$140+ 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 7/18. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Jul 8 — Jul 151
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 June 8, 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 8, 2026.
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 9/192:35 pm
PWM
- SJU
1 stop9h 09m
Delta
Sat 9/261:32 pm
SJU
- PWM
1 stop10h 27m
Delta
Deal found 6/3![Delta logo]()
$302
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/3![American Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/3![Delta logo]()
$340
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 10/206:00 am
PWM
- SJU
2 stops12h 05m
American Airlines
Mon 10/265:25 am
SJU
- PWM
1 stop13h 00m
American Airlines
Deal found 6/4![American Airlines logo]()
$342
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:38 pm
PWM
- PUJ
1 stop17h 51m
American Airlines
Wed 12/95:30 pm
PUJ
- PWM
2 stops19h 41m
American Airlines
Deal found 6/4![American Airlines logo]()
$345
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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
1 stop17h 51m
American Airlines
Mon 12/145:30 pm
PUJ
- PWM
2 stops19h 07m
American Airlines
Deal found 6/4![American Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:00 am
PWM
- NAS
1 stop7h 30m
Delta
Fri 11/201:20 pm
NAS
- PWM
1 stop9h 03m
Delta
Deal found 6/4![Delta logo]()
$350
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 11/96:00 am
PWM
- MBJ
1 stop10h 35m
Delta
Fri 11/131:50 pm
MBJ
- PWM
1 stop9h 59m
Delta
Deal found 6/4![Delta logo]()
$352
This American Airlines deal was found by Cheapflights users on 6/7. 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.
Tue 10/201:05 pm
PWM
- SJU
2 stops10h 45m
American Airlines
Wed 11/42:41 pm
SJU
- PWM
2 stops9h 57m
American Airlines
Deal found 6/7![American Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 12/95:17 pm
PWM
- PUJ
2 stops20h 39m
American Airlines
Sun 12/135:30 pm
PUJ
- PWM
2 stops19h 07m
American Airlines
Deal found 6/4![American Airlines logo]()
$355
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 12/15:37 pm
PWM
- SXM
2 stops21h 48m
American Airlines
Tue 12/83:20 pm
SXM
- PWM
2 stops21h 51m
American Airlines
Deal found 6/4![American Airlines logo]()
$362
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/143:53 pm
PWM
- SJU
1 stop6h 54m
American Airlines
Sat 11/216:25 am
SJU
- PWM
1 stop12h 48m
American Airlines
Deal found 6/6![American Airlines logo]()
$362
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 8, 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 8, 2026.
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/62:35 pm
PWM
- SJU
1 stop9h 21m
Delta
Sun 10/117:00 am
SJU
- PWM
1 stop6h 53m
Delta
Deal found 6/3![Delta logo]()
$302
This United Airlines deal was found by Cheapflights users on 6/7. 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 10/206:00 am
PWM
- SJU
1 stop7h 45m
United Airlines
Wed 11/47:45 am
SJU
- PWM
2 stops16h 12m
United Airlines
Deal found 6/7![United Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:17 pm
PWM
- PUJ
2 stops20h 39m
American Airlines
Wed 12/95:30 pm
PUJ
- PWM
2 stops19h 07m
American Airlines
Deal found 6/4![American Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Wed 10/710:25 am
PWM
- SJU
2 stops11h 50m
Southwest
Mon 10/125:00 am
SJU
- PWM
2 stops11h 55m
Southwest
Deal found 6/3![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 9/196:05 am
PWM
- SJU
1 stop10h 26m
Delta
Sat 9/267:00 am
SJU
- PWM
1 stop6h 54m
Delta
Deal found 6/4![Delta logo]()
$302
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:35 pm
PWM
- SJU
1 stop9h 21m
Delta
Mon 10/267:00 am
