$232+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Nov 24 — Dec 11
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Portland to Caribbean
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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 October 25, 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 October 25, 2026.
This Mytrip deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:09 pm -
2 stops13h 31m
Wed 12/95:01 am -
2 stops34h 52m
Deal found 10/24![Frontier logo]()
$493
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Sat 12/1211:13 pm -
2 stops12h 49m
Tue 12/221:09 pm -
2 stops15h 00m
Deal found 10/20![American Airlines logo]()
$500
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1111:00 pm -
1 stop9h 16m
Wed 11/183:15 pm -
1 stop12h 44m
Deal found 10/22![American Airlines logo]()
$524
This Southwest deal was found by Cheapflights users on 10/20. 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.
Mon 11/97:00 pm -
2 stops12h 40m
Mon 11/2311:20 am -
2 stops14h 30m
Deal found 10/20![Southwest logo]()
$525
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Thu 11/1212:02 pm -
2 stops17h 28m
Thu 11/195:30 pm -
1 stop30h 02m
Deal found 10/20![Multiple Airlines logo]()
$527
This WAYA deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:15 am -
1 stop13h 52m
Fri 12/115:01 am -
1 stop19h 30m
Deal found 10/24![Multiple Airlines logo]()
$535
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/611:09 pm -
2 stops13h 26m
Tue 11/101:07 pm -
2 stops14h 36m
Deal found 10/22![American Airlines logo]()
$538
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Sat 12/1211:13 pm -
2 stops12h 29m
Thu 12/1712:59 pm -
1 stop15h 35m
Deal found 10/20![American Airlines logo]()
$538
This Southwest deal was found by Cheapflights users on 10/20. 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.
Mon 11/97:00 pm -
2 stops14h 15m
Wed 11/181:10 pm -
2 stops13h 15m
Deal found 10/20![Southwest logo]()
$543
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:58 pm -
2 stops41h 22m
Thu 12/109:38 am -
1 stop15h 04m
Deal found 10/22![Multiple Airlines logo]()
$547
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:00 am -
1 stop10h 29m
Wed 12/161:28 pm -
1 stop11h 14m
Deal found 10/23![Multiple Airlines logo]()
$552
This Mytrip deal was found by Cheapflights users on 10/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:02 pm -
2 stops18h 13m
Sat 10/3110:20 am -
2 stops28h 52m
Deal found 10/21![Frontier logo]()
$553
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 October 25, 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 October 25, 2026.
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Sat 12/1211:13 pm -
2 stops12h 49m
Tue 12/221:09 pm -
2 stops15h 00m
Deal found 10/20![American Airlines logo]()
$500
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/115:24 pm -
2 stops16h 36m
Fri 1/151:54 pm -
1 stop12h 15m
Deal found 10/24![Delta logo]()
$500
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Sat 11/711:30 pm -
2 stops11h 10m
Tue 11/178:25 am -
2 stops13h 44m
Deal found 10/20![United Airlines logo]()
$634
This Southwest deal was found by Cheapflights users on 10/20. 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.
Sat 12/51:40 pm -
2 stops19h 35m
Sat 12/121:55 pm -
2 stops10h 30m
Deal found 10/20![Southwest logo]()
$665
This Air Canada deal was found by Cheapflights users on 10/21. 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 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 10/21![Air Canada logo]()
$678
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 2/97:00 am -
1 stop10h 45m
Thu 2/186:10 am -
2 stops31h 15m
Deal found 10/20![Multiple Airlines logo]()
$738
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/57:40 pm -
2 stops13h 00m
Wed 1/201:50 pm -
1 stop12h 36m
Deal found 10/22![Delta logo]()
$500
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/112:48 pm -
2 stops17h 36m
Fri 1/151:14 pm -
1 stop15h 45m
Deal found 10/22![American Airlines logo]()
$520
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1111:00 pm -
1 stop9h 16m
Wed 11/183:15 pm -
1 stop12h 44m
Deal found 10/22![American Airlines logo]()
$524
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/51:45 pm -
2 stops18h 25m
Thu 1/144:50 pm -
2 stops18h 51m
Deal found 10/23![Delta logo]()
$538
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1611:10 pm -
1 stop10h 03m
Thu 11/192:54 pm -
1 stop10h 33m
Deal found 10/24![United Airlines logo]()
