$144+ Cheap flights from Portland, ME (PWM) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Aug 23 — Aug 301
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Caribbean with Cheapflights
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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 July 24, 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 July 24, 2026.
This American Airlines deal was found by Cheapflights users on 7/22. 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 10/294:40 pm
PWM
- STT
2 stops20h 18m
American Airlines
Tue 11/32:01 pm
STT
- PWM
1 stop8h 35m
American Airlines
Deal found 7/22![American Airlines logo]()
$280
This American Airlines deal was found by Cheapflights users on 7/22. 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 10/284:54 pm
PWM
- STT
2 stops20h 04m
American Airlines
Sun 11/14:53 pm
STT
- PWM
2 stops18h 44m
American Airlines
Deal found 7/22![American Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 7/22. 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 9/196:00 am
PWM
- SJU
1 stop10h 49m
Delta
Sat 9/261:16 pm
SJU
- PWM
1 stop10h 40m
Delta
Deal found 7/22![Delta logo]()
$342
This Delta deal was found by Cheapflights users on 7/21. 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.
Mon 11/306:00 am
PWM
- MBJ
1 stop8h 15m
Delta
Sat 12/52:20 pm
MBJ
- PWM
1 stop8h 03m
Delta
Deal found 7/21![Delta logo]()
$352
This Southwest deal was found by Cheapflights users on 7/23. 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.
Sun 11/15:20 am
PWM
- SJU
2 stops10h 40m
Southwest
Fri 11/65:35 am
SJU
- PWM
2 stops11h 55m
Southwest
Deal found 7/23![Southwest logo]()
$353
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Tue 8/188:00 am
PWM
- SJU
2 stops16h 56m
Multiple Airlines
Tue 8/255:37 pm
SJU
- PWM
1 stop24h 21m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$355
This Delta deal was found by Cheapflights users on 7/21. 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.
Mon 11/306:00 am
PWM
- MBJ
1 stop6h 55m
Delta
Wed 12/22:20 pm
MBJ
- PWM
2 stops21h 33m
Delta
Deal found 7/21![Delta logo]()
$357
This American Airlines deal was found by Cheapflights users on 7/19. 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.
Thu 10/294:40 pm
PWM
- STT
2 stops20h 18m
American Airlines
Mon 11/22:01 pm
STT
- PWM
1 stop8h 35m
American Airlines
Deal found 7/19![American Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 7/20. 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 8/246:03 am
PWM
- SJU
1 stop8h 41m
United Airlines
Fri 8/284:55 pm
SJU
- PWM
1 stop7h 04m
United Airlines
Deal found 7/20![United Airlines logo]()
$360
This United Airlines deal was found by Cheapflights users on 7/19. 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 11/76:00 am
PWM
- SJU
2 stops14h 00m
United Airlines
Sat 11/148:05 am
SJU
- PWM
1 stop7h 28m
United Airlines
Deal found 7/19![United Airlines logo]()
$361
This United Airlines deal was found by Cheapflights users on 7/20. 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 9/265:15 am
PWM
- STT
1 stop7h 43m
United Airlines
Sat 10/34:45 pm
STT
- PWM
1 stop7h 14m
United Airlines
Deal found 7/20![United Airlines logo]()
$368
This United Airlines deal was found by Cheapflights users on 7/20. 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.
Tue 10/275:30 am
PWM
- STT
1 stop7h 26m
United Airlines
Mon 11/23:00 pm
STT
- PWM
1 stop9h 23m
United Airlines
Deal found 7/20![United Airlines logo]()
$376
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 July 24, 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 July 24, 2026.
This United Airlines deal was found by Cheapflights users on 7/21. 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.
