$135+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Oct 11 — Oct 181
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
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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 September 11, 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 September 11, 2026.
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/207:26 pm -
2 stops16h 05m
Mon 10/2612:41 pm -
1 stop9h 55m
Deal found 9/9![American Airlines logo]()
$278
This United Airlines deal was found by Cheapflights users on 9/10. 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 50m
Fri 11/65:50 pm -
1 stop7h 09m
Deal found 9/10![United Airlines logo]()
$296
This United Airlines deal was found by Cheapflights users on 9/8. 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 10/66:00 am -
1 stop7h 45m
Tue 10/137:00 am -
2 stops16h 28m
Deal found 9/8![United Airlines logo]()
$313
This United Airlines deal was found by Cheapflights users on 9/6. 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 10/186:00 am -
1 stop7h 45m
Sat 10/241:05 am -
1 stop7h 55m
Deal found 9/6![United Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 9/10. 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 11/24:15 pm -
1 stop7h 37m
Tue 11/107:00 am -
1 stop9h 16m
Deal found 9/10![Delta logo]()
$316
This United Airlines deal was found by Cheapflights users on 9/10. 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 10/136:00 am -
1 stop7h 45m
Mon 10/191:00 am -
1 stop8h 08m
Deal found 9/10![United Airlines logo]()
$318
This American Airlines deal was found by Cheapflights users on 9/8. 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 10/157:24 pm -
1 stop15h 56m
Wed 10/2112:41 pm -
1 stop9h 55m
Deal found 9/8![American Airlines logo]()
$320
This United Airlines deal was found by Cheapflights users on 9/8. 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 11/125:50 am -
1 stop7h 50m
Mon 11/165:50 pm -
1 stop7h 09m
Deal found 9/8![United Airlines logo]()
$321
This American Airlines deal was found by Cheapflights users on 9/9. 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 11/1812:13 pm -
2 stops23h 02m
Tue 11/244:30 pm -
2 stops19h 08m
Deal found 9/9![American Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 9/7. 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 10/295:30 am -
1 stop7h 05m
Wed 11/47:00 am -
2 stops15h 36m
Deal found 9/7![American Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 9/10. 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 9/10![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 9/6. 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 10/166:00 am -
1 stop7h 45m
Sat 10/171:00 am -
1 stop8h 08m
Deal found 9/6![United Airlines logo]()
$337
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 September 11, 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 September 11, 2026.
This Delta deal was found by Cheapflights users on 9/10. 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 1/242:35 pm -
1 stop8h 20m
Wed 2/33:55 pm -
1 stop7h 28m
Deal found 9/10![Delta logo]()
$316
This United Airlines deal was found by Cheapflights users on 9/10. 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 12/92:55 pm -
1 stop5h 47m
Deal found 9/10![United Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 9/7. 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 -
2 stops19h 23m
Tue 11/175:59 pm -
2 stops17h 38m
Deal found 9/7![American Airlines logo]()
$340
This JetBlue deal was found by Cheapflights users on 9/7. 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 10/266:30 am -
1 stop7h 18m
Fri 10/3011:45 am -
1 stop10h 58m
Deal found 9/7![JetBlue logo]()
$484
This Delta deal was found by Cheapflights users on 9/6. 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
Fri 11/204:58 pm -
1 stop6h 33m
Deal found 9/6![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 9/6. 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 10/166:00 am -
1 stop7h 45m
Sat 10/171:00 am -
1 stop8h 08m
Deal found 9/6![United Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 9/10. 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 12/66:47 pm -
2 stops19h 22m
Thu 12/105:25 pm -
2 stops18h 12m
Deal found 9/10![American Airlines logo]()
$360
This United Airlines deal was found by Cheapflights users on 9/10. 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 10/136:00 am -
1 stop7h 45m
Tue 10/207:00 am -
2 stops16h 28m
Deal found 9/10![United Airlines logo]()
$338
This Delta deal was found by Cheapflights users on 9/6. 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 11/214:58 pm -
1 stop6h 33m
Deal found 9/6![Delta logo]()
$343
This Delta deal was found by Cheapflights users on 9/6. 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 12/96:00 am -
1 stop9h 36m
Sat 12/121:22 pm -
1 stop10h 59m
Deal found 9/6![Delta logo]()
$343
This American Airlines deal was found by Cheapflights users on 9/7. 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 10/295:30 am -
1 stop7h 05m
Wed 11/42:55 pm -
1 stop9h 02m
Deal found 9/7![American Airlines logo]()
$383
This United Airlines deal was found by Cheapflights users on 9/10. 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 1/233:15 pm -
1 stop8h 21m
Fri 2/52:05 am -
1 stop7h 14m
Deal found 9/10![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 9/7. 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 11/146:00 am -
1 stop5h 53m
Sat 11/214:58 pm -
1 stop6h 33m
Deal found 9/7![Delta logo]()
$360
This American Airlines deal was found by Cheapflights users on 9/9. 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 stops18h 52m
