$172+ Cheap flights from Oregon 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Nov 3 — Nov 101
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 October 4, 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 October 4, 2026.
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/257:15 pm -
2 stops12h 50m
Sun 11/13:35 pm -
1 stop11h 40m
Deal found 9/29![United Airlines logo]()
$460
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 stops19h 08m
Wed 11/112:54 pm -
1 stop10h 33m
Deal found 9/30![United Airlines logo]()
$472
This Delta deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 10/2![Delta logo]()
$473
This American Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/1![American Airlines logo]()
$483
This American Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 11/3011:01 pm -
1 stop11h 24m
Mon 12/73:27 pm -
2 stops23h 35m
Deal found 10/1![American Airlines logo]()
$500
This Southwest deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/411:40 am -
2 stops22h 10m
Fri 11/133:45 pm -
2 stops13h 40m
Deal found 10/3![Southwest logo]()
$504
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/2311:30 pm -
2 stops12h 00m
Sat 10/312:45 pm -
2 stops21h 51m
Deal found 9/30![United Airlines logo]()
$513
This American Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:55 pm -
2 stops12h 32m
Sat 10/315:13 pm -
2 stops23h 20m
Deal found 9/29![American Airlines logo]()
$519
This United Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:00 am -
1 stop10h 24m
Wed 11/117:40 am -
2 stops14h 40m
Deal found 10/3![United Airlines logo]()
$521
This American Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/122:25 pm -
2 stops17h 52m
Thu 12/316:44 pm -
2 stops22h 25m
Deal found 10/2![American Airlines logo]()
$526
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 -
3 stops14h 57m
Tue 11/31:09 am -
3 stops16h 13m
Deal found 9/30![United Airlines logo]()
$526
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 stops14h 05m
Thu 10/2912:55 pm -
2 stops14h 04m
Deal found 9/30![Delta logo]()
$526
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 October 4, 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 October 4, 2026.
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 1/95:45 pm -
2 stops15h 35m
Thu 1/141:50 pm -
2 stops12h 46m
Deal found 9/29![Delta logo]()
$460
This Southwest deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 1/91:15 pm -
2 stops20h 05m
Thu 1/142:10 pm -
2 stops21h 40m
Deal found 10/1![Southwest logo]()
$460
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 stops19h 08m
Wed 11/112:54 pm -
1 stop10h 33m
Deal found 9/29![United Airlines logo]()
$472
This American Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 2/111:49 pm -
2 stops11h 46m
Sun 2/76:05 pm -
2 stops20h 06m
Deal found 9/29![American Airlines logo]()
$483
This Air Canada deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/163:15 pm -
2 stops17h 15m
Thu 11/199:25 pm -
2 stops24h 06m
Deal found 10/3![Air Canada logo]()
$726
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/411:40 am -
2 stops22h 10m
Fri 11/133:45 pm -
2 stops13h 40m
Deal found 9/29![Southwest logo]()
$460
This Delta deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/1![Delta logo]()
$472
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/313:40 pm -
2 stops20h 59m
Sat 11/72:54 pm -
1 stop10h 33m
Deal found 10/1![United Airlines logo]()
$473
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/2311:30 pm -
2 stops12h 00m
Sat 10/312:45 pm -
2 stops21h 51m
Deal found 9/30![United Airlines logo]()
$513
This Southwest deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:55 am -
2 stops11h 25m
Fri 11/1312:40 pm -
2 stops14h 05m
Deal found 10/1![Southwest logo]()
$526
This American Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/275:25 am -
2 stops11h 27m
Sat 3/61:56 pm -
1 stop13h 03m
Deal found 10/3![American Airlines logo]()
$615
This United Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/115:00 am -
2 stops14h 57m
Tue 11/171:09 am -
3 stops16h 13m
Deal found 10/3![United Airlines logo]()
$526
This American Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/149:50 pm -
2 stops14h 01m
Sat 11/216:00 pm -
2 stops21h 07m
Deal found 10/3![American Airlines logo]()
$637
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 1/249:45 pm -
1 stop14h 57m
Sun 1/316:06 pm -
2 stops26h 07m
Deal found 9/29![Delta logo]()
$637
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/281:10 pm -
2 stops21h 05m
Wed 11/41:10 pm -
2 stops13h 15m
Deal found 9/30![Southwest logo]()
$614
