$161+ Cheap flights from Caribbean to Portland (PDX)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Oct 11 — Oct 181
Round-trip
1 adult, Economy
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Find cheap flights from Caribbean to Portland with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Caribbean to Portland
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Cheapest flights from Caribbean to PortlandExplore the most affordable flight options available from Caribbean to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2026.
Explore the most affordable flight options available from Caribbean to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2026.
This American Airlines deal was found by Cheapflights users on 9/10. 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 11/510:32 am -
1 stop17h 27m
Fri 11/1311:09 pm -
2 stops11h 54m
Deal found 9/10![American Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/152:53 pm -
1 stop12h 06m
Mon 10/1910:55 pm -
1 stop12h 08m
Deal found 9/7![American Airlines logo]()
$328
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Tue 10/206:30 am -
2 stops13h 33m
Tue 10/275:10 am -
2 stops13h 59m
Deal found 9/9![American Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 9/8. 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.
Wed 10/72:53 pm -
1 stop12h 06m
Wed 10/146:09 pm -
2 stops14h 22m
Deal found 9/8![American Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/2212:21 pm -
2 stops14h 38m
Fri 11/1311:09 pm -
2 stops11h 54m
Deal found 9/10![American Airlines logo]()
$342
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Tue 10/272:01 pm -
2 stops21h 35m
Tue 11/171:15 pm -
2 stops19h 58m
Deal found 9/9![United Airlines logo]()
$392
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/182:54 pm -
2 stops21h 42m
Thu 12/37:21 pm -
2 stops42h 29m
Deal found 9/6![United Airlines logo]()
$405
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:21 pm -
3 stops27h 59m
Sun 12/2711:42 pm -
1 stop13h 37m
Deal found 9/7![United Airlines logo]()
$407
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Fri 11/68:30 am -
1 stop17h 29m
Tue 11/1011:00 pm -
1 stop9h 10m
Deal found 9/9![American Airlines logo]()
$414
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Tue 10/202:53 pm -
1 stop12h 06m
Wed 10/286:30 am -
2 stops26h 01m
Deal found 9/9![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/82:27 pm -
1 stop11h 38m
Tue 10/139:44 pm -
1 stop10h 36m
Deal found 9/6![American Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/2212:13 pm -
1 stop10h 31m
Thu 10/292:25 pm -
1 stop23h 47m
Deal found 9/7![American Airlines logo]()
$424
Best flights from Caribbean to PortlandDiscover carefully curated flight deals from Caribbean to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 11, 2026.
Discover carefully curated flight deals from Caribbean to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 11, 2026.
This American Airlines deal was found by Cheapflights users on 9/8. 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 10/92:27 pm -
1 stop11h 38m
Mon 10/1910:55 pm -
1 stop12h 08m
Deal found 9/8![American Airlines logo]()
$322
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Tue 10/272:01 pm -
2 stops21h 35m
Tue 11/171:15 pm -
2 stops19h 58m
Deal found 9/9![United Airlines logo]()
$392
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 2/126:15 am -
2 stops14h 09m
Sat 2/205:45 pm -
2 stops15h 20m
Deal found 9/6![Delta logo]()
$506
This Air Canada deal was found by Cheapflights users on 9/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:20 pm -
2 stops29h 51m
Sun 10/257:15 pm -
2 stops22h 25m
Deal found 9/9![Air Canada logo]()
$568
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 2/262:00 pm -
2 stops13h 20m
Fri 3/55:50 am -
2 stops14h 40m
Deal found 9/7![Southwest logo]()
$611
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/2912:41 pm -
1 stop11h 03m
Mon 11/211:00 pm -
1 stop9h 10m
Deal found 9/10![American Airlines logo]()
$342
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/2212:41 pm -
1 stop11h 03m
Fri 11/1311:09 pm -
2 stops11h 54m
Deal found 9/10![American Airlines logo]()
$342
This Mytrip deal was found by Cheapflights users on 9/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:05 pm -
2 stops44h 26m
Fri 10/162:30 pm -
2 stops22h 00m
Deal found 9/10![Multiple Airlines logo]()
$761
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/182:54 pm -
2 stops21h 42m
Thu 12/37:21 pm -
2 stops42h 29m
Deal found 9/6![United Airlines logo]()
$405
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/2212:52 pm -
2 stops35h 31m
Thu 10/2911:30 pm -
1 stop11h 18m
Deal found 9/7![United Airlines logo]()
$405
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:21 pm -
2 stops19h 18m
Sun 12/2711:42 pm -
1 stop13h 37m
Deal found 9/7![United Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 9/9. 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.
