$187+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Jul 10 — Jul 171
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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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
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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 June 10, 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 June 10, 2026.
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Sun 8/2311:34 pm
PDX
- STT
2 stops12h 25m
American Airlines
Mon 8/314:42 pm
STT
- PDX
2 stops21h 52m
American Airlines
Deal found 6/8![American Airlines logo]()
$420
This Delta deal was found by Cheapflights users on 6/10. 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.
Tue 10/1310:05 pm
PDX
- MBJ
1 stop11h 20m
Delta
Tue 10/201:32 pm
MBJ
- PDX
1 stop10h 54m
Delta
Deal found 6/10![Delta logo]()
$422
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Wed 11/1110:45 pm
PDX
- STT
1 stop9h 22m
American Airlines
Wed 11/186:17 pm
STT
- PDX
2 stops20h 53m
American Airlines
Deal found 6/10![American Airlines logo]()
$425
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 11/27:40 pm
PDX
- MBJ
2 stops13h 45m
Delta
Wed 11/116:00 pm
MBJ
- PDX
2 stops18h 31m
Delta
Deal found 6/8![Delta logo]()
$427
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:00 pm
PDX
- MBJ
1 stop11h 25m
Delta
Thu 9/241:25 pm
MBJ
- PDX
1 stop10h 20m
Delta
Deal found 6/5![Delta logo]()
$432
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:50 pm
PDX
- MBJ
2 stops19h 44m
Delta
Wed 9/231:25 pm
MBJ
- PDX
2 stops24h 31m
Delta
Deal found 6/5![Delta logo]()
$437
This Southwest deal was found by Cheapflights users on 6/7. 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.
Mon 8/247:00 pm
PDX
- SJU
2 stops13h 00m
Southwest
Mon 8/315:00 am
SJU
- PDX
2 stops13h 00m
Southwest
Deal found 6/7![Southwest logo]()
$451
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:00 pm
PDX
- MBJ
2 stops14h 20m
Southwest
Tue 9/2211:50 am
MBJ
- PDX
2 stops13h 20m
Southwest
Deal found 6/5![Southwest logo]()
$459
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Sun 8/2311:34 pm
PDX
- PUJ
1 stop11h 31m
American Airlines
Fri 8/283:05 pm
PUJ
- PDX
1 stop11h 54m
American Airlines
Deal found 6/10![American Airlines logo]()
$464
This American Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/210:45 pm
PDX
- SJU
1 stop10h 56m
American Airlines
Wed 12/28:18 am
SJU
- PDX
1 stop16h 49m
American Airlines
Deal found 6/8![American Airlines logo]()
$465
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 11/910:55 pm
PDX
- SJU
1 stop11h 05m
Delta
Tue 11/177:15 am
SJU
- PDX
2 stops15h 02m
Delta
Deal found 6/8![Delta logo]()
$466
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Sun 11/110:56 pm
PDX
- MBJ
1 stop12h 33m
United Airlines
Sat 11/71:40 pm
MBJ
- PDX
1 stop11h 58m
United Airlines
Deal found 6/8![United Airlines logo]()
$469
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 June 10, 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 June 10, 2026.
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:05 pm
PDX
- MBJ
1 stop11h 20m
Delta
Tue 10/201:32 pm
MBJ
- PDX
1 stop10h 54m
Delta
Deal found 6/8![Delta logo]()
$422
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Wed 11/1110:45 pm
PDX
- STT
1 stop9h 22m
American Airlines
Wed 11/186:17 pm
STT
- PDX
2 stops20h 53m
American Airlines
Deal found 6/10![American Airlines logo]()
$425
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:50 am
PDX
- SJU
2 stops12h 15m
Southwest
Wed 8/1911:50 am
SJU
- PDX
2 stops13h 05m
Southwest
Deal found 6/6![Southwest logo]()
$466
This United Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/210:59 pm
PDX
- MBJ
1 stop11h 47m
United Airlines
Wed 11/112:48 pm
MBJ
- PDX
1 stop12h 14m
United Airlines
Deal found 6/5![United Airlines logo]()
$522
This FlightHub deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:27 pm
PDX
- SXM
2 stops31h 35m
JetBlue
Sun 9/63:02 pm
SXM
- PDX
2 stops25h 02m
JetBlue
Deal found 6/6![JetBlue logo]()
$657
This Air Canada deal was found by Cheapflights users on 6/8. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/13:15 pm
PDX
- BGI
2 stops19h 20m
Air Canada
Thu 11/54:10 pm
BGI
- PDX
2 stops26h 31m
Air Canada
Deal found 6/8![Air Canada logo]()
$712
This FlightHub deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:45 pm
PDX
- GCM
2 stops37h 45m
Multiple Airlines
Sun 9/276:10 pm
GCM
- PDX
1 stop20h 49m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$777
This Delta deal was found by Cheapflights users on 6/7. 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.
