$233+ Cheap flights from Portland (PDX) to Caribbean Islands
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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Jul 19 — Jul 261
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Caribbean Islands 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
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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 Islands
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Cheapest flights from Portland to Caribbean IslandsExplore the most affordable flight options available from Portland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 19, 2026.
Explore the most affordable flight options available from Portland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 19, 2026.
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/2311:34 pm
PDX
- STT
2 stops13h 18m
American Airlines
Mon 8/314:42 pm
STT
- PDX
2 stops21h 52m
American Airlines
Deal found 6/17![American Airlines logo]()
$420
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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
1 stop11h 38m
American Airlines
Fri 8/282:12 pm
MBJ
- PDX
1 stop11h 47m
American Airlines
Deal found 6/16![American Airlines logo]()
$422
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 11/23:50 pm
PDX
- MBJ
2 stops17h 35m
Delta
Tue 11/106:00 pm
MBJ
- PDX
2 stops18h 31m
Delta
Deal found 6/16![Delta logo]()
$427
This United Airlines deal was found by Cheapflights users on 6/18. 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.
Mon 11/210:59 pm
PDX
- MBJ
1 stop11h 47m
United Airlines
Wed 11/112:48 pm
MBJ
- PDX
1 stop12h 14m
United Airlines
Deal found 6/18![United Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 11/25:45 pm
PDX
- MBJ
2 stops15h 40m
Delta
Wed 11/116:00 pm
MBJ
- PDX
2 stops18h 31m
Delta
Deal found 6/16![Delta logo]()
$437
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 12/111:28 pm
PDX
- MBJ
1 stop20h 52m
American Airlines
Thu 12/172:19 pm
MBJ
- PDX
1 stop13h 40m
American Airlines
Deal found 6/17![American Airlines logo]()
$442
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 9/267:00 am
PDX
- SJU
1 stop13h 44m
Delta
Sat 10/3112:46 pm
SJU
- PDX
2 stops14h 01m
Delta
Deal found 6/16![Delta logo]()
$466
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 11/210:45 pm
PDX
- MBJ
1 stop11h 10m
American Airlines
Wed 11/114:02 pm
MBJ
- PDX
1 stop9h 57m
American Airlines
Deal found 6/16![American Airlines logo]()
$468
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/195:15 am
PDX
- SJU
2 stops13h 40m
American Airlines
Thu 8/276:00 am
SJU
- PDX
2 stops13h 51m
American Airlines
Deal found 6/16![American Airlines logo]()
$471
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 6/17![Southwest logo]()
$476
This American Airlines deal was found by Cheapflights users on 6/19. 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 10/276:33 pm
PDX
- MBJ
2 stops12h 32m
American Airlines
Tue 11/104:05 pm
MBJ
- PDX
2 stops21h 53m
American Airlines
Deal found 6/19![American Airlines logo]()
$478
This American Airlines deal was found by Cheapflights users on 6/18. 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.
Wed 8/1211:34 pm
PDX
- SJU
1 stop20h 41m
American Airlines
Fri 8/216:00 am
SJU
- PDX
2 stops13h 51m
American Airlines
Deal found 6/18![American Airlines logo]()
$481
Best flights from Portland to Caribbean IslandsDiscover carefully curated flight deals from Portland to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 19, 2026.
Discover carefully curated flight deals from Portland to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 19, 2026.
