$220+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Jul 15 — Jul 221
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
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Cheapest flights from Portland to CaribbeanExplore the most affordable flight options available from Portland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 15, 2026.
Explore the most affordable flight options available from Portland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 15, 2026.
This American Airlines deal was found by Cheapflights users on 6/11. 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.
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 6/11![American Airlines logo]()
$422
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.
Mon 11/27:14 pm
PDX
- MBJ
2 stops14h 11m
Delta
Tue 11/106:00 pm
MBJ
- PDX
2 stops18h 31m
Delta
Deal found 6/15![Delta logo]()
$427
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.
Sat 12/121:28 pm
PDX
- MBJ
1 stop20h 52m
American Airlines
Wed 12/163:55 pm
MBJ
- PDX
1 stop10h 01m
American Airlines
Deal found 6/14![American Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 6/12. 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 8/235:59 pm
PDX
- MBJ
2 stops15h 38m
American Airlines
Sun 8/302:12 pm
MBJ
- PDX
1 stop11h 47m
American Airlines
Deal found 6/12![American Airlines logo]()
$432
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2410:45 pm
PDX
- SJU
1 stop11h 05m
Southwest
Thu 8/278:55 pm
SJU
- PDX
2 stops17h 45m
Southwest
Deal found 6/11![Southwest logo]()
$436
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:35 pm
PDX
- SJU
2 stops10h 35m
Southwest
Thu 9/248:55 pm
SJU
- PDX
2 stops17h 45m
Southwest
Deal found 6/11![Southwest logo]()
$451
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Sat 10/315:20 am
PDX
- SJU
1 stop15h 13m
American Airlines
Sun 11/110:29 am
SJU
- PDX
1 stop17h 22m
American Airlines
Deal found 6/11![American Airlines logo]()
$461
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 11/95:15 am
PDX
- SJU
1 stop9h 10m
United Airlines
Tue 11/171:00 pm
SJU
- PDX
1 stop12h 21m
United Airlines
Deal found 6/14![United Airlines logo]()
$466
This American Airlines deal was found by Cheapflights users on 6/10. 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 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 6/10![American Airlines logo]()
$468
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Wed 8/1211:34 pm
PDX
- SJU
1 stop20h 41m
American Airlines
Thu 8/2012:55 am
SJU
- PDX
1 stop13h 39m
American Airlines
Deal found 6/10![American Airlines logo]()
$471
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 8/195:59 am
PDX
- SJU
2 stops15h 00m
American Airlines
Wed 8/267:30 am
SJU
- PDX
1 stop15h 18m
American Airlines
Deal found 6/11![American Airlines logo]()
$472
This American Airlines deal was found by Cheapflights users on 6/10. 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 10/273:49 pm
PDX
- MBJ
2 stops15h 16m
American Airlines
Tue 11/104:05 pm
MBJ
- PDX
2 stops22h 05m
American Airlines
Deal found 6/10![American Airlines logo]()
$473
Best flights from Portland to CaribbeanDiscover carefully curated flight deals from Portland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 15, 2026.
Discover carefully curated flight deals from Portland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 15, 2026.
This Delta deal was found by Cheapflights users on 6/11. 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 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 6/11![Delta logo]()
$422
This Southwest deal was found by Cheapflights users on 6/10. 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.
Mon 11/97:00 pm
PDX
- SJU
2 stops12h 45m
Southwest
Tue 11/175:45 am
SJU
- PDX
2 stops13h 15m
Southwest
Deal found 6/10![Southwest logo]()
$466
This United Airlines deal was found by Cheapflights users on 6/12. 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.
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 6/12![United Airlines logo]()
$466
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Wed 9/233:00 pm
PDX
- PUJ
2 stops16h 58m
American Airlines
Wed 9/301:44 pm
PUJ
- PDX
2 stops24h 11m
American Airlines
Deal found 6/10![American Airlines logo]()
$632
This Air Canada 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 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 stops26h 31m
Air Canada
Deal found 6/14![Air Canada logo]()
$695
This FlightHub deal was found by Cheapflights users on 6/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:45 pm
PDX
- GCM
2 stops37h 45m
Multiple Airlines
Sun 9/276:10 pm
GCM
- PDX
1 stop20h 49m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$734
This FlightHub deal was found by Cheapflights users on 6/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/311:29 pm
PDX
- BGI
2 stops34h 23m
JetBlue
Sat 7/111:30 pm
BGI
- PDX
1 stop26h 33m
JetBlue
Deal found 6/11![JetBlue logo]()
$755
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/210:05 pm
PDX
- MBJ
1 stop11h 20m
Delta
Tue 11/106:00 pm
MBJ
- PDX
2 stops18h 16m
Delta
Deal found 6/11![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 6/10. 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.