Mon 11/23:50 pm
PDX
- MBJ
2 stops17h 35m
Delta
Tue 11/106:00 pm
MBJ
- PDX
2 stops18h 16m
Delta
Deal found 6/7![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:10 pm
PDX
- SJU
2 stops11h 35m
Southwest
Tue 11/175:45 am
SJU
- PDX
2 stops13h 15m
Southwest
Deal found 6/6![Southwest logo]()
$466
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/210:05 pm
PDX
- MBJ
1 stop11h 20m
Delta
Wed 11/116:00 pm
MBJ
- PDX
2 stops18h 16m
Delta
Deal found 6/5![Delta logo]()
$437
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2111:17 pm
PDX
- MBJ
1 stop10h 26m
United Airlines
Thu 9/2412:52 pm
MBJ
- PDX
2 stops22h 35m
United Airlines
Deal found 6/7![United Airlines logo]()
$527
This Delta deal was found by Cheapflights users on 6/9. 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.
Sat 9/2610:00 pm
PDX
- SJU
1 stop11h 13m
Delta
Sat 10/3112:46 pm
SJU
- PDX
2 stops14h 05m
Delta
Deal found 6/9![Delta logo]()
$466
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:05 pm
PDX
- SJU
1 stop10h 51m
Delta
Sat 10/171:06 pm
SJU
- PDX
1 stop11h 21m
Delta
Deal found 6/5![Delta logo]()
$476
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Mon 11/25:15 am
PDX
- PUJ
1 stop9h 03m
United Airlines
Thu 11/57:30 pm
PUJ
- PDX
1 stop17h 51m
United Airlines
Deal found 6/8![United Airlines logo]()
$584
This Southwest deal was found by Cheapflights users on 6/8. 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.
Sun 9/610:45 pm
PDX
- STT
2 stops12h 05m
Southwest
Sun 9/202:10 pm
STT
- PDX
2 stops12h 30m
Southwest
Deal found 6/8![Southwest logo]()
$593
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:40 pm
PDX
- SJU
2 stops13h 16m
Delta
Wed 10/217:30 am
SJU
- PDX
2 stops19h 21m
Delta
Deal found 6/5![Delta logo]()
$476
This American Airlines deal was found by Cheapflights users on 6/9. 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.
Thu 11/510:45 pm
PDX
- SXM
1 stop13h 35m
American Airlines
Fri 11/205:24 pm
SXM
- PDX
2 stops23h 33m
American Airlines
Deal found 6/9![American Airlines logo]()
$702
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:55 pm
PDX
- SJU
2 stops14h 02m
United Airlines
Tue 10/132:00 pm
SJU
- PDX
1 stop10h 10m
United Airlines
Deal found 6/7![United Airlines logo]()
$589
This Southwest deal was found by Cheapflights users on 6/8. 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.
Mon 10/56:15 pm
PDX
- NAS
2 stops16h 00m
Southwest
Tue 10/132:10 pm
NAS
- PDX
2 stops11h 10m
Southwest
Deal found 6/8![Southwest logo]()
$594
This Air Canada deal was found by Cheapflights users on 6/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:10 pm
PDX
- BGI
2 stops15h 25m
Air Canada
Fri 12/44:10 pm
BGI
- PDX
2 stops30h 21m
Air Canada
Deal found 6/9![Air Canada logo]()
$719
This Justfly.com deal was found by Cheapflights users on 6/7. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/32:20 pm
PDX
- BGI
1 stop18h 42m
JetBlue
Sat 7/111:30 pm
BGI
- PDX
1 stop26h 33m
JetBlue
Deal found 6/7![JetBlue logo]()
$731
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/311:34 pm
PDX
- SDQ
2 stops12h 50m
American Airlines
Sat 9/127:34 pm
SDQ
- PDX
2 stops18h 21m
American Airlines
Deal found 6/5![American Airlines logo]()
$713
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Sat 10/2411:30 pm
PDX
- STT
1 stop12h 48m
United Airlines
Sat 10/3112:02 pm
STT
- PDX
2 stops13h 36m
United Airlines
Deal found 6/8![United Airlines logo]()
$627
This Southwest deal was found by Cheapflights users on 6/7. 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.
Tue 11/101:00 pm
PDX
- NAS
2 stops20h 15m
Southwest
Sun 11/151:10 pm
NAS
- PDX
2 stops13h 45m
Southwest
Deal found 6/7![Southwest logo]()
$634
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/131:38 pm
PDX
- POP
2 stops20h 06m
American Airlines
Thu 8/201:34 pm
POP
- PDX
2 stops24h 20m
American Airlines
Deal found 6/6![American Airlines logo]()
$715
This American Airlines deal was found by Cheapflights users on 6/9. 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.
