$106+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Apr 11 — Apr 181
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 March 12, 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 March 12, 2026.
This American Airlines deal was found by Cheapflights users on 3/8. 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 4/306:00 am
PWM
- STT
1 stop6h 35m
American Airlines
Fri 5/82:05 pm
STT
- PWM
2 stops20h 18m
American Airlines
Deal found 3/8![American Airlines logo]()
$200
This American Airlines deal was found by Cheapflights users on 3/9. 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 11/256:39 pm
PWM
- STT
2 stops21h 16m
American Airlines
Wed 12/24:22 pm
STT
- PWM
2 stops20h 49m
American Airlines
Deal found 3/9![American Airlines logo]()
$249
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Wed 9/235:15 am
PWM
- SJU
1 stop7h 39m
United Airlines
Tue 9/291:05 am
SJU
- PWM
1 stop8h 06m
United Airlines
Deal found 3/12![United Airlines logo]()
$262
This American Airlines deal was found by Cheapflights users on 3/9. 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 3/176:29 pm
PWM
- STT
2 stops20h 17m
American Airlines
Tue 3/242:03 pm
STT
- PWM
2 stops9h 52m
American Airlines
Deal found 3/9![American Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 3/8. 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.
Tue 5/52:51 pm
PWM
- SJU
1 stop9h 08m
Delta
Tue 5/127:05 am
SJU
- PWM
1 stop6h 53m
Delta
Deal found 3/8![Delta logo]()
$276
This American Airlines deal was found by Cheapflights users on 3/8. 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.
Wed 3/186:29 pm
PWM
- STT
2 stops16h 37m
American Airlines
Wed 3/2512:02 pm
STT
- PWM
2 stops11h 53m
American Airlines
Deal found 3/8![American Airlines logo]()
$280
This United Airlines deal was found by Cheapflights users on 3/10. 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 4/226:04 am
PWM
- STT
1 stop9h 27m
United Airlines
Thu 4/304:45 pm
STT
- PWM
1 stop7h 14m
United Airlines
Deal found 3/10![United Airlines logo]()
$282
This American Airlines deal was found by Cheapflights users on 3/11. 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.
Sun 4/263:02 pm
PWM
- SJU
1 stop7h 03m
American Airlines
Tue 5/51:31 pm
SJU
- PWM
2 stops9h 56m
American Airlines
Deal found 3/11![American Airlines logo]()
$282
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Wed 9/165:15 am
PWM
- SJU
1 stop7h 39m
United Airlines
Tue 9/221:00 am
SJU
- PWM
2 stops9h 02m
United Airlines
Deal found 3/12![United Airlines logo]()
$284
This American Airlines deal was found by Cheapflights users on 3/12. 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 8/266:00 am
PWM
- SJU
1 stop7h 35m
American Airlines
Wed 9/210:32 am
SJU
- PWM
2 stops13h 15m
American Airlines
Deal found 3/12![American Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 3/12. 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.
Sat 5/22:51 pm
PWM
- SJU
1 stop9h 08m
Delta
Fri 5/81:13 pm
SJU
- PWM
1 stop11h 30m
Delta
Deal found 3/12![Delta logo]()
$296
This United Airlines deal was found by Cheapflights users on 3/8. 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 5/56:00 am
PWM
- SJU
1 stop7h 45m
United Airlines
Tue 5/51:00 am
SJU
- PWM
2 stops9h 18m
United Airlines
Deal found 3/8![United Airlines logo]()
$297
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 March 12, 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 March 12, 2026.
This Delta deal was found by Cheapflights users on 3/8. 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.
Tue 5/52:51 pm
PWM
- SJU
1 stop9h 08m
Delta
Tue 5/127:05 am
SJU
- PWM
1 stop6h 53m
Delta
Deal found 3/8![Delta logo]()
$276
This United Airlines deal was found by Cheapflights users on 3/7. 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 5/56:00 am
PWM
- SJU
1 stop7h 45m
United Airlines
Tue 5/51:00 am
SJU
- PWM
2 stops9h 18m
United Airlines
Deal found 3/7![United Airlines logo]()
$297
This American Airlines deal was found by Cheapflights users on 3/8. 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.
