$162+ Cheap flights from Portland (PDX) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
abr. 11 — abr. 181
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Portland to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Portland to Caribbean
Cheapest
Best
Last-minute
One-way
Cheapest flights from Portland to CaribbeanExplore the most affordable flight options available from Portland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on marzo 12, 2026.
Explore the most affordable flight options available from Portland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on marzo 12, 2026.
This American Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
lun. 11/210:45 pm
PDX
- MBJ
1 stop8h 30m
American Airlines
mié. 11/114:05 pm
MBJ
- PDX
1 stop10h 46m
American Airlines
Deal found 3/11![American Airlines logo]()
$392
This United Airlines deal was found by Cheapflights users on 3/8. 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.
mar. 6/910:52 pm
PDX
- MBJ
1 stop10h 51m
United Airlines
mar. 6/164:12 pm
MBJ
- PDX
2 stops19h 27m
United Airlines
Deal found 3/8![United Airlines logo]()
$405
This American Airlines deal was found by Cheapflights users on 3/9. 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.
mar. 5/510:28 pm
PDX
- MBJ
1 stop15h 09m
American Airlines
lun. 5/114:37 pm
MBJ
- PDX
2 stops20h 24m
American Airlines
Deal found 3/9![American Airlines logo]()
$410
This United Airlines deal was found by Cheapflights users on 3/9. 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.
mié. 4/811:15 pm
PDX
- STT
1 stop10h 53m
United Airlines
mié. 4/152:10 pm
STT
- PDX
1 stop11h 24m
United Airlines
Deal found 3/9![United Airlines logo]()
$420
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
lun. 4/275:10 am
PDX
- SJU
2 stops15h 30m
Southwest
jue. 4/302:00 pm
SJU
- PDX
2 stops13h 10m
Southwest
Deal found 3/10![Southwest logo]()
$424
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
lun. 11/210:59 pm
PDX
- MBJ
2 stops12h 30m
United Airlines
mié. 11/112:48 pm
MBJ
- PDX
2 stops21h 52m
United Airlines
Deal found 3/10![United Airlines logo]()
$425
This American Airlines deal was found by Cheapflights users on 3/9. 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.
mié. 4/811:47 pm
PDX
- STT
2 stops13h 28m
American Airlines
mié. 4/1512:25 pm
STT
- PDX
2 stops13h 24m
American Airlines
Deal found 3/9![American Airlines logo]()
$425
This American Airlines deal was found by Cheapflights users on 3/9. 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.
vie. 4/1711:40 pm
PDX
- SJU
1 stop20h 22m
American Airlines
jue. 4/236:45 am
SJU
- PDX
1 stop20h 09m
American Airlines
Deal found 3/9![American Airlines logo]()
$436
This American Airlines deal was found by Cheapflights users on 3/9. 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.
dom. 3/2910:53 pm
PDX
- STT
1 stop12h 53m
American Airlines
dom. 4/51:08 pm
STT
- PDX
1 stop14h 07m
American Airlines
Deal found 3/9![American Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 3/8. 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.
mié. 4/1511:40 pm
PDX
- SJU
1 stop20h 22m
American Airlines
jue. 4/303:34 pm
SJU
- PDX
1 stop11h 20m
American Airlines
Deal found 3/8![American Airlines logo]()
$441
This United Airlines deal was found by Cheapflights users on 3/8. 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.
sáb. 9/1910:50 pm
PDX
- MBJ
1 stop10h 53m
United Airlines
sáb. 9/2612:52 pm
MBJ
- PDX
1 stop11h 46m
United Airlines
Deal found 3/8![United Airlines logo]()
$442
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
lun. 8/107:35 pm
PDX
- SJU
2 stops12h 25m
Southwest
jue. 8/208:55 pm
SJU
- PDX
2 stops17h 45m
Southwest
Deal found 3/11![Southwest logo]()
$446
Best flights from Portland to CaribbeanDiscover carefully curated flight deals from Portland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated marzo 12, 2026.
Discover carefully curated flight deals from Portland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated marzo 12, 2026.
