$159+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
May 21 — May 281
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Caribbean with Cheapflights
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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 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 21, 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 21, 2026.
This American Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/210:45 pm
PDX
- MBJ
1 stop12h 29m
American Airlines
Tue 11/1011:15 am
MBJ
- PDX
1 stop15h 36m
American Airlines
Deal found 4/17![American Airlines logo]()
$392
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 4/20![United Airlines logo]()
$397
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 11/210:05 pm
PDX
- MBJ
1 stop11h 20m
Delta
Tue 11/106:00 pm
MBJ
- PDX
2 stops18h 31m
Delta
Deal found 4/20![Delta logo]()
$427
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/45:35 pm
PDX
- MBJ
2 stops17h 55m
United Airlines
Thu 5/142:40 pm
MBJ
- PDX
1 stop10h 19m
United Airlines
Deal found 4/19![United Airlines logo]()
$444
This American Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/410:23 pm
PDX
- MBJ
2 stops15h 14m
American Airlines
Thu 5/2112:31 pm
MBJ
- PDX
1 stop13h 28m
American Airlines
Deal found 4/16![American Airlines logo]()
$449
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 8/1410:45 pm
PDX
- SJU
1 stop11h 25m
Southwest
Sun 8/239:25 pm
SJU
- PDX
2 stops18h 25m
Southwest
Deal found 4/20![Southwest logo]()
$466
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 8/2410:59 pm
PDX
- PUJ
1 stop10h 37m
American Airlines
Fri 8/283:20 pm
PUJ
- PDX
1 stop11h 02m
American Airlines
Deal found 4/20![American Airlines logo]()
$486
This American Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/110:23 pm
PDX
- MBJ
2 stops15h 14m
American Airlines
Sat 5/94:37 pm
MBJ
- PDX
2 stops19h 43m
American Airlines
Deal found 4/18![American Airlines logo]()
$489
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/511:23 pm
PDX
- MBJ
1 stop10h 01m
American Airlines
Sat 5/91:15 pm
MBJ
- PDX
1 stop12h 33m
American Airlines
Deal found 4/20![American Airlines logo]()
$496
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/212:30 am
PDX
- SJU
2 stops12h 53m
Delta
Wed 5/62:03 pm
SJU
- PDX
2 stops12h 59m
Delta
Deal found 4/19![Delta logo]()
$496
This Southwest deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/510:45 pm
PDX
- SJU
1 stop12h 45m
Southwest
Mon 8/175:30 am
SJU
- PDX
1 stop12h 30m
Southwest
Deal found 4/18![Southwest logo]()
$498
This American Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1311:58 pm
PDX
- MBJ
1 stop10h 08m
American Airlines
Tue 10/202:27 pm
MBJ
- PDX
1 stop20h 47m
American Airlines
Deal found 4/16![American Airlines logo]()
$512
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 21, 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 21, 2026.
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/45:35 pm
PDX
- MBJ
2 stops17h 55m
United Airlines
Thu 5/142:40 pm
MBJ
- PDX
1 stop10h 19m
United Airlines
Deal found 4/19![United Airlines logo]()
$444
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1610:35 pm
PDX
- SJU
1 stop15h 03m
Delta
Mon 7/206:00 am
SJU
- PDX
2 stops17h 15m
Delta
Deal found 4/17![Delta logo]()
$530
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Fri 5/111:40 pm
PDX
- MBJ
2 stops13h 57m
American Airlines
Sat 5/91:15 pm
MBJ
- PDX
1 stop12h 33m
American Airlines
Deal found 4/21![American Airlines logo]()
$541
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/315:50 pm
PDX
- MBJ
2 stops15h 25m
Southwest
Sun 6/711:35 am
MBJ
- PDX
2 stops14h 30m
Southwest
Deal found 4/16![Southwest logo]()
$581
This Justfly.com deal was found by Cheapflights users on 4/21. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:45 pm
PDX
- UVF
2 stops39h 35m
Air Canada
Fri 7/173:05 pm
UVF
- PDX
2 stops21h 26m
Air Canada
Deal found 4/21![Air Canada logo]()
$656