Tue 5/57:23 pm
PWM
- PLS
2 stops18h 37m
American Airlines
Tue 5/123:13 pm
PLS
- PWM
2 stops18h 54m
American Airlines
Deal found 3/8![American Airlines logo]()
$326
This JetBlue deal was found by Cheapflights users on 3/10. 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 5/56:00 am
PWM
- NAS
1 stop6h 27m
JetBlue
Thu 5/71:46 pm
NAS
- PWM
1 stop9h 50m
JetBlue
Deal found 3/10![JetBlue logo]()
$348
This Southwest deal was found by Cheapflights users on 3/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:30 am
PWM
- SJU
2 stops11h 35m
Southwest
Tue 5/55:35 am
SJU
- PWM
2 stops9h 45m
Southwest
Deal found 3/11![Southwest logo]()
$397
This Delta deal was found by Cheapflights users on 3/8. 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.
Tue 5/55:21 am
PWM
- PLS
1 stop8h 49m
Delta
Tue 5/122:05 pm
PLS
- PWM
1 stop9h 07m
Delta
Deal found 3/8![Delta logo]()
$321
This United Airlines deal was found by Cheapflights users on 3/8. 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.
Sat 4/256:00 am
PWM
- GCM
1 stop7h 35m
United Airlines
Sat 5/24:10 pm
GCM
- PWM
1 stop17h 08m
United Airlines
Deal found 3/8![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 3/11. 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 4/216:30 am
PWM
- STT
1 stop6h 43m
Delta
Wed 4/293:59 pm
STT
- PWM
1 stop8h 47m
Delta
Deal found 3/11![Delta logo]()
$331
This United Airlines deal was found by Cheapflights users on 3/8. 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.
Fri 4/246:04 am
PWM
- GCM
1 stop7h 41m
United Airlines
Tue 5/51:35 pm
GCM
- PWM
2 stops19h 48m
United Airlines
Deal found 3/8![United Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 3/12. 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.
Thu 4/97:23 pm
PWM
- STT
2 stops16h 12m
American Airlines
Tue 4/1412:47 pm
STT
- PWM
2 stops11h 07m
American Airlines
Deal found 3/12![American Airlines logo]()
$368
This JetBlue deal was found by Cheapflights users on 3/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:00 am
PWM
- PLS
1 stop7h 15m
JetBlue
Wed 4/153:20 pm
PLS
- PWM
1 stop7h 39m
JetBlue
Deal found 3/11![JetBlue logo]()
$385
This American Airlines deal was found by Cheapflights users on 3/11. 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.
Mon 5/117:23 pm
PWM
- PLS
2 stops17h 02m
American Airlines
Sat 5/162:12 pm
PLS
- PWM
1 stop9h 15m
American Airlines
Deal found 3/11![American Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 3/8. 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.
Tue 4/285:21 am
PWM
- STT
1 stop8h 30m
Delta
Mon 5/43:59 pm
STT
- PWM
1 stop8h 47m
Delta
Deal found 3/8![Delta logo]()
$355
This United Airlines deal was found by Cheapflights users on 3/10. 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 4/226:04 am
PWM
- STT
1 stop9h 27m
United Airlines
Thu 4/302:10 pm
STT
- PWM
2 stops9h 49m
United Airlines
Deal found 3/10![United Airlines logo]()
$360
This Priceline deal was found by Cheapflights users on 3/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:30 am
PWM
- PUJ
1 stop10h 45m
JetBlue
Sat 5/3012:00 pm
PUJ
- PWM
1 stop11h 56m
JetBlue
Deal found 3/11![JetBlue logo]()
$407
This American Airlines deal was found by Cheapflights users on 3/7. 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 5/46:01 pm
PWM
- MBJ
2 stops18h 23m
American Airlines
Fri 5/82:29 pm
MBJ
- PWM
2 stops19h 25m
American Airlines
Deal found 3/7![American Airlines logo]()
$391
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Wed 5/63:39 pm
PWM
- SJU
1 stop8h 11m
United Airlines
Tue 5/121:00 am
SJU
- PWM
1 stop7h 49m
United Airlines
Deal found 3/12![United Airlines logo]()
$375
This KAYAK deal was found by Cheapflights users on 3/9. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
PWM
- SXM
1 stop7h 44m
JetBlue
Sun 6/73:05 pm
SXM
- PWM
1 stop8h 51m
JetBlue
Deal found 3/9![JetBlue logo]()
$422
This Delta deal was found by Cheapflights users on 3/11. 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.