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 10/1711:59 pm
PDX
- MBJ
1 stop11h 31m
United Airlines
Sat 10/242:40 pm
MBJ
- PDX
1 stop9h 41m
United Airlines
Deal found 6/15![United Airlines logo]()
$422
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 11/23:50 pm
PDX
- MBJ
2 stops17h 35m
Delta
Tue 11/106:00 pm
MBJ
- PDX
2 stops18h 31m
Delta
Deal found 6/16![Delta logo]()
$427
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 11/210:45 pm
PDX
- MBJ
1 stop12h 29m
American Airlines
Tue 11/104:05 pm
MBJ
- PDX
2 stops21h 53m
American Airlines
Deal found 6/17![American Airlines logo]()
$437
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/288:05 pm
PDX
- MBJ
2 stops15h 30m
Southwest
Sun 12/63:45 pm
MBJ
- PDX
2 stops21h 55m
Southwest
Deal found 6/14![Southwest logo]()
$555
This Gotogate deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/123:30 pm
PDX
- BGI
2 stops20h 55m
Air Canada
Wed 10/214:20 pm
BGI
- PDX
2 stops25h 31m
Air Canada
Deal found 6/14![Air Canada logo]()
$677
This FlightHub deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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.
Mon 8/2411:27 pm
PDX
- AUA
2 stops33h 48m
JetBlue
Mon 8/312:25 pm
AUA
- PDX
1 stop25h 39m
JetBlue
Deal found 6/17![JetBlue logo]()
$696
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 10/173:50 pm
PDX
- MBJ
2 stops17h 35m
Delta
Sat 10/244:59 pm
MBJ
- PDX
2 stops18h 32m
Delta
Deal found 6/15![Delta logo]()
$427
This Mytrip deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:20 pm
PDX
- BGI
3 stops42h 05m
Multiple Airlines
Wed 10/214:20 pm
BGI
- PDX
2 stops25h 31m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$912
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/1010:52 pm
PDX
- SJU
1 stop11h 53m
United Airlines
Tue 7/141:00 am
SJU
- PDX
1 stop11h 25m
United Airlines
Deal found 6/15![United Airlines logo]()
$466
This American Airlines deal was found by Cheapflights users on 6/19. 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 6/19![American Airlines logo]()
$518
This United Airlines deal was found by Cheapflights users on 6/19. 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 10/2411:59 pm
PDX
- STT
1 stop12h 21m
United Airlines
Sat 10/312:05 pm
STT
- PDX
1 stop12h 07m
United Airlines
Deal found 6/19![United Airlines logo]()
$510
This Southwest deal was found by Cheapflights users on 6/18. 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.
Thu 11/57:00 pm
PDX
- NAS
2 stops14h 15m
Southwest
Thu 11/121:10 pm
NAS
- PDX
2 stops13h 45m
Southwest
Deal found 6/18![Southwest logo]()
$577
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/215:54 pm
PDX
- STT
2 stops18h 08m
Delta
Thu 9/32:49 pm
STT
- PDX
1 stop9h 55m
Delta
Deal found 6/16![Delta logo]()
$532
This American Airlines deal was found by Cheapflights users on 6/18. 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 11/510:45 pm
PDX
- NAS
1 stop18h 24m
American Airlines
Thu 11/123:00 pm
NAS
- PDX
1 stop9h 15m
American Airlines
Deal found 6/18![American Airlines logo]()
$590
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/67:00 pm
PDX
- NAS
2 stops14h 15m
Southwest
Fri 12/111:10 pm
NAS
- PDX
2 stops13h 45m
Southwest
Deal found 6/14![Southwest logo]()
$594
This United Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/812:50 pm
PDX
- SJU
2 stops13h 39m
United Airlines
