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$101+ 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 8/3. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$195
(Expedia)

One-way from

$100
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$283

Good round-trip deal

$189 or less

Good one-way deal

$163 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. 20% potential increase in price ($57 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 July 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 July 31, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 8/1510:16 pmSJU - BOS
1 stop16h 14mSpirit Airlines
Mon 8/183:37 pmBOS - SJU
1 stop8h 20mSpirit Airlines
Deal found 7/29$195
This OneTravel deal was found by Cheapflights users on 7/31. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/306:55 pmSJU - BOS
1 stop15h 44mMultiple Airlines
Sat 9/612:20 pmBOS - SJU
1 stop8h 36mMultiple Airlines
Deal found 7/31$209
This Trip.com deal was found by Cheapflights users on 7/30. 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.
Fri 8/88:25 amSJU - BOS
Nonstop4h 09mJetBlue
Mon 8/118:45 pmBOS - SJU
Nonstop4h 04mJetBlue
Deal found 7/30$228
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/155:30 amSJU - BOS
1 stop9h 51mAmerican Airlines
Mon 10/2011:05 amBOS - SJU
1 stop12h 54mAmerican Airlines
Deal found 7/30$253
This Delta deal was found by Cheapflights users on 7/31. 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 10/151:32 pmSJU - BOS
Nonstop4h 13mDelta
Sat 10/188:15 amBOS - SJU
Nonstop4h 06mDelta
Deal found 7/31$254
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 9/2612:10 pmMBJ - BOS
1 stop10h 45mSpirit Airlines
Fri 10/36:49 pmBOS - MBJ
1 stop17h 16mSpirit Airlines
Deal found 7/29$295
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2612:52 pmMBJ - BOS
1 stop9h 05mUnited Airlines
Fri 10/38:47 pmBOS - MBJ
2 stops17h 43mUnited Airlines
Deal found 7/29$321
This SmartFares deal was found by Cheapflights users on 7/30. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/154:01 pmSDQ - BOS
1 stop7h 54mSpirit Airlines
Tue 11/185:45 amBOS - SDQ
1 stop11h 05mSpirit Airlines
Deal found 7/30$325
This CheapOair deal was found by Cheapflights users on 7/29. 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.
Wed 9/34:05 pmPUJ - BOS
1 stop7h 44mSpirit Airlines
Fri 9/196:10 amBOS - PUJ
1 stop8h 04mSpirit Airlines
Deal found 7/29$325
This SmartFares deal was found by Cheapflights users on 7/30. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1312:08 pmKIN - BOS
1 stop10h 47mSpirit Airlines
Sat 9/206:10 amBOS - KIN
1 stop5h 52mSpirit Airlines
Deal found 7/30$327
This American Airlines deal was found by Cheapflights users on 7/29. 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 9/184:09 pmMBJ - BOS
2 stops14h 46mAmerican Airlines
Sun 9/216:00 amBOS - MBJ
2 stops10h 09mAmerican Airlines
Deal found 7/29$329
This Expedia deal was found by Cheapflights users on 7/31. 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.
Wed 11/266:30 amSDQ - BOS
Nonstop4h 15mArajet
Wed 12/311:15 amBOS - SDQ
Nonstop4h 15mArajet
Deal found 7/31$330

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 July 31, 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 8/15

10:16 pm-2:30 pm

1 stop16h 14m

Boston Logan Intl

Mon 8/18

3:37 pm-11:57 pm

1 stop8h 20m

$195

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Sat 8/30

6:55 pm-10:39 am

1 stop15h 44m

Boston Logan Intl

Sat 9/6

12:20 pm-8:56 pm

1 stop8h 36m

$209

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 8/8

8:25 am-12:34 pm

Nonstop4h 09m

Boston Logan Intl

Mon 8/11

8:45 pm-12:49 am

Nonstop4h 04m

$228

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Wed 10/15

5:30 am-3:21 pm

1 stop9h 51m

Boston Logan Intl

Mon 10/20

11:05 am-11:59 pm

1 stop12h 54m

$253

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Wed 10/15

1:32 pm-5:45 pm

Nonstop4h 13m

Boston Logan Intl

Sat 10/18

8:15 am-12:21 pm

Nonstop4h 06m

$254

Montego BayBoston

MBJ - BOS

MBJBOS

Montego Bay Sangster Intl

Fri 9/26

12:10 pm-11:55 pm

1 stop10h 45m

Boston Logan Intl

Fri 10/3

6:49 pm-11:05 am

1 stop17h 16m

$295

Montego BayBoston

MBJ - BOS

MBJBOS

Montego Bay Sangster Intl

Fri 9/26

12:52 pm-10:57 pm

1 stop9h 05m

Boston Logan Intl

Fri 10/3

8:47 pm-1:30 pm

2 stops17h 43m

$321

Santo DomingoBoston

SDQ - BOS

SDQBOS

Santo Domingo Las Americas

Wed 10/15

4:01 pm-11:55 pm

1 stop7h 54m

Boston Logan Intl

Tue 11/18

5:45 am-5:50 pm

1 stop11h 05m

$325

KingstonBoston

KIN - BOS

KINBOS

Kingston Norman Manley

Sat 9/13

12:08 pm-11:55 pm

1 stop10h 47m

Boston Logan Intl

Sat 9/20

6:10 am-11:02 am

1 stop5h 52m

$327

Montego BayBoston

MBJ - BOS

MBJBOS

Montego Bay Sangster Intl

Thu 9/18

4:09 pm-7:55 am

2 stops14h 46m

Boston Logan Intl

Sun 9/21

6:00 am-3:09 pm

2 stops10h 09m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 July 31, 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 July 31, 2025.

The most flights from 0CB to BOS are scheduled on a Thursday (31 on average). You will have fewer flight options on Saturday, 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 July 31, 2025.
See what other customers who have flown with Southwest, Delta, and Finnair 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.
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Finnair
7.6
Good
1,316 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Copa Airlines
7.5
Good
1,493 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 $100 on Spirit Airlines. Other airlines that offer cheap prices include JetBlue from $123 and Southwest from $127 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 KLM (95%), Delta (93%) and WestJet (93%).

  • What are the cheapest flights from Caribbean to Boston?

    On average you can expect to pay $256 for a flight from Caribbean to Boston. The cheapest flight overall is $108 while the most popular route, (Santo Domingo Las Americas - Boston Logan Intl) is currently priced at $292.

  • 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
Watertown
Seabrook
Waltham
Framingham
Lowell
Randolph
Smithfield
Cranston
Chestnut Hill
Warwick
Peabody
Quincy
York Beach
Chelsea
Saco
Hampton Beach
Swansea
Lincoln

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Top 7 airlines flying from Caribbean to Boston

Discover the top 7 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$252FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$86Average$295FlexibilityNo cancel feeOn-time65%
DeltaCheapest$129Average$414FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$133Average$461FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$207Average$384FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$319Average$490FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$338Average$489FlexibilityNo cancel feeOn-time71%

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