$188+ Cheap flights from Portland (PDX) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Aug 16 — Aug 231
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 July 17, 2026.
Explore the most affordable flight options available from Portland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 17, 2026.
This American Airlines deal was found by Cheapflights users on 7/12. 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.
Thu 8/2011:34 pm
PDX
- STT
2 stops13h 18m
American Airlines
Fri 8/284:42 pm
STT
- PDX
2 stops21h 52m
American Airlines
Deal found 7/12![American Airlines logo]()
$420
This Delta deal was found by Cheapflights users on 7/12. 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.
Sat 10/3110:05 pm
PDX
- MBJ
1 stop12h 20m
Delta
Sat 11/144:00 pm
MBJ
- PDX
1 stop10h 47m
Delta
Deal found 7/12![Delta logo]()
$432
This Southwest deal was found by Cheapflights users on 7/13. 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 8/207:35 pm
PDX
- SJU
2 stops10h 35m
Southwest
Thu 8/2710:00 am
SJU
- PDX
2 stops13h 45m
Southwest
Deal found 7/13![Southwest logo]()
$436
This American Airlines deal was found by Cheapflights users on 7/13. 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 8/2111:34 pm
PDX
- MBJ
1 stop11h 38m
American Airlines
Thu 8/275:08 pm
MBJ
- PDX
2 stops20h 26m
American Airlines
Deal found 7/13![American Airlines logo]()
$437
This American Airlines deal was found by Cheapflights users on 7/14. 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.
Thu 12/310:55 pm
PDX
- STT
2 stops12h 30m
American Airlines
Thu 12/102:49 pm
STT
- PDX
1 stop13h 03m
American Airlines
Deal found 7/14![American Airlines logo]()
$440
This Southwest deal was found by Cheapflights users on 7/13. 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 11/97:00 pm
PDX
- SJU
2 stops12h 45m
Southwest
Tue 11/175:45 am
SJU
- PDX
2 stops13h 15m
Southwest
Deal found 7/13![Southwest logo]()
$451
This American Airlines deal was found by Cheapflights users on 7/15. 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.
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 7/15![American Airlines logo]()
$452
This Delta deal was found by Cheapflights users on 7/14. 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.
Mon 11/25:34 pm
PDX
- MBJ
2 stops15h 51m
Delta
Wed 11/116:00 pm
MBJ
- PDX
2 stops18h 31m
Delta
Deal found 7/14![Delta logo]()
$457
This Southwest deal was found by Cheapflights users on 7/14. 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.
Fri 8/2110:45 pm
PDX
- SJU
1 stop11h 25m
Southwest
Thu 8/275:30 am
SJU
- PDX
1 stop12h 30m
Southwest
Deal found 7/14![Southwest logo]()
$461
This United Airlines deal was found by Cheapflights users on 7/12. 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.
Wed 10/2811:00 pm
PDX
- MBJ
1 stop12h 14m
United Airlines
Wed 11/112:54 pm
MBJ
- PDX
1 stop11h 18m
United Airlines
Deal found 7/12![United Airlines logo]()
$462
This United Airlines deal was found by Cheapflights users on 7/14. 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 10/56:55 pm
PDX
- MBJ
2 stops14h 48m
United Airlines
Mon 10/1212:52 pm
MBJ
- PDX
1 stop22h 58m
United Airlines
Deal found 7/14![United Airlines logo]()
$463
This Delta deal was found by Cheapflights users on 7/13. 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.
Fri 10/238:44 pm
PDX
- SJU
2 stops11h 52m
Delta
Thu 10/291:06 pm
SJU
- PDX
2 stops13h 53m
Delta
Deal found 7/13![Delta logo]()
$466
Best flights from Portland to CaribbeanDiscover carefully curated flight deals from Portland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 17, 2026.
Discover carefully curated flight deals from Portland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 17, 2026.
This American Airlines deal was found by Cheapflights users on 7/12. 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.
