$167+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
May 27 — Jun 31
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 April 27, 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 April 27, 2026.
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 11/210:45 pm
PDX
- MBJ
1 stop11h 10m
American Airlines
Wed 11/1111:09 am
MBJ
- PDX
1 stop13h 06m
American Airlines
Deal found 4/27![American Airlines logo]()
$392
This United Airlines deal was found by Cheapflights users on 4/26. 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.
Mon 11/210:59 pm
PDX
- MBJ
1 stop11h 47m
United Airlines
Wed 11/112:48 pm
MBJ
- PDX
2 stops21h 52m
United Airlines
Deal found 4/26![United Airlines logo]()
$397
This United Airlines deal was found by Cheapflights users on 4/22. 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.
Sat 11/145:15 am
PDX
- MBJ
1 stop8h 35m
United Airlines
Sun 11/222:48 pm
MBJ
- PDX
1 stop21h 42m
United Airlines
Deal found 4/22![United Airlines logo]()
$401
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Tue 9/2212:50 pm
PDX
- MBJ
2 stops20h 53m
United Airlines
Sat 9/2612:52 pm
MBJ
- PDX
1 stop10h 13m
United Airlines
Deal found 4/23![United Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Sun 5/1010:15 pm
PDX
- STT
1 stop11h 53m
United Airlines
Thu 5/141:22 pm
STT
- PDX
1 stop12h 37m
United Airlines
Deal found 4/25![United Airlines logo]()
$420
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:45 pm
PDX
- MBJ
2 stops15h 40m
Delta
Tue 11/106:00 pm
MBJ
- PDX
2 stops18h 31m
Delta
Deal found 4/23![Delta logo]()
$427
This United Airlines deal was found by Cheapflights users on 4/26. 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 5/711:59 pm
PDX
- STT
1 stop12h 44m
United Airlines
Tue 5/121:22 pm
STT
- PDX
1 stop12h 37m
United Airlines
Deal found 4/26![United Airlines logo]()
$445
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Tue 7/2811:30 pm
PDX
- MBJ
1 stop13h 40m
United Airlines
Sun 8/92:40 pm
MBJ
- PDX
1 stop10h 08m
United Airlines
Deal found 4/25![United Airlines logo]()
$448
This Southwest deal was found by Cheapflights users on 4/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:45 pm
PDX
- SJU
1 stop11h 15m
Southwest
Thu 9/245:30 am
SJU
- PDX
1 stop12h 30m
Southwest
Deal found 4/25![Southwest logo]()
$466
This United Airlines deal was found by Cheapflights users on 4/22. 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 8/310:40 pm
PDX
- MBJ
2 stops12h 50m
United Airlines
Mon 8/174:12 pm
MBJ
- PDX
2 stops19h 09m
United Airlines
Deal found 4/22![United Airlines logo]()
$470
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Sat 11/145:42 pm
PDX
- MBJ
2 stops13h 33m
American Airlines
Sun 11/224:05 pm
MBJ
- PDX
2 stops22h 05m
American Airlines
Deal found 4/22![American Airlines logo]()
$472
This Southwest deal was found by Cheapflights users on 4/24. 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.
Fri 9/1810:45 pm
PDX
- SJU
1 stop11h 25m
Southwest
Mon 9/215:30 am
SJU
- PDX
1 stop12h 30m
Southwest
Deal found 4/24![Southwest logo]()
$481
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 April 27, 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 April 27, 2026.
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Sun 5/1010:15 pm
PDX
- STT
1 stop11h 53m
United Airlines
Thu 5/141:22 pm
STT
- PDX
1 stop12h 37m
United Airlines
Deal found 4/25![United Airlines logo]()
$420
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Tue 10/1311:58 pm
PDX
- MBJ
2 stops11h 07m
American Airlines
Tue 10/2010:50 am
MBJ
- PDX
2 stops14h 09m
American Airlines
Deal found 4/22![American Airlines logo]()
$517
This Delta deal was found by Cheapflights users on 4/25. 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.