Thu 12/32:11 pm -
1 stop12h 08m
Tue 12/85:30 am -
2 stops14h 29m
Deal found 9/9![Delta logo]()
$506
This American Airlines deal was found by Cheapflights users on 9/10. 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 12/148:30 am -
1 stop17h 29m
Sat 1/211:52 pm -
1 stop10h 56m
Deal found 9/10![American Airlines logo]()
$506
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Fri 9/255:30 am -
1 stop12h 30m
Sun 10/45:45 pm -
2 stops12h 35m
Deal found 9/10![Southwest logo]()
$631
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Mon 11/92:05 am -
3 stops22h 57m
Sun 11/157:15 pm -
2 stops12h 35m
Deal found 9/9![United Airlines logo]()
$596
This Mytrip deal was found by Cheapflights users on 9/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/283:05 pm -
2 stops44h 26m
Mon 10/52:30 pm -
3 stops21h 25m
Deal found 9/10![Multiple Airlines logo]()
$848
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Fri 9/253:35 pm -
1 stop10h 48m
Sat 10/39:44 pm -
1 stop14h 23m
Deal found 9/10![American Airlines logo]()
$645
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Mon 3/81:00 pm -
1 stop12h 21m
Mon 3/157:49 pm -
2 stops13h 28m
Deal found 9/10![United Airlines logo]()
$671
This Delta deal was found by Cheapflights users on 9/10. 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 10/99:15 am -
1 stop11h 54m
Fri 10/1611:12 pm -
2 stops19h 03m
Deal found 9/10![Delta logo]()
$904
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/209:15 am -
1 stop14h 34m
Tue 10/276:50 am -
1 stop11h 25m
Deal found 9/6![Delta logo]()
$1,004
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/202:57 pm -
2 stops22h 36m
Tue 10/272:34 pm -
3 stops21h 21m
Deal found 9/6![United Airlines logo]()
$756
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/226:00 am -
1 stop18h 27m
Mon 10/2611:10 pm -
1 stop10h 31m
Deal found 9/6![United Airlines logo]()
$788
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Thu 10/226:00 am -
1 stop18h 27m
Sun 10/2511:10 pm -
1 stop20h 41m
Deal found 9/9![United Airlines logo]()
$788
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/224:40 pm -
2 stops21h 53m
Sun 10/2511:10 pm -
1 stop10h 39m
Deal found 9/7![United Airlines logo]()
$793
Last-minute flights from Caribbean to PortlandDiscover last-minute flight deals from Caribbean to Portland. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to Portland. Data last updated September 11, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/8. 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.
Wed 10/72:53 pm -
1 stop12h 06m
Wed 10/146:09 pm -
2 stops14h 22m
Deal found 9/8![American Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/82:27 pm -
1 stop11h 38m
Tue 10/139:44 pm -
1 stop10h 36m
Deal found 9/6![American Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Fri 10/92:27 pm -
1 stop11h 38m
Mon 10/1910:55 pm -
2 stops13h 43m
Deal found 9/10![American Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Wed 10/142:27 pm -
1 stop11h 38m
Mon 10/196:09 pm -
2 stops12h 37m
Deal found 9/9![American Airlines logo]()
$428
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/152:53 pm -
1 stop12h 06m
Mon 10/1910:55 pm -
1 stop12h 08m
Deal found 9/7![American Airlines logo]()
$328
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Tue 10/206:30 am -
2 stops13h 33m
Tue 10/275:10 am -
2 stops13h 59m
Deal found 9/9![American Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Tue 10/202:53 pm -
1 stop12h 06m
Wed 10/286:30 am -
2 stops26h 01m
Deal found 9/9![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Wed 10/216:20 am -
2 stops19h 29m
Tue 10/277:30 am -
2 stops11h 39m
Deal found 9/9![American Airlines logo]()
$414
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/2212:41 pm -
1 stop11h 03m
Fri 11/1311:09 pm -
2 stops11h 54m
Deal found 9/10![American Airlines logo]()
$342
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/2212:52 pm -
2 stops35h 31m
Thu 10/2911:30 pm -
1 stop11h 18m
Deal found 9/7![United Airlines logo]()
$405
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/2212:13 pm -
1 stop10h 31m
Thu 10/292:25 pm -
1 stop23h 47m
Deal found 9/7![American Airlines logo]()
$424
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Tue 10/272:01 pm -
2 stops21h 35m
Tue 11/171:15 pm -
2 stops19h 58m
Deal found 9/9![United Airlines logo]()
$392
One-way flights from Caribbean to PortlandSearch for one-way flight options from Caribbean to Portland. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
Search for one-way flight options from Caribbean to Portland. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This American Airlines deal was found by Cheapflights users on 9/10. 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 12/158:30 am -
1 stop17h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$161
This American Airlines deal was found by Cheapflights users on 9/10. 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 11/238:30 am -
1 stop17h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/213:55 am -
2 stops20h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:17 am -
2 stops31h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:21 pm -
2 stops25h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$233
This American Airlines deal was found by Cheapflights users on 9/9. 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 11/87:30 am -
1 stop20h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![American Airlines logo]()
$253
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/213:45 pm -
2 stops36h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![United Airlines logo]()
$261
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Wed 11/251:25 pm -
2 stops28h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![United Airlines logo]()
$263
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Sun 10/117:30 am -
1 stop18h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$263
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/213:31 pm -
1 stop11h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![American Airlines logo]()
$264
This Air Canada deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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.
