$200+ 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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Aug 25 — Sep 11
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
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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 July 26, 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 July 26, 2026.
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/282:52 pm
MBJ
- PDX
2 stops22h 02m
American Airlines
Sat 9/1211:08 pm
PDX
- MBJ
2 stops11h 45m
American Airlines
Deal found 7/26![American Airlines logo]()
$397
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/105:30 am
SJU
- PDX
1 stop12h 30m
Southwest
Mon 9/1410:45 pm
PDX
- SJU
1 stop11h 05m
Southwest
Deal found 7/24![Southwest logo]()
$436
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 10/1412:13 pm
SJU
- PDX
2 stops14h 46m
American Airlines
Mon 10/196:00 pm
PDX
- SJU
2 stops12h 46m
American Airlines
Deal found 7/22![American Airlines logo]()
$445
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/221:45 pm
SJU
- PDX
2 stops12h 30m
Southwest
Tue 9/297:05 am
PDX
- SJU
2 stops12h 00m
Southwest
Deal found 7/24![Southwest logo]()
$451
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:52 pm
MBJ
- PDX
2 stops29h 04m
United Airlines
Wed 9/167:07 pm
PDX
- MBJ
2 stops38h 36m
United Airlines
Deal found 7/26![United Airlines logo]()
$457
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 am
SJU
- PDX
2 stops13h 51m
American Airlines
Thu 9/1011:08 pm
PDX
- SJU
2 stops13h 32m
American Airlines
Deal found 7/26![American Airlines logo]()
$461
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 9/712:55 am
SJU
- PDX
1 stop20h 05m
American Airlines
Wed 9/239:44 pm
PDX
- SJU
1 stop14h 06m
American Airlines
Deal found 7/22![American Airlines logo]()
$466
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:15 pm
MBJ
- PDX
2 stops11h 25m
Southwest
Sat 9/1210:45 pm
PDX
- MBJ
1 stop13h 40m
Southwest
Deal found 7/26![Southwest logo]()
$467
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/171:30 am
SJU
- PDX
1 stop13h 30m
American Airlines
Tue 1/58:00 am
PDX
- SJU
1 stop11h 00m
American Airlines
Deal found 7/22![American Airlines logo]()
$470
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 9/222:22 pm
SJU
- PDX
1 stop12h 06m
American Airlines
Wed 9/309:44 pm
PDX
- SJU
1 stop14h 06m
American Airlines
Deal found 7/23![American Airlines logo]()
$476
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 9/2012:15 am
BQN
- PDX
1 stop12h 35m
United Airlines
Wed 9/305:00 am
PDX
- BQN
2 stops15h 09m
United Airlines
Deal found 7/22![United Airlines logo]()
$486
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:20 am
SJU
- PDX
2 stops16h 09m
American Airlines
Mon 11/211:09 pm
PDX
- SJU
2 stops11h 54m
American Airlines
Deal found 7/26![American Airlines logo]()
$486
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 July 26, 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 July 26, 2026.
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/285:08 pm
MBJ
- PDX
2 stops19h 46m
American Airlines
Sat 9/1211:08 pm
PDX
- MBJ
2 stops11h 45m
American Airlines
Deal found 7/24![American Airlines logo]()
$397
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:55 pm
SJU
- PDX
2 stops17h 45m
Southwest
Tue 8/255:50 am
PDX
- SJU
2 stops12h 15m
Southwest
Deal found 7/23![Southwest logo]()
$436
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/191:00 am
SJU
- PDX
1 stop11h 50m
United Airlines
Tue 8/2511:02 pm
PDX
- SJU
1 stop12h 42m
United Airlines
Deal found 7/23![United Airlines logo]()
$436
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 9/187:30 am
SJU
- PDX
2 stops17h 32m
Delta
Tue 9/228:44 pm
PDX
- SJU
2 stops12h 19m
Delta
Deal found 7/22![Delta logo]()
$466
This Mytrip deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/284:45 pm
MBJ
- PDX
2 stops23h 05m
Multiple Airlines
Sat 9/123:30 pm
PDX
- MBJ
2 stops17h 50m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$812
This FlightHub deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:30 pm
MBJ
- PDX
2 stops23h 01m
Air Canada
