$120+ Cheap flights from Portland, ME (PWM) 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 12/29. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Nov 11 — Nov 181
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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
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Cheapest flights from Portland to CaribbeanExplore the most affordable flight options available from Portland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 12, 2026.
Explore the most affordable flight options available from Portland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 12, 2026.
This United Airlines deal was found by Cheapflights users on 10/8. 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 11/73:41 pm -
1 stop7h 55m
Tue 11/102:05 am -
2 stops13h 11m
Deal found 10/8![United Airlines logo]()
$257
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Sat 11/143:04 pm -
2 stops20h 12m
Sat 11/215:30 pm -
2 stops18h 08m
Deal found 10/8![American Airlines logo]()
$292
This United Airlines deal was found by Cheapflights users on 10/10. 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.
Tue 11/245:50 am -
1 stop7h 58m
Wed 12/22:55 pm -
1 stop8h 29m
Deal found 10/10![United Airlines logo]()
$314
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Thu 10/297:26 pm -
2 stops19h 29m
Mon 11/24:53 pm -
2 stops17h 57m
Deal found 10/8![American Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 10/10. 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.
Mon 11/166:00 am -
1 stop7h 50m
Fri 11/201:15 pm -
1 stop11h 04m
Deal found 10/10![Delta logo]()
$326
This Southwest deal was found by Cheapflights users on 10/11. 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 12/73:25 pm -
1 stop6h 55m
Fri 12/115:50 pm -
1 stop7h 00m
Deal found 10/11![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 10/7. 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.
Mon 11/95:20 am -
1 stop7h 30m
Thu 11/123:45 pm -
1 stop9h 10m
Deal found 10/7![Southwest logo]()
$337
This American Airlines deal was found by Cheapflights users on 10/9. 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 10/284:54 pm -
2 stops22h 01m
Mon 11/24:33 pm -
2 stops18h 17m
Deal found 10/9![American Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 10/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:40 pm -
1 stop10h 30m
Thu 11/125:50 pm -
1 stop7h 05m
Deal found 10/8![Southwest logo]()
$347
This American Airlines deal was found by Cheapflights users on 10/9. 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 11/116:00 am -
2 stops13h 53m
Wed 11/1812:18 pm -
1 stop9h 18m
Deal found 10/9![American Airlines logo]()
$353
This Delta deal was found by Cheapflights users on 10/10. 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.
Wed 12/96:00 am -
1 stop9h 36m
Sat 12/121:22 pm -
1 stop10h 59m
Deal found 10/10![Delta logo]()
$357
This United Airlines deal was found by Cheapflights users on 10/11. 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 12/117:00 am -
1 stop6h 40m
Tue 12/152:52 pm -
1 stop6h 50m
Deal found 10/11![United Airlines logo]()
$360
Best flights from Portland to CaribbeanDiscover carefully curated flight deals from Portland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 12, 2026.
Discover carefully curated flight deals from Portland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 12, 2026.
This American Airlines deal was found by Cheapflights users on 10/7. 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.
Mon 11/96:47 pm -
2 stops20h 16m
Thu 11/124:53 pm -
2 stops18h 44m
Deal found 10/7![American Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 10/10. 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.
Mon 11/166:00 am -
1 stop7h 50m
Fri 11/201:15 pm -
1 stop11h 04m
Deal found 10/10![Delta logo]()
$326
This Southwest deal was found by Cheapflights users on 10/11. 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 12/73:25 pm -
1 stop6h 55m
Fri 12/115:50 pm -
1 stop7h 00m
Deal found 10/11![Southwest logo]()
$336
This United Airlines deal was found by Cheapflights users on 10/9. 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.
Sat 1/307:30 am -
2 stops12h 30m
Fri 2/52:05 am -
2 stops13h 39m
Deal found 10/9![United Airlines logo]()
$436
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Thu 10/297:26 pm -
2 stops19h 29m
Mon 11/24:53 pm -
2 stops17h 57m
Deal found 10/8![American Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 10/10. 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.
Sat 1/302:35 pm -
1 stop8h 20m
Sat 2/67:00 am -
1 stop7h 53m
Deal found 10/10![Delta logo]()
$336
This Southwest deal was found by Cheapflights users on 10/7. 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.
