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Caribbean

$114+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Jul 18 — Jul 251
Sat 7/18
Sat 7/25
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 June 18, 2026.

This eDestinos deal was found by Cheapflights users on 6/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/710:04 am
BOS
-
SJU
1 stop16h 11m
Frontier
Tue 7/143:36 pm
SJU
-
BOS
1 stop19h 28m
Frontier
Deal found 6/15$300
This Flysmarter deal was found by Cheapflights users on 6/14. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/48:55 am
BOS
-
STT
Nonstop4h 05m
JetBlue
Fri 7/102:49 pm
STT
-
BOS
Nonstop5h 38m
JetBlue
Deal found 6/14$302
This Cheapflightsfares deal was found by Cheapflights users on 6/15. 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.
Fri 7/179:56 am
BOS
-
STT
Nonstop4h 03m
JetBlue
Fri 7/242:49 pm
STT
-
BOS
1 stop5h 38m
JetBlue
Deal found 6/15$306
This Cheapflightsfares deal was found by Cheapflights users on 6/14. 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 9/207:20 pm
BOS
-
SJU
Nonstop4h 38m
JetBlue
Fri 9/257:35 pm
SJU
-
BOS
Nonstop4h 08m
JetBlue
Deal found 6/14$308
This Justfly.com deal was found by Cheapflights users on 6/13. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:56 am
BOS
-
STT
Nonstop4h 03m
JetBlue
Tue 7/142:53 pm
STT
-
BOS
1 stop5h 38m
JetBlue
Deal found 6/13$311
This Delta deal was found by Cheapflights users on 6/16. 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.
Sat 9/198:55 am
BOS
-
SJU
Nonstop4h 06m
Delta
Sat 9/262:06 pm
SJU
-
BOS
Nonstop4h 05m
Delta
Deal found 6/16$313
This Cheapflightsfares deal was found by Cheapflights users on 6/18. 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.
Fri 9/117:20 pm
BOS
-
SJU
Nonstop4h 38m
JetBlue
Wed 9/167:35 pm
SJU
-
BOS
Nonstop4h 08m
JetBlue
Deal found 6/18$315
This eDestinos deal was found by Cheapflights users on 6/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1310:04 am
BOS
-
SJU
1 stop25h 12m
Frontier
Tue 7/143:36 pm
SJU
-
BOS
1 stop19h 28m
Frontier
Deal found 6/15$316
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Thu 8/205:00 am
BOS
-
STT
1 stop10h 52m
American Airlines
Sat 8/292:20 pm
STT
-
BOS
1 stop8h 30m
American Airlines
Deal found 6/14$320
This JetBlue deal was found by Cheapflights users on 6/17. 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.
Tue 7/710:00 am
BOS
-
STT
Nonstop4h 03m
JetBlue
Fri 7/172:49 pm
STT
-
BOS
1 stop5h 38m
JetBlue
Deal found 6/17$321
This Delta deal was found by Cheapflights users on 6/16. 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.
Sat 9/196:05 am
BOS
-
SJU
1 stop6h 08m
Delta
Mon 9/211:32 pm
SJU
-
BOS
1 stop9h 38m
Delta
Deal found 6/16$322
This Delta deal was found by Cheapflights users on 6/17. 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.
Tue 10/278:55 am
BOS
-
SJU
Nonstop4h 06m
Delta
Wed 11/43:06 pm
SJU
-
BOS
Nonstop4h 13m
Delta
Deal found 6/17$323

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 June 18, 2026.

Round-trip from

$300
(eDestinos)

One-way from

$114
(Kiwi.com)

Popular in

April

Cheapest in

July

Average price

$674
From Maine to Caribbean
Search Deals
One-way flight from Maine to Caribbean
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 18, 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

Sat 7/4

8:55 am-1:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Fri 7/10

2:49 pm-8:27 pm

1 stop5h 38m

$311

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 9/9

5:30 am-1:47 pm

1 stop8h 17m

San Juan Luis Munoz Marin Intl

Wed 9/16

5:41 pm-1:17 am

1 stop7h 36m

$322

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 8/17

5:45 am-12:54 pm

1 stop7h 09m

San Juan Luis Munoz Marin Intl

Sun 8/23

1:00 am-9:48 am

1 stop8h 48m

$322

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 9/9

12:20 pm-10:19 pm

1 stop9h 59m

San Juan Luis Munoz Marin Intl

Mon 9/14

5:41 pm-1:17 am

1 stop7h 36m

$322

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 9/11

8:55 am-12:57 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Mon 9/28

7:00 am-2:52 pm

1 stop7h 52m

$328

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 9/3

8:50 am-12:57 pm

Nonstop4h 07m

San Juan Luis Munoz Marin Intl

Sun 9/6

7:30 am-4:13 pm

1 stop8h 43m

$328

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 9/11

5:30 am-1:53 pm

1 stop8h 23m

Simpson Bay Princess Juliana

Sat 9/19

3:20 pm-1:17 am

1 stop9h 57m

$347

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 7/4

9:50 am-8:34 pm

1 stop10h 44m

San Juan Luis Munoz Marin Intl

Tue 7/7

1:00 am-10:20 am

2 stops9h 20m

$350

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 9/5

6:00 am-12:33 pm

1 stop6h 33m

Simpson Bay Princess Juliana

Sat 9/12

1:35 pm-10:54 am

2 stops21h 19m

$360

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 7/20

5:45 am-12:33 pm

1 stop6h 48m

Simpson Bay Princess Juliana

Fri 7/24

3:50 pm-11:59 pm

1 stop8h 09m

$365

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/13

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, February is the cheapest month in which you can book a flight from Maine to Caribbean (average of $101). Flying from Maine to Caribbean in August is currently the most expensive (average of $303). 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.

How far ahead should I book a flight from Maine to Caribbean?

The best time to book flights from Maine to Caribbean is 33 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 $311, JetBlue can have you in Caribbean from Maine in 4h 05m. 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 $141 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, February is the cheapest month in which you can book a flight from Maine to Caribbean (average of $101). Flying from Maine to Caribbean in August is currently the most expensive (average of $303). 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 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 June 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$156Average$575FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$417FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$235Average$698FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$256Average$607FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$300Average$755FlexibilityNo cancel feeOn-time63%

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