$109+ Cheap flights from Portland, ME (PWM) 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 12/30. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Nov 20 — Nov 271
Round-trip
1 adult, Economy
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Find cheap flights from Portland 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 Portland to Caribbean
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Cheapest flights from Portland to CaribbeanExplore the most affordable flight options available from Portland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 21, 2026.
Explore the most affordable flight options available from Portland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 21, 2026.
This Delta deal was found by Cheapflights users on 10/18. 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 stop7h 50m
Fri 11/201:15 pm -
1 stop11h 04m
Deal found 10/18![Delta logo]()
$328
This United Airlines deal was found by Cheapflights users on 10/19. 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 12/37:00 am -
1 stop6h 48m
Thu 12/1012:55 pm -
1 stop8h 17m
Deal found 10/19![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 10/21. 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.
Sat 12/124:00 pm -
1 stop6h 58m
Fri 12/186:10 pm -
1 stop7h 11m
Deal found 10/21![Delta logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 12/57:12 pm -
1 stop14h 11m
Sat 12/123:27 pm -
2 stops50h 28m
Deal found 10/19![Multiple Airlines logo]()
$358
This American Airlines deal was found by Cheapflights users on 10/18. 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 stops17h 35m
Tue 12/83:13 pm -
2 stops20h 17m
Deal found 10/18![American Airlines logo]()
$360
This American Airlines deal was found by Cheapflights users on 10/18. 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 12/26:00 am -
2 stops15h 35m
Tue 12/88:30 am -
1 stop15h 49m
Deal found 10/18![American Airlines logo]()
$361
This Delta deal was found by Cheapflights users on 10/20. 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.
Wed 11/186:00 am -
1 stop9h 33m
Sun 11/223:15 pm -
1 stop8h 16m
Deal found 10/20![Delta logo]()
$368
This American Airlines deal was found by Cheapflights users on 10/18. 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 11/176:47 pm -
2 stops21h 00m
Sun 11/224:25 pm -
2 stops19h 13m
Deal found 10/18![American Airlines logo]()
$387
This American Airlines deal was found by Cheapflights users on 10/21. 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 10/21![American Airlines logo]()
$388
This United Airlines deal was found by Cheapflights users on 10/20. 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 12/123:41 pm -
1 stop7h 55m
Thu 12/177:40 am -
2 stops16h 05m
Deal found 10/20![United Airlines logo]()
$401
This United Airlines deal was found by Cheapflights users on 10/19. 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 12/57:00 am -
1 stop6h 40m
Sat 12/128:05 am -
1 stop7h 32m
Deal found 10/19![United Airlines logo]()
$402
This American Airlines deal was found by Cheapflights users on 10/21. 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 12/56:44 pm -
1 stop18h 15m
Sat 12/125:59 pm -
2 stops17h 31m
Deal found 10/21![American Airlines logo]()
$404
Best flights from Portland to CaribbeanDiscover carefully curated flight deals from Portland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 21, 2026.
Discover carefully curated flight deals from Portland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 21, 2026.