Mon 11/95:20 am -
1 stop7h 30m
Thu 11/123:45 pm -
1 stop9h 10m
Deal found 10/7![Southwest logo]()
$337
This American Airlines deal was found by Cheapflights users on 10/12. 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.
Sun 11/86:47 pm -
2 stops19h 51m
Tue 11/174:53 pm -
2 stops18h 44m
Deal found 10/12![American Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/116:00 am -
1 stop9h 15m
Thu 1/144:25 pm -
1 stop6h 41m
Deal found 10/7![Delta logo]()
$348
This Delta deal was found by Cheapflights users on 10/8. 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 1/246:00 am -
1 stop9h 15m
Fri 1/292:55 pm -
2 stops8h 11m
Deal found 10/8![Delta logo]()
$353
This Southwest deal was found by Cheapflights users on 10/12. 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 11/265:15 am -
2 stops12h 20m
Fri 12/42:25 pm -
1 stop8h 20m
Deal found 10/12![Southwest logo]()
$395
This United Airlines deal was found by Cheapflights users on 10/10. 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 11/95:35 am -
1 stop6h 38m
Mon 11/161:25 pm -
2 stops20h 42m
Deal found 10/10![United Airlines logo]()
$443
This American Airlines deal was found by Cheapflights users on 10/7. 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.
Mon 1/256:36 pm -
1 stop18h 13m
Sat 2/65:59 pm -
2 stops18h 20m
Deal found 10/7![American Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 10/10. 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.
Wed 12/96:00 am -
1 stop9h 36m
Sat 12/121:22 pm -
1 stop10h 59m
Deal found 10/10![Delta logo]()
$357
This United Airlines deal was found by Cheapflights users on 10/11. 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.
Mon 12/77:00 am -
1 stop6h 48m
Wed 12/912:55 pm -
1 stop6h 30m
Deal found 10/11![United Airlines logo]()
$444
This American Airlines deal was found by Cheapflights users on 10/7. 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.
Sun 2/2110:59 am -
1 stop25h 47m
Thu 2/255:42 pm -
2 stops19h 02m
Deal found 10/7![American Airlines logo]()
$373
This Delta deal was found by Cheapflights users on 10/10. 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.
Mon 11/164:50 pm -
2 stops20h 38m
Tue 11/242:51 pm -
1 stop10h 28m
Deal found 10/10![Delta logo]()
$362
This United Airlines deal was found by Cheapflights users on 10/12. 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 11/76:00 am -
2 stops10h 19m
Sat 11/145:21 pm -
2 stops15h 39m
Deal found 10/12![United Airlines logo]()
$449
This American Airlines deal was found by Cheapflights users on 10/7. 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.
Sat 2/63:47 pm -
1 stop18h 38m
Sat 2/1310:22 am -
1 stop12h 34m
Deal found 10/7![American Airlines logo]()
$380
This Southwest deal was found by Cheapflights users on 10/7. 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 10/233:25 pm -
1 stop8h 45m
Tue 10/275:05 am -
2 stops10h 25m
Deal found 10/7![Southwest logo]()
$469
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Mon 12/77:00 am -
1 stop7h 14m
Mon 12/143:20 pm -
1 stop8h 04m
Deal found 10/12![United Airlines logo]()
$456
This American Airlines deal was found by Cheapflights users on 10/7. 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.
Tue 2/210:52 am -
1 stop25h 31m
Tue 2/91:23 pm -
1 stop20h 56m
Deal found 10/7![American Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 10/12. 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.
Mon 2/12:35 pm -
1 stop8h 20m
Mon 2/83:55 pm -
1 stop7h 28m
Deal found 10/12![Delta logo]()
$404
This United Airlines deal was found by Cheapflights users on 10/9. 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 12/17:55 pm -
1 stop16h 18m
Tue 12/81:25 pm -
1 stop7h 17m
Deal found 10/9![United Airlines logo]()
$468
This Southwest deal was found by Cheapflights users on 10/7. 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.
Sun 1/175:35 am -
2 stops9h 15m
Sun 1/245:45 am -
2 stops9h 55m
Deal found 10/7![Southwest logo]()
$517
This Delta deal was found by Cheapflights users on 10/11. 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.
Sat 10/316:01 am -
1 stop10h 47m
Fri 11/66:10 pm -
1 stop7h 00m
Deal found 10/11![Delta logo]()
$404
This American Airlines deal was found by Cheapflights users on 10/7. 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.