Deal found 9/9![American Airlines logo]()
$402
This United Airlines deal was found by Cheapflights users on 9/6. 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 9/286:00 am -
1 stop7h 45m
Sun 10/41:00 am -
1 stop8h 08m
Deal found 9/6![United Airlines logo]()
$377
This JetBlue deal was found by Cheapflights users on 9/10. 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 10m
Thu 11/124:45 pm -
1 stop7h 58m
Deal found 9/10![JetBlue logo]()
$523
This Delta deal was found by Cheapflights users on 9/7. 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 2/16:30 am -
1 stop9h 20m
Mon 2/87:00 am -
1 stop7h 53m
Deal found 9/7![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 9/10. 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 1/297:00 am -
1 stop28h 59m
Wed 2/171:50 pm -
1 stop9h 09m
Deal found 9/10![American Airlines logo]()
$406
This United Airlines deal was found by Cheapflights users on 9/8. 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 10/66:00 am -
2 stops14h 38m
Mon 10/121:00 am -
2 stops9h 02m
Deal found 9/8![United Airlines logo]()
$381
This American Airlines deal was found by Cheapflights users on 9/6. 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 10/97:26 pm -
2 stops18h 28m
Sat 10/175:13 pm -
2 stops16h 50m
Deal found 9/6![American Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 9/10. 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 1/266:30 am -
1 stop9h 20m
Fri 1/296:05 pm -
1 stop6h 44m
Deal found 9/10![Delta logo]()
$384
This United Airlines deal was found by Cheapflights users on 9/8. 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
Wed 10/281:05 am -
1 stop7h 55m
Deal found 9/8![United Airlines logo]()
$386
This United Airlines deal was found by Cheapflights users on 9/10. 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 11/115:50 am -
1 stop8h 16m
Sun 11/154:18 pm -
1 stop8h 03m
Deal found 9/10![United Airlines logo]()
$390
This American Airlines deal was found by Cheapflights users on 9/6. 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 stops8h 42m
Sat 10/243:02 pm -
2 stops18h 42m
Deal found 9/6![American Airlines logo]()
$431
This Delta deal was found by Cheapflights users on 9/8. 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 12/74:00 pm -
2 stops20h 25m
Thu 12/101:40 pm -
1 stop10h 13m
Deal found 9/8![Delta logo]()
$402
This United Airlines deal was found by Cheapflights users on 9/9. 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 10/246:00 am -
1 stop7h 33m
Sat 10/311:05 pm -
1 stop5h 57m
Deal found 9/9![United Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 9/8. 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 12/35:19 pm -
2 stops19h 06m
Mon 12/141:40 pm -
1 stop10h 13m
Deal found 9/8![Delta logo]()
$402
This American Airlines deal was found by Cheapflights users on 9/10. 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 11/1112:50 pm -
2 stops20h 29m
Sun 11/156:00 am -
2 stops17h 57m
Deal found 9/10![American Airlines logo]()
$449
This United Airlines deal was found by Cheapflights users on 9/9. 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 10/255:50 am -
1 stop8h 24m
Sun 11/12:54 pm -
2 stops18h 06m
Deal found 9/9![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 9/7. 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 2/26:00 am -
1 stop9h 25m
Tue 2/92:00 pm -
1 stop9h 49m
Deal found 9/7![Delta logo]()
$405
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated September 11, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/8. 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 10/66:00 am -
1 stop7h 45m
Tue 10/137:00 am -
2 stops16h 28m
Deal found 9/8![United Airlines logo]()
$313
This United Airlines deal was found by Cheapflights users on 9/10. 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 10/136:00 am -
1 stop7h 45m
Mon 10/191:00 am -
1 stop8h 08m
Deal found 9/10![United Airlines logo]()
$318
This United Airlines deal was found by Cheapflights users on 9/8. 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 10/146:00 am -
1 stop7h 45m
Thu 10/224:55 pm -
1 stop7h 04m
Deal found 9/8![United Airlines logo]()
$345
This American Airlines deal was found by Cheapflights users on 9/8. 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 10/157:24 pm -
1 stop15h 56m
Wed 10/2112:41 pm -
1 stop9h 55m
Deal found 9/8![American Airlines logo]()
$320
This United Airlines deal was found by Cheapflights users on 9/6. 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 10/166:00 am -
1 stop7h 45m
Sat 10/171:00 am -
1 stop8h 08m
Deal found 9/6![United Airlines logo]()
$337
This United Airlines deal was found by Cheapflights users on 9/6. 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 10/186:00 am -
1 stop7h 45m
Sat 10/241:05 am -
1 stop7h 55m
Deal found 9/6![United Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/207:26 pm -
2 stops16h 05m
Mon 10/2612:21 pm -
2 stops11h 15m
Deal found 9/9![American Airlines logo]()
$278
This United Airlines deal was found by Cheapflights users on 9/10. 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 10/206:00 am -
1 stop7h 45m
Sun 10/251:05 am -
1 stop7h 55m
Deal found 9/10![United Airlines logo]()
$316
This American Airlines deal was found by Cheapflights users on 9/10. 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 -
1 stop15h 56m
Mon 10/2610:36 am -
2 stops13h 00m
Deal found 9/10![American Airlines logo]()
$340
This United Airlines deal was found by Cheapflights users on 9/9. 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 10/246:00 am -
1 stop7h 33m
Sat 10/311:05 pm -
1 stop5h 57m
Deal found 9/9![United Airlines logo]()
$395
