$224+ Cheap flights from Caribbean to Portland (PDX)
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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
May 19 — May 261
Round-trip
1 adult, Economy
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Find cheap flights from Caribbean to Portland 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 Caribbean to Portland
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Cheapest flights from Caribbean to PortlandExplore the most affordable flight options available from Caribbean to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 19, 2026.
Explore the most affordable flight options available from Caribbean to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 19, 2026.
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/304:33 pm
MBJ
- PDX
2 stops19h 47m
United Airlines
Sat 6/61:14 pm
PDX
- MBJ
2 stops24h 12m
United Airlines
Deal found 4/15![United Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 4/16. 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 7/142:23 pm
MBJ
- PDX
1 stop11h 34m
American Airlines
Sat 8/110:57 pm
PDX
- MBJ
1 stop12h 26m
American Airlines
Deal found 4/16![American Airlines logo]()
$356
This United Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/22:40 pm
MBJ
- PDX
2 stops20h 59m
United Airlines
Tue 6/911:30 pm
PDX
- MBJ
1 stop13h 40m
United Airlines
Deal found 4/18![United Airlines logo]()
$426
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/144:12 pm
MBJ
- PDX
3 stops21h 55m
United Airlines
Sat 8/111:30 pm
PDX
- MBJ
1 stop13h 40m
United Airlines
Deal found 4/16![United Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 4/16. 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.
Thu 9/245:00 am
SJU
- PDX
2 stops13h 00m
Southwest
Sun 9/2710:45 pm
PDX
- SJU
1 stop12h 45m
Southwest
Deal found 4/16![Southwest logo]()
$466
This Delta deal was found by Cheapflights users on 4/16. 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.
Thu 5/72:35 pm
SJU
- PDX
2 stops12h 09m
Delta
Tue 5/125:30 am
PDX
- SJU
2 stops15h 05m
Delta
Deal found 4/16![Delta logo]()
$496
This American Airlines deal was found by Cheapflights users on 4/14. 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 8/181:38 pm
SJU
- PDX
2 stops12h 44m
American Airlines
Tue 8/2510:59 pm
PDX
- SJU
1 stop12h 52m
American Airlines
Deal found 4/14![American Airlines logo]()
$530
This American Airlines deal was found by Cheapflights users on 4/17. 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 8/251:38 pm
SJU
- PDX
2 stops12h 29m
American Airlines
Wed 9/211:59 pm
PDX
- SJU
1 stop11h 55m
American Airlines
Deal found 4/17![American Airlines logo]()
$535
This American Airlines deal was found by Cheapflights users on 4/13. 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 8/216:00 am
SJU
- PDX
2 stops14h 21m
American Airlines
Sat 8/2911:59 pm
PDX
- SJU
1 stop11h 55m
American Airlines
Deal found 4/13![American Airlines logo]()
$542
This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:00 am
SJU
- PDX
1 stop19h 59m
American Airlines
Tue 6/25:07 am
PDX
- SJU
1 stop20h 18m
American Airlines
Deal found 4/15![American Airlines logo]()
$543
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1910:17 am
MBJ
- PDX
1 stop12h 46m
American Airlines
Mon 4/2010:28 pm
PDX
- MBJ
1 stop11h 23m
American Airlines
Deal found 4/19![American Airlines logo]()
$545
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/112:59 am
SJU
- PDX
1 stop12h 00m
American Airlines
Wed 6/105:49 am
PDX
- SJU
1 stop13h 56m
American Airlines
Deal found 4/14![American Airlines logo]()
$553
Best flights from Caribbean to PortlandDiscover carefully curated flight deals from Caribbean to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 19, 2026.
Discover carefully curated flight deals from Caribbean to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 19, 2026.
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/304:33 pm
MBJ
- PDX
2 stops19h 47m
United Airlines
Sat 6/61:14 pm
PDX
- MBJ
2 stops24h 12m
United Airlines
Deal found 4/15![United Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 4/16. 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 7/142:23 pm
MBJ
- PDX
1 stop11h 34m
American Airlines
Sat 8/110:57 pm
PDX
- MBJ
1 stop12h 26m
American Airlines
Deal found 4/16![American Airlines logo]()
$356
This Delta deal was found by Cheapflights users on 4/16. 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.
