$134+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Mar 16 — Mar 231
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 February 14, 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 February 14, 2026.
This United Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/811:59 pm
PDX
- MBJ
1 stop10h 47m
United Airlines
Wed 3/111:48 pm
MBJ
- PDX
1 stop10h 57m
United Airlines
Deal found 2/13![United Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 4/77:25 pm
PDX
- SJU
2 stops12h 10m
Southwest
Tue 4/145:05 am
SJU
- PDX
2 stops18h 55m
Southwest
Deal found 2/13![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 5/43:00 pm
PDX
- SJU
2 stops16h 35m
Southwest
Fri 5/810:00 am
SJU
- PDX
2 stops15h 40m
Southwest
Deal found 2/13![Southwest logo]()
$405
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:30 am
PDX
- SJU
2 stops13h 10m
Southwest
Tue 5/195:05 am
SJU
- PDX
2 stops18h 55m
Southwest
Deal found 2/12![Southwest logo]()
$417
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 4/135:10 am
PDX
- SJU
2 stops11h 50m
Southwest
Tue 4/215:05 am
SJU
- PDX
2 stops18h 55m
Southwest
Deal found 2/13![Southwest logo]()
$424
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 4/303:00 pm
PDX
- SJU
2 stops15h 10m
Southwest
Tue 5/55:05 am
SJU
- PDX
2 stops18h 55m
Southwest
Deal found 2/13![Southwest logo]()
$429
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/110:56 pm
PDX
- SJU
1 stop11h 44m
United Airlines
Mon 11/22:05 am
SJU
- PDX
2 stops15h 10m
United Airlines
Deal found 2/9![United Airlines logo]()
$445
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:40 pm
PDX
- SJU
2 stops10h 25m
Southwest
Tue 5/195:05 am
SJU
- PDX
2 stops18h 55m
Southwest
Deal found 2/12![Southwest logo]()
$449
This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/612:30 am
PDX
- SJU
1 stop10h 45m
Delta
Wed 4/157:15 am
SJU
- PDX
2 stops19h 40m
Delta
Deal found 2/13![Delta logo]()
$450
This American Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2012:59 am
PDX
- SJU
2 stops14h 11m
American Airlines
Mon 5/411:59 pm
SJU
- PDX
1 stop20h 00m
American Airlines
Deal found 2/13![American Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:00 am
PDX
- SJU
1 stop10h 50m
United Airlines
Tue 6/23:56 pm
SJU
- PDX
1 stop10h 56m
United Airlines
Deal found 2/9![United Airlines logo]()
$470
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/39:44 pm
PDX
- MBJ
1 stop13h 34m
American Airlines
Wed 3/111:27 pm
MBJ
- PDX
1 stop12h 17m
American Airlines
Deal found 2/10![American Airlines logo]()
$472
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 February 14, 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 February 14, 2026.
This United Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/811:59 pm
PDX
- MBJ
1 stop10h 47m
United Airlines
Wed 3/111:48 pm
MBJ
- PDX
1 stop10h 57m
United Airlines
Deal found 2/13![United Airlines logo]()
$362
This American Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/89:44 pm
PDX
- MBJ
2 stops12h 43m
American Airlines
Wed 3/1110:07 am
MBJ
- PDX
2 stops16h 08m
American Airlines
Deal found 2/12![American Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:05 pm
PDX
- SJU
2 stops15h 07m
Delta
Wed 4/291:25 pm
SJU
- PDX
1 stop11h 51m
Delta
Deal found 2/9![Delta logo]()
$450
This Priceline deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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.