Tue 10/205:15 am
PWM
- SJU
1 stop7h 19m
United Airlines
Mon 10/267:25 am
SJU
- PWM
2 stops15h 58m
United Airlines
Deal found 7/21![United Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 7/22. 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 9/196:00 am
PWM
- SJU
1 stop10h 49m
Delta
Sat 9/261:16 pm
SJU
- PWM
1 stop10h 40m
Delta
Deal found 7/22![Delta logo]()
$342
This American Airlines deal was found by Cheapflights users on 7/22. 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 10/35:06 pm
PWM
- SXM
2 stops20h 17m
American Airlines
Sat 10/102:23 pm
SXM
- PWM
2 stops20h 33m
American Airlines
Deal found 7/22![American Airlines logo]()
$380
This Southwest deal was found by Cheapflights users on 7/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:20 am
PWM
- SXM
1 stop8h 00m
Southwest
Fri 11/134:40 pm
SXM
- PWM
1 stop8h 10m
Southwest
Deal found 7/18![Southwest logo]()
$462
This JetBlue deal was found by Cheapflights users on 7/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:30 am
PWM
- KIN
1 stop10h 28m
JetBlue
Fri 10/3010:09 am
KIN
- PWM
1 stop12h 34m
JetBlue
Deal found 7/21![JetBlue logo]()
$515
This Delta deal was found by Cheapflights users on 7/21. 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.
Tue 10/204:15 pm
PWM
- SJU
1 stop7h 41m
Delta
Mon 10/267:00 am
SJU
- PWM
1 stop6h 53m
Delta
Deal found 7/21![Delta logo]()
$342
This United Airlines deal was found by Cheapflights users on 7/20. 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.
Tue 10/275:30 am
PWM
- STT
1 stop7h 26m
United Airlines
Fri 10/302:00 pm
STT
- PWM
1 stop9h 23m
United Airlines
Deal found 7/20![United Airlines logo]()
$376
This American Airlines deal was found by Cheapflights users on 7/19. 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.
Sat 10/247:24 pm
PWM
- NAS
1 stop15h 54m
American Airlines
Sat 10/312:23 pm
NAS
- PWM
1 stop8h 13m
American Airlines
Deal found 7/19![American Airlines logo]()
$380
This Delta deal was found by Cheapflights users on 7/19. 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 11/166:00 am
PWM
- NAS
1 stop7h 30m
Delta
Fri 11/201:00 pm
NAS
- PWM
1 stop10h 49m
Delta
Deal found 7/19![Delta logo]()
$380
This United Airlines deal was found by Cheapflights users on 7/21. 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 9/266:00 am
PWM
- SXM
1 stop6h 33m
United Airlines
Sat 10/101:35 pm
SXM
- PWM
1 stop9h 53m
United Airlines
Deal found 7/21![United Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 7/21. 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 9/265:18 pm
PWM
- SXM
2 stops20h 05m
American Airlines
Sat 10/102:50 pm
SXM
- PWM
2 stops20h 06m
American Airlines
Deal found 7/21![American Airlines logo]()
$402
This Delta deal was found by Cheapflights users on 7/21. 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 10/246:00 am
PWM
- NAS
1 stop9h 25m
Delta
Sat 10/3112:55 pm
NAS
- PWM
1 stop10h 54m
Delta
Deal found 7/21![Delta logo]()
$380
This United Airlines deal was found by Cheapflights users on 7/19. 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 10/245:15 am
PWM
- STT
1 stop7h 43m
United Airlines
Fri 10/3012:07 pm
STT
- PWM
2 stops11h 16m
United Airlines
Deal found 7/19![United Airlines logo]()
$405
This American Airlines deal was found by Cheapflights users on 7/22. 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 9/217:00 am
PWM
- PLS
1 stop7h 17m
American Airlines
Thu 10/13:19 pm
PLS
- PWM
1 stop6h 54m
American Airlines
Deal found 7/22![American Airlines logo]()
$423
This Delta deal was found by Cheapflights users on 7/22. 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 8/286:00 am
PWM
- PUJ
1 stop6h 35m
Delta
Sat 9/51:10 pm
PUJ
- PWM
1 stop8h 21m
Delta
Deal found 7/22![Delta logo]()
$390
This JetBlue deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:41 am
PWM
- PLS
1 stop6h 12m
JetBlue
Wed 9/22:13 pm
PLS
- PWM
1 stop10h 12m
JetBlue
Deal found 7/22![JetBlue logo]()
$543
This United Airlines deal was found by Cheapflights users on 7/20. 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 10/265:30 am
PWM
- STT
1 stop7h 26m
United Airlines
Thu 10/292:00 pm
STT
- PWM
1 stop9h 23m
United Airlines
Deal found 7/20![United Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 7/22. 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 9/206:00 am
PWM
- PLS
2 stops8h 26m
American Airlines
Thu 10/13:19 pm
PLS
- PWM
1 stop6h 54m
American Airlines
Deal found 7/22![American Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 7/23. 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 10/224:15 pm
PWM
- SJU
1 stop7h 41m
Delta
Mon 10/261:06 pm
SJU
- PWM
1 stop10h 43m
Delta
Deal found 7/23![Delta logo]()
$403
This American Airlines deal was found by Cheapflights users on 7/19. 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 8/186:09 pm
PWM
- PLS
2 stops20h 04m
American Airlines
Tue 8/251:05 pm
PLS
- PWM
2 stops21h 26m
American Airlines
Deal found 7/19![American Airlines logo]()
$428
This United Airlines deal was found by Cheapflights users on 7/20. 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 9/196:06 am
PWM
- SJU
2 stops14h 32m
United Airlines
Sat 9/261:25 pm
SJU
- PWM
2 stops10h 34m
United Airlines
Deal found 7/20![United Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 7/21. 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.