Thu 5/72:35 pm
SJU
- PDX
2 stops12h 09m
Delta
Tue 5/127:00 am
PDX
- SJU
1 stop13h 35m
Delta
Deal found 4/16![Delta logo]()
$496
This eDestinos deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/253:56 pm
PUJ
- PDX
2 stops28h 01m
Frontier
Sun 7/126:19 pm
PDX
- PUJ
2 stops17h 06m
Frontier
Deal found 4/18![Frontier logo]()
$777
This United Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/22:40 pm
MBJ
- PDX
2 stops20h 59m
United Airlines
Tue 6/911:30 pm
PDX
- MBJ
1 stop13h 40m
United Airlines
Deal found 4/18![United Airlines logo]()
$426
This Southwest deal was found by Cheapflights users on 4/16. 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.
Sun 7/123:35 pm
PUJ
- PDX
1 stop11h 30m
Southwest
Sat 7/187:40 pm
PDX
- PUJ
2 stops14h 40m
Southwest
Deal found 4/16![Southwest logo]()
$854
This Mytrip deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/255:05 pm
PUJ
- PDX
3 stops32h 38m
Multiple Airlines
Sun 7/1211:15 pm
PDX
- PUJ
2 stops21h 00m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$908
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/144:12 pm
MBJ
- PDX
3 stops21h 55m
United Airlines
Sat 8/111:30 pm
PDX
- MBJ
1 stop13h 40m
United Airlines
Deal found 4/16![United Airlines logo]()
$427
This American Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:17 pm
MBJ
- PDX
2 stops21h 27m
American Airlines
Mon 6/811:43 pm
PDX
- MBJ
2 stops11h 48m
American Airlines
Deal found 4/17![American Airlines logo]()
$574
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:15 am
SJU
- PDX
2 stops14h 51m
Delta
Sat 5/165:30 am
PDX
- SJU
2 stops15h 05m
Delta
Deal found 4/17![Delta logo]()
$576
This United Airlines deal was found by Cheapflights users on 4/17. 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 6/14:12 pm
MBJ
- PDX
2 stops19h 35m
United Airlines
Mon 6/810:52 pm
PDX
- MBJ
1 stop10h 51m
United Airlines
Deal found 4/17![United Airlines logo]()
$563
This Delta deal was found by Cheapflights users on 4/14. 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.
Fri 5/227:35 pm
SDQ
- PDX
1 stop19h 11m
Delta
Mon 6/811:15 pm
PDX
- SDQ
2 stops15h 49m
Delta
Deal found 4/14![Delta logo]()
$625
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:35 pm
SDQ
- PDX
1 stop19h 11m
Delta
Wed 6/1010:35 pm
PDX
- SDQ
1 stop16h 29m
Delta
Deal found 4/17![Delta logo]()
$625
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Thu 4/301:40 pm
SJU
- PDX
1 stop12h 14m
United Airlines
Sun 5/38:04 am
PDX
- SJU
1 stop10h 20m
United Airlines
Deal found 4/15![United Airlines logo]()
$586
This eDestinos deal was found by Cheapflights users on 4/16. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/123:39 pm
PUJ
- PDX
2 stops28h 45m
Frontier
Sat 7/1812:26 pm
PDX
- PUJ
2 stops23h 03m
Frontier
Deal found 4/16![Frontier logo]()
$825
This American Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/254:11 pm
PUJ
- PDX
1 stop10h 48m
American Airlines
Sun 7/1211:43 pm
PDX
- PUJ
1 stop13h 21m
American Airlines
Deal found 4/18![American Airlines logo]()
$893
This United Airlines deal was found by Cheapflights users on 4/16. 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 5/612:15 am
BQN
- PDX
2 stops17h 48m
United Airlines
Sun 5/107:05 pm
PDX
- BQN
2 stops25h 04m
United Airlines
Deal found 4/16![United Airlines logo]()
$780
This Delta deal was found by Cheapflights users on 4/14. 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 5/211:05 pm
PUJ
- PDX
1 stop11h 41m
Delta
Fri 5/2911:12 pm
PDX
- PUJ
1 stop10h 46m
Delta
Deal found 4/14![Delta logo]()
$886
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/141:32 pm
STI
- PDX
2 stops23h 48m
American Airlines
