Caribbean

$60+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
ene. 14 — ene. 211
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Cheap flight deals from Boston to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 9, 2025.

Round-trip from

$109
(Cheapflightsfares)

One-way from

$60
(Frontier)
From Boston Logan Intl to Caribbean
One-way flight from Boston Logan Intl to Caribbean

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 enero 9, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 1/9. 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.
lun. 2/36:00 amBOS - SJU
1 stop7h 56mFrontier
mar. 2/115:35 amSJU - BOS
Nonstop4h 28mFrontier
Deal found 1/9$109
This Cheapflightsfares deal was found by Cheapflights users on 1/8. 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.
sáb. 1/2510:18 amBOS - SJU
Nonstop4h 04mMultiple Airlines
mar. 2/254:03 pmSJU - BOS
Nonstop4h 34mMultiple Airlines
Deal found 1/8$116
This Cheapflightsfares deal was found by Cheapflights users on 1/9. 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.
vie. 2/285:07 pmBOS - SJU
1 stop15h 36mSpirit Airlines
mié. 3/54:47 pmSJU - BOS
Nonstop4h 07mSpirit Airlines
Deal found 1/9$120
This United Airlines deal was found by Cheapflights users on 1/8. 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.
mié. 1/2210:35 amBOS - SJU
2 stops10h 47mUnited Airlines
mar. 1/282:05 amSJU - BOS
2 stops12h 56mUnited Airlines
Deal found 1/8$194
This American Airlines deal was found by Cheapflights users on 1/9. 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.
mar. 1/217:45 pmBOS - STT
1 stop16h 44mAmerican Airlines
mar. 1/282:44 pmSTT - BOS
1 stop17h 28mAmerican Airlines
Deal found 1/9$229
This Mytrip deal was found by Cheapflights users on 1/8. 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.
mié. 1/2212:15 pmBOS - STT
2 stops21h 31mSpirit Airlines
mar. 2/411:51 amSTT - BOS
1 stop12h 41mSpirit Airlines
Deal found 1/8$231
This JetBlue deal was found by Cheapflights users on 1/8. 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.
mar. 3/115:45 amBOS - SJU
1 stop6h 56mJetBlue
mar. 3/184:13 pmSJU - BOS
1 stop8h 05mJetBlue
Deal found 1/8$237
This Trip.com deal was found by Cheapflights users on 1/8. 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. 1/196:56 pmBOS - STT
1 stop17h 52mMultiple Airlines
sáb. 1/252:01 pmSTT - BOS
1 stop20h 02mMultiple Airlines
Deal found 1/8$256
This JetBlue deal was found by Cheapflights users on 1/8. 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.
mar. 3/257:00 amBOS - STT
Nonstop4h 02mJetBlue
mar. 4/12:53 pmSTT - BOS
1 stop5h 54mJetBlue
Deal found 1/8$266
This Delta deal was found by Cheapflights users on 1/8. 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.
vie. 2/76:00 amBOS - STT
1 stop6h 40mDelta
jue. 2/134:00 pmSTT - BOS
1 stop9h 58mDelta
Deal found 1/8$289
This Cheapflightsfares deal was found by Cheapflights users on 1/8. 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. 2/96:00 amBOS - AUA
1 stop8h 40mSpirit Airlines
jue. 2/134:47 pmAUA - BOS
1 stop8h 00mSpirit Airlines
Deal found 1/8$290
This Cheapflightsfares deal was found by Cheapflights users on 1/8. 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.
mié. 1/226:00 amBOS - MBJ
1 stop6h 10mSpirit Airlines
mar. 2/41:16 pmMBJ - BOS
1 stop10h 16mSpirit Airlines
Deal found 1/8$292

Find flights from Boston to Caribbean within your budget

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 enero 9, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mié. 1/22

10:03 am-3:07 pm

Nonstop4h 04m

San Juan Luis Munoz Marin Intl

mar. 2/4

5:07 pm-12:39 am

1 stop8h 32m

$109

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mar. 2/11

6:25 am-2:30 pm

1 stop7h 05m

San Juan Luis Munoz Marin Intl

jue. 2/13

4:03 pm-7:37 pm

Nonstop4h 34m

$111

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

sáb. 1/25

10:18 am-3:22 pm

Nonstop4h 04m

San Juan Luis Munoz Marin Intl

mar. 2/25

4:03 pm-7:37 pm

Nonstop4h 34m

$116

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mié. 1/22

10:35 am-10:22 pm

2 stops10h 47m

San Juan Luis Munoz Marin Intl

mar. 1/28

2:05 am-2:01 pm

2 stops12h 56m

$194

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

mar. 1/21

7:45 pm-1:29 pm

1 stop16h 44m

Saint Thomas Island Cyril E King

mar. 1/28

2:44 pm-7:12 am

1 stop17h 28m

$229

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

mié. 1/22

12:15 pm-10:46 am

2 stops21h 31m

Saint Thomas Island Cyril E King

mar. 2/4

11:51 am-11:32 pm

1 stop12h 41m

$231

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mar. 3/11

5:45 am-12:41 pm

1 stop6h 56m

San Juan Luis Munoz Marin Intl

mar. 3/18

4:13 pm-12:18 am

1 stop8h 05m

$237

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

dom. 1/19

6:56 pm-1:48 pm

1 stop17h 52m

Saint Thomas Island Cyril E King

sáb. 1/25

2:01 pm-9:03 am

1 stop20h 02m

$256

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

mar. 3/25

7:00 am-11:02 am

Nonstop4h 02m

Saint Thomas Island Cyril E King

mar. 4/1

2:53 pm-8:47 pm

1 stop5h 54m

$266

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

vie. 2/7

6:00 am-1:40 pm

1 stop6h 40m

Saint Thomas Island Cyril E King

jue. 2/13

4:00 pm-12:58 am

1 stop9h 58m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/8

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.

Travel insights for flights from Boston to Caribbean

Get recent, data-driven insights about flights from Boston to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $380). 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 enero 9, 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 enero 9, 2025.

The most flights from BOS to 0CB are scheduled on a Thursday (16 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (4 on average).

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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

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 enero 9, 2025.
8.1
Very good
4,650 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,650 reviews
8.1
Very good
4,650 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,501 reviews
8.1
Very good
4,650 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
9,634 reviews
8.1
Very good
4,650 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.7
Good
1,648 reviews
8.1
Very good
4,650 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.5
Good
1,846 reviews
8.1
Very good
4,650 reviews

Boarding

8.2

Comfort

8.1

Food

7.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier, with whom users have recently found tickets for as low as $60. However, be on the lookout for offers from Spirit Airlines and Delta, 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?

  • 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: Delta (72%), EL AL (54%), Etihad Airways( 54%).

  • What are the cheapest flights from Boston to Caribbean?

    The cheapest flight price from Boston to Caribbean is $57. On average you can expect to pay $821. The most popular route, (Boston Logan Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $104.

  • 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 March is currently the most expensive (average of $380). 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

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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.

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 enero 9, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$74Average$332FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$99Average$396FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$142Average$544FlexibilityNo cancel feeOn-time62%
DeltaCheapest$143Average$505FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$200Average$527FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$244Average$601FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$263Average$608FlexibilityNo cancel feeOn-time69%
AviancaCheapest$292Average$505FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$427Average$812FlexibilityNo cancel feeOn-time63%
Air CanadaCheapest$444Average$780FlexibilityNo cancel feeOn-time67%
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