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Caribbean Islands

$65+ Cheap flights from Maine to Caribbean Islands

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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
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Cheap flight deals from Maine to Caribbean Islands

Cheapest flights from Maine to Caribbean Islands
Explore the most affordable flight options available from Maine to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.

This Orbitz deal was found by Cheapflights users on 2/1. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:27 am
BOS
-
SJU
1 stop9h 04m
Spirit Airlines
Thu 3/511:52 am
SJU
-
BOS
1 stop13h 07m
Spirit Airlines
Deal found 2/1$143
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia 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
Multiple Airlines
Sat 2/146:00 am
SJU
-
BOS
Nonstop4h 19m
Multiple Airlines
Deal found 2/1$144
This Expedia deal was found by Cheapflights users on 2/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:32 pm
BOS
-
SJU
1 stop17h 59m
Multiple Airlines
Sat 2/286:00 am
SJU
-
BOS
Nonstop4h 19m
Multiple Airlines
Deal found 2/3$145
This Orbitz deal was found by Cheapflights users on 2/1. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/45:27 am
BOS
-
SJU
1 stop9h 04m
Spirit Airlines
Tue 3/105:00 am
SJU
-
BOS
1 stop6h 48m
Spirit Airlines
Deal found 2/1$146
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:32 pm
BOS
-
SJU
1 stop17h 59m
Multiple Airlines
Fri 2/276:00 am
SJU
-
BOS
Nonstop4h 19m
Multiple Airlines
Deal found 2/2$147
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/63:18 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Tue 2/1010:52 am
SJU
-
BOS
Nonstop4h 20m
Spirit Airlines
Deal found 2/1$148
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 2/235:27 am
BOS
-
SJU
1 stop9h 04m
Spirit Airlines
Tue 3/311:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 2/3$149
This Travelocity deal was found by Cheapflights users on 2/2. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:01 pm
BOS
-
SJU
Nonstop4h 07m
Spirit Airlines
Tue 3/3112:55 pm
SJU
-
BOS
1 stop11h 04m
Spirit Airlines
Deal found 2/2$151
This Orbitz deal was found by Cheapflights users on 2/1. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/103:43 pm
BOS
-
SJU
1 stop17h 04m
Multiple Airlines
Fri 2/136:00 am
SJU
-
BOS
Nonstop4h 19m
Multiple Airlines
Deal found 2/1$152
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/253:00 pm
BOS
-
SJU
Nonstop4h 06m
Multiple Airlines
Wed 3/44:06 pm
SJU
-
BOS
1 stop10h 07m
Multiple Airlines
Deal found 2/3$153
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/73:18 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Sat 2/1411:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 2/3$154
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:10 pm
BOS
-
STT
1 stop20h 24m
Spirit Airlines
Tue 3/104:40 pm
STT
-
BOS
1 stop7h 04m
Spirit Airlines
Deal found 2/1$217

Find flight deals from Maine to Caribbean Islands

Keep the following information in mind while searching for Maine to Caribbean Islands flight deals. Data was last updated February 3, 2026.

Round-trip from

$143
(Orbitz)

One-way from

$65
(Expedia)

Popular in

February

Cheapest in

November

Average price

$645
From Maine to Caribbean Islands
Search Deals
One-way flight from Maine to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($57 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 February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maine to Caribbean Islands 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 February 3, 2026.
Use the filters below to find and compare flights from Maine to Caribbean Islands that are best for you.

Fly from

Maine

Fly to

Caribbean Islands

Route

Depart

Return

Price

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Thu 4/2

8:40 am-12:43 pm

Nonstop4h 03m

Saint Thomas Island Cyril E King

Wed 4/8

2:45 pm-7:04 pm

Nonstop4h 19m

$231

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Thu 3/5

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

$231

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 4/5

8:40 am-12:43 pm

Nonstop4h 03m

Saint Thomas Island Cyril E King

Thu 4/9

2:45 pm-7:04 pm

Nonstop4h 19m

$231

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 2/20

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Thu 2/26

2:32 pm-5:53 pm

Nonstop4h 21m

$231

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

2:35 pm-7:01 pm

Nonstop4h 26m

$231

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 2/24

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Fri 3/6

2:32 pm-5:53 pm

Nonstop4h 21m

$231

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 2/24

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Tue 3/3

4:15 pm-1:09 am

1 stop9h 54m

$236

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Mon 2/23

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Tue 3/3

1:50 pm-9:34 pm

1 stop8h 44m

$236

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Thu 4/9

6:00 am-1:00 pm

1 stop7h 00m

Saint Thomas Island Cyril E King

Wed 4/15

2:35 pm-7:01 pm

Nonstop4h 26m

$236

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 4/15

6:00 am-1:08 pm

1 stop7h 08m

Saint Thomas Island Cyril E King

Mon 4/20

2:10 pm-12:59 am

1 stop10h 49m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

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

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

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

Currently, July is the cheapest month in which you can book a flight from Maine to Caribbean Islands (average of $165). Flying from Maine to Caribbean Islands in December is currently the most expensive (average of $302). 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 Islands. 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 Islands?

    Departing from Maine to Caribbean Islands will take you 3h 57m. The distance between Maine and Caribbean Islands is about 1678 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $86 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on American Airlines and Southwest, with prices starting from $146 and $150, respectively.

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

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

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

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

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

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

    Currently, July is the cheapest month in which you can book a flight from Maine to Caribbean Islands (average of $165). Flying from Maine to Caribbean Islands in December is currently the most expensive (average of $302). 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 Islands

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 Islands

Discover the top 5 airlines that operate flights from Maine to Caribbean Islands. 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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$113Average$506FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$190Average$613FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$230Average$692FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$256Average$616FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$648FlexibilityNo cancel feeOn-time63%

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