$161+ Cheap flights from Oregon to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Sep 12 — Sep 191
Round-trip
1 adult, Economy
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Find cheap flights from Oregon 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 Oregon to Caribbean
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Cheapest flights from Oregon to CaribbeanExplore the most affordable flight options available from Oregon to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2026.
Explore the most affordable flight options available from Oregon to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2026.
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 11/97:00 am -
1 stop13h 16m
Tue 11/179:45 am -
1 stop18h 14m
Deal found 8/11![American Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:59 am -
2 stops15h 00m
Wed 9/97:00 am -
1 stop19h 28m
Deal found 8/10![American Airlines logo]()
$327
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 10/247:00 am -
1 stop14h 20m
Tue 11/311:34 am -
2 stops14h 08m
Deal found 8/11![American Airlines logo]()
$354
This Trip.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:35 pm -
2 stops16h 41m
Mon 10/196:31 pm -
2 stops25h 04m
Deal found 8/10![Frontier logo]()
$370
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:59 am -
1 stop13h 55m
Sat 9/122:22 pm -
1 stop12h 06m
Deal found 8/11![American Airlines logo]()
$404
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 10/1411:49 pm -
1 stop20h 31m
Mon 10/197:30 am -
1 stop18h 35m
Deal found 8/12![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:00 pm -
2 stops15h 24m
Sat 10/316:30 am -
2 stops13h 33m
Deal found 8/13![American Airlines logo]()
$414
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:55 pm -
2 stops13h 00m
Sat 10/313:58 pm -
2 stops24h 35m
Deal found 8/11![American Airlines logo]()
$420
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/83:00 pm -
2 stops17h 00m
Tue 9/152:22 pm -
1 stop12h 06m
Deal found 8/11![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 10/132:02 pm -
2 stops19h 29m
Sat 10/176:00 am -
1 stop9h 51m
Deal found 8/11![American Airlines logo]()
$446
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/912:01 pm -
2 stops18h 23m
Tue 9/222:22 pm -
1 stop12h 06m
Deal found 8/11![American Airlines logo]()
$449
This Expedia deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:10 am -
2 stops24h 25m
Tue 10/2712:30 pm -
2 stops23h 56m
Deal found 8/10![Air Canada logo]()
$450
Best flights from Oregon to CaribbeanDiscover carefully curated flight deals from Oregon to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2026.
Discover carefully curated flight deals from Oregon to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2026.
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/234:05 pm -
2 stops18h 41m
Sat 1/303:20 pm -
1 stop10h 58m
Deal found 8/10![United Airlines logo]()
$453
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/810:15 pm -
1 stop11h 10m
Sat 11/144:00 pm -
1 stop10h 59m
Deal found 8/8![Delta logo]()
$462
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/115:45 pm -
2 stops15h 15m
Wed 10/2112:00 pm -
2 stops13h 05m
Deal found 8/9![Southwest logo]()
$462
This American Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/29:50 pm -
1 stop11h 23m
Fri 12/116:17 pm -
2 stops20h 40m
Deal found 8/8![American Airlines logo]()
$538
This Alaska Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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.
