$175+ Cheap flights from Caribbean to Portland (PDX)
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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Nov 21 — Nov 281
Round-trip
1 adult, Economy
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Find cheap flights from Caribbean to Portland 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 Caribbean to Portland
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Cheapest flights from Caribbean to PortlandExplore the most affordable flight options available from Caribbean to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 22, 2026.
Explore the most affordable flight options available from Caribbean to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 22, 2026.
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/32:54 pm -
1 stop30h 48m
Thu 12/104:27 pm -
2 stops18h 47m
Deal found 10/19![United Airlines logo]()
$443
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.
Thu 11/52:16 pm -
1 stop10h 33m
Mon 11/911:10 pm -
1 stop14h 47m
Deal found 10/21![Delta logo]()
$511
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 11/511:05 am -
2 stops14h 05m
Mon 11/911:09 pm -
2 stops12h 13m
Deal found 10/21![American Airlines logo]()
$513
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:30 pm -
2 stops14h 55m
Mon 12/76:20 am -
2 stops12h 05m
Deal found 10/19![Southwest logo]()
$513
This eDestinos deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/108:45 am -
2 stops19h 09m
Mon 11/165:05 am -
2 stops30h 14m
Deal found 10/18![Multiple Airlines logo]()
$515
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:20 pm -
2 stops21h 16m
Sun 11/87:15 pm -
2 stops15h 59m
Deal found 10/19![United Airlines logo]()
$523
This eDestinos deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:15 am -
3 stops54h 56m
Sun 11/156:08 am -
2 stops27h 17m
Deal found 10/19![Multiple Airlines logo]()
$540
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.
Mon 12/218:00 am -
1 stop20h 34m
Wed 12/3011:28 pm -
1 stop18h 42m
Deal found 10/20![American Airlines logo]()
$560
This WAYA deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/23:28 am -
1 stop21h 14m
Mon 12/77:00 am -
1 stop14h 58m
Deal found 10/19![Multiple Airlines logo]()
$564
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 11/113:20 pm -
1 stop10h 50m
Mon 11/167:35 pm -
2 stops13h 20m
Deal found 10/21![Delta logo]()
$566
This eDestinos deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:55 pm -
2 stops23h 17m
Sun 11/155:05 am -
2 stops28h 20m
Deal found 10/19![Multiple Airlines logo]()
$567
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.
Tue 11/107:30 am -
1 stop20h 29m
Mon 11/1611:00 pm -
1 stop19h 39m
Deal found 10/21![American Airlines logo]()
$582
Best flights from Caribbean to PortlandDiscover carefully curated flight deals from Caribbean to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 22, 2026.
Discover carefully curated flight deals from Caribbean to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 22, 2026.
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/32:54 pm -
1 stop30h 48m
Thu 12/104:27 pm -
2 stops18h 47m
Deal found 10/19![United Airlines logo]()
$443
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.
Thu 11/52:16 pm -
1 stop10h 33m
Mon 11/911:20 pm -
2 stops14h 37m
Deal found 10/21![Delta logo]()
$511
This American Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:26 pm -
1 stop11h 35m
Thu 12/105:00 am -
1 stop9h 07m
Deal found 10/19![American Airlines logo]()
$598
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/112:30 pm -
2 stops14h 55m
Sat 1/91:15 pm -
2 stops18h 10m
Deal found 10/19![Southwest logo]()
$630
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:16 pm -
1 stop10h 33m
Sun 11/810:15 pm -
2 stops15h 42m
Deal found 10/19![Delta logo]()
$511
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:20 pm -
2 stops21h 16m
Sun 11/87:15 pm -
2 stops15h 59m
Deal found 10/19![United Airlines logo]()
$523
This American Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1411:34 am -
1 stop16h 39m
Sat 1/211:36 pm -
2 stops12h 05m
Deal found 10/17![American Airlines logo]()
$609
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/113:20 pm -
1 stop10h 50m
Sun 11/155:51 pm -
2 stops15h 04m
Deal found 10/19![Delta logo]()
$566
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:40 am -
2 stops13h 20m
Wed 11/2511:30 pm -
2 stops11h 45m
Deal found 10/19![Southwest logo]()
$630
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.
Wed 11/113:20 pm -
2 stops12h 31m
Mon 11/167:35 pm -
2 stops15h 30m
Deal found 10/20![Delta logo]()
$566
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/103:20 pm -
1 stop10h 50m
Mon 11/167:35 pm -
2 stops13h 07m
Deal found 10/18![Delta logo]()
$566
This United Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:35 pm -
2 stops20h 01m
Wed 12/23:44 pm -
2 stops17h 56m
Deal found 10/18![United Airlines logo]()
$722
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/103:20 pm -
2 stops12h 31m
Sun 11/155:51 pm -
2 stops14h 51m
Deal found 10/18![Delta logo]()
$566
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.