This Justfly.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/52:30 pm
PDX
- AUA
1 stop19h 40m
JetBlue
Sun 6/76:00 pm
AUA
- PDX
1 stop22h 07m
JetBlue
Deal found 4/17![JetBlue logo]()
$768
This Trip.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
Tue 8/252:30 pm
PDX
- UVF
2 stops44h 10m
WestJet
Sun 8/302:30 pm
UVF
- PDX
2 stops26h 20m
WestJet
Deal found 4/20![WestJet logo]()
$781
This Mytrip deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/207:45 pm
PDX
- UVF
2 stops14h 55m
Multiple Airlines
Sun 6/282:30 pm
UVF
- PDX
3 stops26h 20m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$849
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2910:40 pm
PDX
- MBJ
2 stops12h 50m
United Airlines
Fri 7/104:12 pm
MBJ
- PDX
2 stops19h 35m
United Airlines
Deal found 4/16![United Airlines logo]()
$489
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/47:05 pm
PDX
- SJU
2 stops14h 29m
United Airlines
Thu 5/71:40 pm
SJU
- PDX
1 stop10h 29m
United Airlines
Deal found 4/20![United Airlines logo]()
$496
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:25 pm
PDX
- SJU
2 stops12h 10m
Southwest
Tue 6/28:10 am
SJU
- PDX
2 stops13h 20m
Southwest
Deal found 4/20![Southwest logo]()
$590
This United Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:15 pm
PDX
- SJU
1 stop10h 49m
United Airlines
Fri 5/291:00 am
SJU
- PDX
1 stop11h 28m
United Airlines
Deal found 4/18![United Airlines logo]()
$513
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Mon 8/2410:59 pm
PDX
- PUJ
1 stop10h 37m
American Airlines
Mon 8/313:20 pm
PUJ
- PDX
1 stop21h 04m
American Airlines
Deal found 4/21![American Airlines logo]()
$628
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/66:55 am
PDX
- SDQ
1 stop14h 46m
Delta
Thu 6/116:06 am
SDQ
- PDX
1 stop18h 05m
Delta
Deal found 4/20![Delta logo]()
$648
This Southwest deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:55 pm
PDX
- SJU
2 stops14h 40m
Southwest
Thu 5/146:50 am
SJU
- PDX
2 stops16h 20m
Southwest
Deal found 4/17![Southwest logo]()
$611
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/305:00 pm
PDX
- MBJ
2 stops18h 30m
United Airlines
Thu 7/94:12 pm
MBJ
- PDX
2 stops19h 22m
United Airlines
Deal found 4/17![United Airlines logo]()
$517
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2911:47 pm
PDX
- MBJ
1 stop10h 26m
American Airlines
Sun 5/31:15 pm
MBJ
- PDX
1 stop12h 42m
American Airlines
Deal found 4/19![American Airlines logo]()
$646
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2211:03 pm
PDX
- SDQ
1 stop15h 58m
Delta
Thu 5/286:05 am
SDQ
- PDX
2 stops20h 39m
Delta
Deal found 4/16![Delta logo]()
$653
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1511:55 pm
PDX
- NAS
2 stops15h 35m
Southwest
Wed 5/208:45 am
NAS
- PDX
2 stops12h 45m
Southwest
Deal found 4/15![Southwest logo]()
$614
This Air Canada deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 4/19![Air Canada logo]()
$774
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/25:30 am
PDX
- SDQ
2 stops16h 11m
Delta
Mon 6/86:06 am
SDQ
- PDX
2 stops15h 43m
Delta
Deal found 4/20![Delta logo]()
$653
This United Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/611:55 pm
PDX
- SJU
1 stop11h 49m
United Airlines
Mon 5/111:40 pm
SJU
- PDX
1 stop12h 14m
United Airlines
Deal found 4/18![United Airlines logo]()
$549
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/111:39 pm
PDX
- NAS
1 stop18h 50m
American Airlines
Sat 7/1812:29 pm
NAS
- PDX
1 stop12h 20m
American Airlines
Deal found 4/19![American Airlines logo]()
$668
This Mytrip deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/313:30 pm
PDX
- UVF
2 stops43h 40m
Multiple Airlines
Sun 6/72:30 pm
UVF
- PDX
3 stops26h 20m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$860
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/36:50 am
PDX
- SDQ
2 stops14h 51m
Delta
Tue 6/96:06 am
SDQ
- PDX
2 stops17h 11m
Delta
Deal found 4/20![Delta logo]()
$653
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/268:35 am