Fri 10/236:04 pm -
2 stops19h 19m
Tue 10/276:00 am -
3 stops18h 06m
Deal found 8/11![Alaska Airlines logo]()
$891
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:35 pm -
1 stop10h 33m
Sat 9/127:00 am -
2 stops13h 31m
Deal found 8/12![Delta logo]()
$466
This United Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/811:10 pm -
1 stop11h 30m
Sat 11/148:25 am -
2 stops13h 59m
Deal found 8/9![United Airlines logo]()
$486
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3011:30 pm -
2 stops14h 25m
Sat 9/125:05 am -
2 stops11h 55m
Deal found 8/9![Southwest logo]()
$486
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:44 pm -
2 stops13h 05m
Thu 10/2912:55 pm -
2 stops14h 04m
Deal found 8/8![Delta logo]()
$486
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:33 pm -
2 stops14h 58m
Sat 10/312:35 pm -
1 stop11h 42m
Deal found 8/10![United Airlines logo]()
$510
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 10/297:55 am -
2 stops14h 10m
Thu 11/1212:40 pm -
2 stops14h 25m
Deal found 8/12![Southwest logo]()
$536
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 1/118:15 am -
2 stops10h 45m
Mon 1/255:45 am -
2 stops13h 20m
Deal found 8/12![Southwest logo]()
$536
This United Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:30 pm -
1 stop11h 01m
Sun 11/223:00 pm -
1 stop11h 27m
Deal found 8/9![United Airlines logo]()
$538
This business-class.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure business-class.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3011:59 pm -
2 stops12h 11m
Sat 2/63:32 pm -
2 stops26h 14m
Deal found 8/11![Multiple Airlines logo]()
$1,310
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/511:09 pm -
2 stops12h 50m
Wed 12/97:00 am -
2 stops14h 48m
Deal found 8/10![American Airlines logo]()
$714
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:35 pm -
2 stops14h 45m
Thu 10/82:50 pm -
2 stops13h 30m
Deal found 8/11![Southwest logo]()
$538
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:57 pm -
1 stop13h 43m
Wed 9/161:06 pm -
1 stop10h 57m
Deal found 8/9![Delta logo]()
$629
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:02 pm -
1 stop12h 42m
Sat 9/121:25 pm -
1 stop11h 38m
Deal found 8/8![United Airlines logo]()
$576
This American Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2011:06 pm -
2 stops13h 11m
Thu 9/2410:21 am -
2 stops16h 02m
Deal found 8/9![American Airlines logo]()
$723
This Southwest deal was found by Cheapflights users on 8/13. 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.
Mon 9/2810:45 pm -
1 stop11h 05m
Sun 10/115:00 am -
2 stops12h 35m
Deal found 8/13![Southwest logo]()
$556
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/86:04 am -
1 stop10h 56m
Mon 1/186:15 am -
2 stops14h 09m
Deal found 8/9![Delta logo]()
$629
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/161:39 pm -
2 stops12h 32m
Sat 1/232:05 am -
2 stops17h 18m
Deal found 8/8![United Airlines logo]()
$576
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/99:50 pm -
1 stop14h 35m
Tue 12/154:10 pm -
1 stop11h 49m
Deal found 8/11![American Airlines logo]()
$751
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:00 am -
2 stops13h 20m
Mon 12/214:15 pm -
2 stops12h 15m
Deal found 8/11![Southwest logo]()
$566
This Delta deal was found by Cheapflights users on 8/13. 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.
Mon 1/186:04 am -
1 stop7h 41m
Tue 2/21:15 pm -
1 stop8h 53m
Deal found 8/13![Delta logo]()
$630
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/22:34 pm -
1 stop20h 14m
Fri 11/61:25 pm -
2 stops27h 00m
Deal found 8/8![United Airlines logo]()
$577
This Alaska Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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.
Mon 1/118:31 pm -
2 stops22h 08m
Mon 1/256:00 am -
3 stops21h 11m
Deal found 8/12![Alaska Airlines logo]()
$938
This American Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/910:55 pm -
2 stops13h 25m
Sat 10/1710:27 am -
2 stops16h 32m
Deal found 8/8![American Airlines logo]()
$779
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1111:30 pm -
1 stop11h 30m
Mon 12/214:15 pm -
2 stops12h 15m
Deal found 8/9![Southwest logo]()
$586
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:45 am -
1 stop9h 35m
Sat 11/213:45 pm -
1 stop12h 14m
Deal found 8/10![Delta logo]()
$650
Last-minute flights from Oregon to CaribbeanDiscover last-minute flight deals from Oregon to Caribbean. Data last updated August 13, 2026 and is based on user searches.
