to Boston (average of $218). Flying from Caribbean to Boston in July is currently the most expensive (average of $311). 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 September 25, 2025.

When flying from Caribbean to Boston, 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 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 September 25, 2025.

The most flights from 0CB to BOS are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 September 25, 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
8.0
Very good
7,973 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,973 reviews
Delta
8.0
Very good
7,973 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,973 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
JetBlue
7.2
Good
2,914 reviews
Delta
8.0
Very good
7,973 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Spirit Airlines
6.3
Okay
8,045 reviews
Delta
8.0
Very good
7,973 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Frontier
5.8
Fair
3,162 reviews
Delta
8.0
Very good
7,973 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

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 02m. JetBlue provides one of the quickest options available for as low as $238. Airlines will cover a distance of 1678 mi. This flight may include one or multiple stops.

  • 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 $124 on Delta. Other airlines that offer cheap prices include United Airlines from $124 and JetBlue from $163 one-way.

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

    When deciding which route to take from Caribbean to Boston consider San Juan Luis Munoz Marin Intl - Boston Logan Intl, Santo Domingo Las Americas - 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 Delta (91%), KLM (87%) and Etihad Airways (84%).

  • What are the cheapest flights from Caribbean to Boston?

    On average you can expect to pay $670 for a flight from Caribbean to Boston. The cheapest flight overall is $136 while the most popular route, (San Juan Luis Munoz Marin Intl - Boston Logan Intl) is currently priced at $176.

  • 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, January is the cheapest month in which you can book a flight from Caribbean to Boston (average of $218). Flying from Caribbean to Boston in July is currently the most expensive (average of $311). 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
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Warwick
Peabody
Quincy
York Beach
Swansea
Old Orchard Beach
Brockton
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 September 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$78Average$257FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$85Average$287FlexibilityNo cancel feeOn-time65%
DeltaCheapest$136Average$422FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$152Average$468FlexibilityNo cancel feeOn-time62%
ArajetCheapest$178Average$393FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$208Average$480FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$216Average$397FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$338Average$498FlexibilityNo cancel feeOn-time71%

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