SJU
- PWM
1 stop6h 53m
Delta
Deal found 6/7![Delta logo]()
$312
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 12/15:37 pm
PWM
- SXM
2 stops21h 48m
American Airlines
Tue 12/83:20 pm
SXM
- PWM
2 stops21h 51m
American Airlines
Deal found 6/3![American Airlines logo]()
$362
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/217:35 pm
PWM
- AUA
2 stops19h 45m
United Airlines
Tue 8/254:30 pm
AUA
- PWM
1 stop7h 29m
United Airlines
Deal found 6/4![United Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/162:35 pm
PWM
- SJU
1 stop9h 09m
Delta
Wed 9/237:00 am
SJU
- PWM
1 stop6h 54m
Delta
Deal found 6/6![Delta logo]()
$312
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:21 pm
PWM
- SXM
2 stops19h 01m
American Airlines
Sat 9/52:33 pm
SXM
- PWM
1 stop20h 40m
American Airlines
Deal found 6/5![American Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
PWM
- AUA
1 stop9h 35m
United Airlines
Tue 7/284:30 pm
AUA
- PWM
1 stop7h 21m
United Airlines
Deal found 6/6![United Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:35 pm
PWM
- SJU
1 stop9h 21m
Delta
Wed 11/47:00 am
SJU
- PWM
1 stop7h 53m
Delta
Deal found 6/7![Delta logo]()
$312
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 6/5![American Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/286:05 am
PWM
- SJU
1 stop7h 37m
Delta
Sun 8/305:50 pm
SJU
- PWM
1 stop7h 09m
Delta
Deal found 6/4![Delta logo]()
$312
This United Airlines deal was found by Cheapflights users on 6/7. 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.
Sat 8/296:00 am
PWM
- SJU
1 stop7h 45m
United Airlines
Wed 9/24:55 pm
SJU
- PWM
1 stop7h 04m
United Airlines
Deal found 6/7![United Airlines logo]()
$402
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 12/15:37 pm
PWM
- SXM
2 stops21h 48m
American Airlines
Tue 12/155:25 pm
SXM
- PWM
2 stops24h 03m
American Airlines
Deal found 6/4![American Airlines logo]()
$376
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/3![Delta logo]()
$340
This United Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 12/22:45 pm
PWM
- MBJ
2 stops21h 22m
United Airlines
Sat 12/53:36 pm
MBJ
- PWM
1 stop7h 21m
United Airlines
Deal found 6/5![United Airlines logo]()
$421
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:20 pm
PWM
- MBJ
2 stops16h 40m
American Airlines
Sat 10/175:00 pm
MBJ
- PWM
2 stops17h 54m
American Airlines
Deal found 6/3![American Airlines logo]()
$411
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/306:00 am
PWM
- NAS
1 stop5h 51m
Delta
Sun 8/23:26 pm
NAS
- PWM
1 stop7h 48m
Delta
Deal found 6/3![Delta logo]()
$340
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:38 pm
PWM
- AUA
1 stop18h 18m
American Airlines
Thu 12/105:45 pm
AUA
- PWM
2 stops18h 52m
American Airlines
Deal found 6/4![American Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 6/5![Delta logo]()
$350
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am
PWM
- MBJ
1 stop6h 43m
United Airlines
Wed 9/2312:52 pm
MBJ
- PWM
2 stops20h 48m
United Airlines
Deal found 6/6![United Airlines logo]()
$483
This American Airlines deal was found by Cheapflights users on 6/8. 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 11/265:19 pm
PWM
- STT
2 stops17h 48m
American Airlines
Wed 12/26:17 pm
STT
- PWM
2 stops18h 20m
American Airlines
Deal found 6/8![American Airlines logo]()
$418
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 stop10h 37m
Delta
Sun 8/233:22 pm
NAS
- PWM
1 stop7h 51m
Delta
Deal found 6/5![Delta logo]()
$350
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:15 am
PWM
- STT
1 stop7h 43m
United Airlines
Sat 10/34:45 pm
STT
- PWM
2 stops16h 38m
United Airlines