Fri 8/2811:34 pm
PDX
- MBJ
2 stops11h 47m
American Airlines
Wed 9/212:38 pm
MBJ
- PDX
2 stops13h 21m
American Airlines
Deal found 7/12![American Airlines logo]()
$437
This Southwest deal was found by Cheapflights users on 7/12. 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 10/237:50 pm
PDX
- SJU
2 stops13h 20m
Southwest
Thu 10/2910:10 am
SJU
- PDX
2 stops13h 35m
Southwest
Deal found 7/12![Southwest logo]()
$451
This Delta deal was found by Cheapflights users on 7/15. 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 10/1310:15 pm
PDX
- MBJ
1 stop11h 10m
Delta
Tue 10/201:32 pm
MBJ
- PDX
2 stops12h 27m
Delta
Deal found 7/15![Delta logo]()
$457
This United Airlines deal was found by Cheapflights users on 7/14. 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 10/510:33 pm
PDX
- MBJ
1 stop11h 10m
United Airlines
Mon 10/1212:52 pm
MBJ
- PDX
1 stop22h 58m
United Airlines
Deal found 7/14![United Airlines logo]()
$463
This Air Canada deal was found by Cheapflights users on 7/16. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/313:15 pm
PDX
- NAS
2 stops27h 10m
Air Canada
Wed 11/412:30 pm
NAS
- PDX
2 stops23h 56m
Air Canada
Deal found 7/16![Air Canada logo]()
$631
This Expedia deal was found by Cheapflights users on 7/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/313:30 pm
PDX
- UVF
2 stops19h 50m
Multiple Airlines
Mon 9/71:59 pm
UVF
- PDX
2 stops26h 05m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$754
This Southwest deal was found by Cheapflights users on 7/17. 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 7/17![Southwest logo]()
$451
This United Airlines deal was found by Cheapflights users on 7/17. 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.
Wed 9/27:10 am
PDX
- SJU
1 stop10h 28m
United Airlines
Tue 9/81:00 am
SJU
- PDX
2 stops17h 56m
United Airlines
Deal found 7/17![United Airlines logo]()
$466
This American Airlines deal was found by Cheapflights users on 7/12. 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.
Mon 11/911:59 pm
PDX
- SJU
2 stops13h 53m
American Airlines
Tue 11/172:41 pm
SJU
- PDX
1 stop13h 10m
American Airlines
Deal found 7/12![American Airlines logo]()
$466
This Delta deal was found by Cheapflights users on 7/14. 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.
Thu 11/2610:05 pm
PDX
- SJU
1 stop15h 15m
Delta
Tue 12/87:00 am
SJU
- PDX
2 stops16h 43m
Delta
Deal found 7/14![Delta logo]()
$486
This United Airlines deal was found by Cheapflights users on 7/12. 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 10/2311:30 pm
PDX
- SJU
1 stop12h 14m
United Airlines
Thu 10/292:46 pm
SJU
- PDX
1 stop11h 27m
United Airlines
Deal found 7/12![United Airlines logo]()
$466
This Southwest deal was found by Cheapflights users on 7/15. 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.
Thu 9/177:35 pm
PDX
- SJU
2 stops10h 35m
Southwest
Mon 9/212:35 pm
SJU
- PDX
2 stops12h 05m
Southwest
Deal found 7/15![Southwest logo]()
$481
This American Airlines deal was found by Cheapflights users on 7/16. 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.
Tue 10/135:20 am
PDX
- MBJ
1 stop8h 52m
American Airlines
Tue 10/2012:16 pm
MBJ
- PDX
1 stop10h 55m
American Airlines
Deal found 7/16![American Airlines logo]()
$493
This United Airlines deal was found by Cheapflights users on 7/17. 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.
Mon 11/95:00 am
PDX
- SJU
1 stop9h 25m
United Airlines
Tue 11/178:25 am
SJU
- PDX
1 stop10h 58m
United Airlines
Deal found 7/17![United Airlines logo]()
$466
This Delta deal was found by Cheapflights users on 7/13. 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 1/66:04 am
PDX
- SJU
1 stop13h 46m
Delta
Mon 1/116:15 am
SJU
- PDX
2 stops18h 08m
Delta
Deal found 7/13![Delta logo]()
$520
This American Airlines deal was found by Cheapflights users on 7/17. 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 8/1410:59 pm
PDX
- SXM
1 stop11h 34m
American Airlines
Thu 8/202:42 pm
SXM
- PDX
2 stops23h 52m
American Airlines
Deal found 7/17![American Airlines logo]()
$512
This Southwest deal was found by Cheapflights users on 7/13. 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 8/2411:30 pm
PDX
- NAS
2 stops9h 45m
Southwest
Sun 8/301:10 pm
NAS
- PDX
2 stops13h 45m
Southwest
Deal found 7/13![Southwest logo]()
$569
This United Airlines deal was found by Cheapflights users on 7/16. 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.
