$161+ Cheap flights from Portland (PDX) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Oct 7 — Oct 141
Round-trip
1 adult, Economy
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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
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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 September 7, 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 September 7, 2026.
This American Airlines deal was found by Cheapflights users on 9/5. 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 10/2310:55 pm -
2 stops13h 06m
Thu 10/292:27 pm -
1 stop11h 38m
Deal found 9/5![American Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Mon 11/911:09 pm -
2 stops14h 56m
Sat 11/146:05 am -
2 stops15h 43m
Deal found 9/5![American Airlines logo]()
$414
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Wed 11/1111:00 pm -
1 stop11h 19m
Wed 11/183:17 pm -
1 stop12h 42m
Deal found 9/5![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Sat 10/2410:55 pm -
2 stops13h 00m
Sat 10/313:58 pm -
2 stops24h 30m
Deal found 9/5![American Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/78:00 am -
1 stop11h 59m
Fri 12/183:38 pm -
1 stop12h 31m
Deal found 9/2![American Airlines logo]()
$444
This American Airlines deal was found by Cheapflights users on 9/7. 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.
Wed 12/28:00 am -
1 stop11h 59m
Wed 12/97:30 am -
2 stops14h 18m
Deal found 9/7![American Airlines logo]()
$449
This Expedia deal was found by Cheapflights users on 9/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:00 am -
2 stops36h 35m
Wed 12/97:45 pm -
2 stops22h 56m
Deal found 9/5![Air Canada logo]()
$466
This Air Canada deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/257:15 pm -
2 stops22h 25m
Sun 11/17:45 pm -
2 stops22h 56m
Deal found 9/3![Air Canada logo]()
$471
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 11/211:49 pm -
1 stop14h 20m
Wed 11/111:21 pm -
1 stop13h 22m
Deal found 9/3![American Airlines logo]()
$472
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/711:09 pm -
2 stops11h 54m
Fri 12/117:30 am -
2 stops14h 24m
Deal found 9/3![American Airlines logo]()
$474
This Air Canada deal was found by Cheapflights users on 9/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2810:00 am -
2 stops23h 45m
Wed 12/912:35 pm -
2 stops30h 06m
Deal found 9/5![Air Canada logo]()
$476
This Delta deal was found by Cheapflights users on 9/7. 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 11/210:15 pm -
1 stop11h 15m
Wed 11/112:16 pm -
2 stops12h 35m
Deal found 9/7![Delta logo]()
$477
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 September 7, 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 September 7, 2026.
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 11/211:09 pm -
2 stops12h 13m
Tue 11/106:09 pm -
2 stops22h 35m
Deal found 9/3![American Airlines logo]()
$477
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1611:59 pm -
1 stop11h 31m
Fri 10/2312:52 pm -
2 stops22h 39m
Deal found 9/4![United Airlines logo]()
$477
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 12/75:59 pm -
2 stops16h 51m
Mon 3/16:15 am -
2 stops21h 36m
Deal found 9/3![Delta logo]()
$526
This Southwest deal was found by Cheapflights users on 9/6. 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.
Thu 12/106:00 am -
2 stops13h 20m
Mon 12/214:20 pm -
2 stops12h 10m
Deal found 9/6![Southwest logo]()
$566
This Air Canada deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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.
Mon 11/167:00 am -
2 stops25h 30m
Thu 11/192:05 pm -
2 stops33h 41m
Deal found 9/2![Air Canada logo]()
$571
This Mytrip deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/1710:10 am -
2 stops25h 10m
Sat 10/246:00 pm -
2 stops27h 31m
Deal found 9/2![Multiple Airlines logo]()
$660
This Alaska Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/237:02 am -
1 stop17h 58m
Tue 3/26:50 am -
2 stops29h 16m
Deal found 9/4![Alaska Airlines logo]()
$804
This Delta deal was found by Cheapflights users on 9/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:00 pm -
1 stop11h 03m
Sat 10/316:45 am -
2 stops16h 17m
Deal found 9/6![Delta logo]()
$530
This United Airlines deal was found by Cheapflights users on 9/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:30 pm -
1 stop11h 01m
Sat 10/3112:07 pm -
1 stop11h 08m
Deal found 9/6![United Airlines logo]()
$547
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 1/172:05 pm -
2 stops19h 55m
Fri 1/221:55 pm -
2 stops11h 00m
Deal found 9/4![Southwest logo]()
$570
This Air Canada deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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.
