$112+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
May 28 — Jun 41
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 April 28, 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 April 28, 2026.
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/106:00 am
PWM
- STT
1 stop7h 08m
United Airlines
Wed 5/132:10 pm
STT
- PWM
1 stop9h 19m
United Airlines
Deal found 4/24![United Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/36:00 am
PWM
- STT
2 stops10h 15m
American Airlines
Sun 5/1011:27 am
STT
- PWM
1 stop11h 59m
American Airlines
Deal found 4/26![American Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 4/23. 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.
Wed 9/161:35 pm
PWM
- SJU
1 stop8h 25m
Delta
Wed 9/237:00 am
SJU
- PWM
1 stop6h 54m
Delta
Deal found 4/23![Delta logo]()
$276
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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
- STT
2 stops19h 47m
American Airlines
Wed 12/162:49 pm
STT
- PWM
2 stops9h 48m
American Airlines
Deal found 4/24![American Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 10/201:05 pm
PWM
- SJU
2 stops10h 45m
American Airlines
Mon 10/265:25 am
SJU
- PWM
1 stop13h 51m
American Airlines
Deal found 4/27![American Airlines logo]()
$302
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Tue 8/186:00 am
PWM
- SJU
2 stops17h 59m
American Airlines
Fri 8/216:51 am
SJU
- PWM
1 stop13h 26m
American Airlines
Deal found 4/23![American Airlines logo]()
$304
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/2710:57 am
PWM
- SJU
1 stop12h 04m
American Airlines
Wed 6/310:29 am
SJU
- PWM
2 stops13h 22m
American Airlines
Deal found 4/27![American Airlines logo]()
$307
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Wed 8/195:13 pm
PWM
- SJU
2 stops21h 25m
American Airlines
Sat 8/223:44 pm
SJU
- PWM
2 stops24h 49m
American Airlines
Deal found 4/23![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/276:00 am
PWM
- GCM
1 stop6h 54m
Delta
Tue 6/21:19 pm
GCM
- PWM
1 stop8h 50m
Delta
Deal found 4/24![Delta logo]()
$321
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/1311:08 am
PWM
- SJU
2 stops10h 16m
United Airlines
Tue 5/191:00 am
SJU
- PWM
1 stop7h 49m
United Airlines
Deal found 4/24![United Airlines logo]()
$323
This United Airlines deal was found by Cheapflights users on 4/23. 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 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 4/23![United Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/261:18 pm
PWM
- GCM
2 stops23h 36m
Delta
Tue 6/21:19 pm
GCM
- PWM
1 stop8h 50m
Delta
Deal found 4/24![Delta logo]()
$326
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 April 28, 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 April 28, 2026.
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/105:30 am
PWM
- STT
1 stop6h 50m
United Airlines
Wed 5/134:45 pm
STT
- PWM
1 stop7h 14m
United Airlines
Deal found 4/26![United Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/107:23 pm
PWM
- STT
1 stop17h 12m
American Airlines
Wed 5/1312:25 pm
STT
- PWM
2 stops11h 01m
American Airlines
Deal found 4/24![American Airlines logo]()
$250
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/46:30 am
PWM
- SJU
1 stop10h 01m
Delta
Mon 5/112:48 pm
SJU
- PWM
1 stop8h 21m
Delta
Deal found 4/27![Delta logo]()
$407
This Southwest deal was found by Cheapflights users on 4/23. 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.