Fri 4/179:53 am
PDX
- MBJ
2 stops24h 19m
Frontier
Sat 4/251:22 pm
MBJ
- PDX
2 stops47h 41m
Frontier
Deal found 2/13![Frontier logo]()
$479
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:00 pm
PDX
- NAS
2 stops17h 15m
Southwest
Thu 4/308:45 am
NAS
- PDX
2 stops14h 25m
Southwest
Deal found 2/12![Southwest logo]()
$490
This Air Canada deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/277:05 pm
PDX
- NAS
2 stops22h 00m
Air Canada
Thu 4/309:10 pm
NAS
- PDX
2 stops20h 35m
Air Canada
Deal found 2/9![Air Canada logo]()
$529
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/177:00 am
PDX
- PUJ
1 stop26h 30m
Multiple Airlines
Tue 3/243:32 pm
PUJ
- PDX
1 stop30h 23m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$648
This Copa Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/314:15 pm
PDX
- PUJ
2 stops18h 45m
Copa Airlines
Wed 4/85:35 am
PUJ
- PDX
2 stops20h 19m
Copa Airlines
Deal found 2/12![Copa Airlines logo]()
$655
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:05 am
PDX
- SJU
1 stop10h 19m
United Airlines
Thu 4/301:40 pm
SJU
- PDX
1 stop10h 29m
United Airlines
Deal found 2/9![United Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:00 am
PDX
- SJU
1 stop13h 59m
Delta
Sat 5/27:15 am
SJU
- PDX
2 stops18h 06m
Delta
Deal found 2/9![Delta logo]()
$450
This American Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/510:28 pm
PDX
- MBJ
1 stop15h 09m
American Airlines
Mon 5/1112:56 pm
MBJ
- PDX
1 stop12h 57m
American Airlines
Deal found 2/12![American Airlines logo]()
$476
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/210:16 pm
PDX
- SJU
1 stop10h 48m
United Airlines
Fri 5/81:00 am
SJU
- PDX
2 stops15h 15m
United Airlines
Deal found 2/9![United Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/197:32 pm
PDX
- SJU
2 stops13h 40m
Delta
Sat 5/27:15 am
SJU
- PDX
2 stops18h 06m
Delta
Deal found 2/9![Delta logo]()
$450
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/244:55 pm
PDX
- STT
2 stops17h 15m
Southwest
Thu 4/302:30 pm
STT
- PDX
2 stops12h 40m
Southwest
Deal found 2/12![Southwest logo]()
$500
This Expedia deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/143:15 pm
PDX
- NAS
2 stops25h 50m
Air Canada
Mon 4/209:10 pm
NAS
- PDX
2 stops20h 30m
Air Canada
Deal found 2/11![Air Canada logo]()
$529
This American Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1011:59 pm
PDX
- MBJ
1 stop10h 12m
American Airlines
Sun 3/151:27 pm
MBJ
- PDX
1 stop12h 17m
American Airlines
Deal found 2/13![American Airlines logo]()
$481
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2011:15 pm
PDX
- SJU
1 stop10h 37m
Delta
Wed 4/291:25 pm
SJU
- PDX
1 stop11h 51m
Delta
Deal found 2/9![Delta logo]()
$450
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:10 am
PDX
- NAS
2 stops10h 20m
Southwest
Tue 4/212:10 pm
NAS
- PDX
2 stops12h 00m
Southwest
Deal found 2/12![Southwest logo]()
$520
This American Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2211:47 pm
PDX
- MBJ
2 stops13h 50m
American Airlines
Wed 4/291:15 pm
MBJ
- PDX
1 stop12h 42m
American Airlines
Deal found 2/12![American Airlines logo]()
$481
This Travelocity deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:05 pm
PDX
- NAS
2 stops38h 50m
Air Canada
Sat 4/259:10 pm
NAS
- PDX
2 stops39h 00m
Air Canada
Deal found 2/10![Air Canada logo]()
$535
This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:32 pm
PDX
- SJU
2 stops13h 18m
Delta
Thu 4/162:03 pm
SJU
- PDX
2 stops12h 52m
Delta
Deal found 2/13![Delta logo]()
$450
This United Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1311:59 pm
PDX
- NAS
1 stop11h 58m
United Airlines
Tue 4/212:35 pm
NAS
- PDX
1 stop10h 24m
United Airlines
Deal found 2/12![United Airlines logo]()
$528
This Travelocity deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/37:05 pm
PDX
- NAS
2 stops38h 20m
Air Canada
Wed 4/159:10 pm
NAS
- PDX
2 stops20h 30m
Air Canada
Deal found 2/11![Air Canada logo]()
$542
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2411:15 pm
PDX
- SJU
1 stop10h 37m
Delta
Sat 5/22:03 pm
SJU
- PDX
1 stop10h 39m
Delta
Deal found 2/9![Delta logo]()
$450