PDX
- MBJ
2 stops28h 51m
United Airlines
Tue 7/74:12 pm
MBJ
- PDX
2 stops32h 51m
United Airlines
Deal found 4/17![United Airlines logo]()
$550
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/255:10 am
PDX
- NAS
2 stops10h 20m
Southwest
Thu 5/288:45 am
NAS
- PDX
2 stops14h 25m
Southwest
Deal found 4/19![Southwest logo]()
$668
This WestJet deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/102:30 pm
PDX
- SXM
2 stops20h 50m
WestJet
Thu 5/143:20 pm
SXM
- PDX
2 stops25h 30m
WestJet
Deal found 4/18![WestJet logo]()
$907
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:57 pm
PDX
- PUJ
2 stops13h 10m
American Airlines
Sat 7/1111:44 am
PUJ
- PDX
2 stops14h 08m
American Airlines
Deal found 4/19![American Airlines logo]()
$695
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:00 am
PDX
- SDQ
1 stop14h 41m
Delta
Fri 5/296:05 am
SDQ
- PDX
2 stops20h 39m
Delta
Deal found 4/16![Delta logo]()
$653
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated April 21, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated April 21, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/110:23 pm
PDX
- MBJ
2 stops15h 14m
American Airlines
Sat 5/94:37 pm
MBJ
- PDX
2 stops19h 43m
American Airlines
Deal found 4/18![American Airlines logo]()
$489
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:40 pm
PDX
- SJU
2 stops10h 25m
Southwest
Sun 5/105:35 am
SJU
- PDX
2 stops13h 20m
Southwest
Deal found 4/16![Southwest logo]()
$551
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/310:55 pm
PDX
- SJU
1 stop12h 49m
United Airlines
Wed 5/62:55 pm
SJU
- PDX
1 stop11h 04m
United Airlines
Deal found 4/19![United Airlines logo]()
$496
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/410:15 pm
PDX
- MBJ
1 stop11h 28m
United Airlines
Thu 5/142:40 pm
MBJ
- PDX
1 stop10h 19m
United Airlines
Deal found 4/19![United Airlines logo]()
$444
This American Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/410:23 pm
PDX
- MBJ
2 stops15h 14m
American Airlines
Thu 5/2112:31 pm
MBJ
- PDX
1 stop13h 28m
American Airlines
Deal found 4/16![American Airlines logo]()
$449
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/511:23 pm
PDX
- MBJ
1 stop10h 01m
American Airlines
Sat 5/91:15 pm
MBJ
- PDX
1 stop12h 33m
American Airlines
Deal found 4/20![American Airlines logo]()
$496
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/511:59 pm
PDX
- MBJ
1 stop11h 31m
United Airlines
Sat 5/912:52 pm
MBJ
- PDX
1 stop10h 17m
United Airlines
Deal found 4/17![United Airlines logo]()
$564
This United Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/611:55 pm
PDX
- SJU
1 stop11h 49m
United Airlines
Mon 5/111:40 pm
SJU
- PDX
1 stop12h 14m
United Airlines
Deal found 4/18![United Airlines logo]()
$549
This American Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1111:47 pm
PDX
- MBJ
1 stop10h 26m
American Airlines
Tue 5/1912:56 pm
MBJ
- PDX
2 stops23h 24m
American Airlines
Deal found 4/18![American Airlines logo]()
$555
This United Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:15 pm
PDX
- SJU
1 stop10h 49m
United Airlines
Fri 5/291:00 am
SJU
- PDX
1 stop11h 28m
United Airlines
Deal found 4/18![United Airlines logo]()
$513
This United Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:52 pm
PDX
- MBJ
1 stop10h 51m
United Airlines
Tue 6/24:12 pm
MBJ
- PDX
2 stops19h 35m
United Airlines
Deal found 4/18![United Airlines logo]()
$572
This American Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:15 am
PDX
- SJU
2 stops13h 30m
American Airlines
Sun 6/76:20 am
SJU
- PDX
1 stop20h 03m
American Airlines
Deal found 4/16![American Airlines 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 21, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/95:20 pm
PDX
- SJU
2 stops27h 55m
Frontier
Deal found 4/20![Frontier logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:38 pm
PDX
- SJU
2 stops32h 51m
Frontier
Deal found 4/16![Frontier logo]()
$217