Sat 10/2411:59 pm
PDX
- STT
1 stop12h 21m
United Airlines
Sat 10/312:00 pm
STT
- PDX
1 stop12h 12m
United Airlines
Deal found 7/16![United Airlines logo]()
$530
This American Airlines deal was found by Cheapflights users on 7/12. 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.
Thu 8/2010:59 pm
PDX
- STT
1 stop13h 00m
American Airlines
Fri 8/284:42 pm
STT
- PDX
2 stops23h 06m
American Airlines
Deal found 7/12![American Airlines logo]()
$542
This Delta deal was found by Cheapflights users on 7/15. 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.
Fri 11/279:45 pm
PDX
- NAS
1 stop12h 45m
Delta
Thu 12/31:20 pm
NAS
- PDX
1 stop8h 48m
Delta
Deal found 7/15![Delta logo]()
$610
This Southwest deal was found by Cheapflights users on 7/12. 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 9/47:35 pm
PDX
- STT
2 stops14h 45m
Southwest
Thu 9/102:35 pm
STT
- PDX
2 stops12h 05m
Southwest
Deal found 7/12![Southwest logo]()
$600
This Delta deal was found by Cheapflights users on 7/15. 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 11/22:20 pm
PDX
- NAS
1 stop18h 31m
Delta
Wed 11/252:55 pm
NAS
- PDX
1 stop10h 31m
Delta
Deal found 7/15![Delta logo]()
$610
This Mytrip deal was found by Cheapflights users on 7/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/210:00 am
PDX
- UVF
3 stops24h 50m
Multiple Airlines
Mon 11/95:40 pm
UVF
- PDX
2 stops25h 01m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$829
This American Airlines deal was found by Cheapflights users on 7/16. 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 8/283:00 pm
PDX
- SXM
2 stops19h 22m
American Airlines
Mon 9/74:39 pm
SXM
- PDX
2 stops24h 13m
American Airlines
Deal found 7/16![American Airlines logo]()
$606
This United Airlines deal was found by Cheapflights users on 7/15. 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.
Sun 11/17:07 pm
PDX
- NAS
2 stops15h 26m
United Airlines
Thu 11/2612:55 pm
NAS
- PDX
1 stop12h 11m
United Airlines
Deal found 7/15![United Airlines logo]()
$610
This Delta deal was found by Cheapflights users on 7/15. 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.
Thu 11/269:40 am
PDX
- NAS
2 stops24h 50m
Delta
Wed 12/21:00 pm
NAS
- PDX
1 stop11h 27m
Delta
Deal found 7/15![Delta logo]()
$614
This United deal was found by Cheapflights users on 7/15. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:07 pm
PDX
- STT
2 stops14h 51m
Multiple Airlines
Sat 8/225:45 pm
STT
- PDX
2 stops19h 05m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$839
This Delta deal was found by Cheapflights users on 7/15. 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 11/210:05 pm
PDX
- NAS
1 stop10h 25m
Delta
Thu 11/261:20 pm
NAS
- PDX
2 stops11h 33m
Delta
Deal found 7/15![Delta logo]()
$614
This United Airlines deal was found by Cheapflights users on 7/16. 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.
Sat 8/155:00 am
PDX
- MBJ
2 stops32h 10m
United Airlines
Sat 8/222:40 pm
MBJ
- PDX
3 stops21h 31m
United Airlines
Deal found 7/16![United Airlines logo]()
$638
This American Airlines deal was found by Cheapflights users on 7/12. 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.
Fri 10/3010:55 pm
PDX
- PUJ
1 stop12h 08m
American Airlines
Sat 11/712:46 pm
PUJ
- PDX
2 stops15h 13m
American Airlines
Deal found 7/12![American Airlines logo]()
$665
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated July 17, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated July 17, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/16. 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 8/125:59 am
PDX
- SJU
1 stop14h 16m
American Airlines
Fri 8/217:30 am
SJU
- PDX
1 stop15h 18m
American Airlines
Deal found 7/16![American Airlines logo]()
$471
This American Airlines deal was found by Cheapflights users on 7/13. 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.