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/311:55 pm
PDX
- PUJ
2 stops12h 05m
Southwest
Thu 5/72:05 pm
PUJ
- PDX
2 stops13h 05m
Southwest
Deal found 2/10![Southwest logo]()
$566
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1010:35 pm
PDX
- MBJ
1 stop10h 49m
American Airlines
Sat 3/141:37 pm
MBJ
- PDX
1 stop12h 07m
American Airlines
Deal found 2/11![American Airlines logo]()
$516
This United Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2710:55 pm
PDX
- NAS
1 stop13h 02m
United Airlines
Thu 4/303:59 pm
NAS
- PDX
1 stop10h 51m
United Airlines
Deal found 2/12![United Airlines logo]()
$528
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:00 am
PDX
- SJU
1 stop13h 59m
Delta
Sat 4/186:15 am
SJU
- PDX
2 stops12h 52m
Delta
Deal found 2/9![Delta logo]()
$450
This Air Canada deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/253:15 pm
PDX
- NAS
2 stops25h 55m
Air Canada
Mon 3/29:10 pm
NAS
- PDX
2 stops24h 20m
Air Canada
Deal found 2/10![Air Canada logo]()
$545
This American Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/311:35 pm
PDX
- MBJ
1 stop10h 51m
American Airlines
Wed 3/1110:07 am
MBJ
- PDX
1 stop15h 37m
American Airlines
Deal found 2/12![American Airlines logo]()
$539
Last-minute flights from Portland to Caribbean IslandsDiscover last-minute flight deals from Portland to Caribbean Islands. Data last updated February 14, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean Islands. Data last updated February 14, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/39:44 pm
PDX
- MBJ
1 stop13h 34m
American Airlines
Wed 3/111:27 pm
MBJ
- PDX
1 stop12h 17m
American Airlines
Deal found 2/10![American Airlines logo]()
$472
This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/49:45 pm
PDX
- SJU
1 stop12h 47m
Delta
Thu 3/122:07 pm
SJU
- PDX
1 stop10h 46m
Delta
Deal found 2/13![Delta logo]()
$513
This United Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/71:39 pm
PDX
- SJU
2 stops12h 32m
United Airlines
Thu 3/121:25 pm
SJU
- PDX
1 stop12h 35m
United Airlines
Deal found 2/12![United Airlines logo]()
$535
This United Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/811:59 pm
PDX
- MBJ
1 stop10h 47m
United Airlines
Wed 3/111:48 pm
MBJ
- PDX
1 stop10h 57m
United Airlines
Deal found 2/13![United Airlines logo]()
$362
This American Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1011:59 pm
PDX
- MBJ
1 stop10h 12m
American Airlines
Sun 3/151:27 pm
MBJ
- PDX
1 stop12h 17m
American Airlines
Deal found 2/13![American Airlines logo]()
$481
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1010:35 pm
PDX
- MBJ
1 stop10h 49m
American Airlines
Sat 3/141:37 pm
MBJ
- PDX
1 stop12h 07m
American Airlines
Deal found 2/11![American Airlines logo]()
$516
This American Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:40 am
PDX
- SJU
1 stop13h 51m
American Airlines
Sat 5/27:25 am
SJU
- PDX
1 stop16h 38m
American Airlines
Deal found 2/13![American Airlines logo]()
$504
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/239:44 pm
PDX
- SJU
1 stop15h 08m
American Airlines
Wed 4/16:00 am
SJU
- PDX
1 stop21h 22m
American Airlines
Deal found 2/10![American Airlines logo]()
$521
This Expedia deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/237:05 pm
PDX
- NAS
2 stops22h 05m
Air Canada
Mon 3/309:10 pm
NAS
- PDX
2 stops24h 20m
Air Canada
Deal found 2/12![Air Canada logo]()
$530
This American Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:40 am
PDX
- SJU
1 stop19h 48m
American Airlines
Wed 4/17:11 am
SJU
- PDX
1 stop20h 11m
American Airlines
Deal found 2/13![American Airlines logo]()
$488
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3110:35 pm
PDX
- SJU
1 stop13h 53m
American Airlines
Tue 4/711:43 am
SJU
- PDX
2 stops14h 06m
American Airlines
Deal found 2/11![American Airlines logo]()
$450
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/315:40 am
PDX
- SJU
2 stops12h 10m
American Airlines
Fri 4/1010:03 am
SJU
- PDX
1 stop16h 50m
American Airlines
Deal found 2/11![American Airlines logo]()
$486
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 February 14, 2026.