Mon 8/172:14 pm
PWM
- SJU
1 stop8h 15m
Delta
Fri 8/215:50 pm
SJU
- PWM
1 stop7h 09m
Delta
Deal found 7/21![Delta logo]()
$403
This United Airlines deal was found by Cheapflights users on 7/19. 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 11/76:00 am
PWM
- SJU
2 stops14h 00m
United Airlines
Sat 11/147:40 am
SJU
- PWM
2 stops14h 35m
United Airlines
Deal found 7/19![United Airlines logo]()
$432
This American Airlines deal was found by Cheapflights users on 7/23. 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 11/266:47 pm
PWM
- STT
2 stops20h 11m
American Airlines
Wed 12/24:22 pm
STT
- PWM
2 stops20h 49m
American Airlines
Deal found 7/23![American Airlines logo]()
$438
This Cheapflightsfares deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:00 am
PWM
- AUA
1 stop10h 00m
JetBlue
Sun 10/183:50 pm
AUA
- PWM
1 stop8h 02m
JetBlue
Deal found 7/23![JetBlue logo]()
$666
This Delta deal was found by Cheapflights users on 7/22. 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 9/56:00 am
PWM
- NAS
2 stops10h 39m
Delta
Sat 9/121:06 pm
NAS
- PWM
1 stop10h 50m
Delta
Deal found 7/22![Delta logo]()
$424
This United Airlines deal was found by Cheapflights users on 7/21. 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 9/195:15 am
PWM
- SJU
1 stop7h 19m
United Airlines
Wed 9/237:00 am
SJU
- PWM
2 stops16h 32m
United Airlines
Deal found 7/21![United Airlines logo]()
$432
This JetBlue deal was found by Cheapflights users on 7/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:00 am
PWM
- AUA
1 stop8h 53m
JetBlue
Wed 9/21:30 pm
AUA
- PWM
1 stop10h 55m
JetBlue
Deal found 7/19![JetBlue logo]()
$682
This American Airlines deal was found by Cheapflights users on 7/21. 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.
Tue 8/185:30 am
PWM
- AUA
1 stop7h 20m
American Airlines
Tue 8/252:59 pm
AUA
- PWM
2 stops19h 32m
American Airlines
Deal found 7/21![American Airlines logo]()
$466
This United Airlines deal was found by Cheapflights users on 7/21. 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.
Wed 1/65:06 pm
PWM
- AUA
2 stops19h 44m
United Airlines
Wed 1/134:25 pm
AUA
- PWM
1 stop16h 54m
United Airlines
Deal found 7/21![United Airlines logo]()
$439
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated July 24, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated July 24, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 7/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:25 pm
PWM
- SJU
1 stop9h 34m
JetBlue
Sat 8/155:01 am
SJU
- PWM
1 stop8h 44m
JetBlue
Deal found 7/21![JetBlue logo]()
$459
This Expedia deal was found by Cheapflights users on 7/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/142:45 pm
PWM
- SJU
1 stop9h 28m
JetBlue
Tue 8/188:30 pm
SJU
- PWM
2 stops17h 15m
JetBlue
Deal found 7/21![JetBlue logo]()
$439
This Delta deal was found by Cheapflights users on 7/21. 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.