Mon 12/77:10 pm -
2 stops41h 20m
Mon 12/145:25 pm -
2 stops29h 06m
Deal found 9/3![Air Canada logo]()
$589
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/267:26 pm -
2 stops14h 30m
Thu 10/2912:07 pm -
2 stops15h 37m
Deal found 9/3![United Airlines logo]()
$559
This Southwest deal was found by Cheapflights users on 9/6. 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 11/91:45 pm -
2 stops19h 30m
Thu 11/121:10 pm -
2 stops13h 45m
Deal found 9/6![Southwest logo]()
$576
This American Airlines deal was found by Cheapflights users on 9/7. 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.
Sat 10/249:44 pm -
1 stop11h 57m
Sat 10/311:21 pm -
1 stop10h 23m
Deal found 9/7![American Airlines logo]()
$637
This Delta deal was found by Cheapflights users on 9/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/410:00 pm -
1 stop11h 33m
Thu 10/81:16 pm -
1 stop10h 33m
Deal found 9/6![Delta logo]()
$585
This Air Canada deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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.
Mon 10/267:05 am -
2 stops26h 20m
Thu 10/291:20 pm -
2 stops34h 26m
Deal found 9/4![Air Canada logo]()
$628
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 2/2710:55 pm -
2 stops12h 52m
Sat 3/612:48 pm -
1 stop10h 56m
Deal found 9/4![American Airlines logo]()
$654
This United Airlines deal was found by Cheapflights users on 9/7. 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 10/210:33 pm -
1 stop11h 10m
Tue 10/612:52 pm -
2 stops22h 36m
Deal found 9/7![United Airlines logo]()
$596
This Southwest deal was found by Cheapflights users on 9/7. 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.
Thu 9/247:35 pm -
2 stops10h 35m
Wed 9/3011:50 am -
2 stops13h 10m
Deal found 9/7![Southwest logo]()
$611
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 12/125:35 am -
2 stops13h 38m
Fri 3/57:00 am -
2 stops20h 32m
Deal found 9/3![Delta logo]()
$626
This Mytrip deal was found by Cheapflights users on 9/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/410:00 am -
2 stops23h 25m
Tue 2/92:25 pm -
2 stops27h 16m
Deal found 9/5![Air Canada logo]()
$639
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/265:30 am -
2 stops29h 18m
Fri 10/302:01 pm -
2 stops22h 17m
Deal found 9/3![United Airlines logo]()
$597
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 1/2711:00 pm -
1 stop10h 04m
Sun 1/315:05 pm -
2 stops22h 04m
Deal found 9/3![American Airlines logo]()
$659
This Delta deal was found by Cheapflights users on 9/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/39:45 pm -
1 stop12h 45m
Sun 2/71:20 pm -
1 stop11h 07m
Deal found 9/6![Delta logo]()
$650
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/167:50 pm -
2 stops14h 55m
Fri 10/233:05 pm -
2 stops22h 20m
Deal found 9/3![Southwest logo]()
$654
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 10/2711:30 pm -
1 stop12h 10m
Fri 10/301:05 am -
2 stops15h 20m
Deal found 9/2![United Airlines logo]()
$616
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” 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 11/511:00 pm -
1 stop13h 31m
Tue 11/103:26 pm -
1 stop12h 33m
Deal found 9/2![American Airlines logo]()
$715
This Delta deal was found by Cheapflights users on 9/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:25 pm -
2 stops19h 16m
Thu 1/72:40 pm -
2 stops11h 52m
Deal found 9/6![Delta logo]()
$654
This Southwest deal was found by Cheapflights users on 9/6. 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.
Sun 12/67:00 pm -
2 stops15h 45m
Sun 12/132:40 pm -
2 stops23h 00m
Deal found 9/6![Southwest logo]()
$666
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 11/29:00 am -
3 stops26h 14m
Tue 11/103:20 pm -
2 stops26h 14m
Deal found 9/3![United Airlines logo]()
$617
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated September 7, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated September 7, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/2511:06 pm -
1 stop12h 44m
Wed 9/302:22 pm -
1 stop12h 06m
Deal found 9/4![American Airlines logo]()
$491
This United Airlines deal was found by Cheapflights users on 9/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:29 pm -
2 stops14h 05m
Sun 10/41:00 am -
1 stop11h 50m
Deal found 9/6![United Airlines logo]()
$506
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:08 pm -
2 stops11h 49m
Sat 10/317:30 am -
1 stop17h 23m
Deal found 9/3![American Airlines logo]()
$489
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Fri 10/22:07 pm -
1 stop24h 09m
Tue 10/612:18 pm -
1 stop10h 53m
Deal found 9/6![American Airlines logo]()
$482
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/165:20 am -
1 stop8h 52m
Fri 10/2312:18 pm -
1 stop10h 53m
Deal found 9/3![American Airlines logo]()
$472
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1611:30 pm -
2 stops12h 00m
Fri 10/2312:52 pm -
2 stops22h 39m
Deal found 9/3![United Airlines logo]()
$497
This American Airlines deal was found by Cheapflights users on 9/5. 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 10/2310:55 pm -
2 stops13h 06m
Thu 10/292:27 pm -
1 stop11h 38m
Deal found 9/5![American Airlines logo]()
$322
This Justfly.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/237:45 pm -
2 stops36h 25m
Sat 10/3110:40 pm -
2 stops20h 01m
Deal found 9/3![Air Canada logo]()
$486
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Sat 10/2410:55 pm -
2 stops13h 00m
Sat 10/313:58 pm -
2 stops24h 30m
Deal found 9/5![American Airlines logo]()
$440
This United Airlines deal was found by Cheapflights users on 9/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:59 pm -
1 stop11h 40m
Tue 10/272:01 pm -
2 stops22h 17m
Deal found 9/6![United Airlines logo]()
$477
This Air Canada deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/257:15 pm -
2 stops22h 25m
Sun 11/17:45 pm -
2 stops22h 56m
Deal found 9/3![Air Canada logo]()
$471
This Air Canada deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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.