This Delta deal was found by Cheapflights users on 10/18. 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 stop7h 50m
Fri 11/201:15 pm -
1 stop11h 04m
Deal found 10/18![Delta logo]()
$328
This United Airlines deal was found by Cheapflights users on 10/19. 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 12/37:00 am -
1 stop6h 48m
Thu 12/1012:55 pm -
1 stop8h 17m
Deal found 10/19![United Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 10/19. 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 2/236:03 pm -
2 stops21h 17m
Wed 3/35:12 pm -
2 stops18h 20m
Deal found 10/19![American Airlines logo]()
$360
This JetBlue deal was found by Cheapflights users on 10/20. 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 11/36:30 am -
1 stop9h 25m
Sat 11/710:00 am -
1 stop10h 25m
Deal found 10/20![JetBlue logo]()
$560
This Southwest deal was found by Cheapflights users on 10/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:45 pm -
2 stops11h 05m
Sun 11/155:35 am -
2 stops11h 55m
Deal found 10/20![Southwest logo]()
$626
This Delta deal was found by Cheapflights users on 10/19. 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 -
2 stops21h 15m
Wed 1/204:25 pm -
2 stops19h 28m
Deal found 10/19![Delta logo]()
$333
This Delta deal was found by Cheapflights users on 10/19. 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 1/186:00 am -
1 stop7h 30m
Thu 1/212:55 pm -
2 stops20h 06m
Deal found 10/19![Delta logo]()
$333
This United Airlines deal was found by Cheapflights users on 10/20. 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 12/47:55 pm -
1 stop15h 54m
Fri 12/112:55 pm -
1 stop5h 47m
Deal found 10/20![United Airlines logo]()
$368
This American Airlines deal was found by Cheapflights users on 10/20. 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 1/305:39 pm -
2 stops22h 10m
Sat 2/64:19 pm -
2 stops19h 06m
Deal found 10/20![American Airlines logo]()
$404
This United Airlines deal was found by Cheapflights users on 10/20. 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 1/307:45 pm -
2 stops19h 55m
Sat 2/66:00 pm -
1 stop16h 04m
Deal found 10/20![United Airlines logo]()
$404
This American Airlines deal was found by Cheapflights users on 10/21. 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 12/56:44 pm -
2 stops19h 25m
Sat 12/125:59 pm -
2 stops19h 03m
Deal found 10/21![American Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 10/19. 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 1/176:00 am -
1 stop9h 15m
Sun 1/246:10 pm -
2 stops16h 51m
Deal found 10/19![Delta logo]()
$373
This United Airlines deal was found by Cheapflights users on 10/20. 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 12/47:55 pm -
2 stops18h 44m
Fri 12/111:25 pm -
1 stop7h 17m
Deal found 10/20![United Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 10/19. 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.
Sat 1/166:30 am -
1 stop6h 25m
Fri 1/221:15 pm -
2 stops21h 46m
Deal found 10/19![Delta logo]()
$373
This American Airlines deal was found by Cheapflights users on 10/18. 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 11/276:47 pm -
1 stop17h 19m
Fri 12/118:15 am -
2 stops14h 33m
Deal found 10/18![American Airlines logo]()
$422
This JetBlue deal was found by Cheapflights users on 10/20. 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 11/36:30 am -
1 stop9h 25m
Mon 11/910:00 am -
1 stop10h 25m
Deal found 10/20![JetBlue logo]()
$560
This United Airlines deal was found by Cheapflights users on 10/20. 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 10/20![United Airlines logo]()
$436
This American Airlines deal was found by Cheapflights users on 10/20. 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 27m
Sat 12/128:15 am -
2 stops15h 04m
Deal found 10/20![American Airlines logo]()
$453
This JetBlue deal was found by Cheapflights users on 10/17. 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 10/276:30 am -
1 stop9h 25m
Thu 10/293:20 pm -
1 stop8h 23m
Deal found 10/17![JetBlue logo]()
$584
This Southwest deal was found by Cheapflights users on 10/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/211:10 pm -
2 stops11h 35m
Fri 12/256:40 am -
1 stop9h 05m
Deal found 10/16![Southwest logo]()
$643
This United Airlines deal was found by Cheapflights users on 10/21. 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 11/79:46 am -
1 stop6h 33m
Sat 11/145:21 pm -
1 stop16h 46m
Deal found 10/21![United Airlines logo]()
$455
This American Airlines deal was found by Cheapflights users on 10/18. 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 1/294:47 pm -
2 stops19h 01m
Mon 2/88:25 am -
2 stops13h 04m
Deal found 10/18![American Airlines logo]()
$462
This United Airlines deal was found by Cheapflights users on 10/18. 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 1/106:00 am -
1 stop6h 32m
Sat 1/162:05 am -
1 stop7h 59m
Deal found 10/18![United Airlines logo]()
$459
This American Airlines deal was found by Cheapflights users on 10/17. 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 4/56:03 pm -
2 stops19h 12m
Thu 4/152:05 pm -
2 stops20h 13m
Deal found 10/17![American Airlines logo]()
$468
This Delta deal was found by Cheapflights users on 10/20. 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.
