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$100+ Cheap flights from Caribbean Islands 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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Nov 1 — Nov 81
Sat 11/1
Sat 11/8
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Boston

Keep the following information in mind while searching for Caribbean Islands to Boston flight deals. Data was last updated October 2, 2025.

Round-trip from

$156
(American Airlines)

One-way from

$100
(Cheapflightsfares)
From Caribbean Islands to Boston Logan Intl
Search Deals
One-way flight from Caribbean Islands to Boston Logan Intl
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Find flight deals from Caribbean Islands to Boston

Cheapest flights from Caribbean Islands to Boston
Explore the most affordable flight options available from Caribbean Islands to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 2, 2025.

This American Airlines deal was found by Cheapflights users on 9/30. 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.
Sat 11/15:30 amSJU - BOS
1 stop6h 54mAmerican Airlines
Sat 11/13:00 pmBOS - SJU
2 stops8h 55mAmerican Airlines
Deal found 9/30$156
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Tue 10/215:00 pmSJU - BOS
1 stop7h 34mAmerican Airlines
Wed 10/226:00 amBOS - SJU
2 stops9h 54mAmerican Airlines
Deal found 9/29$161
This Mytrip deal was found by Cheapflights users on 10/1. 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.
Tue 10/212:49 amSJU - BOS
1 stop10h 31mMultiple Airlines
Mon 10/279:18 amBOS - SJU
1 stop16h 51mMultiple Airlines
Deal found 10/1$204
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/202:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Sat 10/252:15 pmBOS - SJU
1 stop10h 39mSpirit Airlines
Deal found 9/30$211
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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.
Thu 12/42:59 amSJU - BOS
1 stop8h 09mSpirit Airlines
Mon 12/86:00 amBOS - SJU
1 stop9h 23mSpirit Airlines
Deal found 9/29$214
This SmartFares deal was found by Cheapflights users on 10/2. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/226:05 pmSJU - BOS
1 stop6h 09mJetBlue
Mon 10/277:52 pmBOS - SJU
1 stop6h 56mJetBlue
Deal found 10/2$221
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/42:59 amSJU - BOS
1 stop8h 09mSpirit Airlines
Sun 12/711:13 amBOS - SJU
1 stop7h 08mSpirit Airlines
Deal found 9/30$224
This SmartFares deal was found by Cheapflights users on 10/1. 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.
Thu 10/305:25 amSJU - BOS
1 stop6h 18mJetBlue
Sun 11/28:30 pmBOS - SJU
1 stop6h 18mJetBlue
Deal found 10/1$226
This CheapOair deal was found by Cheapflights users on 9/29. 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.
Tue 10/218:22 pmSJU - BOS
Nonstop4h 02mJetBlue
Wed 10/225:23 amBOS - SJU
1 stop15h 31mJetBlue
Deal found 9/29$227
This SmartFares deal was found by Cheapflights users on 9/30. 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.
Thu 10/166:05 pmSJU - BOS
1 stop6h 09mJetBlue
Tue 10/2110:14 amBOS - SJU
1 stop6h 28mJetBlue
Deal found 9/30$228
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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.
Mon 10/202:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Wed 10/222:15 pmBOS - SJU
1 stop11h 29mSpirit Airlines
Deal found 9/29$230
This Mytrip deal was found by Cheapflights users on 10/2. 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.
Tue 10/212:49 amSJU - BOS
1 stop10h 31mMultiple Airlines
Sun 10/268:31 amBOS - SJU
1 stop16h 11mMultiple Airlines
Deal found 10/2$231

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands 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 October 2, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Boston that are best for you.

