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Caribbean

$94+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Jun 5 — Jun 121
Fri 6/5
Fri 6/12
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 May 6, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/1. 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 5/166:00 am
BOS
-
SJU
1 stop8h 07m
Frontier
Wed 5/205:15 pm
SJU
-
BOS
1 stop8h 09m
Frontier
Deal found 5/1$210
This Trip.com deal was found by Cheapflights users on 5/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1810:17 am
BOS
-
SJU
1 stop7h 13m
Frontier
Thu 5/285:15 pm
SJU
-
BOS
1 stop14h 34m
Frontier
Deal found 5/4$211
This Priceline deal was found by Cheapflights users on 5/4. 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.
Mon 5/1810:17 am
BOS
-
SJU
1 stop7h 13m
Frontier
Tue 5/195:15 pm
SJU
-
BOS
1 stop8h 09m
Frontier
Deal found 5/4$212
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Mon 6/16:00 am
BOS
-
SJU
1 stop8h 07m
Frontier
Sat 6/65:15 pm
SJU
-
BOS
1 stop8h 09m
Frontier
Deal found 5/1$214
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Fri 5/159:57 am
BOS
-
SJU
1 stop7h 17m
Frontier
Tue 5/198:30 am
SJU
-
BOS
1 stop26h 36m
Frontier
Deal found 5/1$216
This Flightnetwork deal was found by Cheapflights users on 5/4. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:00 am
BOS
-
SJU
1 stop8h 07m
Frontier
Thu 6/45:15 pm
SJU
-
BOS
1 stop8h 09m
Frontier
Deal found 5/4$220
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Mon 5/1810:17 am
BOS
-
SJU
1 stop12h 26m
Frontier
Sat 6/135:15 pm
SJU
-
BOS
1 stop8h 12m
Frontier
Deal found 5/1$223
This Frontier deal was found by Cheapflights users on 5/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/76:00 am
BOS
-
SJU
1 stop8h 07m
Frontier
Tue 6/165:15 pm
SJU
-
BOS
1 stop14h 37m
Frontier
Deal found 5/3$224
This United Airlines deal was found by Cheapflights users on 5/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:30 am
BOS
-
STT
1 stop9h 30m
United Airlines
Wed 5/204:45 pm
STT
-
BOS
1 stop7h 14m
United Airlines
Deal found 5/1$230
This CheapOair deal was found by Cheapflights users on 5/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:07 am
BOS
-
SJU
1 stop16h 01m
Frontier
Wed 5/205:15 pm
SJU
-
BOS
1 stop14h 34m
Frontier
Deal found 5/1$233
This Priceline deal was found by Cheapflights users on 5/4. 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.
Mon 5/1810:17 am
BOS
-
SJU
1 stop7h 13m
Frontier
Sat 5/235:15 pm
SJU
-
BOS
1 stop8h 09m
Frontier
Deal found 5/4$234
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:07 am
BOS
-
SJU
1 stop16h 01m
Frontier
Tue 5/125:15 pm
SJU
-
BOS
1 stop8h 09m
Frontier
Deal found 5/1$235

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 May 6, 2026.

Round-trip from

$210
(Kiwi.com)

One-way from

$94
(United Airlines)

Popular in

April

Cheapest in

October

Average price

$342
From Maine to Caribbean
Search Deals
One-way flight from Maine to Caribbean
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 6, 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

Fri 6/12

10:32 am-2:35 pm

Nonstop4h 03m

Saint Thomas Island Cyril E King

Tue 6/16

2:58 pm-8:37 pm

1 stop5h 39m

$301

BostonBridgetown

BOS - BGI

BOSBGI

Boston Logan Intl

Sat 6/6

7:30 am-3:25 pm

1 stop7h 55m

Bridgetown Grantley Adams Intl

Sat 6/13

4:35 pm-9:12 am

1 stop16h 37m

$304

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 6/6

9:05 am-4:29 pm

1 stop7h 24m

San Juan Luis Munoz Marin Intl

Wed 6/10

2:05 pm-6:14 pm

Nonstop4h 09m

$308

BostonSanto Domingo

BOS - SDQ

BOSSDQ

Boston Logan Intl

Thu 6/18

10:20 pm-2:35 am

Nonstop4h 15m

Santo Domingo Las Americas

Sun 6/21

4:35 pm-8:50 pm

Nonstop4h 15m

$345

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Mon 5/11

6:00 am-1:08 pm

1 stop7h 08m

Saint Thomas Island Cyril E King

Sat 5/16

2:10 pm-12:59 am

1 stop10h 49m

$345

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 6/14

6:06 am-4:29 pm

1 stop10h 23m

San Juan Luis Munoz Marin Intl

Sat 6/20

7:05 am-4:04 pm

1 stop8h 59m

$352

BostonBridgetown

BOS - BGI

BOSBGI

Boston Logan Intl

Tue 5/26

5:35 am-2:20 pm

1 stop8h 45m

Bridgetown Grantley Adams Intl

Tue 6/2

3:40 pm-1:28 am

1 stop9h 48m

$354

BostonBridgetown

BOS - BGI

BOSBGI

Boston Logan Intl

Sat 6/13

6:00 am-3:25 pm

1 stop9h 25m

Bridgetown Grantley Adams Intl

Sat 7/4

4:35 pm-9:51 am

1 stop17h 16m

$358

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

Tue 7/7

2:58 pm-8:37 pm

1 stop5h 39m

$361

BostonBridgetown

BOS - BGI

BOSBGI

Boston Logan Intl

Sun 5/24

5:35 am-2:20 pm

1 stop8h 45m

Bridgetown Grantley Adams Intl

Fri 5/29

3:30 pm-1:28 am

1 stop9h 58m

$361

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/2

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

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

The best time to book flights from Maine to Caribbean is 31 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.

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 December is currently the most expensive (average of $298). 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 $301, United Airlines can have you in Caribbean from Maine in 4h 03m. 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 December is currently the most expensive (average of $298). 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 May 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$156Average$584FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$423FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$235Average$670FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$256Average$607FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$645FlexibilityNo cancel feeOn-time63%

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