$110+ Cheap flights from Maine to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Nov 2 — Nov 91
Round-trip
1 adult, Economy
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Find cheap flights from Maine to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Maine to Caribbean
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Cheapest flights from Maine to CaribbeanExplore 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 October 3, 2026.
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 October 3, 2026.
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Tue 10/275:30 am -
1 stop6h 45m
Tue 11/31:00 pm -
1 stop6h 49m
Deal found 9/29![United Airlines logo]()
$316
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Mon 11/96:47 pm -
1 stop17h 58m
Tue 11/175:59 pm -
2 stops17h 25m
Deal found 9/29![American Airlines logo]()
$340
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Fri 10/305:50 am -
1 stop7h 21m
Sat 10/312:05 am -
2 stops13h 11m
Deal found 9/30![United Airlines logo]()
$343
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Fri 11/136:47 pm -
1 stop16h 52m
Wed 11/183:00 pm -
1 stop8h 57m
Deal found 9/30![American Airlines logo]()
$346
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Fri 11/137:35 pm -
2 stops16h 14m
Fri 11/2012:55 pm -
1 stop10h 26m
Deal found 9/29![United Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 9/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:30 am -
1 stop17h 27m
Mon 10/262:18 pm -
2 stops9h 18m
Deal found 9/28![American Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/215:30 am -
2 stops16h 39m
Sat 10/317:30 am -
2 stops15h 14m
Deal found 9/30![American Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Mon 11/166:47 pm -
2 stops15h 57m
Sat 11/212:22 pm -
1 stop9h 33m
Deal found 9/30![American Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 10/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:45 am -
2 stops15h 31m
Wed 11/1111:45 am -
1 stop9h 51m
Deal found 10/1![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Fri 11/136:47 pm -
2 stops19h 23m
Fri 11/204:25 pm -
2 stops19h 13m
Deal found 9/29![American Airlines logo]()
$364
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Mon 11/236:47 pm -
2 stops20h 11m
Wed 12/22:02 pm -
1 stop8h 38m
Deal found 9/30![American Airlines logo]()
$370
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Tue 12/16:47 pm -
2 stops20h 39m
Tue 12/153:27 pm -
2 stops21h 31m
Deal found 9/30![American Airlines logo]()
$380
Best flights from Maine to CaribbeanDiscover carefully curated flight deals from Maine to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 3, 2026.
Discover carefully curated flight deals from Maine to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 3, 2026.
This United Airlines deal was found by Cheapflights users on 10/1. 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 10/316:00 am -
2 stops14h 00m
Fri 11/65:50 pm -
1 stop7h 09m
Deal found 10/1![United Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 10/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/246:00 am -
1 stop7h 30m
Fri 1/294:25 pm -
1 stop6h 41m
Deal found 10/2![Delta logo]()
$328
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Mon 11/166:47 pm -
2 stops15h 57m
Sat 11/212:22 pm -
1 stop9h 33m
Deal found 9/30![American Airlines logo]()
$356
This JetBlue deal was found by Cheapflights users on 9/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:30 am -
1 stop9h 10m
Tue 11/172:20 pm -
1 stop10h 23m
Deal found 9/28![JetBlue logo]()
$477
This United deal was found by Cheapflights users on 10/2. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:50 am -
2 stops26h 00m
Mon 11/23:00 pm -
1 stop9h 21m
Deal found 10/2![Multiple Airlines logo]()
$589
This United Airlines deal was found by Cheapflights users on 10/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/303:14 pm -
1 stop8h 22m
Sat 2/67:40 am -
2 stops14h 23m
Deal found 10/2![United Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Sun 1/176:00 am -
1 stop6h 32m
Tue 1/262:05 am -
1 stop7h 14m
Deal found 9/29![United Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:00 am -
1 stop9h 33m
Sat 11/213:10 pm -
1 stop6h 19m
Deal found 9/29![Delta logo]()
$348
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Fri 12/46:44 pm -
2 stops20h 46m
Sun 12/133:15 pm -
2 stops20h 15m
Deal found 9/30![American Airlines logo]()
$370
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Fri 11/66:47 pm -
2 stops20h 44m
Wed 11/113:26 pm -
2 stops19h 35m
Deal found 9/29![American Airlines logo]()
$380
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/12:35 pm -
1 stop8h 20m
Mon 2/83:55 pm -
1 stop7h 28m
Deal found 9/29![Delta logo]()
$384
This United Airlines deal was found by Cheapflights users on 9/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/57:43 pm -
2 stops16h 25m
Thu 1/1412:56 pm -
2 stops9h 52m
Deal found 9/28![United Airlines logo]()
$355
This Delta deal was found by Cheapflights users on 10/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/172:35 pm -
1 stop8h 20m
Sat 1/237:00 am -
1 stop7h 53m
Deal found 10/1![Delta logo]()
$384
This American Airlines deal was found by Cheapflights users on 10/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/66:29 pm -
2 stops21h 07m
Wed 3/102:14 pm -
1 stop9h 26m
Deal found 10/2![American Airlines logo]()
$404
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Mon 1/187:23 am -