Wed 10/2810:00 am -
2 stops23h 45m
Wed 11/117:45 pm -
2 stops22h 56m
Deal found 9/3![Air Canada logo]()
$466
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 September 7, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 11/1311:09 pm -
2 stops11h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![American Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/112:38 pm -
2 stops31h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 11/1212:02 pm -
2 stops34h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/412:38 pm -
2 stops31h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$195
This Delta deal was found by Cheapflights users on 9/5. 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 12/75:34 pm -
2 stops15h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Delta logo]()
$212
This Delta deal was found by Cheapflights users on 9/7. 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.
Thu 1/287:40 pm -
2 stops13h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/1911:06 am -
2 stops26h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1812:38 pm -
2 stops17h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$249
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 12/111:01 pm -
1 stop15h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![American Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:38 pm -
2 stops22h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$254
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/195:20 am -
1 stop15h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![American Airlines logo]()
$255
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Wed 12/28:00 am -
1 stop11h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$258
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 September 7, 2026.
Round-trip from | $322 (American Airlines) |
|---|---|
One-way from | $161 (American Airlines) |
Popular in | March |
Cheapest in | September |
Average price | $466 |
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 7,457,451 searches. Data last updated September 7, 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
Quickest round-trip
PortlandMontego Bay
PDX Portland - MBJ Montego Bay Sangster Intl
PDXMBJ
Portland
Mon 12/7
11:03 pm-10:15 am
1 stop8h 12m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$212
PortlandMontego Bay
PDX Portland - MBJ Montego Bay Sangster Intl
PDXMBJ
Portland
Sun 11/15
7:35 pm-12:30 pm
2 stops13h 55m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$212
PortlandMontego Bay
PDX Portland - MBJ Montego Bay Sangster Intl
PDXMBJ
Portland
Mon 12/7
5:34 pm-12:27 pm
2 stops15h 53m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$212
PortlandSaint Thomas Island
PDX Portland - STT Saint Thomas Island Cyril E King
PDXSTT
Portland
Fri 12/11
7:21 pm-2:31 pm
2 stops15h 10m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$218
PortlandSaint Thomas Island
PDX Portland - STT Saint Thomas Island Cyril E King
PDXSTT
Portland
Thu 1/28
7:40 pm-1:20 pm
2 stops13h 40m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$218
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Wed 12/9
6:30 am-9:50 pm
2 stops11h 20m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$253
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Sat 1/2
7:36 pm-1:05 pm
2 stops13h 29m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$253
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Sun 10/4
10:00 pm-12:03 pm
1 stop11h 03m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$253
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Tue 12/15
5:34 pm-12:36 pm
2 stops15h 02m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$253
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Wed 12/9
8:00 am-11:59 pm
1 stop11h 59m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$258
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-STT
PDX-PUJ
PDX-MBJ
PDX-NAS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Caribbean
PDX-0CB
PDX-SJU
PDX-STT
PDX-PUJ
PDX-MBJ
What is the cheapest month to book a flight from Portland to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Portland to Caribbean (average of $645). Flying from Portland to Caribbean in December is currently the most expensive (average of $850). 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 September 7, 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
Entertainment
7.5
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Related info for your journey
Find useful and relevant information for your journey from Portland to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 September 7, 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 7,457,451 searches. Data last updated September 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$235 | Average$705 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$247 | Average$709 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$261 | Average$478 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$392 | Average$811 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$408 | Average$640 | FlexibilityNo cancel fee | On-time63% |