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Caribbean

$56+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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 January 28, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 1/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/103:18 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Sun 2/1511:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 1/26$142
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/33:43 pm
BOS
-
SJU
1 stop6h 50m
Spirit Airlines
Tue 2/1010:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Deal found 1/27$143
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/73:43 pm
BOS
-
SJU
1 stop6h 50m
Spirit Airlines
Sat 2/1411:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 1/27$144
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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.
Sat 1/313:43 pm
BOS
-
SJU
1 stop6h 50m
Spirit Airlines
Wed 2/410:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Deal found 1/28$145
This Priceline deal was found by Cheapflights users on 1/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/313:18 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Tue 2/310:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Deal found 1/27$146
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/313:18 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Fri 2/610:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Deal found 1/27$147
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/78:01 pm
BOS
-
SJU
Nonstop4h 07m
Spirit Airlines
Wed 3/1810:00 am
SJU
-
BOS
Nonstop4h 18m
Spirit Airlines
Deal found 1/27$148
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/43:43 pm
BOS
-
SJU
1 stop6h 50m
Spirit Airlines
Thu 2/54:40 pm
SJU
-
BOS
1 stop8h 17m
Spirit Airlines
Deal found 1/27$149
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:27 am
BOS
-
SJU
1 stop9h 04m
Multiple Airlines
Thu 3/56:00 am
SJU
-
BOS
Nonstop4h 19m
Multiple Airlines
Deal found 1/27$150
This CheapOair deal was found by Cheapflights users on 1/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/73:18 pm
BOS
-
SJU
Nonstop4h 06m
Multiple Airlines
Fri 2/276:00 am
SJU
-
BOS
Nonstop4h 19m
Multiple Airlines
Deal found 1/26$152
This CheapOair deal was found by Cheapflights users on 1/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/23:18 pm
BOS
-
SJU
Nonstop4h 06m
Multiple Airlines
Thu 2/57:15 pm
SJU
-
BOS
Nonstop4h 13m
Multiple Airlines
Deal found 1/26$153
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:27 am
BOS
-
STT
1 stop10h 07m
Spirit Airlines
Wed 2/255:40 pm
STT
-
BOS
1 stop7h 04m
Spirit Airlines
Deal found 1/27$219

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 January 28, 2026.

Round-trip from

$142
(Cheapflightsfares)

One-way from

$56
(FlightHub)

Popular in

February

Cheapest in

November

Average price

$367
From Maine to Caribbean
Search Deals
One-way flight from Maine to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 28, 2026.
Use the filters below to find and compare flights from Maine to Caribbean that are best for you.

Fly from

Maine

Fly to

Caribbean

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 3/2

5:27 am-3:31 pm

1 stop9h 04m

San Juan Luis Munoz Marin Intl

Sat 3/7

3:30 pm-6:56 pm

Nonstop4h 26m

$201

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 5/10

10:40 pm-2:39 am

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Sun 5/31

12:30 pm-4:39 pm

Nonstop4h 09m

$203

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 5/13

8:20 am-12:28 pm

Nonstop4h 08m

San Juan Luis Munoz Marin Intl

Fri 5/15

1:30 pm-5:53 pm

Nonstop4h 23m

$203

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 4/23

6:10 pm-10:12 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Wed 4/29

11:25 pm-3:25 am

Nonstop4h 00m

$203

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 2/25

1:35 pm-11:58 pm

1 stop9h 23m

San Juan Luis Munoz Marin Intl

Thu 3/5

7:00 am-3:15 pm

1 stop9h 15m

$212

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 3/3

11:15 am-11:58 pm

1 stop11h 43m

San Juan Luis Munoz Marin Intl

Thu 3/5

7:00 am-3:15 pm

1 stop9h 15m

$212

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Thu 2/26

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Tue 3/3

2:32 pm-5:53 pm

Nonstop4h 21m

$245

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Thu 3/19

8:40 am-12:43 pm

Nonstop4h 03m

Saint Thomas Island Cyril E King

Thu 3/26

2:45 pm-7:04 pm

Nonstop4h 19m

$245

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 3/3

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Wed 3/11

2:45 pm-7:04 pm

Nonstop4h 19m

$245

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 2/27

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Tue 3/3

5:32 pm-10:48 pm

1 stop6h 16m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 60 results
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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 $329). 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 $203, Spirit Airlines can have you in Caribbean from Maine in 3h 59m. Maine 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 Maine to Caribbean one-way?

    One-way options have recently been found by users for as low as $86 on Frontier. Other airlines that offer cheap prices include American Airlines from $146 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 $329). 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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$176Average$487FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$190Average$610FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$230Average$684FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$256Average$621FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$648FlexibilityNo cancel feeOn-time63%

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