Fri 5/295:05 pm
PDX
- SJU
2 stops15h 56m
Delta
Thu 6/41:16 pm
SJU
- PDX
2 stops13h 28m
Delta
Deal found 4/25![Delta logo]()
$530
This Southwest deal was found by Cheapflights users on 4/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/3111:30 pm
PDX
- SJU
1 stop11h 15m
Southwest
Fri 8/76:30 am
SJU
- PDX
2 stops13h 05m
Southwest
Deal found 4/25![Southwest logo]()
$568
This Air Canada deal was found by Cheapflights users on 4/22. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/307:45 pm
PDX
- BGI
2 stops40h 40m
Air Canada
Tue 7/74:20 pm
BGI
- PDX
2 stops44h 11m
Air Canada
Deal found 4/22![Air Canada logo]()
$607
This Justfly.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/102:30 pm
PDX
- MBJ
1 stop22h 23m
JetBlue
Sun 6/143:39 pm
MBJ
- PDX
1 stop23h 26m
JetBlue
Deal found 4/27![JetBlue logo]()
$678
This Mytrip deal was found by Cheapflights users on 4/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/73:30 pm
PDX
- SXM
3 stops19h 50m
Multiple Airlines
Sun 6/143:20 pm
SXM
- PDX
2 stops25h 30m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$809
This United Airlines deal was found by Cheapflights users on 4/24. 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 9/1811:15 pm
PDX
- MBJ
2 stops12h 15m
United Airlines
Sat 9/2612:52 pm
MBJ
- PDX
1 stop12h 00m
United Airlines
Deal found 4/24![United Airlines logo]()
$517
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Mon 5/2511:30 pm
PDX
- SJU
1 stop10h 04m
United Airlines
Sun 5/311:00 am
SJU
- PDX
1 stop11h 25m
United Airlines
Deal found 4/25![United Airlines logo]()
$530
This FlightHub deal was found by Cheapflights users on 4/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/73:30 pm
PDX
- MBJ
2 stops17h 50m
Air Canada
Mon 10/1212:30 pm
MBJ
- PDX
2 stops23h 01m
Air Canada
Deal found 4/22![Air Canada logo]()
$627
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:00 am
PDX
- SJU
1 stop13h 53m
Delta
Tue 7/2812:56 pm
SJU
- PDX
2 stops13h 48m
Delta
Deal found 4/23![Delta logo]()
$636
This United Airlines deal was found by Cheapflights users on 4/22. 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 10/66:56 am
PDX
- SJU
1 stop10h 42m
United Airlines
Thu 10/82:00 pm
SJU
- PDX
1 stop11h 52m
United Airlines
Deal found 4/22![United Airlines logo]()
$530
This American Airlines deal was found by Cheapflights users on 4/26. 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 6/169:47 pm
PDX
- NAS
1 stop9h 15m
American Airlines
Tue 6/232:55 pm
NAS
- PDX
2 stops12h 04m
American Airlines
Deal found 4/26![American Airlines logo]()
$668
This Delta deal was found by Cheapflights users on 4/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:05 pm
PDX
- SDQ
1 stop16h 59m
Delta
Sat 9/57:29 pm
SDQ
- PDX
1 stop19h 14m
Delta
Deal found 4/24![Delta logo]()
$648
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/296:50 pm
PDX
- MBJ
2 stops18h 20m
United Airlines
Mon 8/32:40 pm
MBJ
- PDX
2 stops21h 07m
United Airlines
Deal found 4/27![United Airlines logo]()
$547
This Southwest deal was found by Cheapflights users on 4/24. 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.