Tue 11/244:25 pm -
1 stop11h 47m
Wed 12/210:00 pm -
1 stop12h 22m
Deal found 10/21![American Airlines logo]()
$892
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 2/225:25 pm -
2 stops23h 50m
Thu 3/47:49 pm -
2 stops14h 42m
Deal found 10/21![United Airlines logo]()
$822
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 12/37:50 am -
1 stop20h 23m
Thu 12/3111:28 pm -
1 stop20h 24m
Deal found 10/21![American Airlines logo]()
$895
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 2/225:25 pm -
2 stops20h 15m
Sun 2/286:59 pm -
2 stops13h 06m
Deal found 10/21![United Airlines logo]()
$833
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.
Thu 2/252:15 pm -
1 stop12h 23m
Mon 3/16:59 pm -
1 stop19h 19m
Deal found 10/20![United Airlines logo]()
$836
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.
Thu 2/251:50 pm -
1 stop12h 36m
Sun 2/289:45 pm -
1 stop10h 55m
Deal found 10/21![Delta logo]()
$783
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.
Thu 2/256:00 am -
1 stop20h 08m
Mon 3/110:56 pm -
1 stop12h 10m
Deal found 10/20![United Airlines logo]()
$859
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.
Thu 11/263:38 pm -
2 stops24h 48m
Thu 12/36:37 pm -
2 stops13h 40m
Deal found 10/20![American Airlines logo]()
$1,049
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.
Thu 12/34:29 pm -
1 stop22h 20m
Thu 12/3111:05 am -
2 stops24h 15m
Deal found 10/22![Delta logo]()
$886
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.
Thu 11/261:07 pm -
1 stop11h 08m
Thu 12/33:44 pm -
2 stops18h 12m
Deal found 10/22![United Airlines logo]()
$985
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.
Fri 2/193:00 pm -
2 stops33h 33m
Thu 3/411:47 pm -
1 stop10h 44m
Deal found 10/21![United Airlines logo]()
$1,122
Last-minute flights from Caribbean to PortlandDiscover last-minute flight deals from Caribbean to Portland. Data last updated October 22, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to Portland. Data last updated October 22, 2026 and is based on user searches.
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.
Thu 11/52:16 pm -
1 stop10h 33m
Mon 11/911:10 pm -
1 stop14h 47m
Deal found 10/21![Delta logo]()
$511
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 11/511:05 am -
2 stops14h 05m
Mon 11/911:09 pm -
2 stops12h 13m
Deal found 10/21![American Airlines logo]()
$513
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:20 pm -
2 stops21h 16m
Sun 11/87:15 pm -
2 stops15h 59m
Deal found 10/19![United Airlines logo]()
$523
This eDestinos deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:55 pm -
2 stops23h 17m
Sun 11/155:05 am -
2 stops28h 20m
Deal found 10/19![Multiple Airlines logo]()
$567
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:55 pm -
2 stops23h 17m
Sun 11/1512:07 pm -
2 stops32h 52m
Deal found 10/20![Frontier logo]()
$610
This eDestinos deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/108:45 am -
2 stops19h 09m
Mon 11/165:05 am -
2 stops30h 14m
Deal found 10/18![Multiple Airlines logo]()
$515
This eDestinos deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:15 am -
3 stops54h 56m
Sun 11/156:08 am -
2 stops27h 17m
Deal found 10/19![Multiple Airlines logo]()
$540
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.
Tue 11/107:30 am -
1 stop20h 29m
Mon 11/1611:00 pm -
1 stop19h 39m
Deal found 10/21![American Airlines logo]()
$582
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 11/113:20 pm -
1 stop10h 50m
Mon 11/167:35 pm -
2 stops13h 20m
Deal found 10/21![Delta logo]()
$566
This American Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:30 am -
1 stop20h 29m
Mon 11/2311:01 pm -
1 stop11h 21m
Deal found 10/19![American Airlines logo]()
$616
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/181:00 pm -
2 stops14h 09m
Wed 11/258:30 am -
1 stop9h 52m
Deal found 10/19![United Airlines logo]()
$608
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.
Thu 11/1912:30 pm -
2 stops14h 55m
Wed 11/2511:30 pm -
2 stops11h 45m
Deal found 10/21![Southwest logo]()
$613
One-way flights from Caribbean to PortlandSearch for one-way flight options from Caribbean to Portland. Find affordable one-way fares based on user searches. Data last updated October 22, 2026.
Search for one-way flight options from Caribbean to Portland. Find affordable one-way fares based on user searches. Data last updated October 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:55 am -
2 stops35h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/73:43 am -
2 stops16h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$186
This WAYA deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/153:28 am -
1 stop21h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Multiple Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/169:02 pm -
2 stops19h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/143:43 am -
2 stops16h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:25 am -
3 stops34h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$238
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 11/174:52 pm -
2 stops46h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/153:55 am -
2 stops35h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:25 pm -
2 stops44h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$243
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:30 pm -
2 stops29h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$317
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.
Wed 10/2812:18 pm -
1 stop10h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$351
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:38 am -
1 stop14h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$352
Find flight deals from Caribbean to Portland
Keep the following information in mind while searching for Caribbean to Portland flight deals. Data was last updated October 22, 2026.