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
mar. 5/1911:59 pm
PDX
- MBJ
1 stop11h 31m
United Airlines
vie. 5/294:12 pm
MBJ
- PDX
2 stops19h 35m
United Airlines
Deal found 3/10![United Airlines logo]()
$425
This Southwest deal was found by Cheapflights users on 3/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/610:45 pm
PDX
- SJU
2 stops12h 00m
Southwest
sáb. 9/128:20 am
SJU
- PDX
2 stops14h 40m
Southwest
Deal found 3/8![Southwest logo]()
$470
This American Airlines deal was found by Cheapflights users on 3/7. 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.
lun. 6/2210:59 pm
PDX
- SJU
2 stops13h 49m
American Airlines
lun. 6/296:20 am
SJU
- PDX
1 stop20h 03m
American Airlines
Deal found 3/7![American Airlines logo]()
$518
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/239:46 pm
PDX
- SDQ
1 stop25h 49m
Multiple Airlines
vie. 5/296:30 am
SDQ
- PDX
1 stop29h 41m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$575
This Delta deal was found by Cheapflights users on 3/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/239:45 pm
PDX
- STT
1 stop13h 07m
Delta
sáb. 8/291:27 pm
STT
- PDX
2 stops13h 14m
Delta
Deal found 3/7![Delta logo]()
$610
This FlightHub deal was found by Cheapflights users on 3/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/95:19 pm
PDX
- SDQ
2 stops18h 34m
Frontier
lun. 4/133:01 pm
SDQ
- PDX
2 stops25h 01m
Frontier
Deal found 3/8![Frontier logo]()
$681
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
mar. 4/215:00 am
PDX
- SJU
2 stops13h 24m
United Airlines
mar. 4/282:55 pm
SJU
- PDX
1 stop11h 03m
United Airlines
Deal found 3/10![United Airlines logo]()
$456
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
mar. 4/285:40 am
PDX
- SJU
2 stops12h 25m
Southwest
mié. 5/611:25 am
SJU
- PDX
2 stops14h 45m
Southwest
Deal found 3/10![Southwest logo]()
$472
This American Airlines deal was found by Cheapflights users on 3/7. 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.
dom. 3/299:44 pm
PDX
- STT
1 stop10h 22m
American Airlines
dom. 4/53:40 pm
STT
- PDX
1 stop11h 42m
American Airlines
Deal found 3/7![American Airlines logo]()
$540
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
lun. 5/117:05 pm
PDX
- MBJ
2 stops14h 38m
United Airlines
jue. 5/214:12 pm
MBJ
- PDX
2 stops19h 35m
United Airlines
Deal found 3/11![United Airlines logo]()
$493
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
mié. 7/87:40 pm
PDX
- SJU
2 stops12h 05m
Southwest
lun. 7/136:30 am
SJU
- PDX
2 stops12h 50m
Southwest
Deal found 3/10![Southwest logo]()
$528
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
jue. 4/910:56 pm
PDX
- SJU
1 stop12h 48m
United Airlines
jue. 4/162:55 pm
SJU
- PDX
1 stop11h 03m
United Airlines
Deal found 3/11![United Airlines logo]()
$501
This Delta deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
dom. 8/239:45 pm
PDX
- NAS
1 stop12h 50m
Delta
sáb. 8/2912:58 pm
NAS
- PDX
1 stop11h 37m
Delta
Deal found 3/11![Delta logo]()
$628
This Southwest deal was found by Cheapflights users on 3/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/85:40 am
PDX
- SJU
2 stops12h 25m
Southwest
jue. 4/910:00 am
SJU
- PDX
2 stops15h 40m
Southwest
Deal found 3/7![Southwest logo]()
$533
This Travelocity deal was found by Cheapflights users on 3/7. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/147:00 am
PDX
- GCM
1 stop31h 05m
Multiple Airlines
mar. 4/2111:30 am
GCM
- PDX
1 stop11h 05m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$668
This United Airlines deal was found by Cheapflights users on 3/8. 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.