Sun 10/114:25 pm
PDX
- SXM
2 stops18h 35m
Southwest
Mon 10/193:00 pm
SXM
- PDX
2 stops22h 35m
Southwest
Deal found 4/24![Southwest logo]()
$735
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Thu 5/1411:47 pm
PDX
- NAS
2 stops13h 41m
American Airlines
Wed 5/2012:00 pm
NAS
- PDX
1 stop14h 53m
American Airlines
Deal found 4/23![American Airlines logo]()
$672
This Air Canada deal was found by Cheapflights users on 4/26. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/77:45 pm
PDX
- PUJ
2 stops41h 45m
Air Canada
Wed 6/174:25 pm
PUJ
- PDX
2 stops44h 06m
Air Canada
Deal found 4/26![Air Canada logo]()
$701
This Delta deal was found by Cheapflights users on 4/22. 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 8/237:14 pm
PDX
- SDQ
2 stops14h 58m
Delta
Fri 8/287:29 pm
SDQ
- PDX
1 stop19h 14m
Delta
Deal found 4/22![Delta logo]()
$653
This United Airlines deal was found by Cheapflights users on 4/24. 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.
Sat 10/1710:59 pm
PDX
- PUJ
1 stop13h 01m
United Airlines
Sat 10/241:25 pm
PUJ
- PDX
1 stop10h 40m
United Airlines
Deal found 4/24![United Airlines logo]()
$556
This American Airlines deal was found by Cheapflights users on 4/24. 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 6/29:47 pm
PDX
- AUA
1 stop14h 53m
American Airlines
Wed 6/103:00 pm
AUA
- PDX
1 stop11h 59m
American Airlines
Deal found 4/24![American Airlines logo]()
$717
This Delta deal was found by Cheapflights users on 4/22. 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.
Thu 5/287:00 am
PDX
- SDQ
1 stop14h 41m
Delta
Tue 6/22:48 pm
SDQ
- PDX
2 stops21h 04m
Delta
Deal found 4/22![Delta logo]()
$653
This United Airlines deal was found by Cheapflights users on 4/22. 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.
Wed 7/2210:52 pm
PDX
- SJU
1 stop10h 12m
United Airlines
Wed 8/53:56 pm
SJU
- PDX
1 stop11h 06m
United Airlines
Deal found 4/22![United Airlines logo]()
$564
This Delta deal was found by Cheapflights users on 4/26. 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 8/510:35 pm
PDX
- SDQ
1 stop11h 04m
Delta
Tue 8/112:37 pm
SDQ
- PDX
2 stops21h 48m
Delta
Deal found 4/26![Delta logo]()
$653
This American Airlines deal was found by Cheapflights users on 4/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/911:43 pm
PDX
- AUA
2 stops13h 07m
American Airlines
Tue 6/165:59 pm
AUA
- PDX
2 stops20h 10m
American Airlines
Deal found 4/25![American Airlines logo]()
$722
This United Airlines deal was found by Cheapflights users on 4/24. 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.
Sat 5/910:15 pm
PDX
- SJU
1 stop10h 49m
United Airlines
Wed 5/133:56 pm
SJU
- PDX
1 stop10h 59m
United Airlines
Deal found 4/24![United Airlines logo]()
$586
This Delta deal was found by Cheapflights users on 4/22. 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.
Thu 8/610:35 pm
PDX
- SDQ
1 stop16h 31m
Delta
Tue 8/112:37 pm
SDQ
- PDX
2 stops21h 48m
Delta
Deal found 4/22![Delta logo]()
$653
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/213:30 pm
PDX
- CUR
2 stops20h 20m
Multiple Airlines
Thu 5/284:00 pm
CUR
- PDX
3 stops24h 50m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$1,060
This Delta deal was found by Cheapflights users on 4/22. 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 8/237:14 pm
PDX
- NAS
2 stops13h 34m
Delta
Thu 8/271:13 pm
NAS
- PDX
1 stop11h 41m
Delta
Deal found 4/22![Delta logo]()
$668
This United Airlines deal was found by Cheapflights users on 4/22. 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 6/711:40 pm
PDX
- MBJ
2 stops11h 50m
United Airlines
Sun 6/144:33 pm
MBJ
- PDX
2 stops19h 14m
United Airlines
Deal found 4/22![United Airlines logo]()
$611
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated April 27, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated April 27, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Sun 4/2610:23 pm
PDX
- MBJ
1 stop11h 01m
American Airlines
Tue 4/281:15 pm
MBJ