Fri 8/216:05 am
PDX
- SJU
2 stops13h 05m
Southwest
Sat 8/298:20 am
SJU
- PDX
2 stops14h 40m
Southwest
Deal found 6/10![Southwest logo]()
$466
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:10 pm
PDX
- MBJ
2 stops16h 15m
Delta
Tue 11/106:00 pm
MBJ
- PDX
2 stops18h 31m
Delta
Deal found 6/12![Delta logo]()
$427
This United Airlines deal was found by Cheapflights users on 6/11. 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 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 7/1812:52 pm
MBJ
- PDX
2 stops13h 58m
United Airlines
Deal found 6/11![United Airlines logo]()
$504
This Delta deal was found by Cheapflights users on 6/10. 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 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
Wed 11/116:00 pm
MBJ
- PDX
2 stops18h 31m
Delta
Deal found 6/10![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 6/10. 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.
Wed 9/3010:45 pm
PDX
- MBJ
1 stop12h 40m
Southwest
Sun 10/42:40 pm
MBJ
- PDX
2 stops12h 30m
Southwest
Deal found 6/10![Southwest logo]()
$511
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3010:33 pm
PDX
- MBJ
1 stop11h 10m
United Airlines
Sun 10/42:40 pm
MBJ
- PDX
1 stop9h 41m
United Airlines
Deal found 6/10![United Airlines logo]()
$517
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2610:00 pm
PDX
- SJU
1 stop11h 13m
Delta
Sat 10/312:31 pm
SJU
- PDX
1 stop10h 55m
Delta
Deal found 6/11![Delta logo]()
$466
This Southwest deal was found by Cheapflights users on 6/12. 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 8/115:50 am
PDX
- SJU
2 stops12h 15m
Southwest
Sat 8/1510:25 am
SJU
- PDX
2 stops14h 00m
Southwest
Deal found 6/12![Southwest logo]()
$531
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.
Fri 7/1711:40 pm
PDX
- MBJ
1 stop11h 10m
United Airlines
Wed 7/222:40 pm
MBJ
- PDX
2 stops21h 07m
United Airlines
Deal found 6/14![United Airlines logo]()
$543
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Thu 8/273:00 pm
PDX
- SDQ
2 stops15h 25m
American Airlines
Wed 9/99:30 am
SDQ
- PDX
2 stops16h 53m
American Airlines
Deal found 6/10![American Airlines logo]()
$663
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:00 am
PDX
- SJU
2 stops14h 56m
Delta
Tue 11/103:10 pm
SJU
- PDX
2 stops12h 37m
Delta
Deal found 6/14![Delta logo]()
$466
This Air Canada deal was found by Cheapflights users on 6/10. 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.
Fri 10/3010:00 am
PDX
- PLS
2 stops23h 25m
Air Canada
Tue 11/31:30 pm
PLS
- PDX
2 stops32h 01m
Air Canada
Deal found 6/10![Air Canada logo]()
$701
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.
Sat 11/285:15 am
PDX
- MBJ
1 stop8h 35m
United Airlines
Sun 12/63:20 pm
MBJ
- PDX
1 stop10h 51m
United Airlines
Deal found 6/14![United Airlines logo]()
$545
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:45 pm
PDX
- SJU
1 stop12h 35m
Delta
Tue 11/177:15 am
SJU
- PDX
2 stops15h 02m
Delta
Deal found 6/10![Delta logo]()
$466
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:42 pm
PDX
- GCM
1 stop20h 18m
Multiple Airlines
Sun 9/136:10 pm
GCM
- PDX
1 stop17h 38m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$761
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 11/410:45 pm
PDX
- SXM
1 stop13h 35m
American Airlines
Fri 11/135:24 pm
SXM
- PDX
2 stops21h 34m
American Airlines
Deal found 6/11![American Airlines logo]()
$705
This Air Canada deal was found by Cheapflights users on 6/10. 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.