Wed 11/47:45 pm -
2 stops26h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Air Canada logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/117:20 am -
2 stops54h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$286
Find flight deals from Caribbean to Portland
Keep the following information in mind while searching for Caribbean to Portland flight deals. Data was last updated September 11, 2026.
Round-trip from | $322 (American Airlines) |
|---|---|
One-way from | $161 (American Airlines) |
Popular in | June |
Cheapest in | January |
Average price | $545 |
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 11, 2026.
Use the filters below to find and compare flights from Caribbean to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Montego BayPortland
MBJ Montego Bay Sangster Intl - PDX Portland
MBJPDX
Montego Bay Sangster Intl
Mon 12/21
3:45 pm-12:47 am
2 stops36h 02m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$261
Montego BayPortland
MBJ Montego Bay Sangster Intl - PDX Portland
MBJPDX
Montego Bay Sangster Intl
Wed 11/25
1:25 pm-3:20 pm
2 stops28h 55m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$263
San JuanPortland
SJU San Juan Luis Munoz Marin Intl - PDX Portland
SJUPDX
San Juan Luis Munoz Marin Intl
Sun 12/20
3:10 pm-5:15 pm
1 stop30h 05m
Portland
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$288
Punta CanaPortland
PUJ Punta Cana - PDX Portland
PUJPDX
Punta Cana
Mon 11/30
10:40 pm-8:46 pm
2 stops26h 06m
Portland
Wed 12/31
12:00 am-3:30 am
Nonstop0h 00m
$293
San JuanPortland
SJU San Juan Luis Munoz Marin Intl - PDX Portland
SJUPDX
San Juan Luis Munoz Marin Intl
Mon 12/14
8:05 am-11:08 pm
2 stops19h 03m
Portland
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$298
San JuanPortland
SJU San Juan Luis Munoz Marin Intl - PDX Portland
SJUPDX
San Juan Luis Munoz Marin Intl
Sun 11/22
2:05 am-9:02 pm
3 stops22h 57m
Portland
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$298
San JuanPortland
SJU San Juan Luis Munoz Marin Intl - PDX Portland
SJUPDX
San Juan Luis Munoz Marin Intl
Fri 10/9
2:27 pm-11:05 pm
1 stop11h 38m
Portland
Mon 10/19
10:55 pm-2:03 pm
1 stop12h 08m
$322
San JuanPortland
SJU San Juan Luis Munoz Marin Intl - PDX Portland
SJUPDX
San Juan Luis Munoz Marin Intl
Sun 12/20
2:10 pm-11:59 pm
2 stops13h 49m
Portland
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$340
San JuanPortland
SJU San Juan Luis Munoz Marin Intl - PDX Portland
SJUPDX
San Juan Luis Munoz Marin Intl
Thu 10/29
12:41 pm-8:44 pm
1 stop11h 03m
Portland
Mon 11/2
11:00 pm-12:10 pm
1 stop9h 10m
$342
San JuanPortland
SJU San Juan Luis Munoz Marin Intl - PDX Portland
SJUPDX
San Juan Luis Munoz Marin Intl
Thu 10/22
12:41 pm-8:44 pm
1 stop11h 03m
Portland
Fri 11/13
11:09 pm-3:03 pm
2 stops11h 54m
$342
Showing 1-10 of 54 resultsSorted by cheapest first
Best time to book a flight from Caribbean to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Caribbean with our price prediction graph.
SJU-PDX
MBJ-PDX
PUJ-PDX
SDQ-PDX
STI-PDX
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Caribbean to Portland
0CB-PDX
SJU-PDX
MBJ-PDX
PUJ-PDX
SDQ-PDX
What is the cheapest month to book a flight from Caribbean to Portland?
Currently, January is the cheapest month in which you can book a flight from Caribbean to Portland (average of $483). Flying from Caribbean to Portland in June is currently the most expensive (average of $686). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Portland
Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated September 11, 2026.
Read through reviews of airlines operating flights from Caribbean to Portland, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.1
Comfort
7.3
Food
6.7
Overall
7.4
Crew
8.1
Boarding
7.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Entertainment
7.1
Comfort
7.3
Food
6.7
Overall
7.4
Crew
8.1
Boarding
7.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Entertainment
7.1
Comfort
7.3
Food
6.7
Overall
7.4
Crew
8.1
Boarding
7.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Caribbean to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsBeaverton
Seaside
Lincoln City
Durham
Longview
Lake Oswego
Vancouver
Kelso
Troutdale
Clackamas
Cannon Beach
McMinnville
The Dalles
Wilsonville
Stevenson
Tillamook
Hillsboro
Astoria
Gresham
Silverton
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Alternative routes for Caribbean to Portland
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Portland by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Caribbean to Portland by cabin class
Find flights from Caribbean to Portland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Caribbean and Portland flights
Browse other Caribbean and Portland flight options. Last updated on September 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Portland
Explore flights to Portland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 11, 2026.
Top 2 airlines flying from Caribbean to Portland
Discover the top 2 airlines that operate flights from Caribbean to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$322 | Average$529 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$447 | Average$590 | FlexibilityNo cancel fee | On-time69% |