1 stop8h 27m
Sun 1/246:00 pm -
1 stop15h 19m
Deal found 10/1![United Airlines logo]()
$383
This JetBlue deal was found by Cheapflights users on 10/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:30 am -
1 stop9h 10m
Tue 11/172:20 pm -
1 stop10h 23m
Deal found 10/2![JetBlue logo]()
$521
This American Airlines deal was found by Cheapflights users on 9/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:47 pm -
2 stops20h 29m
Fri 11/204:25 pm -
2 stops19h 13m
Deal found 9/28![American Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Sun 1/177:43 pm -
1 stop17h 07m
Thu 1/212:52 pm -
1 stop7h 56m
Deal found 10/1![United Airlines logo]()
$403
This American Airlines deal was found by Cheapflights users on 9/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:47 pm -
2 stops21h 00m
Sat 11/145:59 pm -
2 stops17h 38m
Deal found 9/28![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 9/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:44 pm -
2 stops19h 38m
Sun 12/136:09 pm -
2 stops16h 21m
Deal found 9/28![American Airlines logo]()
$414
This United Airlines deal was found by Cheapflights users on 10/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:30 am -
2 stops14h 54m
Wed 10/281:05 am -
2 stops13h 11m
Deal found 10/2![United Airlines logo]()
$416
This United Airlines deal was found by Cheapflights users on 9/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:00 am -
1 stop7h 15m
Wed 11/115:45 pm -
2 stops20h 31m
Deal found 9/28![United Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 10/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/296:36 pm -
2 stops20h 39m
Mon 2/84:07 pm -
2 stops19h 12m
Deal found 10/3![American Airlines logo]()
$422
This United Airlines deal was found by Cheapflights users on 10/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:30 am -
2 stops11h 00m
Tue 11/105:45 pm -
2 stops20h 31m
Deal found 10/3![United Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Sat 11/76:47 pm -
2 stops19h 58m
Sat 11/141:25 pm -
1 stop9h 32m
Deal found 9/30![American Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 9/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:47 pm -
2 stops20h 39m
Tue 12/155:33 pm -
2 stops19h 25m
Deal found 9/28![American Airlines logo]()
$427
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Mon 12/77:55 pm -
1 stop15h 54m
Wed 12/912:55 pm -
1 stop10h 29m
Deal found 9/30![United Airlines logo]()
$458
This American Airlines deal was found by Cheapflights users on 9/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:47 pm -
2 stops19h 58m
Sat 11/143:45 pm -
2 stops18h 04m
Deal found 9/28![American Airlines logo]()
$449
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Mon 11/165:35 am -
1 stop6h 14m
Fri 11/2012:55 pm -
1 stop10h 26m
Deal found 9/29![United Airlines logo]()
$458
This American Airlines deal was found by Cheapflights users on 10/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:45 am -
1 stop5h 33m
Wed 11/1111:45 am -
1 stop9h 51m
Deal found 10/2![American Airlines logo]()
$456
Last-minute flights from Maine to CaribbeanDiscover last-minute flight deals from Maine to Caribbean. Data last updated October 3, 2026 and is based on user searches.
Discover last-minute flight deals from Maine to Caribbean. Data last updated October 3, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/215:30 am -
2 stops16h 39m
Sat 10/317:30 am -
2 stops15h 14m
Deal found 9/30![American Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 9/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:30 am -
1 stop17h 27m
Mon 10/263:51 pm -
1 stop6h 45m
Deal found 9/28![American Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Thu 10/227:24 pm -
2 stops20h 15m
Thu 10/292:23 pm -
2 stops20h 40m
Deal found 9/29![American Airlines logo]()
$380
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Tue 10/275:30 am -
1 stop6h 45m
Tue 11/31:00 pm -
1 stop6h 49m
Deal found 9/29![United Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Fri 10/305:50 am -
1 stop7h 21m
Sat 10/312:05 am -
2 stops13h 11m
Deal found 9/30![United Airlines logo]()
$343
This American Airlines deal was found by Cheapflights users on 10/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:45 am -
2 stops15h 31m
Wed 11/1111:45 am -
1 stop9h 51m
Deal found 10/1![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Mon 11/96:47 pm -
1 stop17h 58m
Tue 11/175:59 pm -
2 stops17h 25m
Deal found 9/29![American Airlines logo]()
$340
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Fri 11/136:47 pm -
1 stop16h 52m
Wed 11/183:00 pm -
1 stop8h 57m
Deal found 9/30![American Airlines logo]()
$346
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Fri 11/137:35 pm -
1 stop16h 24m
Fri 11/202:55 pm -
1 stop8h 26m
Deal found 9/29![United Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Fri 11/136:47 pm -
1 stop17h 58m
Fri 11/204:25 pm -
2 stops19h 13m
Deal found 9/29![American Airlines logo]()
$364
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Mon 11/166:47 pm -
2 stops15h 57m
Sat 11/212:22 pm -
1 stop9h 33m
Deal found 9/30![American Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Mon 11/236:47 pm -
2 stops20h 11m
Wed 12/22:02 pm -
1 stop8h 38m
Deal found 9/30![American Airlines logo]()
$370
One-way flights from Maine to CaribbeanSearch for one-way flight options from Maine to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 3, 2026.