lun. 4/2011:15 pm
PDX
- STT
1 stop10h 53m
United Airlines
mié. 4/222:10 pm
STT
- PDX
1 stop11h 24m
United Airlines
Deal found 3/8![United Airlines logo]()
$510
This Southwest deal was found by Cheapflights users on 3/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/141:35 pm
PDX
- GCM
2 stops20h 35m
Southwest
mar. 4/211:05 pm
GCM
- PDX
2 stops11h 55m
Southwest
Deal found 3/7![Southwest logo]()
$538
This Delta deal was found by Cheapflights users on 3/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/235:10 pm
PDX
- AUA
2 stops18h 00m
Delta
jue. 8/273:25 pm
AUA
- PDX
2 stops23h 48m
Delta
Deal found 3/9![Delta logo]()
$662
This American Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
mié. 4/1510:28 pm
PDX
- AUA
1 stop14h 57m
American Airlines
mar. 4/212:30 pm
AUA
- PDX
1 stop12h 23m
American Airlines
Deal found 3/11![American Airlines logo]()
$682
This United Airlines deal was found by Cheapflights users on 3/8. 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.
sáb. 4/2511:15 pm
PDX
- MBJ
1 stop10h 28m
United Airlines
mar. 4/284:12 pm
MBJ
- PDX
1 stop30h 30m
United Airlines
Deal found 3/8![United Airlines logo]()
$527
This Mytrip deal was found by Cheapflights users on 3/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/147:05 pm
PDX
- AUA
2 stops41h 10m
Multiple Airlines
mar. 4/2111:50 am
AUA
- PDX
3 stops29h 50m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$715
This Delta deal was found by Cheapflights users on 3/8. 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.
dom. 5/2411:03 pm
PDX
- SDQ
1 stop15h 58m
Delta
dom. 6/147:25 pm
SDQ
- PDX
1 stop19h 18m
Delta
Deal found 3/8![Delta logo]()
$668
This Southwest deal was found by Cheapflights users on 3/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/227:40 pm
PDX
- SJU
2 stops11h 45m
Southwest
lun. 6/291:15 pm
SJU
- PDX
2 stops11h 55m
Southwest
Deal found 3/7![Southwest logo]()
$566
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
vie. 6/1910:40 pm
PDX
- MBJ
2 stops14h 46m
United Airlines
vie. 6/264:12 pm
MBJ
- PDX
2 stops19h 27m
United Airlines
Deal found 3/11![United Airlines logo]()
$540
This American Airlines deal was found by Cheapflights users on 3/8. 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.
mié. 4/1510:28 pm
PDX
- PLS
1 stop10h 57m
American Airlines
lun. 4/201:00 pm
PLS
- PDX
2 stops13h 03m
American Airlines
Deal found 3/8![American Airlines logo]()
$731
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
mié. 5/132:06 pm
PDX
- AUA
1 stop18h 54m
Delta
mié. 5/201:15 pm
AUA
- PDX
1 stop11h 31m
Delta
Deal found 3/10![Delta logo]()
$677
This Southwest deal was found by Cheapflights users on 3/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/186:25 pm
PDX
- MBJ
2 stops15h 30m
Southwest
mar. 8/2511:50 am
MBJ
- PDX
2 stops13h 05m
Southwest
Deal found 3/8![Southwest logo]()
$581
This United Airlines deal was found by Cheapflights users on 3/8. 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.
lun. 4/277:14 pm
PDX
- SJU
2 stops15h 31m
United Airlines
vie. 5/13:56 pm
SJU
- PDX
1 stop11h 03m
United Airlines
Deal found 3/8![United Airlines logo]()
$543
This American Airlines deal was found by Cheapflights users on 3/8. 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.
sáb. 4/1810:23 pm
PDX
- GCM
2 stops10h 37m
American Airlines
mié. 4/292:05 pm
GCM
- PDX
2 stops22h 15m
American Airlines
Deal found 3/8![American Airlines logo]()
$742
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
mar. 9/15:05 pm
PDX
- AUA
2 stops16h 35m
Delta
mar. 9/81:55 pm
AUA
- PDX
2 stops25h 18m
Delta
Deal found 3/10![Delta logo]()
$682
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated marzo 12, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated marzo 12, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/9. 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.
dom. 3/2910:53 pm
PDX
- STT
1 stop12h 53m
American Airlines
dom. 4/51:08 pm
STT
- PDX
1 stop14h 07m
American Airlines
Deal found 3/9![American Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 3/9. 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.
lun. 3/3011:59 pm
PDX
- SJU
2 stops11h 51m
American Airlines
mié. 4/83:44 pm
SJU
- PDX
1 stop11h 09m
American Airlines
Deal found 3/9![American Airlines logo]()
$470
This American Airlines deal was found by Cheapflights users on 3/8. 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.
