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Caribbean Islands

$77+ Cheap flights from Boston (BOS) to Caribbean Islands

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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
1 adult, Economy
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Cheap flight deals from Boston to Caribbean Islands

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

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$136
(Cheapflightsfares)

One-way from

$77
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$298
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-San Juan flights.
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From Boston Logan Intl to Caribbean Islands
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One-way flight from Boston Logan Intl to Caribbean Islands
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Highest demand for flights based on searches. 12% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Boston to Caribbean Islands

Cheapest flights from Boston to Caribbean Islands
Explore the most affordable flight options available from Boston to Caribbean Islands. 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 4/2. 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.
Sun 4/277:52 pmBOS - SJU
Nonstop4h 00mSpirit Airlines
Wed 4/305:10 pmSJU - BOS
1 stop7h 35mSpirit Airlines
Deal found 4/2$136
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.
Fri 5/27:52 pmBOS - SJU
Nonstop4h 00mMultiple Airlines
Sun 5/116:30 amSJU - BOS
Nonstop4h 13mMultiple Airlines
Deal found 4/3$153
This Cheapflightsfares deal was found by Cheapflights users on 4/2. 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 4/911:16 amBOS - SJU
Nonstop3h 56mFrontier
Wed 4/166:00 amSJU - BOS
Nonstop4h 16mFrontier
Deal found 4/2$178
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/48:25 amBOS - SJU
Nonstop4h 00mDelta
Fri 5/91:39 pmSJU - BOS
Nonstop4h 18mDelta
Deal found 4/3$254
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2912:45 pmBOS - SJU
2 stops11h 09mUnited Airlines
Sat 5/37:25 amSJU - BOS
2 stops12h 23mUnited Airlines
Deal found 4/3$263
This Mytrip deal was found by Cheapflights users on 4/2. 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.
Wed 4/301:31 pmBOS - STT
2 stops20h 29mSpirit Airlines
Sat 5/311:05 amSTT - BOS
2 stops20h 13mSpirit Airlines
Deal found 4/2$264
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/63:14 pmBOS - MBJ
2 stops20h 48mSpirit Airlines
Wed 5/1412:07 pmMBJ - BOS
1 stop10h 22mSpirit Airlines
Deal found 4/3$278
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.
Sat 5/35:59 amBOS - STT
2 stops11h 00mAmerican Airlines
Sat 5/105:05 pmSTT - BOS
1 stop17h 39mAmerican Airlines
Deal found 4/4$289
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.
Wed 5/712:20 pmBOS - SJU
Nonstop4h 00mJetBlue
Fri 5/93:33 amSJU - BOS
1 stop8h 09mJetBlue
Deal found 4/4$294
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.
Sun 5/116:10 amBOS - AUA
1 stop8h 30mSpirit Airlines
Sun 5/183:45 pmAUA - BOS
1 stop7h 44mSpirit Airlines
Deal found 4/3$309
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/48:30 amBOS - STT
1 stop7h 13mUnited Airlines
Fri 4/112:10 pmSTT - BOS
1 stop8h 17mUnited Airlines
Deal found 4/3$309
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/125:45 amBOS - PUJ
1 stop9h 52mFrontier
Wed 4/1611:37 amPUJ - BOS
1 stop21h 51mFrontier
Deal found 4/3$341

Cheapflights Fare Finder

Customize your flight search to find flights from Boston to Caribbean Islands 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 Boston to Caribbean Islands that are best for you.