Sun 8/165:15 am
PDX
- SJU
2 stops13h 40m
American Airlines
Sat 8/2212:55 am
SJU
- PDX
1 stop13h 39m
American Airlines
Deal found 7/13![American Airlines logo]()
$500
This deal was found by Cheapflights users on 7/15. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:00 am
PDX
- SJU
1 stop13h 52m
Delta
Sat 10/104:18 pm
SJU
- PDX
1 stop10h 26m
Delta
Deal found 7/15![Delta logo]()
$476
This American Airlines deal was found by Cheapflights users on 7/16. 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 8/1911:34 pm
PDX
- SJU
1 stop20h 41m
American Airlines
Wed 8/2612:55 am
SJU
- PDX
1 stop20h 10m
American Airlines
Deal found 7/16![American Airlines logo]()
$481
This American Airlines deal was found by Cheapflights users on 7/12. 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.
Thu 8/2011:34 pm
PDX
- STT
2 stops13h 18m
American Airlines
Fri 8/284:42 pm
STT
- PDX
2 stops21h 52m
American Airlines
Deal found 7/12![American Airlines logo]()
$420
This Southwest deal was found by Cheapflights users on 7/13. 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 8/207:35 pm
PDX
- SJU
2 stops10h 35m
Southwest
Thu 8/275:30 am
SJU
- PDX
1 stop12h 30m
Southwest
Deal found 7/13![Southwest logo]()
$436
This American Airlines deal was found by Cheapflights users on 7/13. 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 8/2111:34 pm
PDX
- MBJ
1 stop11h 38m
American Airlines
Thu 8/272:12 pm
MBJ
- PDX
1 stop11h 47m
American Airlines
Deal found 7/13![American Airlines logo]()
$432
This Southwest deal was found by Cheapflights users on 7/15. 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.
Fri 8/2110:45 pm
PDX
- SJU
1 stop11h 25m
Southwest
Thu 8/275:30 am
SJU
- PDX
1 stop12h 30m
Southwest
Deal found 7/15![Southwest logo]()
$451
This American Airlines deal was found by Cheapflights users on 7/15. 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.
Fri 8/2111:34 pm
PDX
- MBJ
2 stops12h 15m
American Airlines
Fri 8/282:52 pm
MBJ
- PDX
2 stops22h 02m
American Airlines
Deal found 7/15![American Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 7/13. 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.
Sun 8/236:45 am
PDX
- SJU
1 stop12h 44m
Delta
Sun 10/117:00 am
SJU
- PDX
2 stops17h 56m
Delta
Deal found 7/13![Delta logo]()
$466
This Southwest deal was found by Cheapflights users on 7/12. 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.
Thu 8/277:35 pm
PDX
- SJU
2 stops10h 35m
Southwest
Thu 9/35:30 am
SJU
- PDX
1 stop12h 30m
Southwest
Deal found 7/12![Southwest logo]()
$485
This Cheapflightsfares deal was found by Cheapflights users on 7/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:27 pm
PDX
- SJU
1 stop11h 44m
JetBlue
Thu 9/31:50 pm
SJU
- PDX
1 stop11h 59m
JetBlue
Deal found 7/16![JetBlue logo]()
$502
One-way flights from Portland to CaribbeanSearch for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 17, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/13. 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.
Thu 8/136:49 pm
PDX
- SJU
2 stops26h 52m
Frontier
Deal found 7/13![Frontier logo]()
$188
This American Airlines deal was found by Cheapflights users on 7/12. 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.
Fri 9/411:34 pm
PDX
- MBJ
1 stop11h 38m
American Airlines
Deal found 7/12![American Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 7/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/75:49 pm
PDX
- SJU
2 stops27h 52m
Frontier
Deal found 7/15![Frontier logo]()
$199
This Southwest deal was found by Cheapflights users on 7/15. 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.
Mon 11/304:25 pm
PDX
- NAS
2 stops16h 50m
Southwest
Deal found 7/15![Southwest logo]()
$206
This American Airlines deal was found by Cheapflights users on 7/13. 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.
Sat 9/511:34 pm
PDX
- STT
2 stops13h 18m
American Airlines
Deal found 7/13![American Airlines logo]()
$208
This Southwest deal was found by Cheapflights users on 7/13. 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.