- PDX
1 stop12h 42m
American Airlines
Deal found 4/22![American Airlines logo]()
$576
This American Airlines deal was found by Cheapflights users on 4/22. 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 5/410:28 pm
PDX
- MBJ
1 stop15h 09m
American Airlines
Thu 5/2112:31 pm
MBJ
- PDX
1 stop13h 28m
American Airlines
Deal found 4/22![American Airlines logo]()
$484
This United Airlines deal was found by Cheapflights users on 4/26. 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 5/711:59 pm
PDX
- STT
1 stop12h 44m
United Airlines
Tue 5/121:22 pm
STT
- PDX
1 stop12h 37m
United Airlines
Deal found 4/26![United Airlines logo]()
$445
This American Airlines deal was found by Cheapflights users on 4/22. 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 5/710:28 pm
PDX
- STT
1 stop14h 47m
American Airlines
Mon 5/112:05 pm
STT
- PDX
1 stop12h 48m
American Airlines
Deal found 4/22![American Airlines logo]()
$569
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Sun 5/107:05 pm
PDX
- STT
2 stops15h 03m
United Airlines
Thu 5/141:22 pm
STT
- PDX
1 stop12h 37m
United Airlines
Deal found 4/25![United Airlines logo]()
$420
This United Airlines deal was found by Cheapflights users on 4/24. 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.
Sun 5/107:05 pm
PDX
- SJU
2 stops13h 59m
United Airlines
Thu 5/143:56 pm
SJU
- PDX
1 stop10h 59m
United Airlines
Deal found 4/24![United Airlines logo]()
$496
This United Airlines deal was found by Cheapflights users on 4/24. 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.
Sun 5/1011:59 pm
PDX
- SJU
1 stop12h 43m
United Airlines
Sat 6/61:00 am
SJU
- PDX
1 stop11h 25m
United Airlines
Deal found 4/24![United Airlines logo]()
$513
This United Airlines deal was found by Cheapflights users on 4/22. 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 5/1810:15 pm
PDX
- SJU
1 stop10h 49m
United Airlines
Mon 5/251:00 am
SJU
- PDX
1 stop11h 25m
United Airlines
Deal found 4/22![United Airlines logo]()
$549
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Sat 5/2311:30 pm
PDX
- MBJ
1 stop13h 40m
United Airlines
Sat 5/302:40 pm
MBJ
- PDX
1 stop10h 08m
United Airlines
Deal found 4/23![United Airlines logo]()
$520
This American Airlines deal was found by Cheapflights users on 4/26. 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.
Sat 5/2310:59 pm
PDX
- SJU
2 stops13h 49m
American Airlines
Thu 5/286:00 am
SJU
- PDX
2 stops13h 42m
American Airlines
Deal found 4/26![American Airlines logo]()
$548
This United Airlines deal was found by Cheapflights users on 4/26. 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.
Sun 5/2411:30 pm
PDX
- SJU
1 stop10h 04m
United Airlines
Sat 5/301:00 am
SJU
- PDX
1 stop11h 25m
United Airlines
Deal found 4/26![United Airlines logo]()
$568
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:51 pm
PDX
- SJU
2 stops16h 29m
Delta
Thu 6/41:16 pm
SJU
- PDX
2 stops13h 28m
Delta
Deal found 4/23![Delta logo]()
$530
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 April 27, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1812:35 pm
PDX
- SJU
2 stops25h 51m
Frontier
Deal found 4/25![Frontier logo]()
$167
This American Airlines deal was found by Cheapflights users on 4/24. 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.
Thu 7/911:43 pm
PDX
- MBJ
1 stop14h 31m
American Airlines
Deal found 4/24![American Airlines logo]()
$172
This Delta deal was found by Cheapflights users on 4/25. 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.
Mon 5/1811:12 pm
PDX
- MBJ
2 stops14h 22m
Delta
Deal found 4/25![Delta logo]()
$187
This American Airlines deal was found by Cheapflights users on 4/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1910:28 pm
PDX
- MBJ
1 stop15h 09m
American Airlines
Deal found 4/25![American Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/242:44 pm
PDX
- PUJ
3 stops44h 33m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 4/24. 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.