Tue 12/17:10 pm
PDX
- BGI
2 stops15h 25m
Air Canada
Fri 12/44:10 pm
BGI
- PDX
2 stops30h 21m
Air Canada
Deal found 6/10![Air Canada logo]()
$719
This United Airlines deal was found by Cheapflights users on 6/12. 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 9/149:00 am
PDX
- MBJ
2 stops24h 43m
United Airlines
Thu 9/1712:52 pm
MBJ
- PDX
2 stops24h 36m
United Airlines
Deal found 6/12![United Airlines logo]()
$547
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 am
PDX
- SJU
2 stops13h 55m
Delta
Tue 11/172:05 pm
SJU
- PDX
2 stops13h 42m
Delta
Deal found 6/12![Delta logo]()
$466
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Fri 10/1611:58 pm
PDX
- PUJ
2 stops11h 32m
American Airlines
Sat 10/245:20 pm
PUJ
- PDX
2 stops18h 54m
American Airlines
Deal found 6/10![American Airlines logo]()
$705
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 11/18:10 pm
PDX
- PLS
2 stops14h 35m
Southwest
Mon 11/92:40 pm
PLS
- PDX
2 stops12h 15m
Southwest
Deal found 6/14![Southwest logo]()
$641
This Air Canada deal was found by Cheapflights users on 6/10. 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 12/97:10 pm
PDX
- PLS
2 stops38h 15m
Air Canada
Wed 12/161:30 pm
PLS
- PDX
2 stops28h 11m
Air Canada
Deal found 6/10![Air Canada logo]()
$721
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated June 15, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated June 15, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/13. 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.
Fri 7/35:07 am
PDX
- MBJ
1 stop9h 07m
American Airlines
Thu 7/92:36 pm
MBJ
- PDX
1 stop12h 14m
American Airlines
Deal found 6/13![American Airlines logo]()
$562
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 7/85:49 am
PDX
- SJU
1 stop14h 10m
American Airlines
Thu 7/167:00 am
SJU
- PDX
1 stop19h 30m
American Airlines
Deal found 6/11![American Airlines logo]()
$558
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 6/12. 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.
Fri 7/1010:52 pm
PDX
- SJU
1 stop10h 12m
United Airlines
Sun 7/191:00 am
SJU
- PDX
1 stop11h 25m
United Airlines
Deal found 6/12![United Airlines logo]()
$533
This United Airlines deal was found by Cheapflights users on 6/11. 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 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 7/1812:52 pm
MBJ
- PDX
1 stop10h 23m
United Airlines
Deal found 6/11![United Airlines logo]()
$468
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.
Sun 7/125:49 am
PDX
- SJU
1 stop14h 10m
American Airlines
Sat 7/255:45 am
SJU
- PDX
1 stop20h 07m
American Airlines
Deal found 6/14![American Airlines logo]()
$540
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 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.
Fri 7/1711:41 pm
PDX
- MBJ
1 stop14h 33m
American Airlines
Wed 7/222:36 pm
MBJ
- PDX
1 stop12h 14m
American Airlines
Deal found 6/14![American Airlines logo]()
$508
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.
Fri 7/1711:40 pm
PDX
- MBJ
1 stop11h 10m
United Airlines
Wed 7/222:40 pm
MBJ
- PDX
2 stops21h 07m
United Airlines
Deal found 6/14![United Airlines logo]()
$543
This American Airlines deal was found by Cheapflights users on 6/13. 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 7/225:49 am
PDX
- SJU
1 stop14h 10m
American Airlines
Tue 7/287:00 am
SJU
- PDX
1 stop19h 30m
American Airlines
Deal found 6/13![American Airlines logo]()
$545
This American Airlines deal was found by Cheapflights users on 6/12. 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 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 6/12![American Airlines logo]()
$570
This American Airlines deal was found by Cheapflights users on 6/13. 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 7/285:49 am
PDX
- SJU
1 stop14h 10m
American Airlines
Mon 8/37:00 am
SJU
- PDX
1 stop19h 30m
American Airlines
Deal found 6/13![American Airlines logo]()
$518
One-way flights from Portland to CaribbeanSearch for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 15, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 15, 2026.
