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$99+ 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 11/29. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
nov. 28 — dic. 51
vie. 11/28
vie. 12/5
1 adult, Economy
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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 octubre 29, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/78:11 pmBOS - SJU
1 stop13h 22mSpirit Airlines
vie. 12/1211:38 amSJU - BOS
1 stop8h 28mSpirit Airlines
Deal found 10/28$216
This Trip.com deal was found by Cheapflights users on 10/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/146:55 pmBOS - SJU
Nonstop3h 59mJetBlue
jue. 11/209:25 pmSJU - BOS
Nonstop4h 05mJetBlue
Deal found 10/28$223
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/316:00 amBOS - SJU
1 stop16h 54mMultiple Airlines
mié. 1/73:15 pmSJU - BOS
Nonstop4h 24mMultiple Airlines
Deal found 10/26$224
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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.
jue. 11/136:16 amBOS - SJU
1 stop10h 03mSpirit Airlines
jue. 11/2011:55 amSJU - BOS
1 stop12h 58mSpirit Airlines
Deal found 10/27$227
This Trip.com deal was found by Cheapflights users on 10/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/166:55 pmBOS - SJU
Nonstop3h 59mJetBlue
jue. 11/209:25 pmSJU - BOS
Nonstop4h 05mJetBlue
Deal found 10/27$228
This Trip.com deal was found by Cheapflights users on 10/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/117:40 amBOS - SJU
Nonstop4h 04mJetBlue
vie. 11/148:10 pmSJU - BOS
Nonstop4h 06mJetBlue
Deal found 10/29$229
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/68:11 pmBOS - SJU
1 stop13h 22mSpirit Airlines
jue. 12/1111:38 amSJU - BOS
1 stop8h 28mSpirit Airlines
Deal found 10/26$230
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/3111:09 amBOS - SJU
2 stops14h 30mFrontier
jue. 1/88:25 amSJU - BOS
Nonstop4h 23mFrontier
Deal found 10/28$232
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/317:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
jue. 1/810:59 amSJU - BOS
1 stop15h 05mMultiple Airlines
Deal found 10/28$237
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/1511:43 amBOS - SJU
2 stops36h 49mMultiple Airlines
vie. 11/219:54 pmSJU - BOS
1 stop10h 35mMultiple Airlines
Deal found 10/28$238
This Trip.com deal was found by Cheapflights users on 10/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/26:55 pmBOS - SJU
Nonstop3h 59mJetBlue
vie. 12/57:00 amSJU - BOS
1 stop6h 53mJetBlue
Deal found 10/29$240
This Trip.com deal was found by Cheapflights users on 10/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/101:55 pmBOS - SJU
Nonstop4h 02mJetBlue
mar. 11/188:10 amSJU - BOS
Nonstop4h 13mJetBlue
Deal found 10/27$241

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 octubre 29, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$209
(Frontier)

One-way from

$99
(JetBlue)

Popular in

December

Cheapest in

January

Average price

$265

Good round-trip deal

$262 or less

Good one-way deal

$133 or less
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-San Juan flights.
Search Deals
From Boston Logan Intl to Caribbean
Search Deals
One-way flight from Boston Logan Intl to Caribbean
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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

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 octubre 29, 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

mié. 12/31

7:55 pm-12:59 am

Nonstop4h 04m

San Juan Luis Munoz Marin Intl

lun. 1/5

2:05 am-5:14 am

Nonstop4h 09m

$250

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

vie. 12/19

6:50 pm-11:56 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

mié. 12/24

8:35 pm-11:47 pm

Nonstop4h 12m

$250

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

jue. 11/13

8:10 am-1:17 pm

Nonstop4h 07m

San Juan Luis Munoz Marin Intl

jue. 11/20

2:27 pm-5:49 pm

Nonstop4h 22m

$262

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mié. 11/12

10:20 am-10:22 pm

2 stops11h 02m

San Juan Luis Munoz Marin Intl

vie. 11/14

2:05 am-9:12 am

1 stop8h 07m

$271

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mar. 1/20

5:29 am-2:10 pm

1 stop7h 41m

San Juan Luis Munoz Marin Intl

vie. 1/23

6:15 am-5:32 pm

1 stop12h 17m

$271

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

lun. 12/8

5:40 am-2:14 pm

1 stop7h 34m

San Juan Luis Munoz Marin Intl

lun. 12/15

2:10 pm-10:26 pm

1 stop9h 16m

$271

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

vie. 1/16

1:00 pm-6:02 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

lun. 1/19

8:15 am-3:50 pm

1 stop8h 35m

$280

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

lun. 11/3

8:15 am-1:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

mié. 11/5

7:00 am-4:01 pm

1 stop10h 01m

$287

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

dom. 12/28

2:55 pm-10:09 pm

1 stop6h 14m

San Juan Luis Munoz Marin Intl

mar. 1/6

1:00 pm-7:18 pm

1 stop7h 18m

$300

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mié. 12/10

2:00 pm-10:14 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

sáb. 12/20

5:24 pm-12:16 am

1 stop7h 52m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 60 results
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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, January is the cheapest month in which you can book a flight from Boston to Caribbean (average of $85). Flying from Boston to Caribbean in September is currently the most expensive (average of $147). 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 octubre 29, 2025.

It’s typically best to fly out from Boston to Caribbean at noon. Doing so could potentially save you 15% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Boston to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Boston to Caribbean. Price data was last updated on October 26, 2025.

Travelers seeking maximum savings on their Boston to Caribbean flight should consider departing on Friday afternoons when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 octubre 29, 2025.
Get a feel of what it's like to fly with Delta, American Airlines, and JetBlue 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.
Delta
7.9
Good
7,992 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,992 reviews
Delta
7.9
Good
7,992 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,992 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
JetBlue
7.2
Good
2,907 reviews
Delta
7.9
Good
7,992 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Spirit Airlines
6.3
Okay
8,114 reviews
Delta
7.9
Good
7,992 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Frontier
5.8
Fair
3,124 reviews
Delta
7.9
Good
7,992 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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.

  • How long is the flight from Boston to Caribbean?

    A quick flight from Boston to Caribbean can take about 4h 04m. JetBlue provides one of the quickest options available for as low as $250. Boston and Caribbean are separated by a distance of 1678 mi. This flight may include one or multiple stops.

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

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $99. However, be on the lookout for offers from Delta and United Airlines, 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 - Santo Domingo Las Americas and Boston Logan Intl - Oranjestad Reina Beatrix.

  • 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: Hawaiian Airlines (73%), Delta (71%), Icelandair( 70%).

  • What are the cheapest flights from Boston to Caribbean?

    The cheapest flight price from Boston to Caribbean is $123. On average you can expect to pay $297. The most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $168.

  • 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, January is the cheapest month in which you can book a flight from Boston to Caribbean (average of $85). Flying from Boston to Caribbean in September is currently the most expensive (average of $147). 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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Alternative routes for Boston to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Albany to Orlando 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 octubre 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$86Average$397FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$101Average$381FlexibilityNo cancel feeOn-time65%
Air CanadaCheapest$141Average$624FlexibilityNo cancel feeOn-time67%
DeltaCheapest$143Average$482FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$171Average$535FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$190Average$514FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$192Average$387FlexibilityNo cancel feeOn-time70%
ArajetCheapest$226Average$413FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$288Average$588FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$578FlexibilityNo cancel feeOn-time71%

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