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/308:44 pm -
2 stops12h 01m
Tue 11/35:05 pm -
2 stops23h 06m
Deal found 9/29![Delta logo]()
$637
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:26 pm -
2 stops15h 48m
Fri 10/302:01 pm -
2 stops22h 17m
Deal found 10/1![United Airlines logo]()
$607
This Southwest deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 11/63:45 pm -
2 stops13h 40m
Deal found 10/2![Southwest logo]()
$632
This Delta deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:29 pm -
2 stops14h 59m
Sat 11/213:45 pm -
1 stop12h 01m
Deal found 10/3![Delta logo]()
$637
This American Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1611:00 pm -
1 stop11h 26m
Mon 11/233:26 pm -
1 stop12h 46m
Deal found 10/2![American Airlines logo]()
$715
This United Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:00 am -
1 stop8h 14m
Sat 11/71:05 pm -
1 stop10h 10m
Deal found 10/3![United Airlines logo]()
$610
This Southwest deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 11/151:45 pm -
2 stops20h 00m
Sun 11/222:40 pm -
2 stops13h 15m
Deal found 10/1![Southwest logo]()
$637
This American Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/273:00 pm -
2 stops19h 23m
Tue 11/35:33 pm -
2 stops24h 11m
Deal found 9/29![American Airlines logo]()
$720
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 11/1511:30 pm -
1 stop11h 18m
Sun 11/223:45 pm -
1 stop10h 30m
Deal found 10/1![United Airlines logo]()
$613
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 4/27:14 pm -
2 stops14h 41m
Tue 4/203:05 pm -
2 stops11h 46m
Deal found 9/30![Delta logo]()
$702
This American Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 11/149:50 pm -
2 stops12h 36m
Sat 11/213:26 pm -
2 stops23h 41m
Deal found 9/30![American Airlines logo]()
$720
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 12/137:25 pm -
2 stops15h 08m
Sun 12/202:55 pm -
2 stops12h 52m
Deal found 9/29![United Airlines logo]()
$614
This Southwest deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/161:05 pm -
2 stops21h 10m
Mon 11/234:40 pm -
2 stops20h 55m
Deal found 10/2![Southwest logo]()
$681
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 4/27:14 pm -
2 stops14h 41m
Thu 4/156:10 pm -
2 stops17h 31m
Deal found 9/30![Delta logo]()
$702
This American Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/265:41 pm -
2 stops14h 59m
Sat 3/65:42 pm -
2 stops24h 04m
Deal found 10/3![American Airlines logo]()
$727
Last-minute flights from Oregon to CaribbeanDiscover last-minute flight deals from Oregon to Caribbean. Data last updated October 4, 2026 and is based on user searches.
Discover last-minute flight deals from Oregon to Caribbean. Data last updated October 4, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/2311:30 pm -
2 stops12h 00m
Sat 10/312:45 pm -
2 stops21h 51m
Deal found 9/30![United Airlines logo]()
$513
This American Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:55 pm -
2 stops12h 32m
Sat 10/315:13 pm -
2 stops23h 20m
Deal found 9/29![American Airlines logo]()
$519
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 stops14h 05m
Thu 10/2912:55 pm -
2 stops14h 04m
Deal found 9/30![Delta logo]()
$526
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/257:15 pm -
2 stops12h 50m
Sun 11/13:35 pm -
1 stop11h 40m
Deal found 9/29![United Airlines logo]()
$460
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 -
3 stops14h 57m
Tue 11/31:09 am -
3 stops16h 13m
Deal found 9/30![United Airlines logo]()
$526
This Mytrip deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:45 pm -
2 stops27h 07m
Thu 11/56:00 am -
3 stops33h 36m
Deal found 10/1![Multiple Airlines logo]()
$529
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 stops19h 08m
Wed 11/112:54 pm -
1 stop10h 33m
Deal found 9/30![United Airlines logo]()
$472
This Delta deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 10/2![Delta logo]()
$473
This American Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/1![American Airlines logo]()
$483
This Southwest deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/411:40 am -
2 stops22h 10m
Fri 11/133:45 pm -
2 stops13h 40m
Deal found 10/3![Southwest logo]()
$504
This United Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:00 am -
1 stop10h 24m
Wed 11/117:40 am -
2 stops14h 40m
Deal found 10/3![United Airlines logo]()
$521
This American Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 11/3011:01 pm -
1 stop11h 24m
Mon 12/73:27 pm -
2 stops23h 35m
Deal found 10/1![American Airlines logo]()
$500
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 October 4, 2026.