Fly from

Boston

Fly to

Caribbean Islands

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 4/27

7:52 pm-11:52 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Wed 4/30

5:10 pm-12:45 am

1 stop7h 35m

$136

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 5/2

7:52 pm-11:52 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Sun 5/11

6:30 am-10:43 am

Nonstop4h 13m

$153

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 5/15

11:43 am-3:44 pm

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

Sun 5/18

6:30 am-10:43 am

Nonstop4h 13m

$195

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 5/4

8:25 am-12:25 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Fri 5/9

1:39 pm-5:57 pm

Nonstop4h 18m

$254

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 4/29

12:45 pm-11:54 pm

2 stops11h 09m

San Juan Luis Munoz Marin Intl

Sat 5/3

7:25 am-7:48 pm

2 stops12h 23m

$263

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 4/30

1:31 pm-10:00 am

2 stops20h 29m

Saint Thomas Island Cyril E King

Sat 5/3

11:05 am-7:18 am

2 stops20h 13m

$264

BostonMontego Bay

BOS - MBJ

BOSMBJ

Boston Logan Intl

Tue 5/6

3:14 pm-11:02 am

2 stops20h 48m

Montego Bay Sangster Intl

Wed 5/14

12:07 pm-11:29 pm

1 stop10h 22m

$278

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sat 5/3

6:59 am-4:59 pm

2 stops10h 00m

Saint Thomas Island Cyril E King

Thu 5/8

1:25 pm-10:49 pm

1 stop9h 24m

$289

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 5/7

12:20 pm-4:20 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Sat 5/10

5:10 pm-12:17 am

1 stop7h 07m

$294

BostonOranjestad

BOS - AUA

BOSAUA

Boston Logan Intl

Sun 5/11

6:10 am-2:40 pm

1 stop8h 30m

Oranjestad Reina Beatrix

Sun 5/18

3:45 pm-11:29 pm

1 stop7h 44m

$309

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 Boston to Caribbean Islands

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

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

Currently, September is the cheapest month in which you can book a flight from Boston to Caribbean Islands (average of $254). Flying from Boston to Caribbean Islands in December is currently the most expensive (average of $336). 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 EPX?

Find hourly flight availability from Boston to Caribbean Islands. 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 Boston to Caribbean Islands, 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 Islands

Explore weekly flight availability from Boston to Caribbean Islands. 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 April 4, 2025.

The most flights from BOS to zzEPX are scheduled on a Friday (18 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Caribbean Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated April 4, 2025.
To help decide which airline to fly from Boston to Caribbean Islands, see what other customers have to say about Alaska Airlines, Southwest and Delta. 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.
Alaska Airlines
8.0
Very good
9,836 reviews

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,836 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,276 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,897 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Copa Airlines
7.6
Good
1,402 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,618 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Related info for your journey

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

    Most people fly from Boston Logan Intl (BOS) if they book a flight from Boston to Caribbean Islands. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

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

    $77 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and United Airlines, with prices starting from $93 and $103, respectively.

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

    Most travelers choose Boston Logan Intl - San Juan Luis Munoz Marin Intl, Boston Logan Intl - Oranjestad Reina Beatrix or Boston Logan Intl - Punta Cana when deciding on the best route from Boston to Caribbean Islands.

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

    The top 3 most reliable airlines when flying from Boston to Caribbean Islands are TAP AIR PORTUGAL (77%), Japan Airlines (71%) and Delta (69%).

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

    On average you can expect to pay $542 for a flight from Boston to Caribbean Islands. The cheapest flight overall is $99 while the most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl) is currently priced at $139.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Boston to Caribbean Islands (average of $254). Flying from Boston to Caribbean Islands in December is currently the most expensive (average of $336). 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.

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Top 10 airlines flying from Boston to Caribbean Islands

Discover the top 10 airlines that operate flights from Boston to Caribbean Islands. 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$76Average$350FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$86Average$454FlexibilityNo cancel feeOn-time65%
DeltaCheapest$141Average$492FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$141Average$522FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$204Average$544FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$266Average$759FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$282Average$591FlexibilityNo cancel feeOn-time71%
AviancaCheapest$292Average$529FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$364Average$527FlexibilityNo cancel feeOn-time70%
SouthwestCheapest$427Average$790FlexibilityNo cancel feeOn-time63%

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