Sat 9/2612:01 pm
PDX
- POP
2 stops21h 18m
American Airlines
Sat 10/31:10 pm
POP
- PDX
2 stops24h 45m
American Airlines
Deal found 6/9![American Airlines logo]()
$715
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 10/510:00 pm
PDX
- NAS
1 stop10h 30m
Delta
Tue 10/131:16 pm
NAS
- PDX
2 stops13h 31m
Delta
Deal found 6/8![Delta logo]()
$594
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2511:02 pm
PDX
- SDQ
2 stops12h 08m
United Airlines
Wed 9/236:00 am
SDQ
- PDX
2 stops16h 18m
United Airlines
Deal found 6/7![United Airlines logo]()
$663
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/31:00 pm
PDX
- GCM
2 stops20h 35m
Southwest
Wed 11/111:30 pm
GCM
- PDX
2 stops12h 45m
Southwest
Deal found 6/6![Southwest logo]()
$682
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:28 pm
PDX
- POP
2 stops18h 17m
American Airlines
Wed 7/221:26 pm
POP
- PDX
2 stops13h 29m
American Airlines
Deal found 6/5![American Airlines logo]()
$715
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated June 10, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated June 10, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/310:57 pm
PDX
- SJU
2 stops12h 50m
American Airlines
Thu 7/97:00 am
SJU
- PDX
1 stop19h 30m
American Airlines
Deal found 6/7![American Airlines logo]()
$498
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/310:57 pm
PDX
- SJU
2 stops12h 50m
American Airlines
Fri 7/107:25 am
SJU
- PDX
1 stop19h 30m
American Airlines
Deal found 6/5![American Airlines logo]()
$530
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:00 am
PDX
- MBJ
1 stop8h 45m
United Airlines
Thu 7/94:12 pm
MBJ
- PDX
2 stops19h 22m
United Airlines
Deal found 6/7![United Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:07 am
PDX
- SJU
1 stop15h 43m
American Airlines
Sat 7/117:00 am
SJU
- PDX
1 stop19h 30m
American Airlines
Deal found 6/6![American Airlines logo]()
$556
This American Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/85:07 am
PDX
- NAS
1 stop8h 58m
American Airlines
Tue 7/146:05 pm
NAS
- PDX
1 stop9h 50m
American Airlines
Deal found 6/8![American Airlines logo]()
$595
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1011:40 pm
PDX
- SJU
1 stop12h 04m
United Airlines
Mon 7/131:00 am
SJU
- PDX
1 stop11h 25m
United Airlines
Deal found 6/7![United Airlines logo]()
$543
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/115:00 am
PDX
- MBJ
1 stop8h 45m
United Airlines
Sat 7/1812:52 pm
MBJ
- PDX
1 stop10h 23m
United Airlines
Deal found 6/7![United Airlines logo]()
$530
This American Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1411:41 pm
PDX
- NAS
1 stop14h 24m
American Airlines
Tue 7/212:18 pm
NAS
- PDX
1 stop12h 37m
American Airlines
Deal found 6/7![American Airlines logo]()
$590
This American Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2011:15 pm
PDX
- SJU
2 stops13h 32m
American Airlines
Fri 7/247:00 am
SJU
- PDX
1 stop19h 30m
American Airlines
Deal found 6/7![American Airlines logo]()
$588
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Wed 7/225:07 am
PDX
- SJU
2 stops13h 52m
American Airlines
Sat 8/17:25 am
SJU
- PDX
1 stop19h 30m
American Airlines
Deal found 6/10![American Airlines logo]()
$558
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/285:49 am
PDX
- SJU
1 stop14h 10m
American Airlines
Mon 8/37:25 am
SJU
- PDX
1 stop19h 30m
American Airlines
Deal found 6/6![American Airlines logo]()
$520
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/285:49 am
PDX
- SJU
1 stop14h 10m
American Airlines
Fri 8/1412:55 am
SJU
- PDX
1 stop20h 05m
American Airlines
Deal found 6/9![American Airlines logo]()
$568
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 June 10, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
This Delta deal was found by Cheapflights users on 6/10. 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.
Tue 9/110:35 pm
PDX
- MBJ
1 stop10h 59m
Delta
Deal found 6/10![Delta logo]()
$187
This American Airlines deal was found by Cheapflights users on 6/9. 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.
Sun 7/2612:45 am
PDX
- STT
1 stop12h 21m
American Airlines
Deal found 6/9![American Airlines logo]()
$208
This Southwest deal was found by Cheapflights users on 6/8. 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.