Sun 5/35:21 am
PWM
- NAS
1 stop11h 12m
Delta
Sat 5/92:30 pm
NAS
- PWM
1 stop6h 18m
Delta
Deal found 3/11![Delta logo]()
$386
This American Airlines deal was found by Cheapflights users on 3/8. 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.
Wed 4/296:00 am
PWM
- AUA
1 stop6h 55m
American Airlines
Thu 4/301:55 pm
AUA
- PWM
1 stop9h 32m
American Airlines
Deal found 3/8![American Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 3/10. 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 5/35:21 am
PWM
- SXM
1 stop8h 44m
Delta
Fri 5/83:20 pm
SXM
- PWM
2 stops22h 38m
Delta
Deal found 3/10![Delta logo]()
$390
This American Airlines deal was found by Cheapflights users on 3/11. 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 6/45:57 pm
PWM
- NAS
1 stop16h 06m
American Airlines
Sun 6/73:46 pm
NAS
- PWM
1 stop8h 05m
American Airlines
Deal found 3/11![American Airlines logo]()
$401
This United Airlines deal was found by Cheapflights users on 3/11. 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.
Sun 4/267:15 pm
PWM
- PUJ
2 stops17h 25m
United Airlines
Sat 5/304:40 pm
PUJ
- PWM
1 stop7h 11m
United Airlines
Deal found 3/11![United Airlines logo]()
$408
This JetBlue deal was found by Cheapflights users on 3/9. 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.
Tue 4/287:30 am
PWM
- MBJ
1 stop6h 30m
JetBlue
Thu 4/302:09 pm
MBJ
- PWM
1 stop7h 53m
JetBlue
Deal found 3/9![JetBlue logo]()
$469
This American Airlines deal was found by Cheapflights users on 3/12. 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 4/297:10 am
PWM
- MBJ
1 stop7h 15m
American Airlines
Sun 5/34:37 pm
MBJ
- PWM
2 stops17h 38m
American Airlines
Deal found 3/12![American Airlines logo]()
$406
This Delta deal was found by Cheapflights users on 3/12. 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.
Thu 4/95:23 am
PWM
- STT
1 stop9h 25m
Delta
Tue 4/143:59 pm
STT
- PWM
1 stop8h 47m
Delta
Deal found 3/12![Delta logo]()
$421
This United Airlines deal was found by Cheapflights users on 3/8. 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 6/36:00 am
PWM
- SXM
1 stop8h 43m
United Airlines
Sun 6/73:50 pm
SXM
- PWM
1 stop8h 01m
United Airlines
Deal found 3/8![United Airlines logo]()
$431
This JetBlue deal was found by Cheapflights users on 3/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:00 am
PWM
- KIN
1 stop11h 53m
JetBlue
Tue 5/192:36 pm
KIN
- PWM
1 stop8h 00m
JetBlue
Deal found 3/8![JetBlue logo]()
$479
This American Airlines deal was found by Cheapflights users on 3/9. 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 4/66:29 pm
PWM
- NAS
2 stops16h 30m
American Airlines
Mon 4/133:21 pm
NAS
- PWM
1 stop8h 06m
American Airlines
Deal found 3/9![American Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 3/10. 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 4/226:00 am
PWM
- NAS
2 stops10h 33m
Delta
Wed 4/293:28 pm
NAS
- PWM
1 stop7h 55m
Delta
Deal found 3/10![Delta logo]()
$428
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated March 12, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated March 12, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/9. 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 3/176:29 pm
PWM
- STT
2 stops20h 17m
American Airlines
Tue 3/242:03 pm
STT
- PWM
2 stops9h 52m
American Airlines
Deal found 3/9![American Airlines logo]()
$275
This American Airlines deal was found by Cheapflights users on 3/8. 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.
