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$85+ Cheap flights from Caribbean Islands 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Boston

Keep the following information in mind while searching for Caribbean Islands to Boston flight deals. Data was last updated April 4, 2025.

Round-trip from

$139
(Cheapflightsfares)

One-way from

$85
(Cheapflightsfares)
From Caribbean Islands to Boston Logan Intl
Search Deals
One-way flight from Caribbean Islands to Boston Logan Intl
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Find flight deals from Caribbean Islands to Boston

Cheapest flights from Caribbean Islands to Boston
Explore the most affordable flight options available from Caribbean Islands to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 4, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/3. 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 4/3012:57 amSJU - BOS
1 stop6h 21mSpirit Airlines
Tue 5/67:52 pmBOS - SJU
Nonstop4h 00mSpirit Airlines
Deal found 4/3$139
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 4/126:00 amSJU - BOS
Nonstop4h 16mMultiple Airlines
Sun 4/277:52 pmBOS - SJU
Nonstop4h 00mMultiple Airlines
Deal found 4/3$155
This Cheapflightsfares deal was found by Cheapflights users on 4/3. 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 5/1410:52 amSTT - BOS
1 stop12h 37mSpirit Airlines
Sat 5/174:49 pmBOS - STT
1 stop17h 08mSpirit Airlines
Deal found 4/3$176
This Cheapflightsfares deal was found by Cheapflights users on 4/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/86:30 amSJU - BOS
Nonstop4h 13mFrontier
Sun 5/1111:43 amBOS - SJU
Nonstop4h 01mFrontier
Deal found 4/4$196
This American Airlines deal was found by Cheapflights users on 4/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/305:50 pmSTT - BOS
1 stop16h 33mAmerican Airlines
Sun 5/46:00 amBOS - STT
2 stops9h 26mAmerican Airlines
Deal found 4/4$249
This Cheapflightsfares deal was found by Cheapflights users on 4/3. 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 5/161:34 pmKIN - BOS
1 stop8h 55mSpirit Airlines
Tue 5/206:10 amBOS - KIN
1 stop7h 19mSpirit Airlines
Deal found 4/3$250
This JetBlue deal was found by Cheapflights users on 4/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/212:30 amSJU - BOS
Nonstop4h 07mJetBlue
Tue 4/298:45 pmBOS - SJU
Nonstop4h 09mJetBlue
Deal found 4/4$254
This Delta deal was found by Cheapflights users on 4/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/71:39 pmSJU - BOS
Nonstop4h 18mDelta
Sat 5/108:20 amBOS - SJU
Nonstop4h 01mDelta
Deal found 4/4$259
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 5/1512:07 pmMBJ - BOS
1 stop10h 22mSpirit Airlines
Sun 5/186:10 amBOS - MBJ
1 stop5h 52mSpirit Airlines
Deal found 4/3$277
This Cheapflightsfares deal was found by Cheapflights users on 4/3. 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 5/112:39 pmPUJ - BOS
1 stop10h 18mSpirit Airlines
Sun 5/116:10 amBOS - PUJ
1 stop8h 07mSpirit Airlines
Deal found 4/3$297
This Priceline deal was found by Cheapflights users on 4/3. 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.
Sun 5/183:45 pmAUA - BOS
1 stop7h 44mSpirit Airlines
Sun 5/256:10 amBOS - AUA
1 stop8h 30mSpirit Airlines
Deal found 4/3$303
This American Airlines deal was found by Cheapflights users on 4/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/303:50 pmSJU - BOS
2 stops8h 29mAmerican Airlines
Mon 11/35:48 amBOS - SJU
1 stop14h 02mAmerican Airlines
Deal found 4/4$311

Cheapflights Fare Finder

Customize your flight search to find flights from Caribbean Islands 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 April 4, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Boston that are best for you.