Tue 2/166:00 am -
1 stop9h 15m
Tue 2/235:25 pm -
1 stop7h 24m
Deal found 10/20![Delta logo]()
$559
This United Airlines deal was found by Cheapflights users on 10/17. 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.
Wed 12/97:55 pm -
2 stops20h 35m
Mon 12/145:45 pm -
2 stops21h 53m
Deal found 10/17![United Airlines logo]()
$462
This American Airlines deal was found by Cheapflights users on 10/19. 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 1/115:00 am -
2 stops16h 51m
Sat 1/163:51 pm -
2 stops19h 34m
Deal found 10/19![American Airlines logo]()
$503
This United Airlines deal was found by Cheapflights users on 10/20. 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 11/79:46 am -
1 stop6h 49m
Sun 11/155:45 pm -
2 stops20h 31m
Deal found 10/20![United Airlines logo]()
$489
This American Airlines deal was found by Cheapflights users on 10/21. 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 3/266:03 pm -
2 stops21h 01m
Fri 4/23:10 pm -
2 stops18h 22m
Deal found 10/21![American Airlines logo]()
$516
This United Airlines deal was found by Cheapflights users on 10/17. 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 1/57:50 pm -
1 stop16h 23m
Tue 1/122:54 pm -
2 stops23h 39m
Deal found 10/17![United Airlines logo]()
$508
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated October 21, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated October 21, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/18. 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 10/297:26 pm -
2 stops19h 29m
Mon 11/24:53 pm -
2 stops17h 57m
Deal found 10/18![American Airlines logo]()
$405
This Delta deal was found by Cheapflights users on 10/20. 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.
Sat 10/316:01 am -
1 stop10h 47m
Thu 11/124:20 pm -
1 stop8h 11m
Deal found 10/20![Delta logo]()
$424
This American Airlines deal was found by Cheapflights users on 10/21. 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 stop7h 33m
Wed 11/112:18 pm -
1 stop7h 18m
Deal found 10/21![American Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 10/18. 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 11/86:47 pm -
2 stops20h 44m
Thu 11/123:41 pm -
2 stops19h 56m
Deal found 10/18![American Airlines logo]()
$420
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/135:45 am -
1 stop14h 44m
Mon 11/167:05 am -
1 stop15h 31m
Deal found 10/21![American Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 10/18. 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 stop7h 50m
Fri 11/201:15 pm -
1 stop11h 04m
Deal found 10/18![Delta logo]()
$328
This American Airlines deal was found by Cheapflights users on 10/21. 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 10/21![American Airlines logo]()
$388
This American Airlines deal was found by Cheapflights users on 10/18. 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 11/176:47 pm -
2 stops21h 00m
Sun 11/224:25 pm -
2 stops19h 13m
Deal found 10/18![American Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 10/20. 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.
Wed 11/186:00 am -
1 stop9h 33m
Sun 11/223:15 pm -
1 stop8h 16m
Deal found 10/20![Delta logo]()
$368
This American Airlines deal was found by Cheapflights users on 10/20. 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 11/187:10 am -
1 stop6h 05m
Sun 11/2211:49 am -
1 stop10h 57m
Deal found 10/20![American Airlines logo]()
$434
This American Airlines deal was found by Cheapflights users on 10/17. 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 11/196:47 pm -
2 stops20h 37m
Sun 11/223:26 pm -
2 stops20h 12m
Deal found 10/17![American Airlines logo]()
$425
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/276:47 pm -
1 stop17h 19m
Fri 12/113:45 pm -
2 stops17h 43m
Deal found 10/21![American Airlines logo]()
$422
One-way flights from Portland to CaribbeanSearch for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 21, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 21, 2026.
This Delta deal was found by Cheapflights users on 10/21. 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.
Wed 12/305:35 am -
1 stop7h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$109
This American Airlines deal was found by Cheapflights users on 10/18. 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 -
1 stop17h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![American Airlines logo]()
$145
This Delta deal was found by Cheapflights users on 10/21. 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.
