$121+ 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 6/25. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Jul 14 — Jul 211
Round-trip
1 adult, Economy
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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 June 14, 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 June 14, 2026.
This American Airlines deal was found by Cheapflights users on 6/9. 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.
Sat 9/195:06 pm
PWM
- SJU
2 stops17h 54m
American Airlines
Sat 9/266:27 am
SJU
- PWM
2 stops16h 18m
American Airlines
Deal found 6/9![American Airlines logo]()
$218
This American Airlines deal was found by Cheapflights users on 6/10. 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 9/165:42 pm
PWM
- SJU
2 stops20h 12m
American Airlines
Wed 9/236:27 am
SJU
- PWM
2 stops17h 32m
American Airlines
Deal found 6/10![American Airlines logo]()
$223
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 10/55:15 am
PWM
- SJU
1 stop7h 19m
United Airlines
Fri 10/91:00 am
SJU
- PWM
1 stop8h 08m
United Airlines
Deal found 6/11![United Airlines logo]()
$254
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Tue 10/202:55 pm
PWM
- SJU
1 stop8h 55m
American Airlines
Mon 10/265:25 am
SJU
- PWM
1 stop13h 00m
American Airlines
Deal found 6/10![American Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 6/10. 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
PWM
- NAS
1 stop7h 30m
Delta
Fri 11/202:55 pm
NAS
- PWM
1 stop7h 28m
Delta
Deal found 6/10![Delta logo]()
$306
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:02 am
PWM
- SJU
1 stop6h 11m
Delta
Sat 9/267:00 am
SJU
- PWM
1 stop6h 54m
Delta
Deal found 6/9![Delta logo]()
$306
This United Airlines deal was found by Cheapflights users on 6/10. 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 8/295:15 am
PWM
- SJU
1 stop7h 19m
United Airlines
Tue 9/11:00 am
SJU
- PWM
1 stop8h 08m
United Airlines
Deal found 6/10![United Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 6/9. 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.
Sat 12/56:38 pm
PWM
- SXM
2 stops18h 42m
American Airlines
Tue 12/85:25 pm
SXM
- PWM
2 stops19h 46m
American Airlines
Deal found 6/9![American Airlines logo]()
$310
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 10/267:10 am
SJU
- PWM
2 stops12h 14m
United Airlines
Deal found 6/12![United Airlines logo]()
$312
This Delta deal was found by Cheapflights users on 6/10. 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
PWM
- NAS
1 stop9h 30m
Delta
Sat 11/211:00 pm
NAS
- PWM
1 stop10h 49m
Delta
Deal found 6/10![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/86:00 am
PWM
- GCM
1 stop6h 41m
Delta
Sun 9/1312:55 pm
GCM
- PWM
1 stop8h 38m
Delta
Deal found 6/11![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:05 am
PWM
- GCM
1 stop6h 35m
Delta
Mon 9/2812:55 pm
GCM
- PWM
2 stops9h 22m
Delta
Deal found 6/13![Delta logo]()
$336
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 June 14, 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 June 14, 2026.
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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
PWM
- NAS
1 stop7h 33m
United Airlines
Wed 10/212:35 pm
NAS
- PWM
1 stop8h 53m
United Airlines
Deal found 6/11![United Airlines logo]()
$306
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:02 am
PWM
- SJU
1 stop6h 11m
Delta
Sat 9/267:00 am
SJU
- PWM
1 stop6h 54m
Delta
Deal found 6/9![Delta logo]()
$306
This American Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/137:34 pm
PWM
- GCM
2 stops16h 26m
American Airlines
Mon 7/205:10 pm
GCM
- PWM
2 stops20h 06m
American Airlines
Deal found 6/13![American Airlines logo]()
$336
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:35 pm
PWM
- SJU
1 stop7h 00m
Southwest
Mon 10/265:00 am
SJU
- PWM
2 stops11h 55m
Southwest
Deal found 6/10![Southwest logo]()
$347
This Expedia deal was found by Cheapflights users on 6/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/96:00 am
PWM
- UVF
1 stop9h 11m
JetBlue
Wed 7/151:57 pm
UVF
- PWM
1 stop10h 19m
JetBlue
Deal found 6/9![JetBlue logo]()
$575
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/162:35 pm
PWM
- SJU
1 stop9h 09m
Delta
Wed 9/231:32 pm
SJU
- PWM
1 stop10h 27m
Delta
Deal found 6/11![Delta logo]()
$306
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 10/264:50 pm
SJU
- PWM
1 stop7h 09m
United Airlines
Deal found 6/12![United Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:39 pm
PWM
- STT
2 stops21h 16m
American Airlines
Wed 12/24:16 pm
STT
- PWM
2 stops20h 55m
American Airlines
Deal found 6/14![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 6/10. 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 11/166:30 am
PWM
- NAS
2 stops9h 00m
Delta
Fri 11/202:55 pm
NAS
- PWM
1 stop7h 28m
Delta
Deal found 6/10![Delta logo]()