Wed 3/186:29 pm
PWM
- STT
2 stops16h 37m
American Airlines
Wed 3/2512:02 pm
STT
- PWM
2 stops11h 53m
American Airlines
Deal found 3/8![American Airlines logo]()
$280
This Delta deal was found by Cheapflights users on 3/11. 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 4/216:30 am
PWM
- STT
1 stop6h 43m
Delta
Wed 4/293:59 pm
STT
- PWM
1 stop8h 47m
Delta
Deal found 3/11![Delta logo]()
$331
This United Airlines deal was found by Cheapflights users on 3/10. 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 4/226:04 am
PWM
- STT
1 stop9h 27m
United Airlines
Thu 4/304:45 pm
STT
- PWM
1 stop7h 14m
United Airlines
Deal found 3/10![United Airlines logo]()
$282
This United Airlines deal was found by Cheapflights users on 3/9. 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.
Fri 4/246:04 am
PWM
- GCM
1 stop7h 41m
United Airlines
Tue 5/51:35 pm
GCM
- PWM
2 stops19h 48m
United Airlines
Deal found 3/9![United Airlines logo]()
$332
This United Airlines deal was found by Cheapflights users on 3/8. 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.
Sat 4/256:00 am
PWM
- GCM
1 stop7h 35m
United Airlines
Sat 5/24:10 pm
GCM
- PWM
1 stop17h 08m
United Airlines
Deal found 3/8![United Airlines logo]()
$327
This American Airlines deal was found by Cheapflights users on 3/11. 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.
Sun 4/263:02 pm
PWM
- SJU
1 stop7h 03m
American Airlines
Tue 5/51:31 pm
SJU
- PWM
2 stops9h 56m
American Airlines
Deal found 3/11![American Airlines logo]()
$282
This United Airlines deal was found by Cheapflights users on 3/11. 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.
Sun 4/269:49 am
PWM
- SJU
1 stop10h 45m
United Airlines
Mon 5/41:00 am
SJU
- PWM
1 stop7h 49m
United Airlines
Deal found 3/11![United Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 3/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:30 am
PWM
- SJU
1 stop11h 00m
Southwest
Tue 5/55:35 am
SJU
- PWM
2 stops9h 45m
Southwest
Deal found 3/11![Southwest logo]()
$302
This American Airlines deal was found by Cheapflights users on 3/8. 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.
Wed 4/296:00 am
PWM
- AUA
1 stop6h 55m
American Airlines
Thu 4/302:30 pm
AUA
- PWM
2 stops19h 53m
American Airlines
Deal found 3/8![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 3/8. 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 4/306:00 am
PWM
- STT
1 stop6h 35m
American Airlines
Fri 5/82:05 pm
STT
- PWM
2 stops20h 18m
American Airlines
Deal found 3/8![American Airlines logo]()
$200
This United Airlines deal was found by Cheapflights users on 3/9. 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.
Thu 4/306:00 am
PWM
- STT
1 stop7h 08m
United Airlines
Fri 5/82:10 pm
STT
- PWM
1 stop9h 13m
United Airlines
Deal found 3/9![United Airlines logo]()
$332
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 March 12, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated March 12, 2026.
This American Airlines deal was found by Cheapflights users on 3/8. 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.
Sun 4/266:00 am
PWM
- SJU
1 stop16h 05m
American Airlines
Deal found 3/8![American Airlines logo]()
$106
This Delta deal was found by Cheapflights users on 3/9. 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.
Wed 4/225:21 am
PWM
- PLS
1 stop8h 49m
Delta
Deal found 3/9![Delta logo]()
$116
This United Airlines deal was found by Cheapflights users on 3/8. 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 3/316:04 am
PWM
- STT
1 stop9h 27m
United Airlines
Deal found 3/8![United Airlines logo]()
$120
This Delta deal was found by Cheapflights users on 3/10. 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 4/135:21 am
PWM
- GCM
1 stop7h 39m
Delta
Deal found 3/10![Delta logo]()
$121
This American Airlines deal was found by Cheapflights users on 3/12. 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 4/66:29 pm
PWM
- STT
2 stops20h 21m
American Airlines
Deal found 3/12![American Airlines logo]()
$123
This Delta deal was found by Cheapflights users on 3/10. 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.