This American Airlines deal was found by Cheapflights users on 9/7. 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 10/295:30 am -
1 stop7h 05m
Wed 11/47:00 am -
2 stops15h 36m
Deal found 9/7![American Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 9/10. 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 50m
Fri 11/65:50 pm -
1 stop7h 09m
Deal found 9/10![United Airlines logo]()
$296
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 September 11, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This American Airlines deal was found by Cheapflights users on 9/10. 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 9/10![American Airlines logo]()
$135
This American Airlines deal was found by Cheapflights users on 9/10. 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 9/10![American Airlines logo]()
$139
This United Airlines deal was found by Cheapflights users on 9/6. 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 10/175:15 am -
1 stop7h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![United Airlines logo]()
$148
This Southwest deal was found by Cheapflights users on 9/9. 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 11/25:20 am -
2 stops10h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Southwest logo]()
$181
This United Airlines deal was found by Cheapflights users on 9/10. 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 10/285:30 am -
2 stops11h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![United Airlines logo]()
$183
This American Airlines deal was found by Cheapflights users on 9/7. 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 9/265:18 pm -
2 stops18h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$184
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/286:00 am -
1 stop6h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$188
This United Airlines deal was found by Cheapflights users on 9/7. 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 10/196:00 am -
1 stop7h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![United Airlines logo]()
$193
This American Airlines deal was found by Cheapflights users on 9/10. 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 12/106:47 pm -
2 stops20h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$199
This United Airlines deal was found by Cheapflights users on 9/7. 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 9/296:00 am -
1 stop6h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![United Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/197:00 am -
3 stops33h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$223
This Delta deal was found by Cheapflights users on 9/10. 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.
Fri 2/192:35 pm -
1 stop8h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$226
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 September 11, 2026.
Round-trip from | $278 (American Airlines) |
|---|---|
One-way from | $135 (American Airlines) |
Popular in | April |
Cheapest in | November |
Average price | $353 |
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 September 11, 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
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
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
$139
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Mon 11/2
4:15 pm-12:52 am
1 stop7h 37m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$148
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Sat 10/17
5:15 am-12:34 pm
1 stop7h 19m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$148
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Mon 11/2
5:20 am-5:00 pm
2 stops10h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$181
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Wed 10/28
5:30 am-3:30 pm
2 stops11h 00m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$183
Quickest round-trip
PortlandGeorge Town
PWM Portland - GCM George Town Owen Roberts Intl
PWMGCM
Portland
Wed 10/28
6:00 am-11:30 am
1 stop6h 30m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$188
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Mon 10/19
6:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$193
PortlandPunta Cana
PWM Portland - PUJ Punta Cana
PWMPUJ
Portland
Thu 12/10
6:47 pm-3:51 pm
2 stops20h 04m
Punta Cana
Wed 12/31
12:00 am-11:30 pm
Nonstop0h 00m
$199
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Tue 9/29
6:00 am-11:43 am
1 stop6h 43m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$202
Showing 1-10 of 59 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-SJU
PWM-SDQ
PWM-NAS
PWM-AUA
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-SJU
PWM-SDQ
PWM-NAS
PWM-AUA
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 $442). Flying from Portland, Maine to Caribbean in April is currently the most expensive (average of $717). 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 36 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 September 11, 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.
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
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 September 11, 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 September 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$174 | Average$486 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$247 | Average$624 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$275 | Average$423 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$296 | Average$613 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$315 | Average$760 | FlexibilityNo cancel fee | On-time63% |