HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$95+ Cheap flights from Boston (BOS) to Caribbean

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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Boston to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Boston to Caribbean

Keep the following information in mind while searching for Boston to Caribbean flight deals. Data was last updated July 30, 2025.

Round-trip from

$194
(eDestinos)

One-way from

$95
(CheapOair)

Popular in

December

Cheapest in

September

Average price

$303

Good round-trip deal

$274 or less

Good one-way deal

$158 or less
From Boston Logan Intl to Caribbean
Search Deals
One-way flight from Boston Logan Intl to Caribbean
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Caribbean.
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Caribbean.
Search Deals

Find flight deals from Boston to Caribbean

Cheapest flights from Boston to Caribbean
Explore the most affordable flight options available from Boston to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

This CheapOair deal was found by Cheapflights users on 7/28. 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.
Mon 11/106:00 amBOS - SJU
1 stop9h 23mSpirit Airlines
Sat 11/156:00 amSJU - BOS
1 stop18h 25mSpirit Airlines
Deal found 7/28$192
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.
Thu 9/1812:00 pmBOS - SJU
Nonstop4h 06mJetBlue
Wed 9/245:15 pmSJU - BOS
Nonstop4h 03mJetBlue
Deal found 7/30$205
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.
Thu 10/911:25 amBOS - SJU
1 stop9h 09mMultiple Airlines
Tue 10/141:59 amSJU - BOS
1 stop11h 49mMultiple Airlines
Deal found 7/29$226
This CheapOair deal was found by Cheapflights users on 7/28. 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.
Tue 11/116:15 amBOS - STT
1 stop7h 56mSpirit Airlines
Tue 11/181:33 pmSTT - BOS
1 stop12h 07mSpirit Airlines
Deal found 7/28$238
This eDestinos deal was found by Cheapflights users on 7/28. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/59:01 amBOS - SJU
1 stop14h 58mFrontier
Wed 9/101:06 pmSJU - BOS
1 stop19h 37mFrontier
Deal found 7/28$239
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.
Sat 9/136:10 amBOS - MBJ
1 stop5h 55mSpirit Airlines
Sat 9/2012:10 pmMBJ - BOS
2 stops10h 00mSpirit Airlines
Deal found 7/29$310
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 10/155:13 pmBOS - STT
1 stop17h 37mAmerican Airlines
Wed 10/2212:40 pmSTT - BOS
2 stops9h 39mAmerican Airlines
Deal found 7/30$311
This CheapOair deal was found by Cheapflights users on 7/28. 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.
Sat 8/306:05 amBOS - SXM
1 stop7h 55mSpirit Airlines
Wed 9/33:05 pmSXM - BOS
1 stop8h 44mSpirit Airlines
Deal found 7/28$316
This JetBlue deal was found by Cheapflights users on 7/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:00 amBOS - PUJ
Nonstop4h 05mJetBlue
Thu 10/1612:30 pmPUJ - BOS
Nonstop4h 09mJetBlue
Deal found 7/28$330
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:08 amBOS - PUJ
1 stop8h 06mMultiple Airlines
Sun 11/23:35 pmPUJ - BOS
1 stop28h 37mMultiple Airlines
Deal found 7/30$332
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/246:05 amBOS - PUJ
1 stop8h 55mSpirit Airlines
Thu 8/284:05 pmPUJ - BOS
1 stop7h 44mSpirit Airlines
Deal found 7/30$333
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/185:35 amBOS - SXM
1 stop8h 21mDelta
Mon 9/223:20 pmSXM - BOS
1 stop9h 58mDelta
Deal found 7/28$335

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston to Caribbean 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 30, 2025.
Use the filters below to find and compare flights from Boston to Caribbean that are best for you.