Sat 9/1210:10 am
PDX
- MBJ
2 stops23h 10m
Air Canada
Deal found 7/24![Air Canada logo]()
$843
This American Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 9/102:22 pm
SJU
- PDX
1 stop12h 06m
American Airlines
Mon 9/2111:06 pm
PDX
- SJU
1 stop12h 44m
American Airlines
Deal found 7/21![American Airlines logo]()
$436
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:55 pm
SJU
- PDX
2 stops17h 45m
Southwest
Fri 9/47:00 pm
PDX
- SJU
2 stops12h 50m
Southwest
Deal found 7/24![Southwest logo]()
$466
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 10/157:15 am
SJU
- PDX
2 stops15h 43m
Delta
Mon 10/1910:15 pm
PDX
- SJU
1 stop10h 50m
Delta
Deal found 7/26![Delta logo]()
$466
This American Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:55 am
SJU
- PDX
1 stop20h 05m
American Airlines
Sat 8/2911:34 pm
PDX
- SJU
2 stops14h 23m
American Airlines
Deal found 7/21![American Airlines logo]()
$436
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 9/2012:15 am
BQN
- PDX
2 stops15h 59m
United Airlines
Wed 9/305:00 am
PDX
- BQN
2 stops15h 09m
United Airlines
Deal found 7/22![United Airlines logo]()
$486
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:30 am
SJU
- PDX
2 stops13h 05m
Southwest
Sun 9/67:30 pm
PDX
- SJU
2 stops10h 40m
Southwest
Deal found 7/21![Southwest logo]()
$486
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/171:00 am
SJU
- PDX
1 stop11h 50m
United Airlines
Tue 8/257:15 pm
PDX
- SJU
2 stops16h 29m
United Airlines
Deal found 7/22![United Airlines logo]()
$526
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:52 pm
MBJ
- PDX
2 stops22h 37m
United Airlines
Wed 9/1611:09 pm
PDX
- MBJ
1 stop10h 34m
United Airlines
Deal found 7/26![United Airlines logo]()
$578
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 10/83:03 pm
PUJ
- PDX
1 stop24h 19m
American Airlines
Fri 10/169:44 pm
PDX
- PUJ
1 stop9h 55m
American Airlines
Deal found 7/26![American Airlines logo]()
$635
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 10/83:35 pm
PUJ
- PDX
2 stops33h 46m
United Airlines
Fri 10/1611:30 pm
PDX
- PUJ
1 stop11h 57m
United Airlines
Deal found 7/26![United Airlines logo]()
$614
This Mytrip deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 10/87:10 pm
PUJ
- PDX
2 stops25h 07m
Multiple Airlines
Fri 10/163:30 pm
PDX
- PUJ
3 stops22h 40m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$897
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/2812:15 am
BQN
- PDX
2 stops14h 13m
United Airlines
Tue 9/15:00 am
PDX
- BQN
2 stops15h 09m
United Airlines
Deal found 7/24![United Airlines logo]()
$638
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/2410:27 am
SDQ
- PDX
2 stops16h 32m
American Airlines
Mon 8/3111:34 pm
PDX
- SDQ
2 stops16h 10m
American Airlines
Deal found 7/22![American Airlines logo]()
$705
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 9/69:13 am
KIN
- PDX
1 stop14h 31m
Delta
Sun 9/137:00 am
PDX
- KIN
2 stops11h 10m
Delta
Deal found 7/22![Delta logo]()
$884
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/14:24 pm
SDQ
- PDX
2 stops22h 10m
American Airlines
Tue 9/1511:08 pm
PDX
- SDQ
2 stops13h 09m
American Airlines
Deal found 7/24![American Airlines logo]()
$705
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 1/226:00 am
SDQ
- PDX
1 stop19h 21m
United Airlines
Sun 1/2410:56 pm
PDX
- SDQ
1 stop10h 45m
United Airlines
Deal found 7/23![United Airlines logo]()
$701
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:30 am
SDQ
- PDX
2 stops14h 00m
American Airlines
Fri 9/2511:06 pm
PDX
- SDQ
2 stops16h 28m
American Airlines
Deal found 7/23![American Airlines logo]()
$705
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/89:13 am
KIN
- PDX
1 stop14h 31m
Delta
Fri 8/2812:35 am
PDX
- KIN
2 stops17h 38m
Delta
Deal found 7/26![Delta logo]()
$1,021
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:10 pm
SDQ
- PDX
1 stop11h 53m
United Airlines
Fri 9/254:07 pm
PDX
- SDQ
2 stops19h 03m
United Airlines
Deal found 7/23![United Airlines logo]()
$701
This Mytrip deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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.
