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Caribbean

$99+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Maine to Caribbean

Keep the following information in mind while searching for Maine to Caribbean flight deals. Data was last updated September 15, 2025.

Round-trip from

$176
(CheapOair)

One-way from

$99
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$360
From Maine to Caribbean
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One-way flight from Maine to Caribbean
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Highest demand for flights based on searches. 2% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Sat 11/12:15 pmBOS - SJU
1 stop10h 39mSpirit Airlines
Sat 2/75:27 pmSJU - BOS
Nonstop4h 07mSpirit Airlines
Deal found 9/15$195
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/22:53 pmBOS - SJU
1 stop10h 01mSpirit Airlines
Tue 10/72:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Deal found 9/13$202
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Wed 10/112:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
Mon 10/62:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Deal found 9/14$206
This eDestinos deal was found by Cheapflights users on 9/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:49 pmBOS - SJU
1 stop16h 15mSpirit Airlines
Tue 9/306:44 amSJU - BOS
1 stop7h 04mSpirit Airlines
Deal found 9/13$212
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:00 amBOS - SJU
1 stop9h 23mSpirit Airlines
Wed 11/1912:10 pmSJU - BOS
1 stop10h 58mSpirit Airlines
Deal found 9/13$213
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/12:15 pmBOS - SJU
1 stop10h 39mSpirit Airlines
Thu 11/612:10 pmSJU - BOS
1 stop10h 58mSpirit Airlines
Deal found 9/13$214
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:00 amBOS - SJU
1 stop9h 23mSpirit Airlines
Wed 11/1212:10 pmSJU - BOS
1 stop10h 58mSpirit Airlines
Deal found 9/13$215
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/12:15 pmBOS - SJU
1 stop10h 39mSpirit Airlines
Fri 11/712:10 pmSJU - BOS
1 stop10h 58mSpirit Airlines
Deal found 9/15$217
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 12/411:13 amBOS - SJU
1 stop7h 08mSpirit Airlines
Sat 12/66:00 amSJU - BOS
1 stop18h 25mSpirit Airlines
Deal found 9/12$218
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Sat 9/2712:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
Sat 10/46:44 amSJU - BOS
1 stop7h 04mSpirit Airlines
Deal found 9/15$219
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:00 amBOS - SJU
1 stop9h 23mMultiple Airlines
Sat 12/133:59 pmSJU - BOS
1 stop9h 45mMultiple Airlines
Deal found 9/14$223
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Wed 10/112:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
Tue 10/72:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Deal found 9/14$226

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 September 15, 2025.
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

Sun 10/19

8:15 am-12:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Wed 10/22

1:32 pm-5:45 pm

Nonstop4h 13m

$282

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 10/24

8:15 am-12:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Tue 11/4

2:32 pm-5:45 pm

Nonstop4h 13m

$282

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 10/26

8:15 am-12:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Tue 11/4

2:32 pm-5:45 pm

Nonstop4h 13m

$282

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 10/21

8:15 am-12:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Sun 10/26

1:32 pm-5:45 pm

Nonstop4h 13m

$282

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 11/4

8:15 am-1:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Thu 11/13

2:27 pm-5:50 pm

Nonstop4h 23m

$282

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 11/16

8:10 am-1:17 pm

Nonstop4h 07m

San Juan Luis Munoz Marin Intl

Fri 11/21

2:27 pm-5:50 pm

Nonstop4h 23m

$282

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 10/5

8:10 am-12:15 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Thu 10/9

1:32 pm-5:45 pm

Nonstop4h 13m

$282

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 10/15

8:00 am-12:27 pm

Nonstop4h 27m

San Juan Luis Munoz Marin Intl

Sat 10/18

3:03 am-9:45 am

1 stop6h 42m

$284

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 10/21

10:14 am-4:42 pm

1 stop6h 28m

San Juan Luis Munoz Marin Intl

Sun 10/26

5:10 am-9:19 am

Nonstop4h 09m

$284

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 9/25

5:35 am-4:31 pm

1 stop10h 56m

San Juan Luis Munoz Marin Intl

Thu 10/2

1:25 pm-5:30 pm

Nonstop4h 05m

$287

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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, September is the cheapest month in which you can book a flight from Maine to Caribbean (average of $254). Flying from Maine to Caribbean in June is currently the most expensive (average of $339). 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.

What is the cheapest time of day to fly from ME to CB?

Find hourly flight availability from Maine to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Maine to Caribbean as you normally would.

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 $330, Delta 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 $119 on Spirit Airlines. Other airlines that offer cheap prices include Southwest from $119 and Frontier from $122 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, September is the cheapest month in which you can book a flight from Maine to Caribbean (average of $254). Flying from Maine to Caribbean in June is currently the most expensive (average of $339). 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 6 airlines flying from Maine to Caribbean

Discover the top 6 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$228FlexibilityNo cancel feeOn-time62%
DeltaCheapest$274Average$504FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$281Average$694FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$285Average$741FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$361Average$629FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$425Average$753FlexibilityNo cancel feeOn-time63%

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