Discover last-minute flight deals from Oregon to Caribbean. Data last updated August 13, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:59 am -
2 stops15h 00m
Wed 9/97:00 am -
1 stop19h 28m
Deal found 8/10![American Airlines logo]()
$327
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/28:01 am -
2 stops13h 58m
Tue 9/86:00 am -
2 stops18h 11m
Deal found 8/11![American Airlines logo]()
$476
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:59 am -
1 stop13h 55m
Sat 9/122:22 pm -
1 stop12h 06m
Deal found 8/11![American Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:00 am -
2 stops13h 29m
Sat 9/127:00 am -
2 stops16h 16m
Deal found 8/12![Delta logo]()
$466
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/53:50 pm -
2 stops15h 20m
Sat 9/125:05 am -
2 stops11h 55m
Deal found 8/11![Southwest logo]()
$476
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/83:00 pm -
2 stops17h 00m
Tue 9/152:22 pm -
1 stop12h 06m
Deal found 8/11![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/912:01 pm -
2 stops18h 23m
Tue 9/222:22 pm -
1 stop12h 06m
Deal found 8/11![American Airlines logo]()
$449
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/1111:02 pm -
2 stops12h 28m
Wed 9/1612:52 pm -
2 stops22h 37m
Deal found 8/11![United Airlines logo]()
$457
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/161:52 pm -
2 stops17h 32m
Sat 9/266:00 am -
2 stops18h 27m
Deal found 8/11![American Airlines logo]()
$451
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:12 pm -
1 stop24h 04m
Thu 10/15:16 pm -
2 stops19h 39m
Deal found 8/10![American Airlines logo]()
$467
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:00 pm -
2 stops15h 24m
Sat 10/317:30 am -
1 stop17h 23m
Deal found 8/11![American Airlines logo]()
$322
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/2610:33 pm -
1 stop11h 10m
Sat 10/312:52 pm -
1 stop10h 18m
Deal found 8/12![United Airlines logo]()
$472
One-way flights from Oregon to CaribbeanSearch for one-way flight options from Oregon to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
Search for one-way flight options from Oregon to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/2811:06 pm -
1 stop12h 44m
Deal found 8/12![American Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1712:34 pm -
2 stops34h 19m
Deal found 8/9![Frontier logo]()
$186
This Trip.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:17 pm -
2 stops13h 49m
Deal found 8/11![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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.
Sat 8/2912:20 pm -
2 stops19h 46m
Deal found 8/11![Frontier logo]()
$199
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1711:09 pm -
2 stops18h 21m
Deal found 8/10![American Airlines logo]()
$207
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 1/2611:59 pm -
2 stops13h 06m
Deal found 8/12![American Airlines logo]()
$208
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/188:00 am -
1 stop11h 59m
Deal found 8/10![American Airlines logo]()
$212
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 1/2710:55 pm -
2 stops14h 10m
Deal found 8/12![American Airlines logo]()
$213
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3110:45 pm -
1 stop11h 05m
Deal found 8/11![Southwest logo]()
$230
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/215:30 am -
2 stops14h 25m
Deal found 8/11![Delta logo]()
$233
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/67:30 pm -
2 stops15h 20m
Deal found 8/9![Southwest logo]()
$237
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:03 pm -
1 stop19h 26m
Deal found 8/10![American Airlines logo]()
$243
Find flight deals from Oregon to Caribbean
Keep the following information in mind while searching for Oregon to Caribbean flight deals. Data was last updated August 13, 2026.
Round-trip from | $322 (American Airlines) |
|---|---|
One-way from | $161 (American Airlines) |
Popular in | March |
Cheapest in | September |
Average price | $482 |
Cheapflights Fare Finder
Customize your flight search to find flights from Oregon to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 13, 2026.