Sat 4/114:48 pm
PWM
- GCM
2 stops19h 59m
Delta
Deal found 3/10![Delta logo]()
$127
This American Airlines deal was found by Cheapflights users on 3/11. 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 4/226:00 am
PWM
- PLS
2 stops8h 00m
American Airlines
Deal found 3/11![American Airlines logo]()
$131
This United Airlines deal was found by Cheapflights users on 3/10. 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 8/226:00 am
PWM
- SJU
2 stops14h 38m
United Airlines
Deal found 3/10![United Airlines logo]()
$131
This Delta deal was found by Cheapflights users on 3/8. 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.
Sun 4/122:30 pm
PWM
- SJU
1 stop9h 29m
Delta
Deal found 3/8![Delta logo]()
$138
This United Airlines deal was found by Cheapflights users on 3/8. 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 6/36:00 am
PWM
- SXM
1 stop8h 43m
United Airlines
Deal found 3/8![United Airlines logo]()
$145
This American Airlines deal was found by Cheapflights users on 3/9. 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 5/86:00 am
PWM
- AUA
2 stops9h 20m
American Airlines
Deal found 3/9![American Airlines logo]()
$147
This American Airlines deal was found by Cheapflights users on 3/8. 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.
Sun 4/1210:50 am
PWM
- SJU
2 stops28h 02m
American Airlines
Deal found 3/8![American Airlines logo]()
$147
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 March 12, 2026.
Round-trip from | $200 (American Airlines) |
|---|---|
One-way from | $106 (American Airlines) |
Popular in | February |
Cheapest in | October |
Average price | $473 |
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 March 12, 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 5/5
2:51 pm-11:59 pm
1 stop9h 08m
San Juan Luis Munoz Marin Intl
Tue 5/12
7:05 am-1:58 pm
1 stop6h 53m
$276
PortlandSan Juan
PWM - SJU
PWMSJU
Portland
Tue 5/5
6:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Tue 5/5
1:00 am-10:18 am
2 stops9h 18m
$297
PortlandProvidenciales
PWM - PLS
PWMPLS
Portland
Tue 5/5
5:21 am-2:10 pm
1 stop8h 49m
Providenciales
Tue 5/12
2:05 pm-11:12 pm
1 stop9h 07m
$321
PortlandProvidenciales
PWM - PLS
PWMPLS
Portland
Tue 5/5
7:23 pm-2:00 pm
2 stops18h 37m
Providenciales
Tue 5/12
3:13 pm-10:07 am
2 stops18h 54m
$326
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Sat 4/25
6:00 am-12:35 pm
1 stop7h 35m
George Town Owen Roberts Intl
Sat 5/2
4:10 pm-10:18 am
1 stop17h 08m
$327
PortlandSaint Thomas Island
PWM - STT
PWMSTT
Portland
Tue 4/21
6:30 am-1:13 pm
1 stop6h 43m
Saint Thomas Island Cyril E King
Wed 4/29
3:59 pm-12:46 am
1 stop8h 47m
$331
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Fri 4/24
6:04 am-12:45 pm
1 stop7h 41m
George Town Owen Roberts Intl
Tue 5/5
1:35 pm-10:23 am
2 stops19h 48m
$332
PortlandNassau
PWM - NAS
PWMNAS
Portland
Tue 5/5
6:00 am-12:27 pm
1 stop6h 27m
Nassau Intl
Thu 5/7
1:46 pm-11:36 pm
1 stop9h 50m
$348
PortlandSaint Thomas Island
PWM - STT
PWMSTT
Portland
Tue 4/28
5:21 am-1:51 pm
1 stop8h 30m
Saint Thomas Island Cyril E King
Mon 5/4
3:59 pm-12:46 am
1 stop8h 47m
$355
PortlandSaint Thomas Island
PWM - STT
PWMSTT
Portland
Wed 4/22
6:04 am-3:31 pm
1 stop9h 27m
Saint Thomas Island Cyril E King
Thu 4/30
2:10 pm-11:59 pm
2 stops9h 49m
$360
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-STT
PWM-SJU
PWM-GCM
PWM-AUA
PWM-PLS
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-STT
PWM-SJU
PWM-GCM
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 $93). Flying from Portland, Maine to Caribbean in November is currently the most expensive (average of $177). 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.
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 March 12, 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.
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - 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.
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 March 12, 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 March 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$407 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$559 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$241 | Average$623 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$569 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$300 | Average$644 | FlexibilityNo cancel fee | On-time63% |