Search for one-way flight options from Portland to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated February 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2512:27 pm
PDX
- SJU
2 stops22h 41m
Frontier
Deal found 2/12![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/711:48 am
PDX
- SJU
2 stops32h 14m
Frontier
Deal found 2/12![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/1512:04 pm
PDX
- SJU
3 stops56h 54m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/169:53 am
PDX
- SJU
2 stops25h 24m
Frontier
Deal found 2/9![Frontier logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:46 pm
PDX
- SJU
3 stops39h 22m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/1512:04 pm
PDX
- SJU
2 stops28h 58m
Frontier
Deal found 2/9![Frontier logo]()
$203
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/39:44 pm
PDX
- MBJ
2 stops12h 49m
American Airlines
Deal found 2/10![American Airlines logo]()
$212
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2410:35 pm
PDX
- SJU
1 stop9h 05m
American Airlines
Deal found 2/9![American Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/169:53 pm
PDX
- SJU
3 stops42h 57m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$223
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2012:59 am
PDX
- SJU
2 stops14h 11m
American Airlines
Deal found 2/10![American Airlines logo]()
$225
This American Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1111:47 pm
PDX
- SJU
2 stops12h 48m
American Airlines
Deal found 2/12![American Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/2712:04 pm
PDX
- SJU
3 stops56h 54m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$230
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 February 14, 2026.
Round-trip from | $362 (United Airlines) |
|---|---|
One-way from | $134 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $580 |
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 February 14, 2026.
Use the filters below to find and compare flights from Portland to Caribbean Islands that are best for you.
Fly from
Portland
Fly to
Caribbean Islands
Route
Depart
Return
Price
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Sun 3/8
11:59 pm-12:46 pm
1 stop10h 47m
Montego Bay Sangster Intl
Wed 3/11
1:48 pm-10:45 pm
1 stop10h 57m
$362
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Sun 3/8
9:44 pm-12:27 pm
2 stops12h 43m
Montego Bay Sangster Intl
Wed 3/11
10:07 am-12:15 am
2 stops16h 08m
$367
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Sun 4/19
6:05 pm-12:12 pm
2 stops15h 07m
San Juan Luis Munoz Marin Intl
Wed 4/29
1:25 pm-10:16 pm
1 stop11h 51m
$450
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Tue 4/21
8:05 am-9:24 pm
1 stop10h 19m
San Juan Luis Munoz Marin Intl
Thu 4/30
1:40 pm-9:09 pm
1 stop10h 29m
$450
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Sat 4/18
7:00 am-11:59 pm
1 stop13h 59m
San Juan Luis Munoz Marin Intl
Sat 5/2
7:15 am-10:21 pm
2 stops18h 06m
$450
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Sat 5/2
10:16 pm-12:04 pm
1 stop10h 48m
San Juan Luis Munoz Marin Intl
Fri 5/8
1:00 am-1:15 pm
2 stops15h 15m
$450
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Sun 4/19
7:32 pm-12:12 pm
2 stops13h 40m
San Juan Luis Munoz Marin Intl
Sat 5/2
7:15 am-10:21 pm
2 stops18h 06m
$450
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Mon 4/20
11:15 pm-12:52 pm
1 stop10h 37m
San Juan Luis Munoz Marin Intl
Wed 4/29
1:25 pm-10:16 pm
1 stop11h 51m
$450
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Mon 4/13
7:32 pm-11:50 am
2 stops13h 18m
San Juan Luis Munoz Marin Intl
Thu 4/16
2:03 pm-11:55 pm
2 stops12h 52m
$450
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Fri 4/24
11:15 pm-12:52 pm
1 stop10h 37m
San Juan Luis Munoz Marin Intl
Sat 5/2
2:03 pm-9:42 pm
1 stop10h 39m
$450
Showing 1-10 of 60 results
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-SJU
PDX-MBJ
PDX-SXM
PDX-PUJ
PDX-NAS
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-SJU
PDX-MBJ
PDX-SXM
PDX-PUJ
What is the cheapest month to book a flight from Portland to Caribbean Islands?
Currently, August is the cheapest month in which you can book a flight from Portland to Caribbean Islands (average of $187). Flying from Portland to Caribbean Islands in January is currently the most expensive (average of $405). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Caribbean 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 February 14, 2026.
See what other customers who have flown with Southwest, Delta, and United 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
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
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 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 February 14, 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 6 airlines flying from Portland to Caribbean Islands
Discover the top 6 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 February 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$184 | Average$688 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$185 | Average$371 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$213 | Average$379 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$327 | Average$702 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$399 | Average$687 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$445 | Average$728 | FlexibilityNo cancel fee | On-time63% |