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Caribbean

$76+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
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 December 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Sat 1/246:11 pmSJU - BOS
1 stop8h 02mMultiple Airlines
Deal found 12/13$154
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Thu 1/224:40 pmSJU - BOS
1 stop8h 17mSpirit Airlines
Deal found 12/15$166
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 12/298:08 amBOS - SJU
1 stop16h 16mMultiple Airlines
Fri 1/2310:52 amSJU - BOS
Nonstop4h 20mMultiple Airlines
Deal found 12/13$172
This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Sat 1/108:15 amSJU - BOS
2 stops50h 48mMultiple Airlines
Deal found 12/13$179
This JetBlue deal was found by Cheapflights users on 12/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:50 pmBOS - SJU
Nonstop4h 06mJetBlue
Sun 1/412:40 pmSJU - BOS
Nonstop4h 13mJetBlue
Deal found 12/13$186
This CheapOair deal was found by Cheapflights users on 12/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:01 amBOS - SJU
Nonstop3h 59mJetBlue
Wed 1/72:00 pmSJU - BOS
Nonstop4h 13mJetBlue
Deal found 12/15$187
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 12/298:08 amBOS - SJU
1 stop16h 16mFrontier
Sat 1/246:11 pmSJU - BOS
1 stop8h 02mFrontier
Deal found 12/13$189
This JetBlue deal was found by Cheapflights users on 12/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:01 amBOS - SJU
Nonstop3h 59mJetBlue
Fri 1/22:05 amSJU - BOS
Nonstop4h 09mJetBlue
Deal found 12/13$194
This American Airlines deal was found by Cheapflights users on 12/14. 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.
Wed 12/317:56 amBOS - SJU
1 stop10h 47mAmerican Airlines
Wed 1/1411:38 amSJU - BOS
1 stop10h 13mAmerican Airlines
Deal found 12/14$195
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Thu 12/187:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Tue 12/238:00 amSJU - BOS
Nonstop4h 23mMultiple Airlines
Deal found 12/14$208
This CheapOair deal was found by Cheapflights users on 12/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:00 pmBOS - STT
1 stop17h 00mJetBlue
Thu 1/82:00 pmSTT - BOS
1 stop5h 49mJetBlue
Deal found 12/15$267
This Expedia deal was found by Cheapflights users on 12/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:45 amBOS - AUA
Nonstop4h 52mMultiple Airlines
Thu 1/84:40 pmAUA - BOS
1 stop8h 17mMultiple Airlines
Deal found 12/13$302

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 December 15, 2025.

Round-trip from

$149
(Kiwi.com)

One-way from

$76
(Priceline)

Popular in

December

Cheapest in

January

Average price

$386
From Maine to Caribbean
Search Deals
One-way flight from Maine to Caribbean
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 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 1/11

8:20 pm-1:22 am

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Wed 1/14

7:15 pm-10:28 pm

Nonstop4h 13m

$186

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 1/24

8:05 am-1:11 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Thu 1/29

2:25 pm-5:45 pm

Nonstop4h 20m

$186

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 1/24

4:05 pm-6:11 am

2 stops13h 06m

San Juan Luis Munoz Marin Intl

Fri 1/30

2:05 am-9:14 am

1 stop8h 09m

$195

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 2/10

5:35 am-2:31 pm

1 stop7h 56m

San Juan Luis Munoz Marin Intl

Sat 2/14

7:00 am-3:15 pm

1 stop9h 15m

$203

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 5/2

1:55 pm-10:54 pm

1 stop8h 59m

San Juan Luis Munoz Marin Intl

Thu 5/7

1:30 pm-5:53 pm

Nonstop4h 23m

$207

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 1/31

5:50 pm-10:55 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Wed 2/4

8:15 am-3:34 pm

1 stop8h 19m

$226

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 2/1

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Sat 2/7

5:55 pm-10:53 pm

1 stop5h 58m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 3/10

8:00 am-12:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Fri 3/20

2:41 pm-8:34 pm

1 stop5h 53m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 1/9

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Mon 1/12

2:32 pm-5:53 pm

Nonstop4h 21m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Mon 2/2

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Wed 2/11

2:32 pm-5:53 pm

Nonstop4h 21m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

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, February is the cheapest month in which you can book a flight from Maine to Caribbean (average of $157). 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.

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 December 15, 2025.

A simple way to save on the total cost of your ticket is to fly from Maine to Caribbean in the evening. If you’re flexible enough to do this you can expect to save up to 51% on your trip compared to booking a flight in the morning.

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 $186, JetBlue can have you in Caribbean from Maine in 4h 02m. 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 United Airlines from $142 and American Airlines 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, February is the cheapest month in which you can book a flight from Maine to Caribbean (average of $157). 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 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$228FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$237Average$566FlexibilityNo cancel feeOn-time62%
DeltaCheapest$274Average$484FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$296Average$654FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$302Average$708FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$315Average$739FlexibilityNo cancel feeOn-time63%

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