Sat 5/305:40 am
PWM
- SXM
1 stop6h 45m
Southwest
Sat 6/64:05 pm
SXM
- PWM
1 stop7h 35m
Southwest
Deal found 4/23![Southwest logo]()
$469
This JetBlue deal was found by Cheapflights users on 4/23. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/107:20 am
PWM
- PUJ
1 stop7h 30m
JetBlue
Thu 5/142:32 pm
PUJ
- PWM
1 stop8h 31m
JetBlue
Deal found 4/23![JetBlue logo]()
$497
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/132:08 pm
PWM
- SJU
1 stop7h 16m
United Airlines
Tue 5/191:00 am
SJU
- PWM
1 stop7h 49m
United Airlines
Deal found 4/24![United Airlines logo]()
$302
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 8/126:12 pm
PWM
- GCM
2 stops18h 18m
American Airlines
Mon 8/242:10 pm
GCM
- PWM
2 stops21h 30m
American Airlines
Deal found 4/28![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/286:00 am
PWM
- SJU
1 stop17h 01m
American Airlines
Mon 6/16:20 am
SJU
- PWM
1 stop15h 26m
American Airlines
Deal found 4/25![American Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 8/186:00 am
PWM
- NAS
1 stop7h 35m
Delta
Sat 8/223:00 pm
NAS
- PWM
2 stops8h 59m
Delta
Deal found 4/27![Delta logo]()
$411
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/306:00 am
PWM
- SJU
1 stop7h 45m
United Airlines
Wed 6/31:00 am
SJU
- PWM
1 stop8h 11m
United Airlines
Deal found 4/28![United Airlines logo]()
$385
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/16:54 pm
PWM
- AUA
1 stop18h 05m
American Airlines
Mon 6/85:59 pm
AUA
- PWM
2 stops20h 25m
American Airlines
Deal found 4/24![American Airlines logo]()
$366
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 6/105:15 am
PWM
- SXM
1 stop7h 18m
United Airlines
Wed 6/173:50 pm
SXM
- PWM
1 stop8h 01m
United Airlines
Deal found 4/26![United Airlines logo]()
$401
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/87:23 pm
PWM
- AUA
1 stop16h 17m
American Airlines
Fri 5/292:33 pm
AUA
- PWM
2 stops19h 20m
American Airlines
Deal found 4/24![American Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/166:00 am
PWM
- PUJ
1 stop9h 40m
Delta
Tue 5/191:48 pm
PUJ
- PWM
1 stop10h 55m
Delta
Deal found 4/25![Delta logo]()
$460
This Expedia deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
Sun 5/316:00 am
PWM
- PUJ
1 stop28h 53m
JetBlue
Fri 6/512:09 pm
PUJ
- PWM
1 stop25h 26m
JetBlue
Deal found 4/24![JetBlue logo]()
$525
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/286:00 am
PWM
- AUA
1 stop9h 35m
United Airlines
Tue 8/43:10 pm
AUA
- PWM
2 stops18h 01m
United Airlines
Deal found 4/27![United Airlines logo]()
$404
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/36:00 am
PWM
- SXM
1 stop6h 40m
American Airlines
Mon 6/84:43 pm
SXM
- PWM
2 stops21h 41m
American Airlines
Deal found 4/24![American Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 9/36:00 am
PWM
- GCM
1 stop6h 41m
Delta
Sun 9/612:56 pm
GCM
- PWM
1 stop8h 37m
Delta
Deal found 4/28![Delta logo]()
$481
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/246:00 pm
PWM
- MBJ
2 stops18h 47m
American Airlines
Tue 7/285:14 pm
MBJ
- PWM
2 stops20h 02m
American Airlines
Deal found 4/27![American Airlines logo]()
$399
This JetBlue deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/266:00 am
PWM
- UVF
1 stop9h 35m
JetBlue
Thu 5/282:10 pm
UVF
- PWM
1 stop9h 48m
JetBlue
Deal found 4/26![JetBlue logo]()
$585
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/261:18 pm
PWM
- GCM
2 stops23h 36m
Delta
Sun 5/311:19 pm
GCM
- PWM
1 stop8h 50m
Delta
Deal found 4/24![Delta logo]()
$486
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/65:15 am
PWM
- PUJ
1 stop11h 15m
United Airlines
Fri 6/126:45 pm
PUJ
- PWM
1 stop28h 45m
United Airlines
Deal found 4/27![United Airlines logo]()
$465
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 9/257:20 pm
PWM
- MBJ
1 stop14h 50m
American Airlines
Tue 9/292:40 pm
MBJ
- PWM
2 stops20h 08m
American Airlines
Deal found 4/26![American Airlines logo]()
$399
This KAYAK deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Mon 6/156:00 am
PWM
- PLS
1 stop6h 50m
JetBlue