Tue 9/156:25 pm
PDX
- SJU
2 stops13h 35m
Southwest
Deal found 6/8![Southwest logo]()
$218
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/111:34 pm
PDX
- PUJ
2 stops12h 32m
American Airlines
Deal found 6/9![American Airlines logo]()
$220
This Delta deal was found by Cheapflights users on 6/8. 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.
Thu 9/2410:00 pm
PDX
- SJU
1 stop11h 13m
Delta
Deal found 6/8![Delta logo]()
$233
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1210:33 pm
PDX
- SJU
1 stop10h 24m
United Airlines
Deal found 6/7![United Airlines logo]()
$238
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Tue 7/2811:30 pm
PDX
- STT
1 stop9h 50m
United Airlines
Deal found 6/9![United Airlines logo]()
$258
This Southwest deal was found by Cheapflights users on 6/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:00 pm
PDX
- STT
2 stops16h 45m
Southwest
Deal found 6/9![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 6/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/297:40 pm
PDX
- SJU
2 stops12h 50m
Southwest
Deal found 6/9![Southwest logo]()
$265
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2811:15 pm
PDX
- STT
2 stops13h 45m
American Airlines
Deal found 6/9![American Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2910:59 pm
PDX
- SJU
2 stops13h 48m
American Airlines
Deal found 6/8![American Airlines logo]()
$283
This Delta deal was found by Cheapflights users on 6/9. 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.
Sun 7/2610:40 pm
PDX
- STT
1 stop10h 31m
Delta
Deal found 6/9![Delta logo]()
$285
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 June 10, 2026.
Round-trip from | $420 (American Airlines) |
|---|---|
One-way from | $208 (American Airlines) |
Popular in | December |
Cheapest in | September |
Average price | $676 |
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 June 10, 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
Tue 10/13
10:05 pm-11:25 am
1 stop11h 20m
Montego Bay Sangster Intl
Tue 10/20
1:32 pm-10:26 pm
1 stop10h 54m
$422
PortlandSaint Thomas Island
PDX - STT
PDXSTT
Portland
Wed 11/11
10:45 pm-12:07 pm
1 stop9h 22m
Saint Thomas Island Cyril E King
Wed 11/18
6:17 pm-11:10 am
2 stops20h 53m
$425
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Mon 11/2
3:50 pm-12:25 pm
2 stops17h 35m
Montego Bay Sangster Intl
Tue 11/10
6:00 pm-9:16 am
2 stops18h 16m
$427
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Mon 11/2
10:05 pm-12:25 pm
1 stop11h 20m
Montego Bay Sangster Intl
Wed 11/11
6:00 pm-9:16 am
2 stops18h 16m
$437
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Wed 8/5
5:50 am-9:05 pm
2 stops12h 15m
San Juan Luis Munoz Marin Intl
Wed 8/19
11:50 am-9:55 pm
2 stops13h 05m
$466
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Mon 11/9
8:10 pm-11:45 am
2 stops11h 35m
San Juan Luis Munoz Marin Intl
Tue 11/17
5:45 am-3:00 pm
2 stops13h 15m
$466
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Sat 9/26
10:00 pm-12:13 pm
1 stop11h 13m
San Juan Luis Munoz Marin Intl
Sat 10/31
12:46 pm-11:51 pm
2 stops14h 05m
$466
Quickest round-trip
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Thu 10/15
10:05 pm-11:56 am
1 stop10h 51m
San Juan Luis Munoz Marin Intl
Sat 10/17
1:06 pm-9:27 pm
1 stop11h 21m
$476
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Fri 10/16
7:40 pm-11:56 am
2 stops13h 16m
San Juan Luis Munoz Marin Intl
Wed 10/21
7:30 am-11:51 pm
2 stops19h 21m
$476
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Mon 11/2
10:59 pm-1:46 pm
1 stop11h 47m
Montego Bay Sangster Intl
Wed 11/11
2:48 pm-12:02 am
1 stop12h 14m
$522
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-STT
PDX-SJU
PDX-SXM
PDX-BGI
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-STT
PDX-SJU
PDX-SXM
What is the cheapest month to book a flight from Portland to Caribbean?
Currently, March is the cheapest month in which you can book a flight from Portland to Caribbean (average of $191). Flying from Portland to Caribbean in May is currently the most expensive (average of $365). 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.
How far ahead should I book a flight from Portland to Caribbean?
The best time to book flights from Portland to Caribbean is 19 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.
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 June 10, 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.
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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 June 10, 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 June 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$190 | Average$709 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$247 | Average$673 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$261 | Average$478 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$392 | Average$754 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$408 | Average$612 | FlexibilityNo cancel fee | On-time63% |