Sun 8/161:00 am
SJU
- PDX
1 stop11h 50m
United Airlines
Deal found 6/17![United Airlines logo]()
$545
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 10/1310:05 pm
PDX
- MBJ
1 stop11h 20m
Delta
Tue 10/201:32 pm
MBJ
- PDX
1 stop10h 54m
Delta
Deal found 6/16![Delta logo]()
$551
This Air Canada deal was found by Cheapflights users on 6/18. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/210:00 am
PDX
- BGI
2 stops24h 35m
Air Canada
Fri 11/64:10 pm
BGI
- PDX
2 stops32h 36m
Air Canada
Deal found 6/18![Air Canada logo]()
$695
This JetBlue deal was found by Cheapflights users on 6/18. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/212:16 pm
PDX
- AUA
1 stop18h 39m
JetBlue
Mon 7/271:15 pm
AUA
- PDX
1 stop12h 16m
JetBlue
Deal found 6/18![JetBlue logo]()
$716
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 9/154:00 pm
PDX
- NAS
2 stops17h 15m
Southwest
Tue 9/221:10 pm
NAS
- PDX
2 stops13h 00m
Southwest
Deal found 6/15![Southwest logo]()
$594
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2712:45 am
PDX
- SJU
2 stops14h 39m
American Airlines
Mon 8/37:00 am
SJU
- PDX
1 stop19h 30m
American Airlines
Deal found 6/14![American Airlines logo]()
$606
This United Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/711:30 pm
PDX
- MBJ
1 stop13h 40m
United Airlines
Fri 8/144:12 pm
MBJ
- PDX
2 stops19h 20m
United Airlines
Deal found 6/17![United Airlines logo]()
$553
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/2110:55 pm
PDX
- STT
1 stop13h 07m
Delta
Tue 9/12:49 pm
STT
- PDX
1 stop9h 55m
Delta
Deal found 6/16![Delta logo]()
$555
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/288:15 pm
PDX
- NAS
2 stops13h 00m
Southwest
Sun 12/61:10 pm
NAS
- PDX
2 stops13h 45m
Southwest
Deal found 6/14![Southwest logo]()
$594
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3110:05 pm
PDX
- MBJ
1 stop12h 20m
Delta
Wed 11/116:00 pm
MBJ
- PDX
2 stops18h 31m
Delta
Deal found 6/18![Delta logo]()
$556
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/311:59 pm
PDX
- MBJ
1 stop11h 31m
United Airlines
Mon 8/104:12 pm
MBJ
- PDX
2 stops19h 20m
United Airlines
Deal found 6/14![United Airlines logo]()
$584
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2410:59 pm
PDX
- PUJ
1 stop10h 36m
American Airlines
Fri 8/284:18 pm
PUJ
- PDX
2 stops22h 16m
American Airlines
Deal found 6/14![American Airlines logo]()
$645
This Justfly.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/32:20 pm
PDX
- BGI
1 stop18h 42m
JetBlue
Sat 7/111:30 pm
BGI
- PDX
1 stop26h 33m
JetBlue
Deal found 6/15![JetBlue logo]()
$785
This Southwest deal was found by Cheapflights users on 6/18. 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.
Fri 7/109:20 pm
PDX
- NAS
1 stop12h 20m
Southwest
Wed 7/158:45 am
NAS
- PDX
2 stops13h 15m
Southwest
Deal found 6/18![Southwest logo]()
$604
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/268:24 pm
PDX
- STT
2 stops14h 10m
Delta
Thu 9/32:49 pm
STT
- PDX
1 stop9h 55m
Delta
Deal found 6/16![Delta logo]()
$556
Last-minute flights from Portland to Caribbean IslandsDiscover last-minute flight deals from Portland to Caribbean Islands. Data last updated June 19, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean Islands. Data last updated June 19, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/18. 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.