Search for one-way flight options from Maine to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 3, 2026.
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Mon 1/257:43 pm -
1 stop16h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![United Airlines logo]()
$110
This American Airlines deal was found by Cheapflights users on 10/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/257:00 am -
2 stops15h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![American Airlines logo]()
$120
This JetBlue deal was found by Cheapflights users on 10/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:30 am -
1 stop9h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![JetBlue logo]()
$135
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Sun 11/156:47 pm -
2 stops19h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$141
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Tue 12/16:47 pm -
2 stops20h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$149
This United Airlines deal was found by Cheapflights users on 10/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:50 am -
1 stop8h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![United Airlines logo]()
$152
This American Airlines deal was found by Cheapflights users on 10/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/215:07 pm -
2 stops18h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![American Airlines logo]()
$153
This United Airlines deal was found by Cheapflights users on 10/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:55 pm -
2 stops17h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![United Airlines logo]()
$158
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Fri 10/235:30 am -
1 stop17h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$158
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Sat 12/53:18 pm -
2 stops23h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$164
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Thu 12/317:44 pm -
1 stop16h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![United Airlines logo]()
$167
This American Airlines deal was found by Cheapflights users on 10/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/53:18 pm -
2 stops18h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![American Airlines logo]()
$175
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 October 3, 2026.
Round-trip from | $316 (United Airlines) |
|---|---|
One-way from | $110 (United Airlines) |
Popular in | April |
Cheapest in | November |
Average price | $362 |
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 7,457,451 searches. Data last updated October 3, 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
Cheapest round-trip
PortlandNassau
PWM Portland - NAS Nassau Intl
PWMNAS
Portland
Mon 1/25
7:43 pm-11:49 am
1 stop16h 06m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$110
PortlandNassau
PWM Portland - NAS Nassau Intl
PWMNAS
Portland
Mon 1/25
7:00 am-10:22 pm
2 stops15h 22m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$120
PortlandOranjestad
PWM Portland - AUA Oranjestad Reina Beatrix
PWMAUA
Portland
Sun 11/15
6:30 am-4:45 pm
1 stop9h 15m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$135
PortlandOranjestad
PWM Portland - AUA Oranjestad Reina Beatrix
PWMAUA
Portland
Sun 11/15
6:47 pm-1:45 pm
1 stop17h 58m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$135
PortlandSimpson Bay
PWM Portland - SXM Simpson Bay Princess Juliana
PWMSXM
Portland
Tue 12/1
6:47 pm-4:26 pm
2 stops20h 39m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$149
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Mon 11/16
6:30 am-1:58 pm
1 stop7h 28m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$152
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Sun 12/6
6:00 am-2:14 pm
1 stop8h 14m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$152
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Tue 3/9
6:00 am-2:40 pm
1 stop7h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Fri 10/23
5:30 am-10:57 pm
1 stop17h 27m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Tue 1/12
3:15 pm-12:36 am
1 stop8h 21m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
Showing 1-10 of 60 resultsSorted by cheapest first
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.
PWM-SJU
PWM-AUA
PWM-NAS
PWM-STT
PWM-SXM
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
USME-0CB
PWM-SJU
PWM-AUA
PWM-NAS
PWM-STT
What is the cheapest month to book a flight from Maine to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Maine to Caribbean (average of $423). Flying from Maine to Caribbean in April is currently the most expensive (average of $730). 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.
How far ahead should I book a flight from Maine to Caribbean?
The best time to book flights from Maine to Caribbean is 36 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.
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.
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
Complete your trip
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Top destinations
Alternative routes for Maine to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Maine to Caribbean by cabin class
Find flights from Maine to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Maine and Caribbean flights
Browse other Maine and Caribbean flight options. Last updated on October 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Caribbean
Find the right flight back to Maine after your stay in Caribbean
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Maine to Caribbean flights
Consider these flights traveling from Maine to Caribbean.
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 7,457,451 searches. Data last updated October 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$405 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$174 | Average$486 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$227 | Average$626 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$296 | Average$652 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$322 | Average$718 | FlexibilityNo cancel fee | On-time63% |