$138+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Mar 20 — Mar 271
1 adult, Economy
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Find cheap flights from Portland to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Portland to Caribbean
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Cheapest flights from Portland to CaribbeanExplore the most affordable flight options available from Portland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 18, 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 February 18, 2026.
This American Airlines deal was found by Cheapflights users on 2/14. 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 3/811:59 pm
PDX
- MBJ
1 stop12h 05m
American Airlines
Wed 3/111:27 pm
MBJ
- PDX
1 stop12h 17m
American Airlines
Deal found 2/14![American Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 2/17. 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.
Sat 5/23:16 pm
PDX
- MBJ
1 stop18h 57m
American Airlines
Thu 5/74:37 pm
MBJ
- PDX
2 stops20h 24m
American Airlines
Deal found 2/17![American Airlines logo]()
$357
This deal was found by Cheapflights users on 2/16. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:28 pm
PDX
- MBJ
1 stop11h 23m
American Airlines
Fri 4/171:15 pm
MBJ
- PDX
1 stop11h 27m
American Airlines
Deal found 2/16![American Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 2/15. 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 4/273:00 pm
PDX
- SJU
2 stops16h 35m
Southwest
Tue 5/55:05 am
SJU
- PDX
2 stops18h 55m
Southwest
Deal found 2/15![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/289:45 am
PDX
- SJU
2 stops10h 55m
Southwest
Tue 5/55:05 am
SJU
- PDX
2 stops18h 55m
Southwest
Deal found 2/16![Southwest logo]()
$406
This Priceline deal was found by Cheapflights users on 2/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2511:40 pm
PDX
- SJU
1 stop20h 20m
JetBlue
Thu 5/281:45 pm
SJU
- PDX
1 stop11h 40m
JetBlue
Deal found 2/14![JetBlue logo]()
$411
This Delta deal was found by Cheapflights users on 2/14. 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.
Sun 3/87:43 pm
PDX
- MBJ
2 stops13h 38m
Delta
Wed 3/1111:15 am
MBJ
- PDX
2 stops13h 08m
Delta
Deal found 2/14![Delta logo]()
$427
This American Airlines deal was found by Cheapflights users on 2/16. 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.
Sat 4/183:16 pm
PDX
- MBJ
1 stop18h 57m
American Airlines
Sat 4/2512:36 pm
MBJ
- PDX
1 stop10h 27m
American Airlines
Deal found 2/16![American Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 2/17. 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.
Tue 5/511:23 pm
PDX
- MBJ
1 stop12h 02m
American Airlines
Sun 5/101:15 pm
MBJ
- PDX
1 stop12h 42m
American Airlines
Deal found 2/17![American Airlines logo]()
$436
This Southwest deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/225:30 am
PDX
- SJU
2 stops12h 35m
Southwest
Thu 4/232:00 pm
SJU
- PDX
2 stops13h 10m
Southwest
Deal found 2/16![Southwest logo]()
$436
This Southwest deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:10 am
PDX
- SJU
2 stops15h 30m
Southwest
Tue 5/55:05 am
SJU
- PDX
2 stops18h 55m
Southwest
Deal found 2/16![Southwest logo]()
$438
This eDestinos deal was found by Cheapflights users on 2/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/19:30 pm
PDX
- SJU
1 stop14h 47m
Multiple Airlines
Wed 4/153:19 pm
SJU
- PDX
3 stops44h 40m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$441
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 February 18, 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 February 18, 2026.
This American Airlines deal was found by Cheapflights users on 2/17. 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.
Sat 5/211:40 pm
PDX
- MBJ
2 stops13h 57m
American Airlines
Thu 5/74:37 pm
MBJ
- PDX
2 stops20h 24m
American Airlines
Deal found 2/17![American Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 2/14. 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.
Tue 4/287:25 pm
PDX
- SJU
2 stops12h 10m
Southwest
Tue 5/55:05 am
SJU
- PDX
2 stops18h 55m
Southwest
Deal found 2/14![Southwest logo]()
$386
This Delta deal was found by Cheapflights users on 2/14. 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.