Deal found 6/4![United Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 11/96:00 am
PWM
- MBJ
1 stop10h 35m
Delta
Fri 11/131:50 pm
MBJ
- PWM
1 stop9h 59m
Delta
Deal found 6/4![Delta logo]()
$352
This American Airlines deal was found by Cheapflights users on 6/8. 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 11/246:39 pm
PWM
- STT
2 stops19h 36m
American Airlines
Thu 12/32:49 pm
STT
- PWM
2 stops9h 48m
American Airlines
Deal found 6/8![American Airlines logo]()
$435
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:00 am
PWM
- AUA
1 stop8h 10m
Delta
Tue 11/32:55 pm
AUA
- PWM
1 stop9h 54m
Delta
Deal found 6/7![Delta logo]()
$377
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:39 pm
PWM
- AUA
2 stops21h 01m
American Airlines
Tue 11/241:40 pm
AUA
- PWM
1 stop9h 53m
American Airlines
Deal found 6/5![American Airlines logo]()
$464
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated June 8, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated June 8, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 6/116:57 pm
PWM
- NAS
1 stop16h 55m
Delta
Thu 6/183:29 pm
NAS
- PWM
1 stop7h 36m
Delta
Deal found 6/4![Delta logo]()
$400
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 6/117:58 am
PWM
- NAS
2 stops11h 32m
American Airlines
Thu 6/1812:36 pm
NAS
- PWM
1 stop12h 06m
American Airlines
Deal found 6/4![American Airlines logo]()
$404
This Southwest deal was found by Cheapflights users on 6/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/161:05 pm
PWM
- SJU
2 stops11h 10m
Southwest
Fri 6/195:15 pm
SJU
- PWM
1 stop6h 50m
Southwest
Deal found 6/7![Southwest logo]()
$492
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 6/4![Delta logo]()
$340
This American Airlines deal was found by Cheapflights users on 6/7. 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.
Wed 6/245:38 am
PWM
- NAS
2 stops13h 52m
American Airlines
Sun 8/232:36 pm
NAS
- PWM
2 stops9h 01m
American Airlines
Deal found 6/7![American Airlines logo]()
$421
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:24 pm
PWM
- SXM
2 stops20h 20m
American Airlines
Fri 7/101:34 pm
SXM
- PWM
2 stops19h 48m
American Airlines
Deal found 6/6![American Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/46:14 am
PWM
- MBJ
1 stop10h 20m
Delta
Wed 7/1512:59 pm
MBJ
- PWM
1 stop11h 00m
Delta
Deal found 6/3![Delta logo]()
$453
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/86:00 am
PWM
- SJU
2 stops15h 24m
United Airlines
Sat 7/114:55 pm
SJU
- PWM
1 stop6h 56m
United Airlines
Deal found 6/4![United Airlines logo]()
$489
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
PWM
- AUA
1 stop9h 35m
United Airlines
Tue 7/284:30 pm
AUA
- PWM
1 stop7h 21m
United Airlines
Deal found 6/6![United Airlines logo]()
$377
This JetBlue deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Wed 7/222:40 pm
PWM
- SJU
1 stop8h 16m
JetBlue
Tue 7/285:01 am
SJU
- PWM
1 stop7h 29m
JetBlue
Deal found 6/3![JetBlue logo]()
$468
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/286:01 pm
PWM
- MBJ
2 stops18h 46m
American Airlines
Mon 8/32:31 pm
MBJ
- PWM
2 stops19h 00m
American Airlines
Deal found 6/4![American Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/306:00 am
PWM
- NAS
2 stops10h 39m
Delta
Sun 8/21:16 pm
NAS
- PWM
1 stop9h 58m
Delta
Deal found 6/5![Delta logo]()
$354
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 8, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 8, 2026.
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/187:51 pm
PWM
- SXM
2 stops19h 53m
American Airlines
Deal found 6/5![American Airlines logo]()
$140
This American Airlines deal was found by Cheapflights users on 6/7. 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.