Search for one-way flight options from Oregon to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 4, 2026.
This Trip.com deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:02 pm -
2 stops23h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Frontier logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/2011:49 am -
2 stops26h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$177
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 11/15:49 pm -
2 stops15h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Delta logo]()
$212
This American Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/285:20 am -
1 stop8h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![American Airlines logo]()
$217
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/233:23 pm -
2 stops20h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![United Airlines logo]()
$218
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/55:45 pm -
2 stops15h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Delta logo]()
$228
This American Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 11/2811:01 pm -
1 stop12h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$246
This Trip.com deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:02 pm -
2 stops34h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Frontier logo]()
$246
This American Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/3111:55 am -
2 stops20h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 11/912:31 pm -
2 stops41h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$260
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 11/147:00 am -
2 stops12h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![United Airlines logo]()
$263
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![United Airlines logo]()
$263
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 October 4, 2026.
Round-trip from | $460 (Delta) |
|---|---|
One-way from | $172 (Trip.com) |
Popular in | March |
Cheapest in | September |
Average price | $505 |
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 7,457,451 searches. Data last updated October 4, 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 11/14
5:24 pm-2:03 pm
2 stops17h 39m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$212
PortlandMontego Bay
PDX Portland - MBJ Montego Bay Sangster Intl
PDXMBJ
Portland
Mon 12/7
7:25 pm-1:48 pm
2 stops15h 23m
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 10/23
11:49 pm-4:12 pm
1 stop14h 23m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$212
PortlandMontego Bay
PDX Portland - MBJ Montego Bay Sangster Intl
PDXMBJ
Portland
Sun 10/25
11:12 pm-3:27 pm
2 stops14h 15m
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
Tue 12/8
2:26 pm-12:13 pm
2 stops18h 47m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$212
PortlandMontego Bay
PDX Portland - MBJ Montego Bay Sangster Intl
PDXMBJ
Portland
Mon 12/7
5:29 pm-12:27 pm
2 stops15h 58m
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 12/5
2:26 pm-12:13 pm
2 stops18h 47m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$212
PortlandMontego Bay
PDX Portland - MBJ Montego Bay Sangster Intl
PDXMBJ
Portland
Sun 11/1
11:00 pm-4:27 pm
1 stop14h 27m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$212
PortlandSaint Thomas Island
PDX Portland - STT Saint Thomas Island Cyril E King
PDXSTT
Portland
Tue 1/5
11:29 pm-4:14 pm
1 stop12h 45m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$228
PortlandSaint Thomas Island
PDX Portland - STT Saint Thomas Island Cyril E King
PDXSTT
Portland
Sat 1/23
7:24 pm-4:20 pm
2 stops16h 56m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$228
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-STT
PDX-MBJ
PDX-SXM
PDX-SJU
PDX-BQN
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-STT
PDX-MBJ
PDX-SXM
PDX-SJU
What is the cheapest month to book a flight from Oregon to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Oregon to Caribbean (average of $645). Flying from Oregon to Caribbean in March is currently the most expensive (average of $817). 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 90 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 October 4, 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 7,457,451 searches. Data last updated October 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$235 | Average$698 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$247 | Average$727 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$261 | Average$478 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$392 | Average$738 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$408 | Average$623 | FlexibilityNo cancel fee | On-time63% |