Thu 5/215:05 am
PDX
- STI
2 stops13h 08m
American Airlines
Deal found 4/14![American Airlines logo]()
$976
This United Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:50 pm
PUJ
- PDX
2 stops28h 23m
United Airlines
Sun 7/1211:40 pm
PDX
- PUJ
1 stop11h 47m
United Airlines
Deal found 4/18![United Airlines logo]()
$836
This deal was found by Cheapflights users on 4/14. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/181:25 pm
PUJ
- PDX
1 stop12h 29m
United Airlines
Mon 6/111:40 pm
PDX
- PUJ
1 stop11h 47m
United Airlines
Deal found 4/14![United Airlines logo]()
$887
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:07 pm
STI
- PDX
2 stops25h 36m
United Airlines
Sun 5/311:55 pm
PDX
- STI
2 stops12h 17m
United Airlines
Deal found 4/16![United Airlines logo]()
$924
This deal was found by Cheapflights users on 4/15. 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.
Thu 5/211:25 pm
PUJ
- PDX
1 stop12h 30m
United Airlines
Wed 6/35:00 am
PDX
- PUJ
1 stop9h 35m
United Airlines
Deal found 4/15![United Airlines logo]()
$929
This deal was found by Cheapflights users on 4/14. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/201:25 pm
PUJ
- PDX
1 stop12h 29m
United Airlines
Fri 5/2910:52 pm
PDX
- PUJ
1 stop12h 56m
United Airlines
Deal found 4/14![United Airlines logo]()
$933
This deal was found by Cheapflights users on 4/14. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/221:25 pm
PUJ
- PDX
1 stop12h 30m
United Airlines
Fri 5/2910:52 pm
PDX
- PUJ
1 stop12h 56m
United Airlines
Deal found 4/14![United Airlines logo]()
$982
This United Airlines deal was found by Cheapflights users on 4/14. 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 8/1810:48 am
CPX
- PDX
2 stops31h 42m
United Airlines
Wed 8/1911:15 pm
PDX
- CPX
2 stops15h 06m
United Airlines
Deal found 4/14![United Airlines logo]()
$1,006
Last-minute flights from Caribbean to PortlandDiscover last-minute flight deals from Caribbean to Portland. Data last updated April 19, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to Portland. Data last updated April 19, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1910:17 am
MBJ
- PDX
1 stop12h 46m
American Airlines
Mon 4/2010:28 pm
PDX
- MBJ
1 stop11h 23m
American Airlines
Deal found 4/19![American Airlines logo]()
$545
This United Airlines deal was found by Cheapflights users on 4/13. 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.
Fri 5/12:55 pm
SJU
- PDX
1 stop11h 04m
United Airlines
Tue 5/57:45 pm
PDX
- SJU
2 stops16h 57m
United Airlines
Deal found 4/13![United Airlines logo]()
$586
This United Airlines deal was found by Cheapflights users on 4/17. 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 5/612:15 am
BQN
- PDX
2 stops19h 18m
United Airlines
Sun 5/105:00 am
PDX
- BQN
2 stops15h 09m
United Airlines
Deal found 4/17![United Airlines logo]()
$693
This Delta deal was found by Cheapflights users on 4/16. 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.
Thu 5/72:35 pm
SJU
- PDX
2 stops12h 09m
Delta
Tue 5/125:30 am
PDX
- SJU
2 stops15h 05m
Delta
Deal found 4/16![Delta logo]()
$496
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Thu 5/76:00 am
SDQ
- PDX
2 stops18h 09m
United Airlines
Sun 5/1010:15 pm
PDX
- SDQ
1 stop10h 40m
United Airlines
Deal found 4/15![United Airlines logo]()
$648
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/105:45 am
SJU
- PDX
1 stop21h 08m
American Airlines
Fri 5/151:09 pm
PDX
- SJU
2 stops12h 23m
American Airlines
Deal found 4/14![American Airlines logo]()
$530
This United Airlines deal was found by Cheapflights users on 4/14. 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.
