$144+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Mar 11 — Mar 181
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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from 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 February 9, 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 February 9, 2026.
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 5/125:05 am
SJU
- PDX
2 stops18h 55m
Southwest
Sat 5/167:40 pm
PDX
- SJU
2 stops10h 25m
Southwest
Deal found 2/6![Southwest logo]()
$408
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 4/307:30 am
SJU
- PDX
2 stops15h 35m
Delta
Sat 5/307:00 am
PDX
- SJU
1 stop10h 06m
Delta
Deal found 2/6![Delta logo]()
$440
This American Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/83:00 pm
SJU
- PDX
1 stop11h 22m
American Airlines
Wed 9/235:56 am
PDX
- SJU
2 stops15h 03m
American Airlines
Deal found 2/6![American Airlines logo]()
$449
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1810:32 am
SJU
- PDX
2 stops13h 42m
American Airlines
Tue 8/255:38 am
PDX
- SJU
2 stops15h 02m
American Airlines
Deal found 2/9![American Airlines logo]()
$478
This American Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:39 am
SJU
- PDX
1 stop20h 26m
American Airlines
Mon 7/2010:30 pm
PDX
- SJU
1 stop12h 05m
American Airlines
Deal found 2/8![American Airlines logo]()
$487
This American Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 5/1111:59 pm
SJU
- PDX
1 stop15h 59m
American Airlines
Fri 5/1511:47 pm
PDX
- SJU
1 stop11h 32m
American Airlines
Deal found 2/8![American Airlines logo]()
$493
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 4/291:25 pm
SJU
- PDX
1 stop11h 51m
Delta
Sat 5/305:17 am
PDX
- SJU
2 stops15h 26m
Delta
Deal found 2/6![Delta logo]()
$503
This American Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 2/247:33 am
SJU
- PDX
2 stops13h 40m
American Airlines
Sat 2/2811:35 pm
PDX
- SJU
2 stops12h 45m
American Airlines
Deal found 2/6![American Airlines logo]()
$513
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 4/15:55 am
SJU
- PDX
2 stops13h 55m
Southwest
Wed 4/86:30 am
PDX
- SJU
2 stops13h 10m
Southwest
Deal found 2/6![Southwest logo]()
$516
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:05 am
SDQ
- PDX
1 stop19h 11m
Delta
Fri 5/111:06 pm
PDX
- SDQ
2 stops16h 28m
Delta
Deal found 2/6![Delta logo]()
$517
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/241:10 pm
SDQ
- PDX
2 stops23h 38m
United Airlines
Sun 5/310:55 pm
PDX
- SDQ
2 stops12h 15m
United Airlines
Deal found 2/9![United Airlines logo]()
$520
This American Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/231:14 pm
MBJ
- PDX
1 stop13h 01m
American Airlines
Mon 3/309:44 pm
PDX
- MBJ
1 stop10h 37m
American Airlines
Deal found 2/6![American Airlines logo]()
$524
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 February 9, 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 February 9, 2026.
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 4/302:03 pm
SJU
- PDX
1 stop10h 53m
Delta
Sun 5/318:06 pm
PDX
- SJU
2 stops17h 17m
Delta
Deal found 2/6![Delta logo]()
$440
This American Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 4/216:45 am
SJU
- PDX
1 stop19h 04m
American Airlines
Sat 4/2511:40 pm
PDX
- SJU
1 stop12h 02m
American Airlines
Deal found 2/7![American Airlines logo]()
$440
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/241:10 pm
SDQ
- PDX
2 stops31h 35m
United Airlines
Sun 5/310:16 pm
PDX
- SDQ
1 stop10h 39m
United Airlines
Deal found 2/9![United Airlines logo]()
$520
This Kiwi.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/75:47 am
PUJ
- PDX
1 stop15h 03m
Multiple Airlines
Sat 3/77:57 pm
PDX
- PUJ
2 stops16h 29m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$715
This Faresmojo deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/1512:09 am
BQN
- PDX
2 stops16h 35m
Sun Country Air