Tue 12/15:37 pm
PWM
- SXM
2 stops21h 48m
American Airlines
Deal found 6/7![American Airlines logo]()
$145
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:46 pm
PWM
- AUA
1 stop18h 04m
American Airlines
Deal found 6/4![American Airlines logo]()
$151
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:35 pm
PWM
- SJU
1 stop9h 21m
Delta
Deal found 6/4![Delta logo]()
$151
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 9/26:00 am
PWM
- MBJ
1 stop6h 34m
Delta
Deal found 6/3![Delta logo]()
$152
This United Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 9/166:00 am
PWM
- MBJ
1 stop6h 43m
United Airlines
Deal found 6/5![United Airlines logo]()
$155
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Mon 11/96:39 pm
PWM
- AUA
2 stops21h 01m
American Airlines
Deal found 6/8![American Airlines logo]()
$155
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:30 am
PWM
- SJU
1 stop9h 50m
Delta
Deal found 6/7![Delta logo]()
$156
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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
- AUA
2 stops20h 22m
American Airlines
Deal found 6/4![American Airlines logo]()
$157
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/38:15 pm
PWM
- AUA
2 stops18h 45m
United Airlines
Deal found 6/6![United Airlines logo]()
$162
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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
- MBJ
2 stops20h 11m
American Airlines
Deal found 6/5![American Airlines logo]()
$168
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 9/16:09 pm
PWM
- KIN
2 stops19h 50m
American Airlines
Deal found 6/4![American Airlines logo]()
$169
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 8, 2026.
Round-trip from | $302 (Delta) |
|---|---|
One-way from | $134 (Delta) |
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 8, 2026.
Use the filters below to find and compare flights from Portland to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandSan Juan
PWM - SJU
PWMSJU
Portland
Tue 10/6
2:35 pm-11:56 pm
1 stop9h 21m
San Juan Luis Munoz Marin Intl
Sun 10/11
7:00 am-1:53 pm
1 stop6h 53m
$302
PortlandSan Juan
PWM - SJU
PWMSJU
Portland
Sat 9/19
6:05 am-4:31 pm
1 stop10h 26m
San Juan Luis Munoz Marin Intl
Sat 9/26
7:00 am-1:54 pm
1 stop6h 54m
$302
PortlandSan Juan
PWM - SJU
PWMSJU
Portland
Tue 10/20
6:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Wed 11/4
7:45 am-10:57 pm
2 stops16h 12m
$312
PortlandSan Juan
PWM - SJU
PWMSJU
Portland
Tue 10/20
2:35 pm-11:56 pm
1 stop9h 21m
San Juan Luis Munoz Marin Intl
Mon 10/26
7:00 am-1:53 pm
1 stop6h 53m
$312
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
7:00 am-1:54 pm
1 stop6h 54m
$312
PortlandSan Juan
PWM - SJU
PWMSJU
Portland
Tue 10/20
2:35 pm-11:56 pm
1 stop9h 21m
San Juan Luis Munoz Marin Intl
Wed 11/4
7:00 am-1:53 pm
1 stop7h 53m
$312
PortlandSan Juan
PWM - SJU
PWMSJU
Portland
Fri 8/28
6:05 am-1:42 pm
1 stop7h 37m
San Juan Luis Munoz Marin Intl
Sun 8/30
5:50 pm-12:59 am
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
$340
Quickest round-trip
PortlandNassau
PWM - NAS
PWMNAS
Portland
Thu 7/30
6:00 am-11:51 am
1 stop5h 51m
Nassau Intl
Sun 8/2
3:26 pm-11:14 pm
1 stop7h 48m
$340
PortlandNassau
PWM - NAS
PWMNAS
Portland
Mon 11/16
6:00 am-1:30 pm
1 stop7h 30m
Nassau Intl
Fri 11/20
2:55 pm-10:23 pm
1 stop7h 28m
$350
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-NAS
PWM-MBJ
PWM-SXM
PWM-AUA
PWM-SJU
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-NAS
PWM-MBJ
PWM-SXM
PWM-AUA
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 8, 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
Comfort
8.0
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
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 8, 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 8, 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% |