$194+ Cheap flights from Portland (PDX) 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Aug 23 — Aug 301
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Caribbean with Cheapflights
1. Tell us where you want to go
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Portland to Caribbean
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Cheapest flights from Portland to CaribbeanExplore the most affordable flight options available from Portland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 24, 2026.
Explore the most affordable flight options available from Portland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 24, 2026.
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:00 pm
PDX
- STT
2 stops18h 53m
American Airlines
Fri 8/284:42 pm
STT
- PDX
2 stops21h 12m
American Airlines
Deal found 7/19![American Airlines logo]()
$420
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:00 pm
PDX
- SJU
2 stops12h 45m
Southwest
Tue 11/175:45 am
SJU
- PDX
2 stops13h 15m
Southwest
Deal found 7/22![Southwest logo]()
$436
This American Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1211:34 pm
PDX
- SJU
1 stop20h 41m
American Airlines
Thu 8/2012:55 am
SJU
- PDX
1 stop20h 05m
American Airlines
Deal found 7/21![American Airlines logo]()
$441
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/293:00 pm
PDX
- STT
2 stops18h 53m
American Airlines
Sat 9/53:43 pm
STT
- PDX
2 stops22h 51m
American Airlines
Deal found 7/19![American Airlines logo]()
$445
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:05 am
PDX
- SJU
2 stops11h 55m
Southwest
Thu 8/275:30 am
SJU
- PDX
1 stop12h 30m
Southwest
Deal found 7/20![Southwest logo]()
$451
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/211:00 pm
PDX
- MBJ
1 stop12h 14m
United Airlines
Wed 11/113:20 pm
MBJ
- PDX
1 stop21h 01m
United Airlines
Deal found 7/21![United Airlines logo]()
$452
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:00 am
PDX
- SJU
1 stop9h 38m
United Airlines
Sat 10/102:00 pm
SJU
- PDX
1 stop10h 10m
United Airlines
Deal found 7/22![United Airlines logo]()
$456
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/22:20 pm
PDX
- MBJ
2 stops19h 05m
Delta
Wed 11/116:00 pm
MBJ
- PDX
2 stops18h 31m
Delta
Deal found 7/21![Delta logo]()
$457
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:35 am
PDX
- STT
2 stops11h 27m
Delta
Thu 5/131:25 pm
STT
- PDX
1 stop12h 01m
Delta
Deal found 7/21![Delta logo]()
$459
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2612:01 pm
PDX
- SJU
2 stops18h 23m
American Airlines
Sat 10/316:00 am
SJU
- PDX
1 stop10h 32m
American Airlines
Deal found 7/19![American Airlines logo]()
$461
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:20 am
PDX
- MBJ
1 stop8h 52m
American Airlines
Tue 10/2012:16 pm
MBJ
- PDX
1 stop30h 47m
American Airlines
Deal found 7/22![American Airlines logo]()
$462
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/210:05 pm
PDX
- SJU
1 stop15h 15m
Delta
Wed 12/163:35 pm
SJU
- PDX
2 stops12h 16m
Delta
Deal found 7/21![Delta logo]()
$466
Best flights from Portland to CaribbeanDiscover carefully curated flight deals from Portland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 24, 2026.
Discover carefully curated flight deals from Portland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 24, 2026.