Sun 5/102:55 pm
SJU
- PDX
1 stop11h 04m
United Airlines
Thu 5/1410:15 pm
PDX
- SJU
1 stop12h 30m
United Airlines
Deal found 4/14![United Airlines logo]()
$566
This American Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/223:39 pm
SJU
- PDX
1 stop11h 20m
American Airlines
Wed 5/275:49 am
PDX
- SJU
1 stop13h 56m
American Airlines
Deal found 4/18![American Airlines logo]()
$535
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:35 pm
SDQ
- PDX
1 stop19h 11m
Delta
Wed 6/1010:35 pm
PDX
- SDQ
1 stop16h 29m
Delta
Deal found 4/17![Delta logo]()
$625
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/247:00 am
SJU
- PDX
1 stop19h 59m
American Airlines
Tue 6/26:37 am
PDX
- SJU
1 stop18h 48m
American Airlines
Deal found 4/14![American Airlines logo]()
$542
This eDestinos deal was found by Cheapflights users on 4/16. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/249:00 am
SJU
- PDX
2 stops51h 49m
Multiple Airlines
Tue 6/25:46 pm
PDX
- SJU
3 stops33h 38m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$580
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/304:33 pm
MBJ
- PDX
2 stops19h 47m
United Airlines
Sat 6/611:59 pm
PDX
- MBJ
1 stop13h 27m
United Airlines
Deal found 4/15![United Airlines logo]()
$353
One-way flights from Caribbean to PortlandSearch for one-way flight options from Caribbean to Portland. Find affordable one-way fares based on user searches. Data last updated April 19, 2026.
Search for one-way flight options from Caribbean to Portland. Find affordable one-way fares based on user searches. Data last updated April 19, 2026.
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/142:40 pm
MBJ
- PDX
1 stop10h 19m
United Airlines
Deal found 4/16![United Airlines logo]()
$224
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/1410:17 am
MBJ
- PDX
2 stops14h 30m
American Airlines
Deal found 4/14![American Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 4/17. 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 5/212:37 pm
SJU
- PDX
3 stops48h 13m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$258
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/106:45 am
SJU
- PDX
1 stop20h 09m
American Airlines
Deal found 4/14![American Airlines logo]()
$265
This American Airlines deal was found by Cheapflights users on 4/17. 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.
Thu 5/217:00 am
SJU
- PDX
1 stop19h 59m
American Airlines
Deal found 4/17![American Airlines logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/188:00 am
SJU
- PDX
3 stops41h 43m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/191:36 pm
MBJ
- PDX
3 stops46h 44m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/191:16 pm
MBJ
- PDX
2 stops47h 04m
Frontier
Deal found 4/18![Frontier logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 6/257:43 pm
SJU
- PDX
2 stops48h 14m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$295
This eDestinos deal was found by Cheapflights users on 4/15. 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.
Sat 6/135:15 pm
SJU
- PDX
2 stops45h 26m
Frontier
Deal found 4/15![Frontier logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
Sun 6/2812:19 pm
SJU
- PDX
3 stops55h 16m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Fri 5/227:10 pm
SDQ
- PDX
3 stops45h 44m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$323
Find flight deals from Caribbean to Portland
Keep the following information in mind while searching for Caribbean to Portland flight deals. Data was last updated April 19, 2026.
Round-trip from | $353 (United Airlines) |
|---|---|
One-way from | $223 (United Airlines) |
Popular in | June |
Cheapest in | February |
Average price | $541 |
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean to Portland 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 April 19, 2026.
