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$91+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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 January 28, 2026.

This CheapOair deal was found by Cheapflights users on 1/26. 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.
Fri 2/136:00 am
SJU
-
BOS
Nonstop4h 19m
Multiple Airlines
Mon 2/238:01 pm
BOS
-
SJU
Nonstop4h 07m
Multiple Airlines
Deal found 1/26$108
This Cheapflightsfares deal was found by Cheapflights users on 1/26. 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 2/610:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Sun 2/83:18 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Deal found 1/26$115
This Flightnetwork deal was found by Cheapflights users on 1/26. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/410:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Sun 2/83:18 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Deal found 1/26$116
This Cheapflightsfares deal was found by Cheapflights users on 1/26. 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 2/610:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Mon 2/95:34 am
BOS
-
SJU
1 stop9h 01m
Spirit Airlines
Deal found 1/26$121
This Spirit deal was found by Cheapflights users on 1/27. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/54:40 pm
SJU
-
BOS
1 stop8h 17m
Spirit Airlines
Sun 2/83:18 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Deal found 1/27$122
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/276:00 am
SJU
-
BOS
Nonstop4h 19m
Multiple Airlines
Sun 3/18:01 pm
BOS
-
SJU
Nonstop4h 07m
Multiple Airlines
Deal found 1/27$127
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 2/2611:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Sun 3/18:01 pm
BOS
-
SJU
Nonstop4h 07m
Spirit Airlines
Deal found 1/27$128
This Flightnetwork deal was found by Cheapflights users on 1/28. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/310:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Sun 2/83:18 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Deal found 1/28$131
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 2/510:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Mon 2/93:18 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Deal found 1/27$133
This CheapOair deal was found by Cheapflights users on 1/28. 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.
Fri 2/276:00 am
SJU
-
BOS
Nonstop4h 19m
Multiple Airlines
Mon 3/28:01 pm
BOS
-
SJU
Nonstop4h 07m
Multiple Airlines
Deal found 1/28$134
This Priceline deal was found by Cheapflights users on 1/26. 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.
Thu 2/125:40 pm
STT
-
BOS
1 stop7h 04m
Spirit Airlines
Wed 2/255:27 am
BOS
-
STT
1 stop10h 07m
Spirit Airlines
Deal found 1/26$192
This Expedia deal was found by Cheapflights users on 1/27. 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.
Sat 2/141:00 pm
MBJ
-
BOS
1 stop6h 27m
Spirit Airlines
Sat 2/218:32 pm
BOS
-
MBJ
1 stop15h 30m
Spirit Airlines
Deal found 1/27$212

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 January 28, 2026.

Round-trip from

$108
(CheapOair)

One-way from

$91
(CheapOair)

Popular in

July

Cheapest in

February

Average price

$227

Good round-trip deal

$136 or less

Good one-way deal

$176 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. 14% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 28, 2026.
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

Wed 2/25

4:31 pm-11:44 pm

1 stop8h 13m

Boston Logan Intl

Sun 3/1

8:01 pm-1:08 am

Nonstop4h 07m

$135

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Sat 2/7

6:20 pm-11:57 pm

1 stop6h 37m

Boston Logan Intl

Sun 2/8

5:34 am-3:35 pm

1 stop9h 01m

$155

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Sun 2/15

11:22 am-2:43 pm

Nonstop4h 21m

Boston Logan Intl

Sun 2/22

3:00 pm-8:06 pm

Nonstop4h 06m

$160

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Tue 2/17

11:22 am-2:43 pm

Nonstop4h 21m

Boston Logan Intl

Sun 2/22

4:22 pm-10:17 am

1 stop16h 55m

$181

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 4/2

6:00 am-10:16 am

Nonstop4h 16m

Boston Logan Intl

Mon 4/13

3:23 pm-7:19 pm

Nonstop3h 56m

$191

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Wed 4/1

10:00 am-2:18 pm

Nonstop4h 18m

Boston Logan Intl

Sun 4/5

3:23 pm-7:19 pm

Nonstop3h 56m

$191

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 4/2

6:00 am-10:16 am

Nonstop4h 16m

Boston Logan Intl

Tue 4/7

11:18 am-3:17 pm

Nonstop3h 59m

$197

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 5/14

1:30 pm-5:53 pm

Nonstop4h 23m

Boston Logan Intl

Tue 5/19

8:20 am-12:28 pm

Nonstop4h 08m

$203

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 6/5

7:49 pm-11:54 pm

Nonstop4h 05m

Boston Logan Intl

Tue 6/9

6:50 pm-11:00 pm

Nonstop4h 10m

$203

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Tue 5/19

7:00 am-3:19 pm

1 stop8h 19m

Boston Logan Intl

Tue 5/26

8:20 am-12:28 pm

Nonstop4h 08m

$208

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

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 $65). Flying from Caribbean to Boston in November is currently the most expensive (average of $141). 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 January 28, 2026.

It’s typically best to fly out from Caribbean to Boston at noon. Doing so could potentially save you 18% 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 January 24, 2026.

Travelers seeking maximum savings on their Caribbean to Boston flight should consider departing on Tuesday at noon 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 January 28, 2026.

The most flights from 0CB to BOS are scheduled on a Tuesday (20 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (4 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 January 28, 2026.
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
8,120 reviews

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

Comfort

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
8,120 reviews
Delta
7.9
Good
8,120 reviews

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

Comfort

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
11,199 reviews
Delta
7.9
Good
8,120 reviews

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

Comfort

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
2,889 reviews
Delta
7.9
Good
8,120 reviews

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

Comfort

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
8,385 reviews
Delta
7.9
Good
8,120 reviews

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

Comfort

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
5.7
Fair
3,056 reviews
Delta
7.9
Good
8,120 reviews

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

Comfort

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 8h 13m. Spirit Airlines provides one of the quickest options available for as low as $135. 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 $69 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $69 and American Airlines from $98 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 EL AL (85%), Japan Airlines (80%) and Delta (75%).

  • What are the cheapest flights from Caribbean to Boston?

    On average you can expect to pay $249 for a flight from Caribbean to Boston. The cheapest flight overall is $95 while the most popular route, (San Juan Luis Munoz Marin Intl - Boston Logan Intl) is currently priced at $102.

  • 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 $65). Flying from Caribbean to Boston in November is currently the most expensive (average of $141). 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
Medford
Cambridge
Hampton Beach
Watertown
Seekonk
Brockton
Warwick
Seabrook
Cranston
Lincoln
Smithfield
Peabody
Quincy
York Beach
Londonderry
Swansea
Old Orchard Beach
Waltham
Lowell
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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$73Average$278FlexibilityNo cancel feeOn-time65%
FrontierCheapest$86Average$281FlexibilityNo cancel feeOn-time62%
DeltaCheapest$113Average$419FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$137Average$527FlexibilityNo cancel feeOn-time62%
ArajetCheapest$169Average$394FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$192Average$221FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$208Average$474FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$324Average$494FlexibilityNo cancel feeOn-time71%

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