lun. 4/612:59 am
PDX
- SJU
2 stops14h 11m
American Airlines
mar. 4/216:45 am
SJU
- PDX
1 stop19h 04m
American Airlines
Deal found 3/8![American Airlines logo]()
$453
This United Airlines deal was found by Cheapflights users on 3/9. 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.
mié. 4/87:05 pm
PDX
- STT
2 stops15h 03m
United Airlines
mié. 4/152:10 pm
STT
- PDX
1 stop11h 24m
United Airlines
Deal found 3/9![United Airlines logo]()
$420
This American Airlines deal was found by Cheapflights users on 3/9. 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.
mié. 4/811:47 pm
PDX
- STT
2 stops13h 28m
American Airlines
mié. 4/1512:25 pm
STT
- PDX
2 stops13h 24m
American Airlines
Deal found 3/9![American Airlines logo]()
$425
This American Airlines deal was found by Cheapflights users on 3/9. 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.
mié. 4/811:40 pm
PDX
- SJU
1 stop20h 22m
American Airlines
mié. 4/151:31 pm
SJU
- PDX
2 stops13h 26m
American Airlines
Deal found 3/9![American Airlines logo]()
$458
This American Airlines deal was found by Cheapflights users on 3/8. 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.
mié. 4/1511:40 pm
PDX
- SJU
1 stop20h 22m
American Airlines
jue. 4/303:34 pm
SJU
- PDX
1 stop11h 20m
American Airlines
Deal found 3/8![American Airlines logo]()
$441
This American Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/1711:40 pm
PDX
- MBJ
2 stops11h 45m
American Airlines
vie. 4/2412:56 pm
MBJ
- PDX
2 stops11h 53m
American Airlines
Deal found 3/12![American Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 3/9. 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.
vie. 4/1711:47 pm
PDX
- SJU
2 stops12h 48m
American Airlines
jue. 4/236:45 am
SJU
- PDX
1 stop19h 04m
American Airlines
Deal found 3/9![American Airlines logo]()
$436
This American Airlines deal was found by Cheapflights users on 3/9. 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.
mar. 4/2111:23 pm
PDX
- SJU
1 stop18h 28m
American Airlines
lun. 5/46:45 am
SJU
- PDX
1 stop20h 09m
American Airlines
Deal found 3/9![American Airlines logo]()
$455
This American Airlines deal was found by Cheapflights users on 3/8. 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.
lun. 4/2710:23 pm
PDX
- MBJ
1 stop11h 01m
American Airlines
lun. 5/412:56 pm
MBJ
- PDX
1 stop12h 57m
American Airlines
Deal found 3/8![American Airlines logo]()
$405
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
lun. 4/275:10 am
PDX
- SJU
2 stops15h 30m
Southwest
jue. 4/302:00 pm
SJU
- PDX
2 stops13h 10m
Southwest
Deal found 3/10![Southwest logo]()
$424
One-way flights from Portland to CaribbeanSearch for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated marzo 12, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated marzo 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
mar. 4/2112:38 pm
PDX
- SJU
2 stops18h 16m
Frontier
Deal found 3/10![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 3/7. 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.
sáb. 4/2512:27 pm
PDX
- SJU
2 stops33h 31m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
sáb. 4/1812:27 pm
PDX
- SJU
2 stops34h 34m
Frontier
Deal found 3/9![Frontier logo]()
$168
This United Airlines deal was found by Cheapflights users on 3/8. 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.
mar. 5/1911:59 pm
PDX
- MBJ
1 stop11h 31m
United Airlines
Deal found 3/8![United Airlines logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/2611:15 am
PDX
- SJU
2 stops34h 43m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
vie. 4/1011:58 am
PDX
- SJU
2 stops29h 51m
Frontier
Deal found 3/10![Frontier logo]()
$180
This American Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
mar. 5/1911:47 pm
PDX
- MBJ
2 stops13h 50m
American Airlines
Deal found 3/10![American Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
sáb. 4/1812:27 pm
PDX
- SJU
3 stops31h 57m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
mar. 5/191:48 pm
PDX
- SJU
2 stops24h 42m
Frontier
Deal found 3/9![Frontier logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
mar. 4/2112:38 pm
PDX
- SJU
3 stops27h 44m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
lun. 4/209:54 am
PDX
- SJU
2 stops21h 00m
Frontier
Deal found 3/11![Frontier logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
dom. 5/179:53 am
PDX
- SJU
2 stops25h 15m
Frontier
Deal found 3/9![Frontier logo]()
$204
Find flight deals from Portland to Caribbean
Keep the following information in mind while searching for Portland to Caribbean flight deals. Data was last updated marzo 12, 2026.