Thu 12/315:35 am -
1 stop7h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$150
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Wed 12/307:44 pm -
1 stop16h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![United Airlines logo]()
$162
This Delta deal was found by Cheapflights users on 10/19. 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 12/76:00 am -
1 stop10h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$167
This American Airlines deal was found by Cheapflights users on 10/17. 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 12/87:01 am -
2 stops13h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![American Airlines logo]()
$176
This American Airlines deal was found by Cheapflights users on 10/18. 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 1/15:30 am -
1 stop7h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![American Airlines logo]()
$178
This United Airlines deal was found by Cheapflights users on 10/20. 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 2/194:48 pm -
2 stops12h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![United Airlines logo]()
$178
This American Airlines deal was found by Cheapflights users on 10/19. 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 3/317:14 am -
2 stops12h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![American Airlines logo]()
$181
This United Airlines deal was found by Cheapflights users on 10/18. 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 12/315:15 am -
1 stop7h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![United Airlines logo]()
$193
This American Airlines deal was found by Cheapflights users on 10/21. 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 1/15:30 am -
1 stop5h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$195
This American Airlines deal was found by Cheapflights users on 10/17. 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 12/97:01 am -
1 stop28h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![American Airlines logo]()
$197
Find flight deals from Portland to Caribbean
Keep the following information in mind while searching for Portland to Caribbean flight deals. Data was last updated October 21, 2026.
Round-trip from | $328 (Delta) |
|---|---|
One-way from | $145 (American Airlines) |
Popular in | April |
Cheapest in | May |
Average price | $362 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland 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 21, 2026.
Use the filters below to find and compare flights from Portland 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
Wed 12/30
5:35 am-1:28 pm
1 stop7h 53m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$109
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
$145
PortlandNassau
PWM Portland - NAS Nassau Intl
PWMNAS
Portland
Thu 12/31
5:35 am-1:28 pm
1 stop7h 53m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$150
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Mon 12/7
6:00 am-4:57 pm
1 stop10h 57m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$167
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Tue 12/8
7:01 am-8:01 pm
2 stops13h 00m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$176
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Fri 2/19
4:48 pm-6:15 am
2 stops12h 27m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$178
PortlandSaint Thomas Island
PWM Portland - STT Saint Thomas Island Cyril E King
PWMSTT
Portland
Fri 1/1
5:30 am-1:33 pm
1 stop7h 03m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$178
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Wed 12/9
7:01 am-8:01 pm
2 stops13h 00m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$181
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Wed 3/31
7:14 am-6:48 pm
2 stops12h 34m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$181
PortlandSaint Thomas Island
PWM Portland - STT Saint Thomas Island Cyril E King
PWMSTT
Portland
Thu 12/31
5:15 am-1:56 pm
1 stop7h 41m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$193
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Portland to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Portland with our price prediction graph.
PWM-NAS
PWM-AUA
PWM-STT
PWM-SXM
PWM-GCM
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 Portland to Caribbean
PWM-0CB
PWM-NAS
PWM-AUA
PWM-STT
PWM-SXM
What is the cheapest month to book a flight from Portland, Maine to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Caribbean (average of $410). Flying from Portland, Maine to Caribbean in April is currently the most expensive (average of $725). 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 Portland, Maine to Caribbean?
Booking 37 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland, Maine to Caribbean. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated October 21, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Portland to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.4
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Related info for your journey
Find useful and relevant information for your journey from Portland to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Portland 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 Portland to Caribbean by cabin class
Find flights from Portland to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Caribbean flights
Browse other Portland and Caribbean flight options. Last updated on October 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Portland to Caribbean flights
Consider these flights traveling from Portland to Caribbean.
Top 5 airlines flying from Portland to Caribbean
Discover the top 5 airlines that operate flights from Portland 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 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$174 | Average$502 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$247 | Average$604 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$298 | Average$615 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$322 | Average$718 | FlexibilityNo cancel fee | On-time63% |