Sun 3/295:30 am
PDX
- BQN
2 stops14h 39m
Sun Country Air
Deal found 2/9![Sun Country Air logo]()
$750
This Gotogate deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/264:45 pm
PUJ
- PDX
2 stops24h 55m
Air Canada
Thu 4/27:05 pm
PDX
- PUJ
2 stops22h 35m
Air Canada
Deal found 2/9![Air Canada logo]()
$786
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 4/301:25 pm
SJU
- PDX
1 stop11h 51m
Delta
Sat 5/307:00 am
PDX
- SJU
1 stop13h 43m
Delta
Deal found 2/6![Delta logo]()
$440
This American Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 4/301:31 pm
SJU
- PDX
2 stops13h 26m
American Airlines
Tue 5/511:47 pm
PDX
- SJU
2 stops12h 05m
American Airlines
Deal found 2/8![American Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 4/37:11 am
SJU
- PDX
1 stop20h 11m
American Airlines
Mon 4/611:30 pm
PDX
- SJU
1 stop11h 50m
American Airlines
Deal found 2/7![American Airlines logo]()
$440
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 4/307:30 am
SJU
- PDX
2 stops15h 35m
Delta
Fri 5/295:51 pm
PDX
- SJU
2 stops16h 27m
Delta
Deal found 2/6![Delta logo]()
$440
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/273:20 pm
SDQ
- PDX
2 stops21h 28m
United Airlines
Sun 5/310:55 pm
PDX
- SDQ
2 stops12h 15m
United Airlines
Deal found 2/9![United Airlines logo]()
$520
This United Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/232:20 pm
MBJ
- PDX
2 stops30h 27m
United Airlines
Mon 3/302:10 pm
PDX
- MBJ
2 stops23h 00m
United Airlines
Deal found 2/6![United Airlines logo]()
$562
This Delta deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 5/67:59 pm
SDQ
- PDX
1 stop18h 47m
Delta
Wed 5/138:19 pm
PDX
- SDQ
2 stops18h 59m
Delta
Deal found 2/5![Delta logo]()
$517
This American Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/2310:07 am
MBJ
- PDX
1 stop15h 37m
American Airlines
Mon 3/305:38 pm
PDX
- MBJ
2 stops13h 29m
American Airlines
Deal found 2/6![American Airlines logo]()
$529
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:05 am
SDQ
- PDX
2 stops18h 27m
Delta
Fri 5/111:15 pm
PDX
- SDQ
2 stops16h 19m
Delta
Deal found 2/6![Delta logo]()
$517
This United Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 4/3012:15 am
BQN
- PDX
2 stops23h 43m
United Airlines
Tue 5/55:00 am
PDX
- BQN
2 stops15h 09m
United Airlines
Deal found 2/6![United Airlines logo]()
$591
This American Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 2/2411:07 am
MBJ
- PDX
1 stop15h 43m
American Airlines
Tue 3/1011:59 pm
PDX
- MBJ
1 stop12h 05m
American Airlines
Deal found 2/6![American Airlines logo]()
$588
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 2/242:00 pm
MBJ
- PDX
2 stops22h 15m
Delta
Tue 3/107:43 pm
PDX
- MBJ
2 stops17h 45m
Delta
Deal found 2/6![Delta logo]()
$588
This Mytrip deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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.
Fri 3/62:55 pm
KIN
- PDX
2 stops30h 35m
Multiple Airlines
Fri 3/133:15 pm
PDX
- KIN
3 stops20h 15m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$869
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/262:28 pm
PUJ
- PDX
2 stops35h 32m
United Airlines
Thu 4/25:00 am
PDX
- PUJ
1 stop9h 35m
United Airlines
Deal found 2/9![United Airlines logo]()
$784
This American Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 4/257:00 am
KIN
- PDX
1 stop18h 53m
American Airlines
Sat 5/210:28 pm
PDX
- KIN
1 stop18h 26m
American Airlines
Deal found 2/6![American Airlines logo]()
$788
This Booking.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2610:55 pm
PUJ
- PDX
3 stops18h 45m
Multiple Airlines
Thu 4/29:50 am
PDX
- PUJ
3 stops31h 50m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$1,093
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 4/259:00 am
KIN
- PDX
1 stop12h 05m
Delta
Sat 5/26:28 am
PDX
- KIN
1 stop11h 32m
Delta
Deal found 2/6![Delta logo]()
$779