This American Airlines deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:00 pm
PDX
- STT
2 stops18h 53m
American Airlines
Fri 8/284:42 pm
STT
- PDX
2 stops21h 12m
American Airlines
Deal found 7/18![American Airlines logo]()
$420
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:07 pm
PDX
- SJU
2 stops13h 50m
United Airlines
Mon 9/211:25 pm
SJU
- PDX
1 stop11h 38m
United Airlines
Deal found 7/21![United Airlines logo]()
$436
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:50 am
PDX
- SJU
2 stops12h 15m
Southwest
Thu 9/1010:00 am
SJU
- PDX
2 stops13h 45m
Southwest
Deal found 7/21![Southwest logo]()
$436
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/810:05 pm
PDX
- MBJ
1 stop11h 20m
Delta
Sat 11/144:00 pm
MBJ
- PDX
1 stop10h 47m
Delta
Deal found 7/22![Delta logo]()
$452
This Air Canada deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/87:10 pm
PDX
- MBJ
2 stops14h 40m
Air Canada
Sat 11/146:20 pm
MBJ
- PDX
2 stops23h 21m
Air Canada
Deal found 7/23![Air Canada logo]()
$528
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:07 pm
PDX
- SJU
2 stops13h 50m
United Airlines
Sun 9/271:00 am
SJU
- PDX
1 stop11h 50m
United Airlines
Deal found 7/22![United Airlines logo]()
$436
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:50 am
PDX
- SJU
2 stops13h 10m
Southwest
Wed 9/91:20 pm
SJU
- PDX
2 stops11h 55m
Southwest
Deal found 7/22![Southwest logo]()
$436
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:15 pm
PDX
- MBJ
2 stops16h 10m
Delta
Tue 11/106:00 pm
MBJ
- PDX
2 stops18h 16m
Delta
Deal found 7/23![Delta logo]()
$457
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:00 am
PDX
- SJU
2 stops15h 50m
United Airlines
Wed 9/231:25 pm
SJU
- PDX
1 stop11h 38m
United Airlines
Deal found 7/20![United Airlines logo]()
$436
This Southwest deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:00 pm
PDX
- SJU
2 stops12h 45m
Southwest
Tue 11/175:45 am
SJU
- PDX
2 stops13h 15m
Southwest
Deal found 7/18![Southwest logo]()
$436
This FlightHub deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1311:27 pm
PDX
- POP
1 stop32h 32m
JetBlue
Thu 8/203:30 pm
POP
- PDX
2 stops24h 31m
JetBlue
Deal found 7/20![JetBlue logo]()
$1,001
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/199:45 pm
PDX
- MBJ
1 stop10h 25m
Delta
Thu 1/282:10 pm
MBJ
- PDX
2 stops12h 41m
Delta
Deal found 7/23![Delta logo]()
$457
This American Airlines deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/243:00 pm
PDX
- SXM
2 stops19h 22m
American Airlines
Sat 9/122:53 pm
SXM
- PDX
2 stops23h 02m
American Airlines
Deal found 7/18![American Airlines logo]()
$512
This Priceline deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/32:19 pm
PDX
- CUR
2 stops20h 47m
Multiple Airlines
Wed 9/911:35 am
CUR
- PDX
2 stops32h 15m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$1,034
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/311:09 pm
PDX
- SXM
2 stops13h 22m
American Airlines
Mon 11/95:33 pm
SXM
- PDX
2 stops23h 00m
American Airlines
Deal found 7/22![American Airlines logo]()
$512
This United Airlines deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:00 am
PDX
- SJU
2 stops12h 38m
United Airlines
Sat 8/221:25 pm
SJU
- PDX
1 stop11h 38m
United Airlines
Deal found 7/18![United Airlines logo]()
$466
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/121:40 pm
PDX
- SJU
2 stops18h 10m
Southwest
Wed 12/165:45 am
SJU
- PDX
2 stops13h 15m
Southwest
Deal found 7/20![Southwest logo]()
$476
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:35 pm
PDX
- SJU
2 stops10h 35m
Southwest
Mon 9/215:00 am
SJU
- PDX
2 stops13h 00m
Southwest
Deal found 7/21![Southwest logo]()
$481
This American Airlines deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/1710:59 pm
PDX
- STT
1 stop14h 06m
American Airlines
Sat 1/236:39 pm
STT
- PDX
2 stops21h 43m
American Airlines
Deal found 7/18![American Airlines logo]()
$538
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:49 pm
PDX
- SXM
2 stops16h 08m
United Airlines
Sat 12/122:40 pm
SXM
- PDX
1 stop12h 32m
United Airlines
Deal found 7/21![United Airlines logo]()
$507
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/1710:05 pm
PDX
- PUJ
1 stop14h 15m
Delta
Fri 1/225:45 pm
PUJ
- PDX
2 stops26h 42m
Delta
Deal found 7/23![Delta logo]()
$565
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:29 pm
PDX
- STT
2 stops15h 02m
United Airlines
Sat 10/312:35 pm
STT
- PDX
1 stop11h 38m
United Airlines
Deal found 7/19![United Airlines logo]()
$549
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2510:05 pm
PDX
- PUJ
1 stop11h 23m
Delta
Sun 11/14:56 pm
PUJ
- PDX
2 stops23h 37m
Delta
Deal found 7/23![Delta logo]()
$654
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:15 pm
PDX
- SJU
2 stops17h 27m
United Airlines
Fri 9/111:00 am
SJU
- PDX
2 stops13h 28m
United Airlines
Deal found 7/23![United Airlines logo]()
$551
This American Airlines deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/173:00 pm
PDX
- SXM
2 stops19h 22m
American Airlines
Mon 8/242:22 pm
SXM
- PDX
2 stops23h 32m
American Airlines
Deal found 7/18![American Airlines logo]()
$680
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/110:59 pm
PDX
- MBJ
1 stop11h 47m
United Airlines
Fri 12/111:25 pm
MBJ
- PDX
2 stops23h 15m
United Airlines
Deal found 7/21![United Airlines logo]()
$577