$643
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/611:09 pm -
2 stops13h 26m
Tue 11/104:53 pm -
1 stop11h 06m
Deal found 10/22![American Airlines logo]()
$538
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/87:00 am -
1 stop13h 58m
Wed 2/172:15 pm -
2 stops13h 17m
Deal found 10/24![Delta logo]()
$566
This Justfly.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/83:15 pm -
2 stops21h 15m
Mon 12/145:25 pm -
2 stops44h 01m
Deal found 10/25![Air Canada logo]()
$698
This Southwest deal was found by Cheapflights users on 10/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:40 pm -
2 stops21h 30m
Fri 11/202:40 pm -
2 stops22h 15m
Deal found 10/21![Southwest logo]()
$705
This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/117:10 am -
1 stop9h 50m
Wed 1/203:46 pm -
1 stop11h 29m
Deal found 10/21![United Airlines logo]()
$666
This American Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/711:00 pm -
1 stop9h 16m
Wed 11/113:15 pm -
1 stop12h 44m
Deal found 10/23![American Airlines logo]()
$558
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/96:40 am -
1 stop10h 16m
Wed 2/173:55 pm -
1 stop10h 31m
Deal found 10/24![Delta logo]()
$566
This Travelocity deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:00 am -
2 stops27h 15m
Fri 11/209:25 pm -
2 stops24h 06m
Deal found 10/25![Air Canada logo]()
$706
This Southwest deal was found by Cheapflights users on 10/20. 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.
Thu 11/196:20 am -
2 stops11h 35m
Thu 11/269:35 am -
2 stops11h 40m
Deal found 10/20![Southwest logo]()
$714
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/95:30 am -
2 stops15h 06m
Tue 2/233:46 pm -
1 stop11h 22m
Deal found 10/24![United Airlines logo]()
$666
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Sun 1/1711:09 pm -
1 stop13h 05m
Sat 1/235:04 pm -
2 stops22h 07m
Deal found 10/20![American Airlines logo]()
$559
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/25:00 am -
1 stop9h 25m
Fri 2/52:05 am -
2 stops16h 31m
Deal found 10/24![United Airlines logo]()
$666
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/3110:55 pm -
1 stop10h 05m
Tue 4/63:05 pm -
1 stop10h 21m
Deal found 10/22![Delta logo]()
$650
This American Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2211:01 pm -
1 stop9h 14m
Fri 12/44:53 pm -
2 stops22h 09m
Deal found 10/24![American Airlines logo]()
$600
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2811:24 pm -
1 stop11h 50m
Sat 1/92:54 pm -
2 stops21h 46m
Deal found 10/24![United Airlines logo]()
$668
This United Airlines deal was found by Cheapflights users on 10/20. 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 2/85:00 am -
1 stop9h 18m
Thu 2/182:15 pm -
1 stop12h 23m
Deal found 10/20![United Airlines logo]()
$672
This Delta deal was found by Cheapflights users on 10/20. 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 12/511:10 pm -
1 stop11h 40m
Sat 12/121:22 pm -
1 stop11h 56m
Deal found 10/20![Delta logo]()
$674
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1510:55 pm -
1 stop10h 05m
Wed 3/246:10 pm -
2 stops18h 06m
Deal found 10/23![Delta logo]()
$675
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/234:00 pm -
1 stop22h 18m
Sat 1/302:15 pm -
1 stop11h 00m
Deal found 10/22![United Airlines logo]()
$682
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated October 25, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 10/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:02 pm -
2 stops18h 13m
Sat 10/3110:20 am -
2 stops28h 52m
Deal found 10/21![Frontier logo]()
$553
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/611:09 pm -
2 stops13h 26m
Tue 11/101:07 pm -
2 stops14h 36m
Deal found 10/22![American Airlines logo]()
$538
This American Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/711:00 pm -
1 stop9h 16m
Wed 11/113:15 pm -
1 stop12h 44m
Deal found 10/23![American Airlines logo]()
$558
This Southwest deal was found by Cheapflights users on 10/20. 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.
Mon 11/97:00 pm -
2 stops12h 40m
Mon 11/2311:20 am -
2 stops14h 30m
Deal found 10/20![Southwest logo]()
$525
This Southwest deal was found by Cheapflights users on 10/20. 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.
Mon 11/97:00 pm -
2 stops14h 15m
Wed 11/181:10 pm -
2 stops13h 15m
Deal found 10/20![Southwest logo]()
$543
This Southwest deal was found by Cheapflights users on 10/20. 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.