This American Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/67:32 am
KIN
- PDX
2 stops16h 12m
American Airlines
Fri 3/1310:53 pm
PDX
- KIN
1 stop18h 19m
American Airlines
Deal found 2/6![American Airlines logo]()
$792
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/69:00 am
KIN
- PDX
2 stops16h 24m
Delta
Fri 3/1311:15 pm
PDX
- KIN
2 stops18h 45m
Delta
Deal found 2/6![Delta logo]()
$779
This Mytrip deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/236:25 pm
MBJ
- PDX
2 stops26h 05m
Multiple Airlines
Mon 3/303:15 pm
PDX
- MBJ
3 stops25h 02m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$1,261
This United Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/72:05 pm
PUJ
- PDX
1 stop11h 05m
United Airlines
Sat 3/711:28 pm
PDX
- PUJ
1 stop10h 51m
United Airlines
Deal found 2/6![United Airlines logo]()
$1,234
This United Airlines deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 3/610:30 am
CPX
- PDX
2 stops16h 29m
United Airlines
Mon 3/97:00 am
PDX
- CPX
2 stops30h 13m
United Airlines
Deal found 2/5![United Airlines logo]()
$1,830
Last-minute flights from Caribbean to PortlandDiscover last-minute flight deals from Caribbean to Portland. Data last updated February 9, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to Portland. Data last updated February 9, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 2/168:00 am
SJU
- PDX
1 stop19h 50m
American Airlines
Sat 2/2111:40 pm
PDX
- SJU
2 stops12h 09m
American Airlines
Deal found 2/7![American Airlines logo]()
$577
This United Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 2/171:09 am
BQN
- PDX
2 stops14h 46m
United Airlines
Tue 2/245:05 am
PDX
- BQN
2 stops14h 52m
United Airlines
Deal found 2/7![United Airlines logo]()
$656
This American Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 2/247:33 am
SJU
- PDX
2 stops13h 40m
American Airlines
Sat 2/2811:35 pm
PDX
- SJU
2 stops12h 45m
American Airlines
Deal found 2/6![American Airlines logo]()
$513
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/243:10 pm
SJU
- PDX
2 stops13h 05m
Delta
Sat 2/287:00 am
PDX
- SJU
1 stop12h 56m
Delta
Deal found 2/8![Delta logo]()
$566
This Delta deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 2/242:00 pm
MBJ
- PDX
2 stops22h 15m
Delta
Tue 3/107:43 pm
PDX
- MBJ
2 stops17h 45m
Delta
Deal found 2/6![Delta logo]()
$588
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/252:05 am
SJU
- PDX
2 stops16h 49m
United Airlines
Mon 3/210:38 pm
PDX
- SJU
1 stop12h 02m
United Airlines
Deal found 2/8![United Airlines logo]()
$593
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/48:30 am
SJU
- PDX
1 stop10h 57m
United Airlines
Sun 3/82:05 pm
PDX
- SJU
1 stop12h 06m
United Airlines
Deal found 2/8![United Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/76:33 am
SJU
- PDX
1 stop21h 44m
American Airlines
Sat 3/149:44 pm
PDX
- SJU
1 stop19h 50m
American Airlines
Deal found 2/8![American Airlines logo]()
$543
This American Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/231:14 pm
MBJ
- PDX
1 stop13h 01m
American Airlines
Mon 3/309:44 pm
PDX
- MBJ
1 stop10h 37m
American Airlines
Deal found 2/6![American Airlines logo]()
$524
This American Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/231:23 pm
SJU
- PDX
1 stop13h 21m
American Airlines
Mon 3/3010:53 pm
PDX
- SJU
1 stop9h 03m
American Airlines
Deal found 2/6![American Airlines logo]()
$544
This United Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/232:20 pm
MBJ
- PDX
2 stops30h 27m
United Airlines
Mon 3/302:10 pm
PDX
- MBJ
2 stops23h 00m
United Airlines
Deal found 2/6![United Airlines logo]()
$562
This American Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/317:40 am
SJU
- PDX
1 stop16h 51m
American Airlines
Tue 4/1411:40 pm
PDX
- SJU
1 stop12h 02m
American Airlines
Deal found 2/7![American Airlines logo]()
$620
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 February 9, 2026.
