$212+ 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
Oct 18 — Oct 251
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 18, 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 18, 2026.
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/276:15 am -
2 stops13h 55m
Wed 11/412:30 pm -
2 stops14h 55m
Deal found 9/14![Southwest logo]()
$448
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:02 pm -
2 stops33h 57m
Thu 11/53:59 pm -
2 stops23h 37m
Deal found 9/17![Frontier logo]()
$458
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/127:33 pm -
2 stops14h 58m
Tue 12/223:00 pm -
1 stop11h 47m
Deal found 9/18![United Airlines logo]()
$460
This Flightnetwork deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:15 pm -
2 stops19h 30m
Fri 10/306:45 pm -
2 stops22h 56m
Deal found 9/16![Air Canada logo]()
$465
This Air Canada deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:10 am -
2 stops23h 35m
Wed 10/286:45 pm -
2 stops26h 46m
Deal found 9/16![Air Canada logo]()
$467
This Air Canada deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:15 pm -
2 stops19h 30m
Sun 11/17:45 pm -
2 stops22h 56m
Deal found 9/16![Air Canada logo]()
$470
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 -
1 stop10h 41m
Deal found 9/14![Delta logo]()
$472
This Air Canada deal was found by Cheapflights users on 9/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:10 pm -
2 stops22h 30m
Wed 12/912:35 pm -
2 stops24h 51m
Deal found 9/17![Air Canada logo]()
$475
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/304:20 pm -
2 stops18h 45m
Fri 11/62:40 pm -
2 stops13h 15m
Deal found 9/13![Southwest logo]()
$479
This Air Canada deal was found by Cheapflights users on 9/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/223:15 pm -
2 stops28h 20m
Sun 12/67:45 pm -
2 stops26h 46m
Deal found 9/17![Air Canada logo]()
$480
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/29:50 pm -
1 stop11h 12m
Tue 11/103:56 pm -
1 stop23h 32m
Deal found 9/16![American Airlines logo]()
$482
This Air Canada deal was found by Cheapflights users on 9/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/213:15 pm -
2 stops26h 25m
Wed 12/212:35 pm -
2 stops24h 51m
Deal found 9/17![Air Canada logo]()
$485
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 18, 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 18, 2026.
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 11/23:40 pm -
2 stops17h 33m
Wed 11/112:54 pm -
1 stop10h 33m
Deal found 9/13![United Airlines logo]()
$472
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 -
1 stop10h 41m
Deal found 9/14![Delta logo]()
$472
This Expedia deal was found by Cheapflights users on 9/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/163:15 pm -
2 stops17h 15m
Thu 11/192:05 pm -
2 stops27h 36m
Deal found 9/17![Air Canada logo]()
$517
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/175:00 am -
1 stop9h 09m
Mon 11/236:09 pm -
2 stops19h 58m
Deal found 9/18![American Airlines logo]()
$519
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/187:35 pm -
2 stops13h 20m
Sun 11/155:35 am -
2 stops12h 15m
Deal found 9/15![Southwest logo]()
$566
This Sun Country Air deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/197:08 pm -
1 stop14h 59m
Sat 12/263:10 pm -
1 stop11h 43m
Deal found 9/16![Sun Country Air logo]()
$825
This Alaska Airlines deal was found by Cheapflights users on 9/17. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:49 pm -
2 stops17h 56m
Mon 12/76:28 am -
3 stops19h 24m
Deal found 9/17![Alaska Airlines logo]()
$933
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/293:40 pm -
2 stops19h 08m
Thu 11/52:54 pm -
1 stop10h 33m