Sun 12/137:00 pm
PDX
- SXM
2 stops15h 20m
Southwest
Deal found 7/13![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 7/15. 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.
Mon 8/2411:30 pm
PDX
- SJU
2 stops11h 05m
Southwest
Deal found 7/15![Southwest logo]()
$218
This Trip.com deal was found by Cheapflights users on 7/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:49 pm
PDX
- SJU
2 stops14h 27m
Frontier
Deal found 7/17![Frontier logo]()
$222
This SmartFares deal was found by Cheapflights users on 7/12. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:27 pm
PDX
- SJU
1 stop11h 44m
JetBlue
Deal found 7/12![JetBlue logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 7/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:49 pm
PDX
- SJU
2 stops26h 39m
Frontier
Deal found 7/15![Frontier logo]()
$228
This Delta deal was found by Cheapflights users on 7/14. 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.
Mon 11/1610:05 pm
PDX
- SJU
1 stop11h 00m
Delta
Deal found 7/14![Delta logo]()
$233
This American Airlines deal was found by Cheapflights users on 7/13. 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.
Thu 8/1310:58 pm
PDX
- SJU
1 stop20h 26m
American Airlines
Deal found 7/13![American Airlines logo]()
$237
Find flight deals from Portland to Caribbean
Keep the following information in mind while searching for Portland to Caribbean flight deals. Data was last updated July 17, 2026.
Round-trip from | $420 (American Airlines) |
|---|---|
One-way from | $188 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $612 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 17, 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
Fri 8/28
11:34 pm-1:21 pm
2 stops11h 47m
Montego Bay Sangster Intl
Wed 9/2
12:38 pm-11:59 pm
2 stops13h 21m
$437
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Fri 10/23
7:50 pm-12:10 pm
2 stops13h 20m
San Juan Luis Munoz Marin Intl
Thu 10/29
10:10 am-8:45 pm
2 stops13h 35m
$451
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
$451
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Tue 10/13
10:15 pm-11:25 am
1 stop11h 10m
Montego Bay Sangster Intl
Tue 10/20
1:32 pm-11:59 pm
2 stops12h 27m
$457
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Mon 10/5
10:33 pm-11:43 am
1 stop11h 10m
Montego Bay Sangster Intl
Mon 10/12
12:52 pm-9:50 am
1 stop22h 58m
$463
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Wed 9/2
7:10 am-8:38 pm
1 stop10h 28m
San Juan Luis Munoz Marin Intl
Tue 9/8
1:00 am-3:56 pm
2 stops17h 56m
$466
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Mon 11/9
11:59 pm-5:52 pm
2 stops13h 53m
San Juan Luis Munoz Marin Intl
Tue 11/17
2:41 pm-11:51 pm
1 stop13h 10m
$466
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Fri 10/23
11:30 pm-2:44 pm
1 stop12h 14m
San Juan Luis Munoz Marin Intl
Thu 10/29
2:46 pm-11:13 pm
1 stop11h 27m
$466
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Mon 11/9
5:00 am-6:25 pm
1 stop9h 25m
San Juan Luis Munoz Marin Intl
Tue 11/17
8:25 am-3:23 pm
1 stop10h 58m
$466
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Thu 9/17
7:35 pm-9:10 am
2 stops10h 35m
San Juan Luis Munoz Marin Intl
Mon 9/21
2:35 pm-11:40 pm
2 stops12h 05m
$481
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-SJU
PDX-MBJ
PDX-NAS
PDX-SDQ
PDX-STT
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-SJU
PDX-MBJ
PDX-NAS
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 July 17, 2026.
Read through reviews of airlines operating flights from Portland to Caribbean, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Portland to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Portland to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Portland to Caribbean by cabin class
Find flights from Portland to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Caribbean flights
Browse other Portland and Caribbean flight options. Last updated on July 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Portland to Caribbean flights
Consider these flights traveling from Portland to Caribbean.
Top 5 airlines flying from Portland to Caribbean
Discover the top 5 airlines that operate flights from Portland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$190 | Average$715 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$247 | Average$682 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$261 | Average$478 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$392 | Average$723 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$408 | Average$624 | FlexibilityNo cancel fee | On-time63% |