This Orbitz deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1311:27 pm
PDX
- POP
1 stop32h 32m
JetBlue
Sun 8/233:30 pm
POP
- PDX
2 stops24h 31m
JetBlue
Deal found 7/21![JetBlue logo]()
$1,054
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:44 pm
PDX
- POP
2 stops11h 36m
American Airlines
Sat 10/31:10 pm
POP
- PDX
2 stops24h 45m
American Airlines
Deal found 7/19![American Airlines logo]()
$735
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:34 pm
PDX
- AUA
2 stops15h 26m
Delta
Fri 10/23:25 pm
AUA
- PDX
2 stops23h 21m
Delta
Deal found 7/21![Delta logo]()
$760
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2611:00 pm
PDX
- MBJ
1 stop12h 14m
United Airlines
Thu 10/292:20 pm
MBJ
- PDX
3 stops32h 48m
United Airlines
Deal found 7/21![United Airlines logo]()
$577
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated July 24, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated July 24, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1211:34 pm
PDX
- SJU
1 stop20h 41m
American Airlines
Thu 8/2012:55 am
SJU
- PDX
1 stop20h 05m
American Airlines
Deal found 7/21![American Airlines logo]()
$441
This American Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/169:44 pm
PDX
- SJU
1 stop14h 07m
American Airlines
Sat 8/2212:55 am
SJU
- PDX
1 stop13h 39m
American Airlines
Deal found 7/20![American Airlines logo]()
$461
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:05 am
PDX
- SJU
2 stops11h 55m
Southwest
Mon 8/242:35 pm
SJU
- PDX
2 stops12h 05m
Southwest
Deal found 7/19![Southwest logo]()
$481
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:05 am
PDX
- SJU
2 stops11h 55m
Southwest
Thu 8/275:30 am
SJU
- PDX
1 stop12h 30m
Southwest
Deal found 7/20![Southwest logo]()
$451
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:00 am
PDX
- SJU
2 stops15h 50m
United Airlines
Tue 8/251:00 am
SJU
- PDX
1 stop11h 50m
United Airlines
Deal found 7/20![United Airlines logo]()
$483
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:00 pm
PDX
- STT
2 stops18h 53m
American Airlines
Fri 8/284:42 pm
STT
- PDX
2 stops21h 12m
American Airlines
Deal found 7/19![American Airlines logo]()
$420
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2111:34 pm
PDX
- MBJ
2 stops12h 15m
American Airlines
Fri 8/285:08 pm
MBJ
- PDX
2 stops20h 26m
American Airlines
Deal found 7/19![American Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:35 am
PDX
- STT
2 stops11h 27m
Delta
Thu 5/131:25 pm
STT
- PDX
1 stop12h 01m
Delta
Deal found 7/21![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2111:20 pm
PDX
- SJU
1 stop10h 56m
Delta
Wed 9/22:59 pm
SJU
- PDX
1 stop9h 45m
Delta
Deal found 7/20![Delta logo]()
$476
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:10 am
PDX
- SJU
1 stop10h 28m
United Airlines
Sat 8/292:00 pm
SJU
- PDX
1 stop10h 05m
United Airlines
Deal found 7/20![United Airlines logo]()
$436
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/293:00 pm
PDX
- STT
2 stops18h 53m
American Airlines
Sat 9/53:43 pm
STT
- PDX
2 stops22h 51m
American Airlines
Deal found 7/19![American Airlines logo]()
$445
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2910:05 pm
PDX
- SJU
1 stop13h 48m
American Airlines
Thu 9/36:00 am
SJU
- PDX
2 stops13h 51m
American Airlines
Deal found 7/19![American Airlines logo]()
$486
One-way flights from Portland to CaribbeanSearch for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 24, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:49 pm
PDX
- SJU
2 stops27h 52m
Frontier
Deal found 7/18![Frontier logo]()
$194
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/811:00 pm
PDX
- MBJ
1 stop10h 13m
United Airlines
Deal found 7/22![United Airlines logo]()
$202
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:15 am
PDX
- SJU
2 stops13h 40m
American Airlines
Deal found 7/19![American Airlines logo]()
$218
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/66:00 am
PDX
- SJU
1 stop11h 39m
American Airlines
Deal found 7/23![American Airlines logo]()
$223
This American Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/133:00 pm
PDX
- SJU
2 stops15h 43m
American Airlines
Deal found 7/20![American Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:47 pm
PDX
- SJU
2 stops37h 57m
Frontier
Deal found 7/22![Frontier logo]()
$232
This SmartFares deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/311:39 pm
PDX
- SJU
1 stop11h 32m
JetBlue
Deal found 7/22![JetBlue logo]()
$239
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:50 pm
PDX
- MBJ
2 stops16h 40m
United Airlines
Deal found 7/22![United Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/111:34 pm
PDX
- PUJ
1 stop11h 31m
American Airlines
Deal found 7/19![American Airlines logo]()
$263
This Expedia deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:45 pm
PDX
- MBJ
2 stops37h 35m
Air Canada
Deal found 7/19![Air Canada logo]()
$272
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:18 am
PDX
- MBJ
1 stop8h 50m
American Airlines
Deal found 7/23![American Airlines logo]()
$273
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/710:00 am
PDX
- SJU
1 stop10h 36m
United Airlines
Deal found 7/23![United Airlines logo]()
$277
Find flight deals from Portland to Caribbean
Keep the following information in mind while searching for Portland to Caribbean flight deals. Data was last updated July 24, 2026.