This American Airlines deal was found by Cheapflights users on 6/10. 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 9/111:34 pm
PDX
- PUJ
2 stops12h 32m
American Airlines
Deal found 6/10![American Airlines logo]()
$220
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:59 pm
PDX
- SJU
2 stops13h 51m
United Airlines
Deal found 6/11![United Airlines logo]()
$233
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Thu 7/910:40 pm
PDX
- MBJ
2 stops14h 30m
United Airlines
Deal found 6/12![United Airlines logo]()
$234
This American Airlines deal was found by Cheapflights users on 6/10. 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 8/115:59 am
PDX
- SJU
1 stop14h 16m
American Airlines
Deal found 6/10![American Airlines logo]()
$270
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 7/155:49 am
PDX
- SJU
1 stop14h 10m
American Airlines
Deal found 6/11![American Airlines logo]()
$275
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Thu 8/63:00 pm
PDX
- SJU
2 stops15h 43m
American Airlines
Deal found 6/10![American Airlines logo]()
$276
This Southwest deal was found by Cheapflights users on 6/13. 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.
Sat 7/1110:10 am
PDX
- SJU
2 stops12h 10m
Southwest
Deal found 6/13![Southwest 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 Delta deal was found by Cheapflights users on 6/12. 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 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 6/12![Delta logo]()
$308
This United Airlines deal was found by Cheapflights users on 6/13. 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.
Sat 7/1111:40 pm
PDX
- SJU
1 stop12h 04m
United Airlines
Deal found 6/13![United Airlines 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
This American Airlines deal was found by Cheapflights users on 6/13. 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 7/1311:15 pm
PDX
- SDQ
2 stops16h 25m
American Airlines
Deal found 6/13![American Airlines logo]()
$324
Find flight deals from Portland to Caribbean
Keep the following information in mind while searching for Portland to Caribbean flight deals. Data was last updated June 15, 2026.
Round-trip from | $422 (American Airlines) |
|---|---|
One-way from | $187 (Delta) |
Popular in | December |
Cheapest in | September |
Average price | $676 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 15, 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
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
$422
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Mon 11/2
10:05 pm-12:25 pm
1 stop11h 20m
Montego Bay Sangster Intl
Tue 11/10
6:00 pm-9:16 am
2 stops18h 16m
$427
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Tue 10/27
5:10 pm-11:25 am
2 stops16h 15m
Montego Bay Sangster Intl
Tue 11/10
6:00 pm-9:31 am
2 stops18h 31m
$427
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Mon 11/2
3:50 pm-12:25 pm
2 stops17h 35m
Montego Bay Sangster Intl
Wed 11/11
6:00 pm-9:31 am
2 stops18h 31m
$427
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
$466
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
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Fri 8/21
6:05 am-10:10 pm
2 stops13h 05m
San Juan Luis Munoz Marin Intl
Sat 8/29
8:20 am-8:00 pm
2 stops14h 40m
$466
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Sat 9/26
10:00 pm-12:13 pm
1 stop11h 13m
San Juan Luis Munoz Marin Intl
Sat 10/31
2:31 pm-10:26 pm
1 stop10h 55m
$466
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Tue 11/3
6:00 am-12:56 am
2 stops14h 56m
San Juan Luis Munoz Marin Intl
Tue 11/10
3:10 pm-11:47 pm
2 stops12h 37m
$466
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Mon 11/9
9:45 pm-2:20 pm
1 stop12h 35m
San Juan Luis Munoz Marin Intl
Tue 11/17
7:15 am-6:17 pm
2 stops15h 02m
$466
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-PUJ
PDX-SJU
PDX-AUA
PDX-SDQ
PDX-MBJ
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-PUJ
PDX-SJU
PDX-AUA
PDX-SDQ
What is the cheapest month to book a flight from Portland to Caribbean?
Currently, March is the cheapest month in which you can book a flight from Portland to Caribbean (average of $191). Flying from Portland to Caribbean in May is currently the most expensive (average of $365). 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 June 15, 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.
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from Portland to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Portland to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Portland to Caribbean by cabin class
Find flights from Portland to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Caribbean flights
Browse other Portland and Caribbean flight options. Last updated on June 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Portland to Caribbean flights
Consider these flights traveling from Portland to Caribbean.
Top 5 airlines flying from Portland to Caribbean
Discover the top 5 airlines that operate flights from Portland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 15, 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% |