$310
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/86:46 pm
PWM
- GCM
2 stops17h 14m
American Airlines
Sun 9/1312:36 pm
GCM
- PWM
1 stop9h 01m
American Airlines
Deal found 6/11![American Airlines logo]()
$341
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/196:00 am
PWM
- SJU
1 stop7h 45m
United Airlines
Tue 9/221:00 am
SJU
- PWM
2 stops9h 04m
United Airlines
Deal found 6/11![United Airlines logo]()
$348
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 stop9h 30m
Delta
Sat 11/211:00 pm
NAS
- PWM
1 stop10h 49m
Delta
Deal found 6/11![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/86:00 am
PWM
- GCM
1 stop6h 41m
Delta
Sun 9/1312:55 pm
GCM
- PWM
1 stop8h 38m
Delta
Deal found 6/11![Delta logo]()
$331
This American Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:38 pm
PWM
- PUJ
2 stops19h 18m
American Airlines
Sun 12/135:30 pm
PUJ
- PWM
2 stops19h 41m
American Airlines
Deal found 6/13![American Airlines logo]()
$365
This United Airlines deal was found by Cheapflights users on 6/10. 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 8/295:15 am
PWM
- SJU
1 stop7h 19m
United Airlines
Tue 9/11:00 am
SJU
- PWM
2 stops9h 04m
United Airlines
Deal found 6/10![United Airlines logo]()
$365
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/36:59 pm
PWM
- SXM
2 stops20h 45m
American Airlines
Fri 7/101:34 pm
SXM
- PWM
2 stops19h 48m
American Airlines
Deal found 6/11![American Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 6/246:00 am
PWM
- NAS
1 stop8h 04m
Delta
Sun 8/233:22 pm
NAS
- PWM
1 stop7h 51m
Delta
Deal found 6/12![Delta logo]()
$350
This American Airlines deal was found by Cheapflights users on 6/10. 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 8/285:13 pm
PWM
- AUA
2 stops22h 04m
American Airlines
Tue 9/14:50 pm
AUA
- PWM
2 stops21h 34m
American Airlines
Deal found 6/10![American Airlines logo]()
$375
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 11/86:00 am
PWM
- NAS
1 stop7h 49m
Delta
Sat 11/141:00 pm
NAS
- PWM
1 stop10h 49m
Delta
Deal found 6/12![Delta logo]()
$350
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Thu 7/237:16 pm
PWM
- PUJ
2 stops19h 11m
United Airlines
Thu 7/303:35 pm
PUJ
- PWM
1 stop8h 16m
United Airlines
Deal found 6/10![United Airlines logo]()
$427
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 8/236:46 pm
PWM
- SXM
2 stops20h 53m
American Airlines
Sun 8/304:39 pm
SXM
- PWM
2 stops21h 42m
American Airlines
Deal found 6/12![American Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 6/10. 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 11/306:00 am
PWM
- MBJ
1 stop10h 35m
Delta
Thu 12/36:00 pm
MBJ
- PWM
2 stops15h 30m
Delta
Deal found 6/10![Delta logo]()
$363
This JetBlue deal was found by Cheapflights users on 6/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:30 am
PWM
- KIN
1 stop10h 28m
JetBlue
Wed 11/1110:15 am
KIN
- PWM
1 stop13h 28m
JetBlue
Deal found 6/9![JetBlue logo]()
$649
This United Airlines deal was found by Cheapflights users on 6/9. 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 7/185:15 am
PWM
- SXM
1 stop7h 18m
United Airlines
Fri 7/243:50 pm
SXM
- PWM
1 stop8h 01m
United Airlines
Deal found 6/9![United Airlines logo]()
$477
This American Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:50 pm
PWM
- MBJ
2 stops18h 50m
American Airlines
Sat 10/175:00 pm
MBJ
- PWM
2 stops19h 22m
American Airlines
Deal found 6/13![American Airlines logo]()
$396
This Delta deal was found by Cheapflights users on 6/10. 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 12/66:00 am
PWM
- MBJ
1 stop10h 35m
Delta
Tue 12/86:00 pm
MBJ
- PWM
2 stops19h 53m
Delta
Deal found 6/10![Delta logo]()
$363
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 10/97:57 am
PWM
- MBJ
2 stops30h 33m
United Airlines
Sat 10/174:55 pm
MBJ
- PWM
1 stop15h 13m
United Airlines
Deal found 6/11![United Airlines logo]()
$483
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 12/96:38 pm
PWM
- PUJ
2 stops17h 54m
American Airlines
Tue 12/1512:53 pm
PUJ
- PWM
2 stops11h 44m
American Airlines
Deal found 6/12![American Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 6/9. 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 11/75:06 pm
PWM
- MBJ
1 stop21h 23m
United Airlines
Wed 11/113:36 pm
MBJ
- PWM
1 stop7h 21m
United Airlines
Deal found 6/9![United Airlines logo]()
$485
This Delta deal was found by Cheapflights users on 6/9. 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 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 stop10h 35m
Delta
Tue 12/81:50 pm
MBJ
- PWM
1 stop9h 16m
Delta
Deal found 6/9![Delta logo]()
$407
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated June 14, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated June 14, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/9. 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.