Fri 8/146:00 am
PWM
- SJU
1 stop10h 33m
Delta
Tue 8/185:50 pm
SJU
- PWM
1 stop7h 09m
Delta
Deal found 7/21![Delta logo]()
$464
This Delta deal was found by Cheapflights users on 7/21. 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.
Mon 8/172:14 pm
PWM
- SJU
1 stop8h 15m
Delta
Fri 8/215:50 pm
SJU
- PWM
1 stop7h 09m
Delta
Deal found 7/21![Delta logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Tue 8/188:00 am
PWM
- SJU
2 stops16h 56m
Multiple Airlines
Tue 8/255:37 pm
SJU
- PWM
1 stop24h 21m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$355
This American Airlines deal was found by Cheapflights users on 7/19. 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 8/187:28 am
PWM
- SJU
1 stop14h 56m
American Airlines
Tue 8/257:30 am
SJU
- PWM
1 stop14h 30m
American Airlines
Deal found 7/19![American Airlines logo]()
$418
This American Airlines deal was found by Cheapflights users on 7/19. 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 8/186:09 pm
PWM
- PLS
2 stops20h 04m
American Airlines
Tue 8/251:27 pm
PLS
- PWM
1 stop8h 33m
American Airlines
Deal found 7/19![American Airlines logo]()
$428
This American Airlines deal was found by Cheapflights users on 7/21. 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.
Tue 8/185:30 am
PWM
- AUA
1 stop7h 20m
American Airlines
Tue 8/252:59 pm
AUA
- PWM
2 stops19h 32m
American Airlines
Deal found 7/21![American Airlines logo]()
$466
This Delta deal was found by Cheapflights users on 7/21. 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 8/202:53 pm
PWM
- SJU
1 stop8h 59m
Delta
Thu 8/2712:56 pm
SJU
- PWM
1 stop10h 17m
Delta
Deal found 7/21![Delta logo]()
$342
This American Airlines deal was found by Cheapflights users on 7/22. 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 8/227:28 am
PWM
- NAS
1 stop6h 44m
American Airlines
Sat 8/2912:10 pm
NAS
- PWM
1 stop10h 05m
American Airlines
Deal found 7/22![American Airlines logo]()
$420
This United Airlines deal was found by Cheapflights users on 7/20. 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 8/246:03 am
PWM
- SJU
1 stop8h 41m
United Airlines
Fri 8/284:55 pm
SJU
- PWM
1 stop7h 04m
United Airlines
Deal found 7/20![United Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 7/22. 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 8/285:30 pm
PWM
- PUJ
2 stops19h 29m
Delta
Sat 9/52:25 pm
PUJ
- PWM
2 stops19h 24m
Delta
Deal found 7/22![Delta logo]()
$381
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 July 24, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 24, 2026.
This American Airlines deal was found by Cheapflights users on 7/19. 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.
Sat 10/177:26 pm
PWM
- STT
2 stops19h 29m
American Airlines
Deal found 7/19![American Airlines logo]()
$144
This Delta deal was found by Cheapflights users on 7/21. 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 9/306:00 am
PWM
- MBJ
1 stop8h 01m
Delta
Deal found 7/21![Delta logo]()
$152
This Delta deal was found by Cheapflights users on 7/23. 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 9/66:05 am
PWM
- NAS
1 stop7h 52m
Delta
Deal found 7/23![Delta logo]()
$156
This American Airlines deal was found by Cheapflights users on 7/23. 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 9/66:00 am
PWM
- NAS
2 stops11h 39m
American Airlines
Deal found 7/23![American Airlines logo]()
$157
This Delta deal was found by Cheapflights users on 7/22. 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 10/234:15 pm
PWM
- SJU
1 stop7h 41m
Delta
Deal found 7/22![Delta logo]()
$171
This Delta deal was found by Cheapflights users on 7/23. 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 9/102:10 pm
PWM
- KIN
1 stop7h 00m
Delta
Deal found 7/23![Delta logo]()
$183
This Priceline deal was found by Cheapflights users on 7/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/61:17 pm
PWM
- KIN
1 stop11h 17m
JetBlue
Deal found 7/21![JetBlue logo]()
$198
This American Airlines deal was found by Cheapflights users on 7/22. 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
PWM
- AUA
1 stop18h 12m
American Airlines
Deal found 7/22![American Airlines logo]()
$198
This American Airlines deal was found by Cheapflights users on 7/21. 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.