Wed 7/85:07 am
PDX
- SJU
1 stop20h 32m
American Airlines
Thu 7/167:00 am
SJU
- PDX
1 stop19h 30m
American Airlines
Deal found 6/18![American Airlines logo]()
$586
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/1010:52 pm
PDX
- SJU
1 stop11h 53m
United Airlines
Tue 7/141:00 am
SJU
- PDX
1 stop11h 25m
United Airlines
Deal found 6/15![United Airlines logo]()
$466
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/1010:52 pm
PDX
- SJU
1 stop11h 53m
United Airlines
Mon 7/201:00 am
SJU
- PDX
1 stop11h 25m
United Airlines
Deal found 6/15![United Airlines logo]()
$556
This United Airlines deal was found by Cheapflights users on 6/19. 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 7/115:00 am
PDX
- MBJ
1 stop8h 45m
United Airlines
Sat 7/182:40 pm
MBJ
- PDX
1 stop10h 08m
United Airlines
Deal found 6/19![United Airlines logo]()
$543
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/125:49 am
PDX
- SJU
1 stop14h 10m
American Airlines
Sat 7/257:25 am
SJU
- PDX
1 stop19h 30m
American Airlines
Deal found 6/15![American Airlines logo]()
$540
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/1411:30 pm
PDX
- SJU
1 stop10h 04m
United Airlines
Mon 7/201:00 am
SJU
- PDX
1 stop11h 25m
United Airlines
Deal found 6/16![United Airlines logo]()
$500
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:49 am
PDX
- SJU
1 stop14h 10m
American Airlines
Tue 7/217:00 am
SJU
- PDX
1 stop19h 30m
American Airlines
Deal found 6/14![American Airlines logo]()
$566
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1610:40 pm
PDX
- MBJ
2 stops12h 50m
United Airlines
Thu 7/234:12 pm
MBJ
- PDX
2 stops19h 35m
United Airlines
Deal found 6/16![United Airlines logo]()
$588
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:49 am
PDX
- SJU
1 stop14h 10m
American Airlines
Sat 8/17:25 am
SJU
- PDX
1 stop19h 30m
American Airlines
Deal found 6/15![American Airlines logo]()
$573
This American Airlines deal was found by Cheapflights users on 6/18. 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.
Sat 7/2511:15 pm
PDX
- MBJ
2 stops12h 16m
American Airlines
Fri 7/315:14 pm
MBJ
- PDX
2 stops19h 47m
American Airlines
Deal found 6/18![American Airlines logo]()
$552
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/285:49 am
PDX
- SJU
1 stop14h 10m
American Airlines
Mon 8/37:25 am
SJU
- PDX
1 stop19h 30m
American Airlines
Deal found 6/15![American Airlines logo]()
$503
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/3111:15 pm
PDX
- SJU
1 stop10h 56m
Delta
Tue 9/227:00 am
SJU
- PDX
2 stops19h 54m
Delta
Deal found 6/16![Delta logo]()
$571
One-way flights from Portland to Caribbean IslandsSearch for one-way flight options from Portland to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated June 19, 2026.
Search for one-way flight options from Portland to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated June 19, 2026.
This Delta deal was found by Cheapflights users on 6/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:50 pm
PDX
- SJU
2 stops15h 23m
Delta
Deal found 6/19![Delta logo]()
$233
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/136:50 pm
PDX
- SJU
2 stops14h 14m
United Airlines
Deal found 6/16![United Airlines logo]()
$238
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 10/147:35 pm
PDX
- SXM
2 stops15h 25m
Southwest
Deal found 6/16![Southwest logo]()
$266
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/125:49 am
PDX
- SJU
1 stop14h 10m
American Airlines
Deal found 6/15![American Airlines logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 10/247:30 am
PDX
- SDQ
1 stop18h 59m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Tue 10/206:06 am
PDX
- SDQ
2 stops20h 23m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$297
This American Airlines deal was found by Cheapflights users on 6/18. 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.
Sat 7/115:28 pm
PDX
- SXM
2 stops19h 16m
American Airlines
Deal found 6/18![American Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 11/41:00 pm
PDX
- AUA
2 stops22h 00m
Southwest
Deal found 6/15![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 6/18. 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.
Wed 10/214:40 pm
PDX
- PUJ
2 stops16h 45m
Southwest
Deal found 6/18![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 6/18. 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.
Sat 7/119:20 pm
PDX
- SXM
1 stop12h 35m
Southwest
Deal found 6/18![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:35 pm
PDX
- PUJ
2 stops15h 08m
Delta
Deal found 6/15![Delta logo]()
$308
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/2110:40 pm
PDX
- SDQ
2 stops12h 30m
United Airlines
Deal found 6/15![United Airlines logo]()
$317
Find flight deals from Portland to Caribbean Islands
Keep the following information in mind while searching for Portland to Caribbean Islands flight deals. Data was last updated June 19, 2026.