Wed 9/912:30 pm
MBJ
- PDX
3 stops23h 01m
Multiple Airlines
Wed 9/162:30 pm
PDX
- MBJ
3 stops18h 50m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$1,171
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 9/2012:15 am
BQN
- PDX
1 stop12h 35m
United Airlines
Tue 9/2910:33 pm
PDX
- BQN
1 stop21h 36m
United Airlines
Deal found 7/22![United Airlines logo]()
$732
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/92:26 pm
MBJ
- PDX
1 stop9h 21m
Delta
Wed 9/1610:57 pm
PDX
- MBJ
1 stop14h 38m
Delta
Deal found 7/26![Delta logo]()
$1,187
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/85:24 pm
KIN
- PDX
2 stops20h 10m
American Airlines
Sat 8/2911:34 pm
PDX
- KIN
2 stops15h 08m
American Airlines
Deal found 7/24![American Airlines logo]()
$942
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/72:40 pm
MBJ
- PDX
1 stop10h 08m
United Airlines
Sat 8/811:29 pm
PDX
- MBJ
1 stop13h 41m
United Airlines
Deal found 7/23![United Airlines logo]()
$885
Last-minute flights from Caribbean to PortlandDiscover last-minute flight deals from Caribbean to Portland. Data last updated July 26, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to Portland. Data last updated July 26, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/116:00 am
SJU
- PDX
2 stops13h 51m
American Airlines
Mon 8/1711:34 pm
PDX
- SJU
2 stops12h 17m
American Airlines
Deal found 7/23![American Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/111:00 am
SJU
- PDX
1 stop11h 50m
United Airlines
Mon 8/177:15 pm
PDX
- SJU
2 stops17h 27m
United Airlines
Deal found 7/22![United Airlines logo]()
$580
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/171:00 am
SJU
- PDX
1 stop11h 50m
United Airlines
Tue 8/257:15 pm
PDX
- SJU
2 stops16h 29m
United Airlines
Deal found 7/22![United Airlines logo]()
$526
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/176:00 am
SJU
- PDX
2 stops13h 51m
American Airlines
Sun 8/2311:34 pm
PDX
- SJU
2 stops13h 37m
American Airlines
Deal found 7/24![American Airlines logo]()
$566
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:55 am
SJU
- PDX
1 stop20h 10m
American Airlines
Fri 9/411:34 pm
PDX
- SJU
1 stop20h 20m
American Airlines
Deal found 7/24![American Airlines logo]()
$579
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:55 am
SJU
- PDX
1 stop20h 05m
American Airlines
Sat 8/2911:34 pm
PDX
- SJU
2 stops12h 19m
American Airlines
Deal found 7/26![American Airlines logo]()
$436
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:55 pm
SJU
- PDX
2 stops17h 45m
Southwest
Fri 9/47:00 pm
PDX
- SJU
2 stops12h 50m
Southwest
Deal found 7/24![Southwest logo]()
$466
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/2412:55 am
SJU
- PDX
1 stop20h 05m
American Airlines
Wed 9/25:59 am
PDX
- SJU
1 stop14h 16m
American Airlines
Deal found 7/26![American Airlines logo]()
$506
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/2410:27 am
SDQ
- PDX
2 stops16h 32m
American Airlines
Mon 8/3111:34 pm
PDX
- SDQ
2 stops16h 10m
American Airlines
Deal found 7/22![American Airlines logo]()
$705
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/282:52 pm
MBJ
- PDX
2 stops22h 02m
American Airlines
Sat 9/1211:08 pm
PDX
- MBJ
2 stops11h 45m
American Airlines
Deal found 7/26![American Airlines logo]()
$397
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:15 pm
MBJ
- PDX
2 stops11h 25m
Southwest
Sat 9/1210:45 pm
PDX
- MBJ
1 stop13h 40m
Southwest
Deal found 7/26![Southwest logo]()
$467
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/2812:15 am
BQN
- PDX
2 stops14h 13m
United Airlines
Tue 9/15:00 am
PDX
- BQN
2 stops15h 09m
United Airlines
Deal found 7/24![United Airlines logo]()
$638
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 July 26, 2026.