Fly from

Caribbean Islands

Fly to

Boston

Route

Depart

Return

Price

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 11/6

9:30 am-4:37 pm

1 stop8h 07m

Boston Logan Intl

Mon 11/10

7:52 pm-3:48 am

1 stop6h 56m

$242

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 10/23

2:25 pm-9:00 pm

1 stop6h 35m

Boston Logan Intl

Mon 10/27

7:52 pm-2:48 am

1 stop6h 56m

$242

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Wed 10/22

6:00 am-1:50 pm

1 stop7h 50m

Boston Logan Intl

Tue 10/28

1:55 pm-5:57 pm

Nonstop4h 02m

$248

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 11/7

5:01 am-11:43 am

1 stop7h 42m

Boston Logan Intl

Sun 11/9

7:00 pm-11:59 pm

Nonstop3h 59m

$252

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 11/13

8:10 am-11:23 am

Nonstop4h 13m

Boston Logan Intl

Thu 11/20

3:41 pm-1:57 am

1 stop9h 16m

$256

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 10/24

1:25 pm-9:00 pm

1 stop7h 35m

Boston Logan Intl

Mon 10/27

6:55 pm-10:54 pm

Nonstop3h 59m

$257

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Sun 10/26

5:10 am-9:19 am

Nonstop4h 09m

Boston Logan Intl

Wed 10/29

7:52 pm-2:48 am

1 stop6h 56m

$257

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Tue 10/21

8:22 pm-12:24 am

Nonstop4h 02m

Boston Logan Intl

Wed 10/22

12:20 pm-8:54 pm

1 stop8h 34m

$261

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Wed 10/29

1:32 pm-5:45 pm

Nonstop4h 13m

Boston Logan Intl

Wed 11/5

8:15 am-1:21 pm

Nonstop4h 06m

$262

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 12/25

4:34 pm-8:00 pm

Nonstop4h 26m

Boston Logan Intl

Mon 1/5

8:00 am-1:05 pm

Nonstop4h 05m

$262

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/2

Showing 1-10 of 60 results
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Best time to book a flight from Caribbean Islands to Boston

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

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

Currently, January is the cheapest month in which you can book a flight from Caribbean Islands to Boston (average of $218). Flying from Caribbean Islands 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 EPX to BOS?

Find hourly flight availability from Caribbean Islands 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 October 2, 2025.

When flying from Caribbean Islands 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 Islands to Boston

Explore weekly flight availability from Caribbean Islands 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 October 2, 2025.

The most flights from zzEPX to BOS are scheduled on a Thursday (14 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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 October 2, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Caribbean Islands to Boston by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,962 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,962 reviews
Delta
8.0
Very good
7,962 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,933 reviews
Delta
8.0
Very good
7,962 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
11,033 reviews
Delta
8.0
Very good
7,962 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
JetBlue
7.2
Good
2,911 reviews
Delta
8.0
Very good
7,962 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Spirit Airlines
6.3
Okay
8,070 reviews
Delta
8.0
Very good
7,962 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

Related info for your journey

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

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

  • How long is the flight from Caribbean Islands to Boston?

    Departing from Caribbean Islands to Boston will take you 4h 22m. The distance from Caribbean Islands to Boston is about 1697 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The cheapest airlines for a one-way flight from Caribbean Islands to Boston are Spirit Airlines ($132), Delta ($141), and JetBlue ($141).

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

    The most popular flight routes from Caribbean Islands to Boston are San Juan Luis Munoz Marin Intl - Boston Logan Intl, Santo Domingo Las Americas - Boston Logan Intl and Santiago de los Caballeros - Boston Logan Intl.

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

    The top 3 most reliable airlines when flying from Caribbean Islands to Boston are Delta (91%), KLM (87%) and Etihad Airways (84%).

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

    Looking at all options, your cheapest flight can be booked for $141. While the most popular route (San Juan Luis Munoz Marin Intl - Boston Logan Intl) can be booked for $176 on average, our data indicates $669 when flying from Caribbean Islands to Boston.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Caribbean Islands to Boston (average of $218). Flying from Caribbean Islands 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
Hampton Beach
Watertown
Seabrook
Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Peabody
Quincy
York Beach
Warwick
Swansea
Old Orchard Beach
Brockton
Waltham
Chelsea

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Top 8 airlines flying from Caribbean Islands to Boston

Discover the top 8 airlines that operate flights from Caribbean Islands 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 October 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$82Average$258FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$85Average$304FlexibilityNo cancel feeOn-time65%
DeltaCheapest$137Average$422FlexibilityNo cancel feeOn-timeN/A
ArajetCheapest$144Average$408FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$159Average$467FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$485FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$216Average$397FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$335Average$497FlexibilityNo cancel feeOn-time71%

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