Round-trip from | $420 (American Airlines) |
|---|---|
One-way from | $233 (Delta) |
Popular in | December |
Cheapest in | September |
Average price | $676 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Caribbean Islands 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 19, 2026.
Use the filters below to find and compare flights from Portland to Caribbean Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Sat 10/17
11:59 pm-1:30 pm
1 stop11h 31m
Montego Bay Sangster Intl
Sat 10/24
2:40 pm-10:21 pm
1 stop9h 41m
$422
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Mon 11/2
3:50 pm-12:25 pm
2 stops17h 35m
Montego Bay Sangster Intl
Tue 11/10
6:00 pm-9:31 am
2 stops18h 31m
$427
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Sat 10/17
3:50 pm-11:25 am
2 stops17h 35m
Montego Bay Sangster Intl
Sat 10/24
4:59 pm-9:31 am
2 stops18h 32m
$427
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Mon 11/2
10:45 pm-2:14 pm
1 stop12h 29m
Montego Bay Sangster Intl
Tue 11/10
4:05 pm-10:58 am
2 stops21h 53m
$437
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Fri 7/10
10:52 pm-1:45 pm
1 stop11h 53m
San Juan Luis Munoz Marin Intl
Tue 7/14
1:00 am-9:25 am
1 stop11h 25m
$466
PortlandSaint Thomas Island
PDX - STT
PDXSTT
Portland
Sat 10/24
11:59 pm-3:20 pm
1 stop12h 21m
Saint Thomas Island Cyril E King
Sat 10/31
2:05 pm-11:12 pm
1 stop12h 07m
$510
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Fri 8/21
11:34 pm-1:49 pm
2 stops12h 15m
Montego Bay Sangster Intl
Fri 8/28
5:08 pm-11:34 am
2 stops20h 26m
$518
PortlandSaint Thomas Island
PDX - STT
PDXSTT
Portland
Fri 8/21
5:54 pm-3:02 pm
2 stops18h 08m
Saint Thomas Island Cyril E King
Thu 9/3
2:49 pm-9:44 pm
1 stop9h 55m
$532
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Sat 8/8
12:50 pm-5:29 am
2 stops13h 39m
San Juan Luis Munoz Marin Intl
Sun 8/16
1:00 am-9:50 am
1 stop11h 50m
$545
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Tue 10/13
10:05 pm-11:25 am
1 stop11h 20m
Montego Bay Sangster Intl
Tue 10/20
1:32 pm-10:26 pm
1 stop10h 54m
$551
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Portland to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Portland with our price prediction graph.
PDX-STT
PDX-MBJ
PDX-SJU
PDX-BGI
PDX-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 Islands
PDX-zzEPX
PDX-STT
PDX-MBJ
PDX-SJU
PDX-BGI
What is the cheapest month to book a flight from Portland to Caribbean Islands?
Currently, March is the cheapest month in which you can book a flight from Portland to Caribbean Islands (average of $191). Flying from Portland to Caribbean Islands in February is currently the most expensive (average of $466). 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 Islands?
Booking 18 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Caribbean Islands. 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 Islands
Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated June 19, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Portland to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Portland to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Portland to Caribbean Islands
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Portland to Caribbean Islands by cabin class
Find flights from Portland to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Caribbean Islands flights
Browse other Portland and Caribbean Islands flight options. Last updated on June 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Portland to Caribbean Islands flights
Consider these flights traveling from Portland to Caribbean Islands.
Top 5 airlines flying from Portland to Caribbean Islands
Discover the top 5 airlines that operate flights from Portland to Caribbean Islands. 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 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$190 | Average$711 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$247 | Average$674 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$261 | Average$478 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$392 | Average$755 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$408 | Average$651 | FlexibilityNo cancel fee | On-time63% |