Sat 6/202:15 pm
PLS
- PWM
1 stop10h 10m
JetBlue
Deal found 4/27![JetBlue logo]()
$601
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 9/186:00 am
PWM
- MBJ
1 stop10h 34m
Delta
Tue 9/2212:50 pm
MBJ
- PWM
1 stop10h 09m
Delta
Deal found 4/26![Delta logo]()
$507
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/411:08 am
PWM
- SJU
2 stops10h 16m
United Airlines
Mon 5/114:55 pm
SJU
- PWM
1 stop7h 04m
United Airlines
Deal found 4/27![United Airlines logo]()
$466
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/235:57 pm
PWM
- MBJ
2 stops20h 11m
American Airlines
Mon 6/12:08 pm
MBJ
- PWM
2 stops19h 24m
American Airlines
Deal found 4/24![American Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 7/136:00 am
PWM
- NAS
1 stop10h 39m
Delta
Fri 7/243:22 pm
NAS
- PWM
2 stops9h 37m
Delta
Deal found 4/24![Delta logo]()
$519
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/245:15 am
PWM
- MBJ
1 stop10h 55m
United Airlines
Tue 7/284:12 pm
MBJ
- PWM
1 stop6h 39m
United Airlines
Deal found 4/27![United Airlines logo]()
$476
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 8/187:22 am
PWM
- NAS
1 stop5h 26m
American Airlines
Sat 8/2212:11 pm
NAS
- PWM
1 stop10h 07m
American Airlines
Deal found 4/27![American Airlines logo]()
$407
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated April 28, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated April 28, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 4/307:23 pm
PWM
- STT
2 stops16h 12m
American Airlines
Fri 5/82:05 pm
STT
- PWM
2 stops20h 18m
American Airlines
Deal found 4/24![American Airlines logo]()
$365
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/17:10 pm
PWM
- GCM
2 stops18h 20m
United Airlines
Tue 5/51:35 pm
GCM
- PWM
2 stops19h 43m
United Airlines
Deal found 4/27![United Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/210:57 am
PWM
- SJU
1 stop11h 51m
Multiple Airlines
Fri 5/88:59 am
SJU
- PWM
1 stop24h 13m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$378
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/36:00 am
PWM
- STT
2 stops10h 15m
American Airlines
Sun 5/1011:27 am
STT
- PWM
1 stop11h 59m
American Airlines
Deal found 4/26![American Airlines logo]()
$275
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/87:23 pm
PWM
- AUA
1 stop16h 17m
American Airlines
Fri 5/292:33 pm
AUA
- PWM
2 stops19h 20m
American Airlines
Deal found 4/24![American Airlines logo]()
$366
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/106:00 am
PWM
- STT
1 stop7h 08m
United Airlines
Wed 5/132:10 pm
STT
- PWM
1 stop9h 19m
United Airlines
Deal found 4/24![United Airlines logo]()
$250
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/132:08 pm
PWM
- SJU
1 stop7h 16m
United Airlines
Tue 5/191:00 am
SJU
- PWM
1 stop7h 49m
United Airlines
Deal found 4/24![United Airlines logo]()
$302
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/261:18 pm
PWM
- GCM
2 stops23h 36m
Delta
Tue 6/21:19 pm
GCM
- PWM
1 stop8h 50m
Delta
Deal found 4/24![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/2710:57 am
PWM
- SJU
1 stop12h 04m
American Airlines
Wed 6/310:29 am
SJU
- PWM
2 stops13h 22m
American Airlines
Deal found 4/27![American Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/276:00 am
PWM
- GCM
1 stop6h 54m
Delta
Sat 5/301:19 pm
GCM
- PWM
1 stop8h 50m
Delta
Deal found 4/24![Delta logo]()
$321
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/286:00 am
PWM
- SJU
1 stop17h 01m
American Airlines
Mon 6/16:20 am
SJU
- PWM
1 stop17h 31m
American Airlines
Deal found 4/27![American Airlines logo]()
$342
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/295:57 pm
PWM
- GCM
1 stop22h 10m
American Airlines
Mon 6/112:01 pm
GCM
- PWM
2 stops10h 50m
American Airlines
Deal found 4/28![American Airlines logo]()
$333
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 April 28, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
This Delta deal was found by Cheapflights users on 4/23. 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.