Round-trip from | $397 (American Airlines) |
|---|---|
One-way from | $162 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $683 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated marzo 12, 2026.
Use the filters below to find and compare flights from Portland to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
mar. 5/19
11:59 pm-1:30 pm
1 stop11h 31m
Montego Bay Sangster Intl
vie. 5/29
4:12 pm-9:47 am
2 stops19h 35m
$425
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
mar. 4/21
5:00 am-9:24 pm
2 stops13h 24m
San Juan Luis Munoz Marin Intl
mar. 4/28
2:55 pm-10:58 pm
1 stop11h 03m
$456
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
dom. 9/6
10:45 pm-1:45 pm
2 stops12h 00m
San Juan Luis Munoz Marin Intl
sáb. 9/12
8:20 am-8:00 pm
2 stops14h 40m
$470
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
mar. 4/28
5:40 am-9:05 pm
2 stops12h 25m
San Juan Luis Munoz Marin Intl
mié. 5/6
11:25 am-11:10 pm
2 stops14h 45m
$472
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
lun. 5/11
7:05 pm-11:43 am
2 stops14h 38m
Montego Bay Sangster Intl
jue. 5/21
4:12 pm-9:47 am
2 stops19h 35m
$493
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
jue. 4/9
10:56 pm-2:44 pm
1 stop12h 48m
San Juan Luis Munoz Marin Intl
jue. 4/16
2:55 pm-10:58 pm
1 stop11h 03m
$501
PortlandSaint Thomas Island
PDX - STT
PDXSTT
Portland
lun. 4/20
11:15 pm-1:08 pm
1 stop10h 53m
Saint Thomas Island Cyril E King
mié. 4/22
2:10 pm-10:34 pm
1 stop11h 24m
$510
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
lun. 6/22
10:59 pm-3:48 pm
2 stops13h 49m
San Juan Luis Munoz Marin Intl
lun. 6/29
6:20 am-11:23 pm
1 stop20h 03m
$518
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
sáb. 4/25
11:15 pm-11:43 am
1 stop10h 28m
Montego Bay Sangster Intl
mar. 4/28
4:12 pm-8:42 pm
1 stop30h 30m
$527
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
mié. 7/8
7:40 pm-10:45 am
2 stops12h 05m
San Juan Luis Munoz Marin Intl
lun. 7/13
6:30 am-4:20 pm
2 stops12h 50m
$528
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Portland to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Portland with our price prediction graph.
PDX-MBJ
PDX-SJU
PDX-SDQ
PDX-STT
PDX-NAS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Caribbean
PDX-0CB
PDX-MBJ
PDX-SJU
PDX-SDQ
PDX-STT
What is the cheapest month to book a flight from Portland to Caribbean?
Currently, August is the cheapest month in which you can book a flight from Portland to Caribbean (average of $185). Flying from Portland to Caribbean in January is currently the most expensive (average of $405). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated marzo 12, 2026.
Read through reviews of airlines operating flights from Portland to Caribbean, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
Find useful and relevant information for your journey from Portland to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top countries
Top destinations
Alternative routes for Portland to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Portland to Caribbean by cabin class
Find flights from Portland to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Caribbean flights
Browse other Portland and Caribbean flight options. Last updated on marzo 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Portland to Caribbean flights
Consider these flights traveling from Portland to Caribbean.
Top 6 airlines flying from Portland to Caribbean
Discover the top 6 airlines that operate flights from Portland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated marzo 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$184 | Average$649 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$185 | Average$520 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$241 | Average$415 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$327 | Average$675 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$399 | Average$698 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$408 | Average$701 | FlexibilityNo cancel fee | On-time63% |