Sun 3/87:43 pm
PDX
- MBJ
2 stops13h 38m
Delta
Wed 3/1111:15 am
MBJ
- PDX
2 stops13h 08m
Delta
Deal found 2/14![Delta logo]()
$427
This United Airlines deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:00 am
PDX
- SJU
1 stop9h 38m
United Airlines
Sat 4/187:40 am
SJU
- PDX
2 stops16h 34m
United Airlines
Deal found 2/16![United Airlines logo]()
$450
This Frontier deal was found by Cheapflights users on 2/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/912:27 pm
PDX
- PUJ
2 stops19h 10m
Frontier
Sat 5/1611:07 am
PUJ
- PDX
2 stops24h 52m
Frontier
Deal found 2/17![Frontier logo]()
$471
This Air Canada deal was found by Cheapflights users on 2/14. 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 4/273:15 pm
PDX
- NAS
2 stops25h 50m
Air Canada
Thu 4/309:10 pm
NAS
- PDX
2 stops24h 55m
Air Canada
Deal found 2/14![Air Canada logo]()
$529
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Tue 3/175:50 pm
PDX
- SDQ
2 stops32h 17m
Multiple Airlines
Tue 3/245:39 am
SDQ
- PDX
1 stop18h 11m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$563
This Copa Airlines deal was found by Cheapflights users on 2/14. 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 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 stops22h 16m
Copa Airlines
Wed 4/85:35 am
PUJ
- PDX
2 stops20h 19m
Copa Airlines
Deal found 2/14![Copa Airlines logo]()
$655
This deal was found by Cheapflights users on 2/16. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1310:28 pm
PDX
- MBJ
1 stop11h 23m
American Airlines
Fri 4/171:15 pm
MBJ
- PDX
1 stop11h 27m
American Airlines
Deal found 2/16![American Airlines logo]()
$382
This deal was found by Cheapflights users on 2/16. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1110:23 pm
PDX
- MBJ
1 stop13h 02m
American Airlines
Thu 4/161:15 pm
MBJ
- PDX
1 stop11h 27m
American Airlines
Deal found 2/16![American Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 2/17. 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.
Fri 5/15:10 am
PDX
- SJU
2 stops15h 30m
Southwest
Wed 5/68:10 am
SJU
- PDX
2 stops14h 05m
Southwest
Deal found 2/17![Southwest logo]()
$438
This Delta deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/910:05 pm
PDX
- SJU
1 stop15h 25m
Delta
Thu 6/181:09 pm
SJU
- PDX
1 stop13h 50m
Delta
Deal found 2/16![Delta logo]()
$450
This United Airlines deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/110:15 pm
PDX
- SJU
1 stop12h 30m
United Airlines
Wed 5/61:40 pm
SJU
- PDX
1 stop12h 14m
United Airlines
Deal found 2/17![United Airlines logo]()
$450
This Southwest deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:10 am
PDX
- SJU
2 stops15h 30m
Southwest
Tue 5/55:05 am
SJU
- PDX
2 stops18h 55m
Southwest
Deal found 2/16![Southwest logo]()
$438
This Delta deal was found by Cheapflights users on 2/14. 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.
Sat 4/183:35 pm
PDX
- SJU
2 stops17h 37m
Delta
Sat 4/257:15 am
SJU
- PDX
2 stops18h 06m
Delta
Deal found 2/14![Delta logo]()
$450
This United Airlines deal was found by Cheapflights users on 2/16. 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.
Fri 5/87:05 pm
PDX
- SJU
2 stops14h 29m
United Airlines
Fri 5/151:40 pm
SJU
- PDX
1 stop10h 29m
United Airlines
Deal found 2/16![United Airlines logo]()
$450
This American Airlines deal was found by Cheapflights users on 2/16. 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 5/511:47 pm
PDX
- MBJ
1 stop10h 26m
American Airlines
Sat 5/1612:36 pm
MBJ
- PDX
1 stop10h 27m
American Airlines
Deal found 2/16![American Airlines logo]()
$431
This Orbitz deal was found by Cheapflights users on 2/15. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:05 pm
PDX
- NAS
2 stops22h 00m
Air Canada
Sat 4/189:10 pm
NAS
- PDX
2 stops20h 30m
Air Canada
Deal found 2/15![Air Canada logo]()
$529
This United Airlines deal was found by Cheapflights users on 2/14. 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.
