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Caribbean

$89+ Cheap flights from Maine 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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Apr 12 — Apr 191
Sun 4/12
Sun 4/19
1 adult, Economy
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Cheap flight deals from Maine to Caribbean

Cheapest flights from Maine to Caribbean
Explore the most affordable flight options available from Maine to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 13, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/243:23 pm
BOS
-
SJU
Nonstop3h 56m
Multiple Airlines
Thu 4/26:00 am
SJU
-
BOS
Nonstop4h 16m
Multiple Airlines
Deal found 3/8$153
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/283:23 pm
BOS
-
SJU
Nonstop3h 56m
Multiple Airlines
Thu 4/26:00 am
SJU
-
BOS
Nonstop4h 16m
Multiple Airlines
Deal found 3/8$154
This Booking.com deal was found by Cheapflights users on 3/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/293:23 pm
BOS
-
SJU
Nonstop3h 56m
Multiple Airlines
Tue 4/76:00 am
SJU
-
BOS
Nonstop4h 16m
Multiple Airlines
Deal found 3/9$156
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/253:23 pm
BOS
-
SJU
Nonstop3h 56m
Multiple Airlines
Sat 4/46:00 am
SJU
-
BOS
Nonstop4h 16m
Multiple Airlines
Deal found 3/9$158
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/283:23 pm
BOS
-
SJU
Nonstop3h 56m
Multiple Airlines
Sat 4/46:00 am
SJU
-
BOS
Nonstop4h 16m
Multiple Airlines
Deal found 3/9$159
This Cheapflightsfares deal was found by Cheapflights users on 3/9. 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.
Wed 4/13:23 pm
BOS
-
SJU
Nonstop3h 56m
Spirit Airlines
Sat 4/410:00 am
SJU
-
BOS
Nonstop4h 18m
Spirit Airlines
Deal found 3/9$160
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/293:23 pm
BOS
-
SJU
Nonstop3h 56m
Multiple Airlines
Sat 4/46:00 am
SJU
-
BOS
Nonstop4h 16m
Multiple Airlines
Deal found 3/8$162
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/303:23 pm
BOS
-
SJU
Nonstop3h 56m
Multiple Airlines
Sat 4/46:00 am
SJU
-
BOS
Nonstop4h 16m
Multiple Airlines
Deal found 3/9$163
This Priceline deal was found by Cheapflights users on 3/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/273:23 pm
BOS
-
SJU
Nonstop3h 56m
Multiple Airlines
Thu 4/26:00 am
SJU
-
BOS
Nonstop4h 16m
Multiple Airlines
Deal found 3/11$165
This Gotogate deal was found by Cheapflights users on 3/9. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/313:23 pm
BOS
-
SJU
Nonstop3h 56m
Spirit Airlines
Fri 4/310:00 am
SJU
-
BOS
Nonstop4h 18m
Spirit Airlines
Deal found 3/9$166
This Delta deal was found by Cheapflights users on 3/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/238:40 am
BOS
-
STT
Nonstop4h 03m
Delta
Wed 4/12:45 pm
STT
-
BOS
Nonstop4h 19m
Delta
Deal found 3/9$221
This United Airlines deal was found by Cheapflights users on 3/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
BOS
-
STT
1 stop7h 08m
United Airlines
Thu 4/161:22 pm
STT
-
BOS
1 stop8h 32m
United Airlines
Deal found 3/9$230

Find flight deals from Maine to Caribbean

Keep the following information in mind while searching for Maine to Caribbean flight deals. Data was last updated March 13, 2026.

Round-trip from

$153
(Kiwi.com)

One-way from

$89
(Delta)

Popular in

February

Cheapest in

October

Average price

$473
From Maine to Caribbean
Search Deals
One-way flight from Maine to Caribbean
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($72 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maine 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 March 13, 2026.
Use the filters below to find and compare flights from Maine to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 5/3

5:45 am-12:20 pm

1 stop6h 35m

Saint Thomas Island Cyril E King

Thu 5/7

2:10 pm-11:59 pm

2 stops9h 49m

$230

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Mon 3/23

5:35 am-1:47 pm

1 stop8h 12m

Saint Thomas Island Cyril E King

Wed 3/25

3:55 pm-10:54 pm

1 stop6h 59m

$230

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 3/24

8:40 am-12:43 pm

Nonstop4h 03m

Saint Thomas Island Cyril E King

Fri 3/27

2:45 pm-7:04 pm

Nonstop4h 19m

$266

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sat 5/2

6:00 am-5:00 pm

1 stop11h 00m

Saint Thomas Island Cyril E King

Sun 5/10

1:22 pm-11:35 pm

1 stop10h 13m

$295

BostonSanto Domingo

BOS - SDQ

BOSSDQ

Boston Logan Intl

Tue 4/14

6:00 am-12:31 pm

1 stop6h 31m

Santo Domingo Las Americas

Wed 4/22

7:59 pm-7:29 am

1 stop11h 30m

$301

BostonSanto Domingo

BOS - SDQ

BOSSDQ

Boston Logan Intl

Fri 5/8

6:00 am-6:01 pm

1 stop12h 01m

Santo Domingo Las Americas

Fri 5/22

2:00 pm-11:37 pm

1 stop9h 37m

$301

BostonSanto Domingo

BOS - SDQ

BOSSDQ

Boston Logan Intl

Sun 5/31

6:00 am-6:01 pm

1 stop12h 01m

Santo Domingo Las Americas

Fri 6/5

2:00 pm-11:37 pm

1 stop9h 37m

$301

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 4/8

6:00 am-1:00 pm

1 stop7h 00m

Saint Thomas Island Cyril E King

Tue 4/14

2:33 pm-6:59 pm

Nonstop4h 26m

$313

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Thu 4/9

8:40 am-12:43 pm

Nonstop4h 03m

Saint Thomas Island Cyril E King

Thu 4/16

2:33 pm-6:59 pm

Nonstop4h 26m

$318

BostonOranjestad

BOS - AUA

BOSAUA

Boston Logan Intl

Wed 4/15

6:00 am-3:20 pm

1 stop9h 20m

Oranjestad Reina Beatrix

Wed 6/10

1:50 pm-12:59 am

1 stop11h 09m

$321

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/8

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Maine to Caribbean

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

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

Currently, July is the cheapest month in which you can book a flight from Maine to Caribbean (average of $165). Flying from Maine to Caribbean in June is currently the most expensive (average of $307). 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.

Related info for your journey

Find useful and relevant information for your journey from Maine to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Maine to Caribbean?

    For as low as $230, United Airlines can have you in Caribbean from Maine in 6h 35m. Maine and Caribbean are separated by a distance of 1697 mi. This flight may include one or multiple stops.

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

    One-way options have recently been found by users for as low as $106 on United Airlines. Other airlines that offer cheap prices include American Airlines from $108 and Southwest from $150 one-way.

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

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

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

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

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

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

    Currently, July is the cheapest month in which you can book a flight from Maine to Caribbean (average of $165). Flying from Maine to Caribbean in June is currently the most expensive (average of $307). 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 Maine to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Maine to Caribbean

Discover the top 5 airlines that operate flights from Maine 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 March 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$137Average$407FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$156Average$559FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$241Average$677FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$256Average$611FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$300Average$644FlexibilityNo cancel feeOn-time63%

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