Use the filters below to find and compare flights from Caribbean to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Montego BayPortland
MBJ - PDX
MBJPDX
Montego Bay Sangster Intl
Sat 5/30
4:33 pm-10:20 am
2 stops19h 47m
Portland
Sat 6/6
1:14 pm-3:26 pm
2 stops24h 12m
$353
Montego BayPortland
MBJ - PDX
MBJPDX
Montego Bay Sangster Intl
Tue 7/14
2:23 pm-11:57 pm
1 stop11h 34m
Portland
Sat 8/1
10:57 pm-1:23 pm
1 stop12h 26m
$356
Montego BayPortland
MBJ - PDX
MBJPDX
Montego Bay Sangster Intl
Tue 6/2
2:40 pm-9:39 am
2 stops20h 59m
Portland
Tue 6/9
11:30 pm-3:10 pm
1 stop13h 40m
$426
Montego BayPortland
MBJ - PDX
MBJPDX
Montego Bay Sangster Intl
Tue 7/14
4:12 pm-12:07 pm
3 stops21h 55m
Portland
Sat 8/1
11:30 pm-3:10 pm
1 stop13h 40m
$427
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Thu 5/7
2:35 pm-11:44 pm
2 stops12h 09m
Portland
Tue 5/12
7:00 am-11:35 pm
1 stop13h 35m
$496
Montego BayPortland
MBJ - PDX
MBJPDX
Montego Bay Sangster Intl
Mon 6/1
4:12 pm-9:47 am
2 stops19h 35m
Portland
Mon 6/8
10:52 pm-11:43 am
1 stop10h 51m
$563
Montego BayPortland
MBJ - PDX
MBJPDX
Montego Bay Sangster Intl
Mon 6/1
5:17 pm-12:44 pm
2 stops21h 27m
Portland
Mon 6/8
11:43 pm-1:31 pm
2 stops11h 48m
$574
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Thu 5/7
6:15 am-6:06 pm
2 stops14h 51m
Portland
Sat 5/16
5:30 am-11:35 pm
2 stops15h 05m
$576
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Thu 4/30
1:40 pm-10:54 pm
1 stop12h 14m
Portland
Sun 5/3
8:04 am-9:24 pm
1 stop10h 20m
$586
Santo DomingoPortland
SDQ - PDX
SDQPDX
Santo Domingo Las Americas
Fri 5/22
7:35 pm-11:46 am
1 stop19h 11m
Portland
Mon 6/8
11:15 pm-6:04 pm
2 stops15h 49m
$625
Showing 1-10 of 56 resultsSorted by cheapest first
Best time to book a flight from Caribbean to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Caribbean with our price prediction graph.
MBJ-PDX
SJU-PDX
PUJ-PDX
SDQ-PDX
BQN-PDX
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 Caribbean to Portland
0CB-PDX
MBJ-PDX
SJU-PDX
PUJ-PDX
SDQ-PDX
What is the cheapest month to book a flight from Caribbean to Portland?
Currently, June is the cheapest month in which you can book a flight from Caribbean to Portland (average of $185). Flying from Caribbean to Portland in January is currently the most expensive (average of $447). 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 Portland
Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated April 19, 2026.
Read through reviews of airlines operating flights from Caribbean to Portland, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.8
Comfort
7.9
Boarding
8.1
Overall
7.9
Food
7.2
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Comfort
7.9
Boarding
8.1
Overall
7.9
Food
7.2
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Comfort
7.9
Boarding
8.1
Overall
7.9
Food
7.2
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Comfort
7.9
Boarding
8.1
Overall
7.9
Food
7.2
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Related info for your journey
Find useful and relevant information for your journey from Caribbean to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsBeaverton
Seaside
Vancouver
Lincoln City
Longview
Lake Oswego
Hillsboro
Clackamas
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Wilsonville
Depoe Bay
Stevenson
Tillamook
Astoria
Pacific City
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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Portland flight routes
Alternative routes for Caribbean to Portland
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Portland by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Caribbean to Portland by cabin class
Find flights from Caribbean to Portland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Caribbean and Portland flights
Browse other Caribbean and Portland flight options. Last updated on April 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Portland
Explore flights to Portland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 19, 2026.
Top 3 airlines flying from Caribbean to Portland
Discover the top 3 airlines that operate flights from Caribbean to Portland. 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 April 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$184 | Average$522 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$406 | Average$567 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$419 | Average$550 | FlexibilityNo cancel fee | On-time71% |