Tue 6/1610:30 am
PWM
- SJU
2 stops9h 20m
Southwest
Fri 6/195:15 pm
SJU
- PWM
1 stop6h 50m
Southwest
Deal found 6/9![Southwest logo]()
$492
This Delta deal was found by Cheapflights users on 6/10. 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.
Wed 6/246:00 am
PWM
- NAS
1 stop8h 04m
Delta
Sun 8/233:22 pm
NAS
- PWM
1 stop7h 51m
Delta
Deal found 6/10![Delta logo]()
$350
This American Airlines deal was found by Cheapflights users on 6/10. 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 6/245:58 pm
PWM
- NAS
1 stop16h 04m
American Airlines
Sun 8/232:36 pm
NAS
- PWM
2 stops9h 01m
American Airlines
Deal found 6/10![American Airlines logo]()
$421
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/16:54 pm
PWM
- MBJ
2 stops19h 15m
American Airlines
Sun 7/55:14 pm
MBJ
- PWM
2 stops20h 02m
American Airlines
Deal found 6/11![American Airlines logo]()
$488
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/36:59 pm
PWM
- SXM
2 stops20h 45m
American Airlines
Fri 7/101:34 pm
SXM
- PWM
2 stops19h 48m
American Airlines
Deal found 6/11![American Airlines logo]()
$372
This American Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/137:34 pm
PWM
- GCM
2 stops16h 26m
American Airlines
Mon 7/205:10 pm
GCM
- PWM
2 stops20h 06m
American Airlines
Deal found 6/13![American Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:45 am
PWM
- AUA
2 stops9h 35m
American Airlines
Sun 7/195:59 pm
AUA
- PWM
2 stops19h 41m
American Airlines
Deal found 6/13![American Airlines logo]()
$427
This United Airlines deal was found by Cheapflights users on 6/9. 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 7/185:15 am
PWM
- SXM
1 stop7h 18m
United Airlines
Fri 7/243:50 pm
SXM
- PWM
1 stop8h 01m
United Airlines
Deal found 6/9![United Airlines logo]()
$477
This American Airlines deal was found by Cheapflights users on 6/9. 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.
Mon 7/207:34 pm
PWM
- SXM
2 stops20h 10m
American Airlines
Tue 7/284:45 pm
SXM
- PWM
2 stops19h 50m
American Airlines
Deal found 6/9![American Airlines logo]()
$501
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Thu 7/237:16 pm
PWM
- PUJ
2 stops19h 11m
United Airlines
Thu 7/303:35 pm
PUJ
- PWM
1 stop8h 16m
United Airlines
Deal found 6/10![United Airlines logo]()
$427
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/276:01 pm
PWM
- MBJ
2 stops20h 08m
American Airlines
Mon 8/35:14 pm
MBJ
- PWM
2 stops20h 02m
American Airlines
Deal found 6/12![American Airlines logo]()
$458
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/306:01 pm
PWM
- NAS
1 stop16h 00m
American Airlines
Sun 8/212:29 pm
NAS
- PWM
1 stop12h 14m
American Airlines
Deal found 6/11![American Airlines logo]()
$355
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 June 14, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 14, 2026.
This American Airlines deal was found by Cheapflights users on 6/9. 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.