Round-trip from | $420 (American Airlines) |
|---|---|
One-way from | $194 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $612 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 24, 2026.
Use the filters below to find and compare flights from Portland to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandSaint Thomas Island
PDX - STT
PDXSTT
Portland
Thu 8/20
3:00 pm-12:53 pm
2 stops18h 53m
Saint Thomas Island Cyril E King
Fri 8/28
4:42 pm-10:54 am
2 stops21h 12m
$420
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Thu 9/17
7:07 pm-11:57 am
2 stops13h 50m
San Juan Luis Munoz Marin Intl
Mon 9/21
1:25 pm-10:03 pm
1 stop11h 38m
$436
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Wed 9/2
5:50 am-9:05 pm
2 stops12h 15m
San Juan Luis Munoz Marin Intl
Thu 9/10
10:00 am-8:45 pm
2 stops13h 45m
$436
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Wed 9/23
7:07 pm-11:57 am
2 stops13h 50m
San Juan Luis Munoz Marin Intl
Sun 9/27
1:00 am-9:50 am
1 stop11h 50m
$436
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Wed 9/2
5:50 am-10:00 pm
2 stops13h 10m
San Juan Luis Munoz Marin Intl
Wed 9/9
1:20 pm-10:15 pm
2 stops11h 55m
$436
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Wed 9/16
5:00 am-11:50 pm
2 stops15h 50m
San Juan Luis Munoz Marin Intl
Wed 9/23
1:25 pm-10:03 pm
1 stop11h 38m
$436
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Mon 11/9
7:00 pm-11:45 am
2 stops12h 45m
San Juan Luis Munoz Marin Intl
Tue 11/17
5:45 am-3:00 pm
2 stops13h 15m
$436
Quickest round-trip
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Sun 11/8
10:05 pm-12:25 pm
1 stop11h 20m
Montego Bay Sangster Intl
Sat 11/14
4:00 pm-11:47 pm
1 stop10h 47m
$452
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Mon 11/2
5:15 pm-12:25 pm
2 stops16h 10m
Montego Bay Sangster Intl
Tue 11/10
6:00 pm-9:16 am
2 stops18h 16m
$457
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Tue 1/19
9:45 pm-11:10 am
1 stop10h 25m
Montego Bay Sangster Intl
Thu 1/28
2:10 pm-11:51 pm
2 stops12h 41m
$457
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.
PDX-STT
PDX-SJU
PDX-MBJ
PDX-POP
PDX-SXM
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
PDX-0CB
PDX-STT
PDX-SJU
PDX-MBJ
PDX-POP
What is the cheapest month to book a flight from Portland to Caribbean?
Currently, September is the cheapest month in which you can book a flight from Portland to Caribbean (average of $624). Flying from Portland to Caribbean in June is currently the most expensive (average of $791). 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 to Caribbean?
The best time to book flights from Portland to Caribbean is 19 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated July 24, 2026.
Read through reviews of airlines operating flights from Portland to Caribbean, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Portland to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Portland to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Portland to Caribbean by cabin class
Find flights from Portland to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Caribbean flights
Browse other Portland and Caribbean flight options. Last updated on July 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Portland to Caribbean flights
Consider these flights traveling from Portland to Caribbean.
Top 5 airlines flying from Portland to Caribbean
Discover the top 5 airlines that operate flights from Portland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$235 | Average$715 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$247 | Average$686 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$261 | Average$478 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$392 | Average$735 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$408 | Average$624 | FlexibilityNo cancel fee | On-time63% |