Fri 5/1512:35 pm
PDX
- SJU
2 stops47h 37m
Frontier
Deal found 4/24![Frontier logo]()
$222
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:30 pm
PDX
- PUJ
1 stop18h 10m
Delta
Deal found 4/23![Delta logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:44 pm
PDX
- SJU
3 stops58h 17m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 4/24. 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.
Mon 6/811:15 am
PDX
- SDQ
3 stops50h 14m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$233
This Southwest deal was found by Cheapflights users on 4/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:05 am
PDX
- SJU
2 stops13h 10m
Southwest
Deal found 4/25![Southwest logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Sun 5/1012:35 pm
PDX
- SJU
2 stops32h 46m
Frontier
Deal found 4/22![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/177:46 pm
PDX
- SJU
3 stops39h 15m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$240
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 April 27, 2026.
Round-trip from | $392 (American Airlines) |
|---|---|
One-way from | $167 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $555 |
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 April 27, 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
PortlandSaint Thomas Island
PDX - STT
PDXSTT
Portland
Sun 5/10
10:15 pm-1:08 pm
1 stop11h 53m
Saint Thomas Island Cyril E King
Thu 5/14
1:22 pm-10:59 pm
1 stop12h 37m
$420
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Tue 10/13
11:58 pm-1:05 pm
2 stops11h 07m
Montego Bay Sangster Intl
Tue 10/20
10:50 am-10:59 pm
2 stops14h 09m
$517
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Fri 9/18
11:15 pm-1:30 pm
2 stops12h 15m
Montego Bay Sangster Intl
Sat 9/26
12:52 pm-10:52 pm
1 stop12h 00m
$517
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Fri 5/29
5:05 pm-12:01 pm
2 stops15h 56m
San Juan Luis Munoz Marin Intl
Thu 6/4
1:16 pm-11:44 pm
2 stops13h 28m
$530
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Mon 5/25
11:30 pm-12:34 pm
1 stop10h 04m
San Juan Luis Munoz Marin Intl
Sun 5/31
1:00 am-9:25 am
1 stop11h 25m
$530
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Tue 10/6
6:56 am-8:38 pm
1 stop10h 42m
San Juan Luis Munoz Marin Intl
Thu 10/8
2:00 pm-10:52 pm
1 stop11h 52m
$530
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Wed 7/29
6:50 pm-3:10 pm
2 stops18h 20m
Montego Bay Sangster Intl
Mon 8/3
2:40 pm-9:47 am
2 stops21h 07m
$547
PortlandPunta Cana
PDX - PUJ
PDXPUJ
Portland
Sat 10/17
10:59 pm-3:00 pm
1 stop13h 01m
Punta Cana
Sat 10/24
1:25 pm-9:05 pm
1 stop10h 40m
$556
Quickest round-trip
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Wed 7/22
10:52 pm-12:04 pm
1 stop10h 12m
San Juan Luis Munoz Marin Intl
Wed 8/5
3:56 pm-12:02 am
1 stop11h 06m
$564
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Fri 7/31
11:30 pm-1:45 pm
1 stop11h 15m
San Juan Luis Munoz Marin Intl
Fri 8/7
6:30 am-4:35 pm
2 stops13h 05m
$568
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-SJU
PDX-MBJ
PDX-PUJ
PDX-SDQ
PDX-STT
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Caribbean
PDX-0CB
PDX-SJU
PDX-MBJ
PDX-PUJ
PDX-SDQ
How far ahead should I book a flight from Portland to Caribbean?
The best time to book flights from Portland to Caribbean is 46 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Portland to Caribbean?
Currently, May is the cheapest month in which you can book a flight from Portland to Caribbean (average of $179). Flying from Portland to Caribbean in February is currently the most expensive (average of $279). 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 April 27, 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.
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 April 27, 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 5 airlines flying from Portland to Caribbean
Discover the top 5 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 April 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$185 | Average$446 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$190 | Average$662 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$224 | Average$663 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$396 | Average$730 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$408 | Average$682 | FlexibilityNo cancel fee | On-time63% |