Deal found 9/14![United Airlines logo]()
$472
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/177:10 pm -
2 stops16h 35m
Sun 1/2411:40 am -
3 stops34h 51m
Deal found 9/17![Multiple Airlines logo]()
$1,132
This Justfly.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/183:15 pm -
2 stops21h 25m
Mon 11/235:35 pm -
2 stops28h 56m
Deal found 9/15![Air Canada logo]()
$570
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:44 pm -
1 stop11h 57m
Sat 10/313:58 pm -
2 stops24h 30m
Deal found 9/18![American Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:00 am -
2 stops12h 00m
Fri 11/68:25 am -
1 stop10h 58m
Deal found 9/17![United Airlines logo]()
$526
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/176:04 am -
1 stop7h 41m
Fri 1/292:55 pm -
1 stop10h 31m
Deal found 9/16![Delta logo]()
$610
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2711:30 pm -
1 stop12h 10m
Thu 11/52:21 pm -
1 stop12h 48m
Deal found 9/17![United Airlines logo]()
$526
This Justfly.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
Mon 12/77:10 pm -
2 stops41h 20m
Mon 12/145:25 pm -
2 stops29h 06m
Deal found 9/14![Air Canada logo]()
$602
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/151:00 pm -
2 stops20h 55m
Fri 1/291:20 pm -
2 stops13h 12m
Deal found 9/16![Delta logo]()
$614
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1111:00 pm -
1 stop7h 30m
Sun 11/157:47 am -
1 stop19h 12m
Deal found 9/18![American Airlines logo]()
$620
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:15 pm -
2 stops12h 50m
Sat 11/71:07 pm -
1 stop11h 08m
Deal found 9/15![United Airlines logo]()
$529
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/191:05 pm -
2 stops21h 10m
Mon 11/303:15 pm -
2 stops23h 25m
Deal found 9/18![Southwest logo]()
$730
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 1/61:38 pm -
2 stops19h 17m
Wed 1/131:20 pm -
1 stop11h 07m
Deal found 9/13![Delta logo]()
$614
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Sat 11/1411:49 pm -
1 stop11h 34m
Sat 11/2112:36 pm -
1 stop12h 24m
Deal found 9/17![American Airlines logo]()
$632
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/287:15 pm -
2 stops12h 50m
Wed 11/41:07 pm -
1 stop11h 08m
Deal found 9/13![United Airlines logo]()
$550
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 12/42:10 pm -
2 stops20h 10m
Sun 12/134:40 pm -
2 stops22h 00m
Deal found 9/13![Southwest logo]()
$740
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:49 pm -
2 stops14h 52m
Tue 10/201:06 pm -
1 stop10h 44m
Deal found 9/13![Delta logo]()
$614
This Air Canada deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/17:10 pm -
2 stops40h 35m
Mon 2/84:20 pm -
2 stops30h 11m
Deal found 9/15![Air Canada logo]()
$703
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/307:15 pm -
2 stops12h 50m
Wed 11/41:07 pm -
1 stop11h 08m
Deal found 9/13![United Airlines logo]()
$550
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/186:04 am -
1 stop7h 41m
Sun 1/241:20 pm -
2 stops13h 12m
Deal found 9/16![Delta logo]()
$614
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/3010:55 pm -
2 stops13h 13m
Fri 11/61:07 pm -
2 stops14h 36m
Deal found 9/14![American Airlines logo]()
$682
This Air Canada deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 1/1010:00 am -
2 stops26h 40m
Wed 1/135:35 pm -
2 stops28h 56m
Deal found 9/14![Air Canada logo]()
$723
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/3111:30 pm -
1 stop12h 01m
Wed 11/41:07 pm -
2 stops13h 20m
Deal found 9/13![United Airlines logo]()
$569
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated September 18, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated September 18, 2026 and is based on user searches.