Round-trip from | $443 (United Airlines) |
|---|---|
One-way from | $175 (Kiwi.com) |
Popular in | June |
Cheapest in | November |
Average price | $466 |
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean to Portland 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 22, 2026.
Use the filters below to find and compare flights from Caribbean to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JuanPortland
SJU San Juan Luis Munoz Marin Intl - PDX Portland
SJUPDX
San Juan Luis Munoz Marin Intl
Wed 1/6
3:30 am-8:46 pm
2 stops45h 16m
Portland
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$269
San JuanPortland
SJU San Juan Luis Munoz Marin Intl - PDX Portland
SJUPDX
San Juan Luis Munoz Marin Intl
Sat 1/16
5:35 am-2:35 pm
2 stops13h 00m
Portland
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$283
San JuanPortland
SJU San Juan Luis Munoz Marin Intl - PDX Portland
SJUPDX
San Juan Luis Munoz Marin Intl
Tue 12/15
12:59 pm-11:49 pm
2 stops14h 50m
Portland
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$283
San JuanPortland
SJU San Juan Luis Munoz Marin Intl - PDX Portland
SJUPDX
San Juan Luis Munoz Marin Intl
Wed 12/9
2:11 pm-10:18 pm
1 stop12h 07m
Portland
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$283
San JuanPortland
SJU San Juan Luis Munoz Marin Intl - PDX Portland
SJUPDX
San Juan Luis Munoz Marin Intl
Sat 1/16
7:22 am-4:36 pm
2 stops13h 14m
Portland
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$283
San JuanPortland
SJU San Juan Luis Munoz Marin Intl - PDX Portland
SJUPDX
San Juan Luis Munoz Marin Intl
Sun 12/20
5:00 am-12:56 pm
1 stop11h 56m
Portland
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$283
San JuanPortland
SJU San Juan Luis Munoz Marin Intl - PDX Portland
SJUPDX
San Juan Luis Munoz Marin Intl
Sun 12/20
3:10 pm-5:15 pm
1 stop30h 05m
Portland
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$298
San JuanPortland
SJU San Juan Luis Munoz Marin Intl - PDX Portland
SJUPDX
San Juan Luis Munoz Marin Intl
Wed 1/6
7:25 am-4:35 pm
2 stops13h 10m
Portland
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$308
Punta CanaPortland
PUJ Punta Cana - PDX Portland
PUJPDX
Punta Cana
Mon 11/23
7:30 pm-8:32 pm
2 stops29h 02m
Portland
Wed 12/31
12:00 am-3:30 am
Nonstop0h 00m
$317
Quickest round-trip
Montego BayPortland
MBJ Montego Bay Sangster Intl - PDX Portland
MBJPDX
Montego Bay Sangster Intl
Wed 10/28
12:18 pm-9:11 pm
1 stop10h 53m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$351
Showing 1-10 of 54 resultsSorted by cheapest first
Best time to book a flight from Caribbean to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Caribbean with our price prediction graph.
SJU-PDX
PUJ-PDX
MBJ-PDX
PLS-PDX
AUA-PDX
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 Caribbean to Portland
0CB-PDX
SJU-PDX
PUJ-PDX
MBJ-PDX
PLS-PDX
What is the cheapest month to book a flight from Caribbean to Portland?
Currently, November is the cheapest month in which you can book a flight from Caribbean to Portland (average of $451). Flying from Caribbean to Portland in June is currently the most expensive (average of $686). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Portland
Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated October 22, 2026.
Read through reviews of airlines operating flights from Caribbean to Portland, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Entertainment
7.8
Comfort
7.8
Overall
7.8
Food
7.2
Boarding
8.1
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Crew
8.5
Entertainment
7.8
Comfort
7.8
Overall
7.8
Food
7.2
Boarding
8.1
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Crew
8.5
Entertainment
7.8
Comfort
7.8
Overall
7.8
Food
7.2
Boarding
8.1
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Crew
8.5
Entertainment
7.8
Comfort
7.8
Overall
7.8
Food
7.2
Boarding
8.1
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Related info for your journey
Find useful and relevant information for your journey from Caribbean to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsBeaverton
Seaside
Durham
Cannon Beach
Longview
Lake Oswego
Vancouver
Kelso
Troutdale
Lincoln City
Clackamas
McMinnville
The Dalles
Wilsonville
Stevenson
Hillsboro
Tillamook
Astoria
Gresham
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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Portland flight routes
Alternative routes for Caribbean to Portland
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Portland by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Caribbean to Portland by cabin class
Find flights from Caribbean to Portland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Caribbean and Portland flights
Browse other Caribbean and Portland flight options. Last updated on October 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Portland
Explore flights to Portland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 22, 2026.
Top 3 airlines flying from Caribbean to Portland
Discover the top 3 airlines that operate flights from Caribbean to Portland. 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 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$322 | Average$529 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$451 | Average$604 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$466 | Average$610 | FlexibilityNo cancel fee | On-time69% |