Tue 4/287:00 am
PDX
- SJU
1 stop10h 38m
United Airlines
Tue 5/57:20 am
SJU
- PDX
2 stops15h 18m
United Airlines
Deal found 2/14![United Airlines logo]()
$450
This American Airlines deal was found by Cheapflights users on 2/17. 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.
Tue 5/511:23 pm
PDX
- MBJ
1 stop12h 02m
American Airlines
Mon 5/114:37 pm
MBJ
- PDX
2 stops20h 24m
American Airlines
Deal found 2/17![American Airlines logo]()
$436
This Travelocity deal was found by Cheapflights users on 2/14. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:05 pm
PDX
- NAS
2 stops22h 05m
Air Canada
Mon 3/169:30 pm
NAS
- PDX
2 stops20h 10m
Air Canada
Deal found 2/14![Air Canada logo]()
$530
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/67:00 am
PDX
- PUJ
1 stop11h 29m
Multiple Airlines
Tue 4/149:38 am
PUJ
- PDX
1 stop13h 57m
Multiple Airlines
Deal found 2/17![Multiple Airlines logo]()
$595
This United Airlines deal was found by Cheapflights users on 2/15. 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.
Mon 4/2011:59 pm
PDX
- SJU
1 stop11h 45m
United Airlines
Fri 4/243:56 pm
SJU
- PDX
1 stop11h 02m
United Airlines
Deal found 2/15![United Airlines logo]()
$450
This Southwest deal was found by Cheapflights users on 2/14. 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.
Wed 4/16:00 am
PDX
- NAS
2 stops9h 30m
Southwest
Wed 4/82:10 pm
NAS
- PDX
2 stops12h 00m
Southwest
Deal found 2/14![Southwest logo]()
$510
This American Airlines deal was found by Cheapflights users on 2/17. 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.
Tue 3/1011:59 pm
PDX
- MBJ
1 stop10h 12m
American Airlines
Sun 3/151:14 pm
MBJ
- PDX
1 stop13h 01m
American Airlines
Deal found 2/17![American Airlines logo]()
$436
This Delta deal was found by Cheapflights users on 2/14. 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 3/1710:30 pm
PDX
- NAS
1 stop15h 15m
Delta
Tue 3/313:05 pm
NAS
- PDX
1 stop10h 03m
Delta
Deal found 2/14![Delta logo]()
$528
This Air Canada deal was found by Cheapflights users on 2/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/149:50 am
PDX
- NAS
2 stops24h 05m
Air Canada
Mon 4/209:10 pm
NAS
- PDX
2 stops39h 00m
Air Canada
Deal found 2/17![Air Canada logo]()
$535
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/267:00 am
PDX
- SDQ
1 stop16h 40m
Multiple Airlines
Sat 4/43:55 am
SDQ
- PDX
1 stop32h 28m
Multiple Airlines
Deal found 2/17![Multiple Airlines logo]()
$614
This American Airlines deal was found by Cheapflights users on 2/16. 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 5/511:47 pm
PDX
- MBJ
1 stop10h 26m
American Airlines
Sun 5/101:15 pm
MBJ
- PDX
1 stop11h 32m
American Airlines
Deal found 2/16![American Airlines logo]()
$436
This Delta deal was found by Cheapflights users on 2/14. 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 3/175:02 pm
PDX
- NAS
2 stops15h 40m
Delta
Wed 4/16:10 pm
NAS
- PDX
1 stop19h 20m
Delta
Deal found 2/14![Delta logo]()
$532
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated February 18, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated February 18, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/17. 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.