Search for one-way flight options from Caribbean to Portland. Find affordable one-way fares based on user searches. Data last updated July 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:15 pm
SJU
- PDX
2 stops26h 56m
Frontier
Deal found 7/24![Frontier logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/118:37 pm
SJU
- PDX
2 stops48h 27m
Frontier
Deal found 7/22![Frontier logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/113:10 am
SJU
- PDX
2 stops41h 54m
Frontier
Deal found 7/22![Frontier logo]()
$210
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:55 am
SJU
- PDX
1 stop20h 05m
American Airlines
Deal found 7/26![American Airlines logo]()
$218
This United Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:00 am
SJU
- PDX
1 stop11h 50m
United Airlines
Deal found 7/25![United Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/1912:11 pm
SJU
- PDX
2 stops27h 41m
Frontier
Deal found 7/24![Frontier logo]()
$229
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 12/33:35 pm
SJU
- PDX
1 stop10h 51m
Delta
Deal found 7/25![Delta logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/187:30 am
SJU
- PDX
2 stops36h 41m
Frontier
Deal found 7/24![Frontier logo]()
$234
This Trip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1010:48 pm
SJU
- PDX
2 stops20h 43m
Frontier
Deal found 7/24![Frontier logo]()
$237
This Trip.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/133:10 am
SJU
- PDX
2 stops35h 25m
Frontier
Deal found 7/26![Frontier logo]()
$242
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 12/142:05 pm
SJU
- PDX
2 stops13h 54m
American Airlines
Deal found 7/26![American Airlines logo]()
$243
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/1712:05 pm
MBJ
- PDX
1 stop13h 18m
American Airlines
Deal found 7/26![American Airlines logo]()
$254
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 July 26, 2026.
Round-trip from | $397 (American Airlines) |
|---|---|
One-way from | $200 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $590 |
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 July 26, 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
Fri 8/28
5:08 pm-10:54 am
2 stops19h 46m
Portland
Sat 9/12
11:08 pm-12:53 pm
2 stops11h 45m
$397
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Thu 8/20
8:55 pm-11:40 am
2 stops17h 45m
Portland
Tue 8/25
5:50 am-9:05 pm
2 stops12h 15m
$436
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Wed 8/19
1:00 am-9:50 am
1 stop11h 50m
Portland
Tue 8/25
11:02 pm-2:44 pm
1 stop12h 42m
$436
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Thu 9/10
2:22 pm-11:28 pm
1 stop12h 06m
Portland
Mon 9/21
11:06 pm-2:50 pm
1 stop12h 44m
$436
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Thu 8/20
12:55 am-6:00 pm
1 stop20h 05m
Portland
Sat 8/29
11:34 pm-4:57 pm
2 stops14h 23m
$436
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Fri 9/18
7:30 am-10:02 pm
2 stops17h 32m
Portland
Tue 9/22
8:44 pm-12:03 pm
2 stops12h 19m
$466
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Thu 8/20
8:55 pm-11:40 am
2 stops17h 45m
Portland
Fri 9/4
7:00 pm-10:50 am
2 stops12h 50m
$466
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Thu 10/15
7:15 am-7:58 pm
2 stops15h 43m
Portland
Mon 10/19
10:15 pm-12:05 pm
1 stop10h 50m
$466
AguadillaPortland
BQN - PDX
BQNPDX
Aguadilla Borinquen
Sun 9/20
12:15 am-1:14 pm
2 stops15h 59m
Portland
Wed 9/30
5:00 am-11:09 pm
2 stops15h 09m
$486
Quickest round-trip
San JuanPortland
SJU - PDX
SJUPDX
San Juan Luis Munoz Marin Intl
Fri 9/4
6:30 am-4:35 pm
2 stops13h 05m
Portland
Sun 9/6
7:30 pm-9:10 am
2 stops10h 40m
$486
Showing 1-10 of 57 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
BQN-PDX
PUJ-PDX
SDQ-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
BQN-PDX
PUJ-PDX
What is the cheapest month to book a flight from Caribbean to Portland?
Currently, January is the cheapest month in which you can book a flight from Caribbean to Portland (average of $483). Flying from Caribbean to Portland in June is currently the most expensive (average of $686). 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 July 26, 2026.
Read through reviews of airlines operating flights from Caribbean to Portland, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.1
Food
6.6
Comfort
7.3
Entertainment
7.1
Overall
7.4
Boarding
7.7
Reviews
1 / 20
6.0
GoodROHIT,Jun 2026
IND - EWR
Crew
8.1
Food
6.6
Comfort
7.3
Entertainment
7.1
Overall
7.4
Boarding
7.7
Reviews
1 / 20
6.0
GoodROHIT,Jun 2026
IND - EWR
Crew
8.1
Food
6.6
Comfort
7.3
Entertainment
7.1
Overall
7.4
Boarding
7.7
Reviews
1 / 20
6.0
GoodROHIT,Jun 2026
IND - EWR
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
Lincoln City
Vancouver
Longview
Lake Oswego
Hillsboro
Kelso
Clackamas
Troutdale
Cannon Beach
Long Beach
McMinnville
The Dalles
Wilsonville
Depoe Bay
Stevenson
Tillamook
Astoria
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 July 26, 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 July 26, 2026.
Top 2 airlines flying from Caribbean to Portland
Discover the top 2 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 July 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$419 | Average$543 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$588 | FlexibilityNo cancel fee | On-time69% |