This Southwest deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:00 pm
PDX
- SXM
2 stops14h 45m
Southwest
Deal found 4/18![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 4/20![Delta logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2912:38 pm
PDX
- SJU
2 stops34h 23m
Frontier
Deal found 4/20![Frontier logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 stops21h 40m
Frontier
Deal found 4/20![Frontier logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/155:31 pm
PDX
- SJU
3 stops29h 37m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/185:31 pm
PDX
- SJU
3 stops43h 28m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$245
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/1710:55 pm
PDX
- SJU
1 stop12h 49m
United Airlines
Deal found 4/20![United Airlines logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/1712:35 pm
PDX
- SJU
2 stops32h 22m
Frontier
Deal found 4/20![Frontier logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/95:20 pm
PDX
- SJU
3 stops27h 59m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/2210:41 am
PDX
- SJU
3 stops40h 43m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$254
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 21, 2026.
Round-trip from | $392 (American Airlines) |
|---|---|
One-way from | $159 (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 21, 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
Mon 5/4
5:35 pm-1:30 pm
2 stops17h 55m
Montego Bay Sangster Intl
Thu 5/14
2:40 pm-10:59 pm
1 stop10h 19m
$444
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Mon 6/29
10:40 pm-1:30 pm
2 stops12h 50m
Montego Bay Sangster Intl
Fri 7/10
4:12 pm-9:47 am
2 stops19h 35m
$489
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Mon 5/4
7:05 pm-12:34 pm
2 stops14h 29m
San Juan Luis Munoz Marin Intl
Thu 5/7
1:40 pm-9:09 pm
1 stop10h 29m
$496
Quickest round-trip
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Sat 5/16
10:15 pm-12:04 pm
1 stop10h 49m
San Juan Luis Munoz Marin Intl
Fri 5/29
1:00 am-9:28 am
1 stop11h 28m
$513
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Tue 6/30
5:00 pm-1:30 pm
2 stops18h 30m
Montego Bay Sangster Intl
Thu 7/9
4:12 pm-9:34 am
2 stops19h 22m
$517
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Thu 7/16
10:35 pm-4:38 pm
1 stop15h 03m
San Juan Luis Munoz Marin Intl
Mon 7/20
6:00 am-8:15 pm
2 stops17h 15m
$530
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Fri 5/1
11:40 pm-3:37 pm
2 stops13h 57m
Montego Bay Sangster Intl
Sat 5/9
1:15 pm-11:48 pm
1 stop12h 33m
$541
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Wed 5/6
11:55 pm-2:44 pm
1 stop11h 49m
San Juan Luis Munoz Marin Intl
Mon 5/11
1:40 pm-10:54 pm
1 stop12h 14m
$549
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Fri 6/26
8:35 am-3:26 pm
2 stops28h 51m
Montego Bay Sangster Intl
Tue 7/7
4:12 pm-11:03 pm
2 stops32h 51m
$550
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Sun 5/31
5:50 pm-11:15 am
2 stops15h 25m
Montego Bay Sangster Intl
Sun 6/7
11:35 am-12:05 am
2 stops14h 30m
$581
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-PUJ
PDX-SXM
PDX-CUR
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-PUJ
PDX-SXM
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 21, 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.
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
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.
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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 21, 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 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$184 | Average$646 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$185 | Average$445 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$224 | Average$662 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$396 | Average$723 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$408 | Average$684 | FlexibilityNo cancel fee | On-time63% |