Fly from

Boston

Fly to

Caribbean

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 8/31

6:05 am-9:48 pm

1 stop15h 43m

San Juan Luis Munoz Marin Intl

Wed 9/3

1:59 am-1:48 pm

1 stop11h 49m

$194

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 9/18

12:00 pm-4:06 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Wed 9/24

5:15 pm-9:18 pm

Nonstop4h 03m

$205

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 10/9

11:25 am-8:34 pm

1 stop9h 09m

San Juan Luis Munoz Marin Intl

Tue 10/14

1:59 am-1:48 pm

1 stop11h 49m

$226

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 11/11

6:15 am-3:11 pm

1 stop7h 56m

Saint Thomas Island Cyril E King

Tue 11/18

1:33 pm-12:40 am

1 stop12h 07m

$238

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 8/5

9:01 am-11:59 pm

1 stop14h 58m

San Juan Luis Munoz Marin Intl

Wed 9/10

1:06 pm-8:43 am

1 stop19h 37m

$239

BostonMontego Bay

BOS - MBJ

BOSMBJ

Boston Logan Intl

Sat 9/13

6:10 am-11:05 am

1 stop5h 55m

Montego Bay Sangster Intl

Sat 9/20

12:10 pm-11:10 pm

2 stops10h 00m

$310

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 10/15

5:13 pm-10:50 am

1 stop17h 37m

Saint Thomas Island Cyril E King

Wed 10/22

12:40 pm-10:19 pm

2 stops9h 39m

$311

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 8/30

6:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Wed 9/3

3:05 pm-11:49 pm

1 stop8h 44m

$316

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 1/18

8:40 am-1:46 pm

Nonstop4h 06m

Saint Thomas Island Cyril E King

Fri 1/23

2:59 pm-6:20 pm

Nonstop4h 21m

$330

BostonPunta Cana

BOS - PUJ

BOSPUJ

Boston Logan Intl

Fri 9/26

7:00 am-11:05 am

Nonstop4h 05m

Punta Cana

Fri 10/3

12:30 pm-5:09 pm

Nonstop4h 39m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Boston to Caribbean

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

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

Currently, September is the cheapest month in which you can book a flight from Boston to Caribbean (average of $254). Flying from Boston to Caribbean in June is currently the most expensive (average of $339). 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 BOS to CB?

Find hourly flight availability from Boston to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 30, 2025.

When flying from Boston to Caribbean, 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 Boston to Caribbean

Explore weekly flight availability from Boston to Caribbean. 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 30, 2025.

The most flights from BOS to 0CB are scheduled on a Tuesday (15 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated July 30, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Austrian Airlines from Boston to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

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
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

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.
Austrian Airlines
7.6
Good
823 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

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
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

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
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

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

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

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

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $95. However, be on the lookout for offers from JetBlue and Frontier, as they are both options that can get you from Boston to Caribbean for a low price.

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

    The most popular flight routes from Boston to Caribbean are Boston Logan Intl - San Juan Luis Munoz Marin Intl, Boston Logan Intl - Oranjestad Reina Beatrix and Boston Logan Intl - Punta Cana.

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

    Before booking your flight to Caribbean from Boston, check out the most reliable airlines to get you to your destination on time: Spirit Airlines (88%), Delta (87%), EL AL( 87%).

  • What are the cheapest flights from Boston to Caribbean?

    The cheapest flight price from Boston to Caribbean is $108. On average you can expect to pay $581. The most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $154.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Boston to Caribbean (average of $254). Flying from Boston to Caribbean in June is currently the most expensive (average of $339). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Boston to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Las Vegas flights
Boston to Dallas/Fort Worth flights
Boston to O'Hare Intl flights
Boston to Los Angeles flights
Boston to Orlando flights
Boston to Baltimore flights
Boston to Seattle flights
Boston to Heathrow flights
Hartford to Orlando flights
Boston to Luis Munoz Marin Intl flights
Boston to Fort Lauderdale flights
Boston to Reagan-National flights
Boston to Atlanta flights
Boston to Cancún flights
Boston to Newark flights
Boston to Charles de Gaulle flights
Boston to Dulles Intl flights
Boston to Miami flights
Boston to Nashville flights
Boston to San Francisco flights
Boston to Denver flights
Boston to Philadelphia flights
Boston to LaGuardia flights
Hartford to Denver flights
Boston to Leonardo da Vinci/Fiumicino flights
Boston to Narita flights
Boston to Sky Harbor Intl flights
Hartford to Luis Munoz Marin Intl flights
Boston to Hobby flights
Boston to Charleston flights
Boston to Pearson Intl flights
Boston to Dublin flights
Boston to Tampa flights
Boston to John F Kennedy Intl flights
Boston to Lisbon flights
Boston to Athens flights
Boston to Gatwick flights
Boston to George Bush Intcntl flights
Boston to Minneapolis flights
Boston to San Diego flights
Boston to London City flights
Boston to Jose Maria Cordova Intl flights
Boston to Charlotte flights
Boston to Haneda flights
Boston to Portland flights
Boston to Toronto Island flights
Boston to Honolulu flights
Boston to Midway flights
Boston to Salt Lake City flights
Boston to Oranjestad flights

Top 10 airlines flying from Boston to Caribbean

Discover the top 10 airlines that operate flights from Boston to Caribbean. 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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$80Average$375FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$97Average$389FlexibilityNo cancel feeOn-time65%
DeltaCheapest$140Average$483FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$149Average$538FlexibilityNo cancel feeOn-time62%
ArajetCheapest$171Average$337FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$188Average$660FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$204Average$544FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$255Average$520FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$288Average$590FlexibilityNo cancel feeOn-time71%
AviancaCheapest$292Average$539FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.