Wed 8/125:30 am
PWM
- AUA
1 stop7h 20m
American Airlines
Deal found 7/21![American Airlines logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/317:00 am
PWM
- SJU
3 stops17h 56m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$205
This FlightHub deal was found by Cheapflights users on 7/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:40 pm
PWM
- SJU
2 stops27h 22m
JetBlue
Deal found 7/19![JetBlue logo]()
$207
This United Airlines deal was found by Cheapflights users on 7/19. 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 10/106:00 am
PWM
- MBJ
1 stop6h 43m
United Airlines
Deal found 7/19![United Airlines logo]()
$208
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 July 24, 2026.
Round-trip from | $280 (American Airlines) |
|---|---|
One-way from | $144 (American Airlines) |
Popular in | April |
Cheapest in | October |
Average price | $696 |
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 2,558,603 searches. Data last updated July 24, 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
PortlandSan Juan
PWM - SJU
PWMSJU
Portland
Tue 10/20
5:15 am-12:34 pm
1 stop7h 19m
San Juan Luis Munoz Marin Intl
Mon 10/26
7:25 am-11:23 pm
2 stops15h 58m
$342
PortlandSan Juan
PWM - SJU
PWMSJU
Portland
Sat 9/19
6:00 am-4:49 pm
1 stop10h 49m
San Juan Luis Munoz Marin Intl
Sat 9/26
1:16 pm-11:56 pm
1 stop10h 40m
$342
PortlandSan Juan
PWM - SJU
PWMSJU
Portland
Tue 10/20
4:15 pm-11:56 pm
1 stop7h 41m
San Juan Luis Munoz Marin Intl
Mon 10/26
7:00 am-1:53 pm
1 stop6h 53m
$342
PortlandSaint Thomas Island
PWM - STT
PWMSTT
Portland
Tue 10/27
5:30 am-12:56 pm
1 stop7h 26m
Saint Thomas Island Cyril E King
Fri 10/30
2:00 pm-11:23 pm
1 stop9h 23m
$376
PortlandSimpson Bay
PWM - SXM
PWMSXM
Portland
Sat 10/3
5:06 pm-1:23 pm
2 stops20h 17m
Simpson Bay Princess Juliana
Sat 10/10
2:23 pm-10:56 am
2 stops20h 33m
$380
PortlandNassau
PWM - NAS
PWMNAS
Portland
Sat 10/24
7:24 pm-11:18 am
1 stop15h 54m
Nassau Intl
Sat 10/31
2:23 pm-10:36 pm
1 stop8h 13m
$380
PortlandNassau
PWM - NAS
PWMNAS
Portland
Mon 11/16
6:00 am-1:30 pm
1 stop7h 30m
Nassau Intl
Fri 11/20
1:00 pm-11:49 pm
1 stop10h 49m
$380
PortlandNassau
PWM - NAS
PWMNAS
Portland
Sat 10/24
6:00 am-3:25 pm
1 stop9h 25m
Nassau Intl
Sat 10/31
12:55 pm-11:49 pm
1 stop10h 54m
$380
PortlandPunta Cana
PWM - PUJ
PWMPUJ
Portland
Fri 8/28
6:00 am-12:35 pm
1 stop6h 35m
Punta Cana
Sat 9/5
1:10 pm-9:31 pm
1 stop8h 21m
$390
PortlandSimpson Bay
PWM - SXM
PWMSXM
Portland
Sat 9/26
6:00 am-12:33 pm
1 stop6h 33m
Simpson Bay Princess Juliana
Sat 10/10
1:35 pm-11:28 pm
1 stop9h 53m
$397
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-SJU
PWM-PUJ
PWM-NAS
PWM-PLS
PWM-AUA
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-PUJ
PWM-NAS
PWM-PLS
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 $468). Flying from Portland, Maine to Caribbean in July is currently the most expensive (average of $696). 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 43 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 July 24, 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.
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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.
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.
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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 July 24, 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 2,558,603 searches. Data last updated July 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$576 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$216 | Average$446 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$645 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$573 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$300 | Average$755 | FlexibilityNo cancel fee | On-time63% |