Mon 11/98:10 pm -
2 stops11h 30m
Mon 11/1612:30 pm -
2 stops14h 55m
Deal found 10/20![Southwest logo]()
$556
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/1012:02 pm -
2 stops25h 13m
Thu 11/195:30 pm -
1 stop30h 02m
Deal found 10/20![Multiple Airlines logo]()
$563
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1111:00 pm -
1 stop9h 16m
Wed 11/183:15 pm -
1 stop12h 44m
Deal found 10/22![American Airlines logo]()
$524
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Thu 11/1212:02 pm -
2 stops17h 28m
Thu 11/195:30 pm -
1 stop30h 02m
Deal found 10/20![Multiple Airlines logo]()
$527
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 11/1211:00 pm -
1 stop15h 05m
Mon 11/238:25 am -
1 stop19h 47m
Deal found 10/21![American Airlines logo]()
$560
This Mytrip deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:31 pm -
2 stops25h 50m
Mon 11/163:55 pm -
2 stops23h 12m
Deal found 10/23![Frontier logo]()
$561
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 11/126:00 am -
2 stops12h 39m
Fri 11/201:18 pm -
1 stop14h 54m
Deal found 10/21![American Airlines logo]()
$566
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 October 25, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:10 pm -
1 stop14h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$232
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/55:48 pm -
2 stops14h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$248
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/132:48 pm -
2 stops17h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![American Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2910:28 pm -
2 stops43h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/312:02 pm -
2 stops34h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$281
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/117:00 pm -
2 stops15h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$283
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/3112:30 am -
2 stops16h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$283
This Southwest deal was found by Cheapflights users on 10/20. 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.
Sat 2/612:45 pm -
2 stops21h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/36:04 am -
1 stop13h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Delta logo]()
$293
This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/149:00 am -
3 stops26h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![United Airlines logo]()
$297
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Sat 2/65:00 am -
1 stop8h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![United Airlines logo]()
$311
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Wed 3/1710:00 pm -
1 stop16h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![American Airlines logo]()
$316
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 October 25, 2026.
Round-trip from | $493 (Mytrip) |
|---|---|
One-way from | $232 (Delta) |
Popular in | December |
Cheapest in | September |
Average price | $468 |
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 October 25, 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 Portland - MBJ Montego Bay Sangster Intl
PDXMBJ
Portland
Sat 11/14
11:10 pm-4:57 pm
1 stop14h 47m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$232
PortlandSaint Thomas Island
PDX Portland - STT Saint Thomas Island Cyril E King
PDXSTT
Portland
Tue 1/5
11:59 pm-4:14 pm
2 stops12h 15m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$248
PortlandSaint Thomas Island
PDX Portland - STT Saint Thomas Island Cyril E King
PDXSTT
Portland
Tue 1/5
5:48 pm-12:44 pm
2 stops14h 56m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$248
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Fri 12/11
8:25 am-1:00 am
2 stops12h 35m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$283
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Wed 2/3
5:00 am-12:36 am
2 stops15h 36m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$283
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Sat 12/12
6:50 am-12:09 am
1 stop13h 19m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$283
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Sat 12/12
7:00 am-12:36 am
2 stops13h 36m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$283
PortlandMontego Bay
PDX Portland - MBJ Montego Bay Sangster Intl
PDXMBJ
Portland
Sat 11/14
9:00 am-2:14 pm
3 stops26h 14m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$297
PortlandNassau
PDX Portland - NAS Nassau Intl
PDXNAS
Portland
Tue 3/16
12:30 am-1:40 pm
2 stops10h 10m
Nassau Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$311
PortlandNassau
PDX Portland - NAS Nassau Intl
PDXNAS
Portland
Wed 3/17
10:00 pm-5:54 pm
1 stop16h 54m
Nassau Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$316
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-STT
PDX-SJU
PDX-NAS
PDX-AUA
PDX-SDQ
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-STT
PDX-SJU
PDX-NAS
PDX-AUA
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 $648). Flying from Portland to Caribbean in March is currently the most expensive (average of $837). 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 90 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 October 25, 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
Overall
7.9
Crew
8.6
Entertainment
7.4
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.4
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.4
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.4
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.4
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.4
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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.
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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 October 25, 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 October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$234 | Average$698 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$247 | Average$706 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$261 | Average$624 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$392 | Average$748 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$408 | Average$627 | FlexibilityNo cancel fee | On-time63% |