Tue 3/310:53 pm
PDX
- MBJ
1 stop8h 14m
American Airlines
Wed 3/1110:07 am
MBJ
- PDX
1 stop15h 37m
American Airlines
Deal found 2/17![American Airlines logo]()
$494
This Delta deal was found by Cheapflights users on 2/14. 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.
Wed 3/45:30 am
PDX
- SJU
2 stops14h 28m
Delta
Thu 3/122:07 pm
SJU
- PDX
2 stops12h 47m
Delta
Deal found 2/14![Delta logo]()
$513
This American Airlines deal was found by Cheapflights users on 2/14. 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 3/811:59 pm
PDX
- MBJ
1 stop12h 05m
American Airlines
Wed 3/111:27 pm
MBJ
- PDX
1 stop12h 17m
American Airlines
Deal found 2/14![American Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 2/14. 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.
Sun 3/87:43 pm
PDX
- MBJ
2 stops13h 38m
Delta
Wed 3/1111:15 am
MBJ
- PDX
2 stops13h 08m
Delta
Deal found 2/14![Delta logo]()
$427
This American Airlines deal was found by Cheapflights users on 2/15. 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 3/911:59 pm
PDX
- SJU
1 stop19h 32m
American Airlines
Wed 3/117:11 am
SJU
- PDX
1 stop19h 33m
American Airlines
Deal found 2/15![American Airlines logo]()
$445
This American Airlines deal was found by Cheapflights users on 2/17. 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.
Tue 3/1011:59 pm
PDX
- MBJ
1 stop10h 12m
American Airlines
Sun 3/151:14 pm
MBJ
- PDX
1 stop13h 01m
American Airlines
Deal found 2/17![American Airlines logo]()
$436
This American Airlines deal was found by Cheapflights users on 2/14. 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 3/105:00 am
PDX
- SJU
2 stops12h 50m
American Airlines
Tue 3/1712:58 pm
SJU
- PDX
2 stops14h 22m
American Airlines
Deal found 2/14![American Airlines logo]()
$488
This United Airlines deal was found by Cheapflights users on 2/16. 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.
Wed 3/112:05 pm
PDX
- MBJ
1 stop21h 00m
United Airlines
Wed 3/252:20 pm
MBJ
- PDX
1 stop10h 51m
United Airlines
Deal found 2/16![United Airlines logo]()
$460
This American Airlines deal was found by Cheapflights users on 2/14. 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.
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 2/14![American Airlines logo]()
$504
This American Airlines deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1711:59 pm
PDX
- MBJ
1 stop12h 05m
American Airlines
Tue 3/2412:44 pm
MBJ
- PDX
1 stop10h 47m
American Airlines
Deal found 2/15![American Airlines logo]()
$500
This American Airlines deal was found by Cheapflights users on 2/15. 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 3/2310:53 pm
PDX
- SJU
1 stop18h 57m
American Airlines
Wed 4/17:11 am
SJU
- PDX
1 stop20h 11m
American Airlines
Deal found 2/15![American Airlines logo]()
$526
This American Airlines deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3110:35 pm
PDX
- SJU
1 stop9h 05m
American Airlines
Sun 4/57:11 am
SJU
- PDX
1 stop20h 11m
American Airlines
Deal found 2/15![American Airlines logo]()
$450
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 February 18, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated February 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/291:48 pm
PDX
- SJU
2 stops24h 42m
Frontier
Deal found 2/14![Frontier logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:48 pm
PDX
- SJU
2 stops27h 19m
Frontier
Deal found 2/16![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:48 pm
PDX
- SJU
3 stops28h 01m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$179
This Southwest deal was found by Cheapflights users on 2/14. 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.