Use the filters below to find and compare flights from Oregon 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 1/23
4:05 pm-1:46 pm
2 stops18h 41m
Montego Bay Sangster Intl
Sat 1/30
3:20 pm-11:18 pm
1 stop10h 58m
$453
PortlandMontego Bay
PDX Portland - MBJ Montego Bay Sangster Intl
PDXMBJ
Portland
Sun 11/8
10:15 pm-12:25 pm
1 stop11h 10m
Montego Bay Sangster Intl
Sat 11/14
4:00 pm-11:59 pm
1 stop10h 59m
$462
PortlandMontego Bay
PDX Portland - MBJ Montego Bay Sangster Intl
PDXMBJ
Portland
Sun 10/11
5:45 pm-11:00 am
2 stops15h 15m
Montego Bay Sangster Intl
Wed 10/21
12:00 pm-11:05 pm
2 stops13h 05m
$462
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Sat 9/5
10:35 pm-12:08 pm
1 stop10h 33m
San Juan Luis Munoz Marin Intl
Sat 9/12
7:00 am-5:31 pm
2 stops13h 31m
$466
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Sun 11/8
11:10 pm-2:40 pm
1 stop11h 30m
San Juan Luis Munoz Marin Intl
Sat 11/14
8:25 am-6:24 pm
2 stops13h 59m
$486
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Sun 8/30
11:30 pm-4:55 pm
2 stops14h 25m
San Juan Luis Munoz Marin Intl
Sat 9/12
5:05 am-2:00 pm
2 stops11h 55m
$486
PortlandSan Juan
PDX Portland - SJU San Juan Luis Munoz Marin Intl
PDXSJU
Portland
Fri 10/23
8:44 pm-12:49 pm
2 stops13h 05m
San Juan Luis Munoz Marin Intl
Thu 10/29
12:55 pm-11:59 pm
2 stops14h 04m
$486
PortlandSaint Thomas Island
PDX Portland - STT Saint Thomas Island Cyril E King
PDXSTT
Portland
Sat 10/24
7:33 pm-1:31 pm
2 stops14h 58m
Saint Thomas Island Cyril E King
Sat 10/31
2:35 pm-11:17 pm
1 stop11h 42m
$510
BoiseSan Juan
BOI Boise Air Term. Gowen Fld - SJU San Juan Luis Munoz Marin Intl
BOISJU
Boise Air Term. Gowen Fld
Thu 10/29
7:55 am-12:05 am
2 stops14h 10m
San Juan Luis Munoz Marin Intl
Thu 11/12
12:40 pm-12:05 am
2 stops14h 25m
$536
BoiseSan Juan
BOI Boise Air Term. Gowen Fld - SJU San Juan Luis Munoz Marin Intl
BOISJU
Boise Air Term. Gowen Fld
Mon 1/11
8:15 am-10:00 pm
2 stops10h 45m
San Juan Luis Munoz Marin Intl
Mon 1/25
5:45 am-4:05 pm
2 stops13h 20m
$536
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Oregon to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Oregon with our price prediction graph.
PDX-SJU
BOI-SJU
PDX-STT
PDX-NAS
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 Oregon to Caribbean
USOR-0CB
PDX-SJU
BOI-SJU
PDX-STT
PDX-NAS
What is the cheapest month to book a flight from Oregon to Caribbean?
Currently, September is the cheapest month in which you can book a flight from Oregon to Caribbean (average of $602). Flying from Oregon to Caribbean in December is currently the most expensive (average of $802). 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 Oregon to Caribbean?
To ensure you get the cheapest price possible for a flight from Oregon to Caribbean, you should look to book at least 19 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Related info for your journey
Find useful and relevant information for your journey from Oregon to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Oregon 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 Oregon to Caribbean by cabin class
Find flights from Oregon to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Oregon and Caribbean flights
Browse other Oregon and Caribbean flight options. Last updated on August 13, 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.
Oregon to Caribbean flights
Consider these flights traveling from Oregon to Caribbean.
Top 5 airlines flying from Oregon to Caribbean
Discover the top 5 airlines that operate flights from Oregon to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$235 | Average$702 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$247 | Average$714 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$261 | Average$478 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$392 | Average$724 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$408 | Average$615 | FlexibilityNo cancel fee | On-time63% |