Thu 6/257:28 pm
PWM
- NAS
1 stop16h 08m
American Airlines
Deal found 6/9![American Airlines logo]()
$121
This American Airlines deal was found by Cheapflights users on 6/10. 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 8/165:13 pm
PWM
- STT
2 stops19h 40m
American Airlines
Deal found 6/10![American Airlines logo]()
$128
This United Airlines deal was found by Cheapflights users on 6/9. 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 7/185:15 am
PWM
- SXM
1 stop7h 18m
United Airlines
Deal found 6/9![United Airlines logo]()
$139
This American Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/137:34 pm
PWM
- SXM
2 stops20h 10m
American Airlines
Deal found 6/13![American Airlines logo]()
$145
This American Airlines deal was found by Cheapflights users on 6/10. 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 11/156:39 pm
PWM
- AUA
2 stops17h 00m
American Airlines
Deal found 6/10![American Airlines logo]()
$149
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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
- MBJ
1 stop6h 34m
Delta
Deal found 6/11![Delta logo]()
$155
This Delta deal was found by Cheapflights users on 6/10. 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 11/156:00 am
PWM
- PUJ
1 stop7h 25m
Delta
Deal found 6/10![Delta logo]()
$161
This American Airlines deal was found by Cheapflights users on 6/10. 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 11/155:19 pm
PWM
- PUJ
2 stops19h 15m
American Airlines
Deal found 6/10![American Airlines logo]()
$167
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 9/14:30 pm
PWM
- KIN
2 stops21h 29m
American Airlines
Deal found 6/12![American Airlines logo]()
$174
This United Airlines deal was found by Cheapflights users on 6/10. 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 7/318:15 pm
PWM
- NAS
1 stop15h 13m
United Airlines
Deal found 6/10![United Airlines logo]()
$175
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/185:35 am
PWM
- SXM
2 stops9h 30m
Southwest
Deal found 6/13![Southwest logo]()
$178
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:20 pm
PWM
- MBJ
2 stops16h 40m
American Airlines
Deal found 6/14![American Airlines logo]()
$194
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 June 14, 2026.
Round-trip from | $218 (United Airlines) |
|---|---|
One-way from | $121 (American Airlines) |
Popular in | April |
Cheapest in | July |
Average price | $474 |
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 June 14, 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 - NAS
PWMNAS
Portland
Wed 10/14
6:00 am-1:33 pm
1 stop7h 33m
Nassau Intl
Wed 10/21
2:35 pm-11:28 pm
1 stop8h 53m
$306
Quickest round-trip
PortlandSan Juan
PWM - SJU
PWMSJU
Portland
Sat 9/19
6:02 am-12:13 pm
1 stop6h 11m
San Juan Luis Munoz Marin Intl
Sat 9/26
7:00 am-1:54 pm
1 stop6h 54m
$306
PortlandSan Juan
PWM - SJU
PWMSJU
Portland
Wed 9/16
2:35 pm-11:44 pm
1 stop9h 09m
San Juan Luis Munoz Marin Intl
Wed 9/23
1:32 pm-11:59 pm
1 stop10h 27m
$306
PortlandNassau
PWM - NAS
PWMNAS
Portland
Mon 11/16
6:30 am-3:30 pm
2 stops9h 00m
Nassau Intl
Fri 11/20
2:55 pm-10:23 pm
1 stop7h 28m
$310
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
4:50 pm-11:59 pm
1 stop7h 09m
$312
PortlandNassau
PWM - NAS
PWMNAS
Portland
Mon 11/16
6:00 am-3:30 pm
1 stop9h 30m
Nassau Intl
Sat 11/21
1:00 pm-11:49 pm
1 stop10h 49m
$328
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Tue 9/8
6:00 am-11:41 am
1 stop6h 41m
George Town Owen Roberts Intl
Sun 9/13
12:55 pm-10:33 pm
1 stop8h 38m
$331
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Mon 7/13
7:34 pm-11:00 am
2 stops16h 26m
George Town Owen Roberts Intl
Mon 7/20
5:10 pm-2:16 pm
2 stops20h 06m
$336
PortlandSaint Thomas Island
PWM - STT
PWMSTT
Portland
Thu 11/26
6:39 pm-4:55 pm
2 stops21h 16m
Saint Thomas Island Cyril E King
Wed 12/2
4:16 pm-12:11 pm
2 stops20h 55m
$339
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Tue 9/8
6:46 pm-11:00 am
2 stops17h 14m
George Town Owen Roberts Intl
Sun 9/13
12:36 pm-10:37 pm
1 stop9h 01m
$341
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-GCM
PWM-NAS
PWM-SXM
PWM-PUJ
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-GCM
PWM-NAS
PWM-SXM
PWM-PUJ
What is the cheapest month to book a flight from Portland, Maine to Caribbean?
Currently, February is the cheapest month in which you can book a flight from Portland, Maine to Caribbean (average of $101). Flying from Portland, Maine to Caribbean in August is currently the most expensive (average of $303). 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 33 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 June 14, 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
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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 June 14, 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 June 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$575 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$176 | Average$413 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$654 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$562 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$300 | Average$755 | FlexibilityNo cancel fee | On-time63% |