Tue 5/267:25 pm
PDX
- SJU
2 stops12h 10m
Southwest
Deal found 2/14![Southwest logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Mon 3/210:18 pm
PDX
- SJU
3 stops39h 14m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/309:53 am
PDX
- SJU
2 stops25h 13m
Frontier
Deal found 2/14![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/291:48 pm
PDX
- SJU
3 stops21h 43m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Mon 3/210:18 pm
PDX
- SJU
2 stops36h 49m
Frontier
Deal found 2/15![Frontier logo]()
$211
This Priceline deal was found by Cheapflights users on 2/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2211:40 pm
PDX
- SJU
1 stop20h 20m
JetBlue
Deal found 2/15![JetBlue logo]()
$218
This Gotogate deal was found by Cheapflights users on 2/15. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:05 pm
PDX
- NAS
2 stops14h 50m
Air Canada
Deal found 2/15![Air Canada logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/169:53 am
PDX
- SJU
2 stops33h 52m
Frontier
Deal found 2/16![Frontier logo]()
$223
This American Airlines deal was found by Cheapflights users on 2/14. 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 4/2110:28 pm
PDX
- SJU
1 stop9h 25m
American Airlines
Deal found 2/14![American Airlines logo]()
$225
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 February 18, 2026.
Round-trip from | $352 (American Airlines) |
|---|---|
One-way from | $138 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $588 |
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 February 18, 2026.
Use the filters below to find and compare flights from Portland to Caribbean that are best for you.
Fly from
Portland
Fly to
Caribbean
Route
Depart
Return
Price
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Sat 5/2
11:40 pm-3:37 pm
2 stops13h 57m
Montego Bay Sangster Intl
Thu 5/7
4:37 pm-11:01 am
2 stops20h 24m
$357
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Mon 4/13
10:28 pm-11:51 am
1 stop11h 23m
Montego Bay Sangster Intl
Fri 4/17
1:15 pm-10:42 pm
1 stop11h 27m
$382
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Sat 4/11
10:23 pm-1:25 pm
1 stop13h 02m
Montego Bay Sangster Intl
Thu 4/16
1:15 pm-10:42 pm
1 stop11h 27m
$382
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Tue 4/28
7:25 pm-10:35 am
2 stops12h 10m
San Juan Luis Munoz Marin Intl
Tue 5/5
5:05 am-9:00 pm
2 stops18h 55m
$386
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Sun 3/8
7:43 pm-11:21 am
2 stops13h 38m
Montego Bay Sangster Intl
Wed 3/11
11:15 am-10:23 pm
2 stops13h 08m
$427
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Tue 5/5
11:47 pm-12:13 pm
1 stop10h 26m
Montego Bay Sangster Intl
Sat 5/16
12:36 pm-9:03 pm
1 stop10h 27m
$431
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Tue 5/5
11:23 pm-1:25 pm
1 stop12h 02m
Montego Bay Sangster Intl
Mon 5/11
4:37 pm-11:01 am
2 stops20h 24m
$436
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Tue 3/10
11:59 pm-12:11 pm
1 stop10h 12m
Montego Bay Sangster Intl
Sun 3/15
1:14 pm-12:15 am
1 stop13h 01m
$436
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Tue 5/5
11:47 pm-12:13 pm
1 stop10h 26m
Montego Bay Sangster Intl
Sun 5/10
1:15 pm-10:47 pm
1 stop11h 32m
$436
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Fri 5/1
5:10 am-11:40 pm
2 stops15h 30m
San Juan Luis Munoz Marin Intl
Wed 5/6
8:10 am-7:15 pm
2 stops14h 05m
$438
Showing 1-10 of 60 results
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-NAS
PDX-MBJ
PDX-AUA
PDX-SDQ
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-NAS
PDX-MBJ
PDX-AUA
What is the cheapest month to book a flight from Portland to Caribbean?
Currently, August is the cheapest month in which you can book a flight from Portland to Caribbean (average of $188). Flying from Portland to Caribbean 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
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 February 18, 2026.
Read through reviews of airlines operating flights from Portland to Caribbean, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
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. 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 February 18, 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 6 airlines flying from Portland to Caribbean
Discover the top 6 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 February 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$184 | Average$696 | 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$700 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$399 | Average$688 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$408 | Average$722 | FlexibilityNo cancel fee | On-time63% |