Search for one-way flight options from Caribbean to Portland. Find affordable one-way fares based on user searches. Data last updated February 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 5/13:18 pm
SJU
- PDX
2 stops23h 24m
Frontier
Deal found 2/7![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 4/303:19 pm
SJU
- PDX
2 stops22h 44m
Frontier
Deal found 2/7![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 5/34:11 pm
SJU
- PDX
2 stops47h 51m
Frontier
Deal found 2/7![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 4/2911:07 am
SJU
- PDX
2 stops27h 50m
Frontier
Deal found 2/7![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/73:59 am
SJU
- PDX
2 stops34h 10m
Frontier
Deal found 2/6![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/79:38 am
PUJ
- PDX
2 stops28h 31m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1011:07 am
SJU
- PDX
3 stops58h 59m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 4/266:00 am
SJU
- PDX
3 stops58h 02m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/103:19 pm
SJU
- PDX
2 stops47h 33m
Frontier
Deal found 2/9![Frontier logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 5/39:49 pm
SJU
- PDX
3 stops42h 13m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$206
This American Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/197:11 am
SJU
- PDX
1 stop19h 33m
American Airlines
Deal found 2/7![American Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 4/2910:53 am
SJU
- PDX
3 stops25h 06m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$222
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 February 9, 2026.
Round-trip from | $408 (Southwest) |
|---|---|
One-way from | $144 (Kiwi.com) |
Popular in | June |
Cheapest in | September |
Average price | $545 |
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 February 9, 2026.
Use the filters below to find and compare flights from Caribbean to Portland that are best for you.
Fly from
Caribbean
Fly to
Portland
Route
Depart
Return
Price
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Thu 4/30
2:03 pm-9:56 pm
1 stop10h 53m
Portland
Sun 5/31
8:06 pm-4:23 pm
2 stops17h 17m
$440
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Tue 4/21
6:45 am-10:49 pm
1 stop19h 04m
Portland
Sat 4/25
11:40 pm-2:42 pm
1 stop12h 02m
$440
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Thu 4/30
1:25 pm-10:16 pm
1 stop11h 51m
Portland
Sat 5/30
7:00 am-11:43 pm
1 stop13h 43m
$440
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Thu 4/30
1:31 pm-11:57 pm
2 stops13h 26m
Portland
Tue 5/5
11:47 pm-2:52 pm
2 stops12h 05m
$440
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Fri 4/3
7:11 am-12:22 am
1 stop20h 11m
Portland
Mon 4/6
11:30 pm-2:20 pm
1 stop11h 50m
$440
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Thu 4/30
7:30 am-8:05 pm
2 stops15h 35m
Portland
Fri 5/29
5:51 pm-1:18 pm
2 stops16h 27m
$440
Santo DomingoPortland
SDQ - PDX
SDQPDX
Santo Domingo Las Americas
Wed 5/6
7:59 pm-11:46 am
1 stop18h 47m
Portland
Wed 5/13
8:19 pm-6:18 pm
2 stops18h 59m
$517
Santo DomingoPortland
SDQ - PDX
SDQPDX
Santo Domingo Las Americas
Tue 4/28
6:05 am-9:32 pm
2 stops18h 27m
Portland
Fri 5/1
11:15 pm-6:34 pm
2 stops16h 19m
$517
Santo DomingoPortland
SDQ - PDX
SDQPDX
Santo Domingo Las Americas
Fri 4/24
1:10 pm-5:45 pm
2 stops31h 35m
Portland
Sun 5/3
10:16 pm-11:55 am
1 stop10h 39m
$520
Santo DomingoPortland
SDQ - PDX
SDQPDX
Santo Domingo Las Americas
Mon 4/27
3:20 pm-9:48 am
2 stops21h 28m
Portland
Sun 5/3
10:55 pm-2:10 pm
2 stops12h 15m
$520
Showing 1-10 of 58 results
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.
SJU-PDX
SDQ-PDX
MBJ-PDX
PUJ-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
SJU-PDX
SDQ-PDX
MBJ-PDX
PUJ-PDX
What is the cheapest month to book a flight from Caribbean to Portland?
Currently, July is the cheapest month in which you can book a flight from Caribbean to Portland (average of $237). Flying from Caribbean to Portland in October is currently the most expensive (average of $481). 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 February 9, 2026.
Read through reviews of airlines operating flights from Caribbean to Portland, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Boarding
8.1
Food
7.0
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 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 locationsVancouver
Seaside
Clackamas
Lincoln City
Longview
Lake Oswego
Beaverton
Hillsboro
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Depoe Bay
Wilsonville
Stevenson
Tillamook
Pacific City
Gresham
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 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 February 9, 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 February 9, 2026.
Caribbean to Portland flights
Consider these flights traveling from Caribbean to Portland.
Top 4 airlines flying from Caribbean to Portland
Discover the top 4 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 February 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$190 | Average$512 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$379 | Average$550 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$406 | Average$575 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$466 | Average$565 | FlexibilityNo cancel fee | On-time63% |