Mon 11/167:10 am -
1 stop6h 05m
Sat 11/214:21 pm -
1 stop7h 34m
Deal found 10/7![American Airlines logo]()
$430
This Southwest deal was found by Cheapflights users on 10/10. 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.
Tue 1/55:15 am -
1 stop6h 45m
Tue 1/123:10 pm -
1 stop6h 30m
Deal found 10/10![Southwest logo]()
$540
This United Airlines deal was found by Cheapflights users on 10/9. 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 1/57:50 pm -
1 stop16h 23m
Tue 1/122:54 pm -
2 stops23h 39m
Deal found 10/9![United Airlines logo]()
$498
This American Airlines deal was found by Cheapflights users on 10/12. 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.
Fri 1/296:36 pm -
2 stops17h 12m
Mon 2/812:59 pm -
1 stop8h 30m
Deal found 10/12![American Airlines logo]()
$442
Last-minute flights from Portland to CaribbeanDiscover last-minute flight deals from Portland to Caribbean. Data last updated October 12, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Caribbean. Data last updated October 12, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/9. 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 10/284:54 pm -
2 stops22h 01m
Mon 11/24:33 pm -
2 stops18h 17m
Deal found 10/9![American Airlines logo]()
$345
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Thu 10/297:26 pm -
2 stops19h 29m
Mon 11/24:53 pm -
2 stops17h 57m
Deal found 10/8![American Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 10/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:40 pm -
1 stop10h 30m
Thu 11/125:50 pm -
1 stop7h 05m
Deal found 10/8![Southwest logo]()
$347
This American Airlines deal was found by Cheapflights users on 10/9. 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 11/66:47 pm -
2 stops16h 26m
Wed 11/1111:45 am -
1 stop9h 51m
Deal found 10/9![American Airlines logo]()
$375
This United Airlines deal was found by Cheapflights users on 10/8. 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 11/73:41 pm -
1 stop7h 55m
Tue 11/102:05 am -
2 stops13h 11m
Deal found 10/8![United Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 10/7. 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.
Mon 11/95:20 am -
1 stop7h 30m
Thu 11/123:45 pm -
1 stop9h 10m
Deal found 10/7![Southwest logo]()
$337
This American Airlines deal was found by Cheapflights users on 10/7. 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.
Mon 11/96:47 pm -
2 stops20h 16m
Thu 11/124:33 pm -
1 stop7h 00m
Deal found 10/7![American Airlines logo]()
$390
This American Airlines deal was found by Cheapflights users on 10/9. 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 11/116:00 am -
2 stops13h 53m
Wed 11/1812:55 pm -
2 stops10h 02m
Deal found 10/9![American Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Sat 11/143:04 pm -
2 stops20h 12m
Sat 11/215:30 pm -
2 stops18h 08m
Deal found 10/8![American Airlines logo]()
$292
This Delta deal was found by Cheapflights users on 10/10. 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.
Mon 11/166:00 am -
1 stop7h 50m
Fri 11/201:15 pm -
1 stop11h 04m
Deal found 10/10![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 10/10. 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.
Mon 11/164:50 pm -
2 stops20h 38m
Tue 11/242:51 pm -
1 stop10h 28m
Deal found 10/10![Delta logo]()
$362
This United Airlines deal was found by Cheapflights users on 10/10. 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.
Tue 11/245:50 am -
1 stop7h 58m
Wed 12/22:55 pm -
1 stop8h 29m
Deal found 10/10![United Airlines logo]()
$314
One-way flights from Portland to CaribbeanSearch for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 12, 2026.
Search for one-way flight options from Portland to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 12, 2026.
This Delta deal was found by Cheapflights users on 10/9. 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.
Tue 12/296:50 pm -
1 stop16h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Delta logo]()
$120
This Delta deal was found by Cheapflights users on 10/9. 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.