This Justfly.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:45 pm -
2 stops43h 00m
Sat 10/3110:40 pm -
2 stops23h 51m
Deal found 9/17![Air Canada logo]()
$485
This Air Canada deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:10 am -
2 stops23h 35m
Wed 10/286:45 pm -
2 stops26h 46m
Deal found 9/16![Air Canada logo]()
$467
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:55 pm -
2 stops13h 00m
Sat 10/313:58 pm -
2 stops25h 35m
Deal found 9/16![American Airlines logo]()
$494
This Flightnetwork deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:15 pm -
2 stops19h 30m
Fri 10/306:45 pm -
2 stops22h 56m
Deal found 9/16![Air Canada logo]()
$465
This Air Canada deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:15 pm -
2 stops19h 30m
Sun 11/17:45 pm -
2 stops22h 56m
Deal found 9/16![Air Canada logo]()
$470
This Air Canada deal was found by Cheapflights users on 9/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:15 pm -
2 stops24h 20m
Mon 11/210:40 pm -
2 stops23h 51m
Deal found 9/17![Air Canada logo]()
$475
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:35 pm -
2 stops10h 35m
Thu 10/2910:10 am -
2 stops11h 55m
Deal found 9/14![Southwest logo]()
$487
This Air Canada deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:15 pm -
2 stops15h 35m
Thu 10/293:30 pm -
2 stops30h 01m
Deal found 9/15![Air Canada logo]()
$490
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/276:15 am -
2 stops13h 55m
Wed 11/412:30 pm -
2 stops14h 55m
Deal found 9/14![Southwest logo]()
$448
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:02 pm -
2 stops33h 57m
Thu 11/53:59 pm -
2 stops23h 37m
Deal found 9/17![Frontier logo]()
$458
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/292:34 pm -
1 stop20h 14m
Thu 11/52:54 pm -
1 stop10h 33m
Deal found 9/14![United Airlines logo]()
$472
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/304:20 pm -
2 stops18h 45m
Fri 11/62:40 pm -
2 stops13h 15m
Deal found 9/13![Southwest logo]()
$479
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 18, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 18, 2026.
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/142:37 pm -
2 stops18h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![United Airlines logo]()
$212
This Orbitz deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/183:15 pm -
2 stops28h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Air Canada logo]()
$221
This Air Canada deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/163:15 pm -
2 stops28h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Air Canada logo]()
$226
This Air Canada deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:15 pm -
2 stops26h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Air Canada logo]()
$231
This FlightHub deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2310:00 am -
2 stops31h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Air Canada logo]()
$236
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:35 pm -
2 stops10h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$236
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/611:09 pm -
2 stops12h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$246
This Justfly.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2510:00 am -
2 stops33h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Air Canada logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$248
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1111:09 pm -
2 stops12h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![American Airlines logo]()
$251
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/277:15 pm -
2 stops16h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![United Airlines logo]()
$260
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:50 am -
1 stop10h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![United Airlines logo]()
$263
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 18, 2026.
Round-trip from | $448 (Southwest) |
|---|---|
One-way from | $212 (United 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 18, 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
11:49 pm-5:09 pm
1 stop14h 20m
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
Sat 11/14
2:37 pm-12:13 pm
2 stops18h 36m
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
Fri 11/13
12:35 am-4:57 pm
2 stops13h 22m
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
Sat 1/30
4:05 pm-1:48 pm
2 stops18h 43m
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
Sat 1/30
11:00 pm-2:17 pm
1 stop12h 17m
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
Fri 11/27
7:15 pm-4:50 pm
1 stop18h 35m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$212
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Sat 12/12
1:10 pm-10:30 am
2 stops17h 20m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$263
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Wed 11/18
7:35 pm-12:55 pm
2 stops13h 20m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$263
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Thu 10/8
8:35 am-10:57 pm
1 stop11h 22m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$263
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Sat 12/12
11:17 pm-1:53 pm
1 stop10h 36m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$263
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-PUJ
PDX-MBJ
PDX-STT
PDX-AUA
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-PUJ
PDX-MBJ
PDX-STT
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 $646). Flying from Portland to Caribbean in December is currently the most expensive (average of $831). 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 26 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 18, 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.
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
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.
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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 18, 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 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$235 | Average$702 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$247 | Average$719 | 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% |