Fri 5/86:00 am
PWM
- GCM
1 stop6h 54m
Delta
Deal found 4/23![Delta logo]()
$112
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/106:01 pm
PWM
- GCM
2 stops18h 30m
American Airlines
Deal found 4/23![American Airlines logo]()
$118
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/186:00 am
PWM
- STT
1 stop7h 08m
United Airlines
Deal found 4/27![United Airlines logo]()
$123
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/26:00 am
PWM
- SXM
2 stops9h 42m
American Airlines
Deal found 4/24![American Airlines logo]()
$139
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/36:00 am
PWM
- SXM
1 stop6h 40m
American Airlines
Deal found 4/24![American Airlines logo]()
$144
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/296:00 am
PWM
- NAS
1 stop10h 37m
Delta
Deal found 4/24![Delta logo]()
$145
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/87:23 pm
PWM
- AUA
1 stop16h 17m
American Airlines
Deal found 4/24![American Airlines logo]()
$148
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/295:57 pm
PWM
- NAS
2 stops15h 30m
American Airlines
Deal found 4/24![American Airlines logo]()
$151
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 9/16:00 am
PWM
- MBJ
1 stop8h 58m
American Airlines
Deal found 4/24![American Airlines logo]()
$152
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/273:05 pm
PWM
- SJU
1 stop7h 56m
American Airlines
Deal found 4/27![American Airlines logo]()
$156
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 9/27:22 am
PWM
- MBJ
1 stop7h 06m
American Airlines
Deal found 4/24![American Airlines logo]()
$157
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 10/105:27 pm
PWM
- MBJ
2 stops16h 38m
American Airlines
Deal found 4/28![American Airlines logo]()
$158
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 April 28, 2026.
Round-trip from | $250 (United Airlines) |
|---|---|
One-way from | $112 (Delta) |
Popular in | April |
Cheapest in | October |
Average price | $711 |
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 April 28, 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
Quickest round-trip
PortlandSaint Thomas Island
PWM - STT
PWMSTT
Portland
Sun 5/10
5:30 am-12:20 pm
1 stop6h 50m
Saint Thomas Island Cyril E King
Wed 5/13
4:45 pm-11:59 pm
1 stop7h 14m
$250
PortlandSaint Thomas Island
PWM - STT
PWMSTT
Portland
Sun 5/10
7:23 pm-12:35 pm
1 stop17h 12m
Saint Thomas Island Cyril E King
Wed 5/13
12:25 pm-11:26 pm
2 stops11h 01m
$250
PortlandSan Juan
PWM - SJU
PWMSJU
Portland
Wed 5/13
2:08 pm-9:24 pm
1 stop7h 16m
San Juan Luis Munoz Marin Intl
Tue 5/19
1:00 am-8:49 am
1 stop7h 49m
$302
PortlandGeorge Town
PWM - GCM
PWMGCM
Portland
Wed 8/12
6:12 pm-11:30 am
2 stops18h 18m
George Town Owen Roberts Intl
Mon 8/24
2:10 pm-12:40 pm
2 stops21h 30m
$331
PortlandSan Juan
PWM - SJU
PWMSJU
Portland
Thu 5/28
6:00 am-11:01 pm
1 stop17h 01m
San Juan Luis Munoz Marin Intl
Mon 6/1
6:20 am-9:46 pm
1 stop15h 26m
$342
PortlandOranjestad
PWM - AUA
PWMAUA
Portland
Mon 6/1
6:54 pm-12:59 pm
1 stop18h 05m
Oranjestad Reina Beatrix
Mon 6/8
5:59 pm-2:24 pm
2 stops20h 25m
$366
PortlandOranjestad
PWM - AUA
PWMAUA
Portland
Fri 5/8
7:23 pm-11:40 am
1 stop16h 17m
Oranjestad Reina Beatrix
Fri 5/29
2:33 pm-9:53 am
2 stops19h 20m
$366
PortlandSimpson Bay
PWM - SXM
PWMSXM
Portland
Wed 6/3
6:00 am-12:40 pm
1 stop6h 40m
Simpson Bay Princess Juliana
Mon 6/8
4:43 pm-2:24 pm
2 stops21h 41m
$377
PortlandSan Juan
PWM - SJU
PWMSJU
Portland
Sat 5/30
6:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Wed 6/3
1:00 am-9:11 am
1 stop8h 11m
$385
PortlandMontego Bay
PWM - MBJ
PWMMBJ
Portland
Fri 7/24
6:00 pm-11:47 am
2 stops18h 47m
Montego Bay Sangster Intl
Tue 7/28
5:14 pm-2:16 pm
2 stops20h 02m
$399
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-STT
PWM-SXM
PWM-NAS
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-STT
PWM-SXM
PWM-NAS
How far ahead should I book a flight from Portland, Maine to Caribbean?
Booking 31 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.
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 December is currently the most expensive (average of $298). 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 April 28, 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
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 April 28, 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 April 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$589 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$176 | Average$422 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$584 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$565 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$315 | Average$660 | FlexibilityNo cancel fee | On-time63% |