Sat 1/26:50 pm -
1 stop16h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Delta logo]()
$140
This JetBlue deal was found by Cheapflights users on 10/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:30 am -
1 stop9h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![JetBlue logo]()
$145
This JetBlue deal was found by Cheapflights users on 10/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:30 am -
1 stop7h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![JetBlue logo]()
$147
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Sun 11/156:47 pm -
2 stops19h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![American Airlines logo]()
$151
This JetBlue deal was found by Cheapflights users on 10/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:30 am -
1 stop7h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![JetBlue logo]()
$154
This American Airlines deal was found by Cheapflights users on 10/11. 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 11/286:47 pm -
2 stops20h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![American Airlines logo]()
$159
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Sat 10/315:37 pm -
2 stops17h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![American Airlines logo]()
$162
This Delta deal was found by Cheapflights users on 10/12. 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.
Mon 12/76:00 am -
1 stop10h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Delta logo]()
$167
This American Airlines deal was found by Cheapflights users on 10/8. 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 11/26:47 pm -
2 stops19h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![American Airlines logo]()
$168
This American Airlines deal was found by Cheapflights users on 10/11. 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 12/53:18 pm -
2 stops19h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![American Airlines logo]()
$168
This United Airlines deal was found by Cheapflights users on 10/9. 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 12/307:44 pm -
1 stop16h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![United Airlines logo]()
$168
Find flight deals from Portland to Caribbean
Keep the following information in mind while searching for Portland to Caribbean flight deals. Data was last updated October 12, 2026.
Round-trip from | $244 (American Airlines) |
|---|---|
One-way from | $120 (Delta) |
Popular in | April |
Cheapest in | November |
Average price | $362 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 12, 2026.
Use the filters below to find and compare flights from Portland to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandNassau
PWM Portland - NAS Nassau Intl
PWMNAS
Portland
Sat 1/2
5:35 am-4:04 pm
1 stop10h 29m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$140
PortlandOranjestad
PWM Portland - AUA Oranjestad Reina Beatrix
PWMAUA
Portland
Sun 11/15
6:30 am-4:45 pm
1 stop9h 15m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$145
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Sun 11/15
5:50 am-2:14 pm
1 stop8h 24m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$162
PortlandSaint Thomas Island
PWM Portland - STT Saint Thomas Island Cyril E King
PWMSTT
Portland
Sat 12/5
3:18 pm-12:17 pm
2 stops19h 59m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$168
PortlandNassau
PWM Portland - NAS Nassau Intl
PWMNAS
Portland
Wed 12/30
7:44 pm-11:49 am
1 stop16h 05m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$168
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Sat 11/14
6:47 pm-1:12 pm
1 stop18h 25m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$175
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Thu 12/31
7:44 pm-12:13 pm
1 stop16h 29m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$177
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Sat 10/31
5:30 am-3:19 pm
1 stop10h 49m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$198
PortlandOranjestad
PWM Portland - AUA Oranjestad Reina Beatrix
PWMAUA
Portland
Sun 11/15
5:08 pm-1:40 pm
2 stops19h 32m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$200
PortlandNassau
PWM Portland - NAS Nassau Intl
PWMNAS
Portland
Fri 1/1
6:00 am-1:48 pm
1 stop7h 48m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$205
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Portland to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Portland with our price prediction graph.
PWM-STT
PWM-NAS
PWM-SJU
PWM-MBJ
PWM-AUA
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Caribbean
PWM-0CB
PWM-STT
PWM-NAS
PWM-SJU
PWM-MBJ
What is the cheapest month to book a flight from Portland, Maine to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Caribbean (average of $410). Flying from Portland, Maine to Caribbean in April is currently the most expensive (average of $734). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How far ahead should I book a flight from Portland, Maine to Caribbean?
Booking 36 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland, Maine to Caribbean. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated October 12, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Portland to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.5
Overall
7.9
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Entertainment
7.5
Overall
7.9
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Entertainment
7.5
Overall
7.9
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Entertainment
7.5
Overall
7.9
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Entertainment
7.5
Overall
7.9
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Entertainment
7.5
Overall
7.9
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Related info for your journey
Find useful and relevant information for your journey from Portland to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Portland to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Portland to Caribbean by cabin class
Find flights from Portland to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Caribbean flights
Browse other Portland and Caribbean flight options. Last updated on October 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Portland to Caribbean flights
Consider these flights traveling from Portland to Caribbean.
Top 5 airlines flying from Portland to Caribbean
Discover the top 5 airlines that operate flights from Portland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$413 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$174 | Average$502 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$247 | Average$607 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$296 | Average$609 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$322 | Average$718 | FlexibilityNo cancel fee | On-time63% |