Fly from

Caribbean Islands

Fly to

Boston

Route

Depart

Return

Price

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Wed 4/30

12:57 am-7:18 am

1 stop6h 21m

Boston Logan Intl

Tue 5/6

7:52 pm-11:52 pm

Nonstop4h 00m

$139

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Tue 4/22

6:20 am-10:36 am

Nonstop4h 16m

Boston Logan Intl

Tue 4/29

7:52 pm-11:52 pm

Nonstop4h 00m

$158

Saint Thomas IslandBoston

STT - BOS

STTBOS

Saint Thomas Island Cyril E King

Wed 5/14

10:52 am-11:29 pm

1 stop12h 37m

Boston Logan Intl

Sat 5/17

4:49 pm-9:57 am

1 stop17h 08m

$176

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 5/1

6:30 am-10:43 am

Nonstop4h 13m

Boston Logan Intl

Thu 5/8

11:43 am-3:44 pm

Nonstop4h 01m

$195

Saint Thomas IslandBoston

STT - BOS

STTBOS

Saint Thomas Island Cyril E King

Wed 4/30

5:50 pm-10:23 am

1 stop16h 33m

Boston Logan Intl

Sun 5/4

8:00 am-3:26 pm

1 stop7h 26m

$249

KingstonBoston

KIN - BOS

KINBOS

Kingston Norman Manley

Fri 5/16

1:34 pm-11:29 pm

1 stop8h 55m

Boston Logan Intl

Tue 5/20

6:10 am-12:29 pm

1 stop7h 19m

$250

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Mon 4/21

2:30 am-6:37 am

Nonstop4h 07m

Boston Logan Intl

Tue 4/29

8:45 pm-12:54 am

Nonstop4h 09m

$254

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Wed 5/7

1:39 pm-5:57 pm

Nonstop4h 18m

Boston Logan Intl

Sat 5/10

8:20 am-12:21 pm

Nonstop4h 01m

$259

Montego BayBoston

MBJ - BOS

MBJBOS

Montego Bay Sangster Intl

Thu 5/15

12:07 pm-11:29 pm

1 stop10h 22m

Boston Logan Intl

Sun 5/18

6:10 am-11:02 am

1 stop5h 52m

$277

Punta CanaBoston

PUJ - BOS

PUJBOS

Punta Cana

Thu 5/1

12:39 pm-10:57 pm

1 stop10h 18m

Boston Logan Intl

Sun 5/11

6:10 am-2:17 pm

1 stop8h 07m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

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

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

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

Currently, January is the cheapest month in which you can book a flight from Caribbean Islands to Boston (average of $218). Flying from Caribbean Islands 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 EPX to BOS?

Find hourly flight availability from Caribbean Islands 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 April 4, 2025.

When flying from Caribbean Islands 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.

Rainfall in Boston by month

Plan your trip to Boston by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Boston ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Boston when rainfall is around 3.1 in.

Temperature in Boston by month

Plan your trip to Boston by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Boston, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 April 4, 2025.
To help decide which airline to fly from Caribbean Islands to Boston, see what other customers have to say about Delta, Alaska Airlines and Southwest. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,900 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,900 reviews
Delta
8.0
Very good
7,900 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Alaska Airlines
8.0
Very good
9,839 reviews
Delta
8.0
Very good
7,900 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Southwest
8.0
Very good
4,276 reviews
Delta
8.0
Very good
7,900 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Copa Airlines
7.6
Good
1,404 reviews
Delta
8.0
Very good
7,900 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Aeromexico
7.5
Good
1,701 reviews
Delta
8.0
Very good
7,900 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands 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 Islands?

    Boston Logan Intl (BOS), located 2.6 mi from the city center, is the airport you fly into when you book flights from Caribbean Islands to Boston.

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

    The cheapest airlines for a one-way flight from Caribbean Islands to Boston are Spirit Airlines ($85), Frontier ($88), and United Airlines ($127).

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

    The most popular flight routes from Caribbean Islands to Boston are Santo Domingo Las Americas - Boston Logan Intl, San Juan Luis Munoz Marin Intl - Boston Logan Intl and Santiago de los Caballeros - Boston Logan Intl.

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

    The top 3 most reliable airlines when flying from Caribbean Islands to Boston are KLM (90%), Etihad Airways (88%) and Turkish Airlines (83%).

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

    Looking at all options, your cheapest flight can be booked for $87. While the most popular route (Santo Domingo Las Americas - Boston Logan Intl) can be booked for $330 on average our data indicates $1,397 when flying from Caribbean Islands to Boston.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Caribbean Islands to Boston (average of $218). Flying from Caribbean Islands 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 Caribbean Islands?

Book flights to Caribbean Islands if you plan to visit one of these locations
Warwick
Marlborough
Waltham
Cambridge
Framingham
Chestnut Hill
Seekonk
Randolph
Brockton
Lowell
West Yarmouth
Woburn
Somerville
Saco
Burlington
Smithfield
Salem
Chelsea
Seabrook
Brookline

Browse thousands of different options on Cheapflights for your next trip

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Top 7 airlines flying from Caribbean Islands to Boston

Discover the top 7 airlines that operate flights from Caribbean Islands 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 April 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$69Average$248FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$71Average$292FlexibilityNo cancel feeOn-time65%
DeltaCheapest$122Average$395FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$123Average$480FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$207Average$408FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$219Average$462FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$332Average$512FlexibilityNo cancel feeOn-time71%

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