$99+ Cheap flights from Pittsburgh (PIT) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Nov 24 — Dec 11
Round-trip
1 adult, Economy
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Find cheap flights from Pittsburgh 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 Pittsburgh to Caribbean
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Cheapest flights from Pittsburgh to CaribbeanExplore the most affordable flight options available from Pittsburgh to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
Explore the most affordable flight options available from Pittsburgh to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:28 pm -
1 stop6h 45m
Fri 12/118:44 pm -
1 stop21h 49m
Deal found 10/21![Frontier logo]()
$260
This Frontier deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:27 pm -
1 stop7h 19m
Thu 11/127:23 am -
1 stop11h 09m
Deal found 10/21![Frontier logo]()
$273
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:27 pm -
1 stop14h 48m
Tue 11/173:55 am -
1 stop14h 37m
Deal found 10/21![Frontier logo]()
$276
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 12/76:52 pm -
1 stop18h 07m
Tue 12/154:10 pm -
1 stop7h 52m
Deal found 10/21![American Airlines logo]()
$282
This deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:27 pm -
1 stop7h 19m
Sun 11/811:20 am -
1 stop7h 12m
Deal found 10/22![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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.
Thu 12/33:09 pm -
2 stops32h 58m
Thu 12/106:05 am -
1 stop16h 20m
Deal found 10/24![Multiple Airlines logo]()
$286
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 12/67:55 pm -
1 stop17h 24m
Wed 12/95:16 pm -
2 stops18h 03m
Deal found 10/21![American Airlines logo]()
$286
This Cheapflightsfares deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:27 pm -
1 stop7h 19m
Wed 12/24:07 pm -
1 stop26h 21m
Deal found 10/20![Frontier logo]()
$287
This JetBlue deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Wed 12/26:00 am -
1 stop6h 45m
Wed 12/912:25 pm -
1 stop9h 06m
Deal found 10/21![JetBlue logo]()
$288
This Cheapflightsfares deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:27 pm -
1 stop14h 48m
Wed 11/117:23 am -
1 stop11h 09m
Deal found 10/20![Frontier logo]()
$301
This JetBlue deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/67:53 am -
1 stop7h 47m
Thu 12/104:45 pm -
1 stop8h 11m
Deal found 10/20![JetBlue logo]()
$301
This JetBlue deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Sat 12/56:00 am -
1 stop6h 55m
Sat 12/1212:25 pm -
1 stop9h 06m
Deal found 10/21![JetBlue logo]()
$303
Best flights from Pittsburgh to CaribbeanDiscover carefully curated flight deals from Pittsburgh to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
Discover carefully curated flight deals from Pittsburgh to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
This JetBlue deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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.
Wed 12/26:00 am -
1 stop6h 45m
Wed 12/912:25 pm -
1 stop9h 06m
Deal found 10/24![JetBlue logo]()
$302
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 1/177:20 pm -
2 stops17h 30m
Thu 1/215:50 pm -
1 stop6h 38m
Deal found 10/24![United Airlines logo]()
$302
This American Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 4/610:55 am -
2 stops9h 56m
Thu 4/154:30 pm -
1 stop17h 13m
Deal found 10/24![American Airlines logo]()
$320
This Breeze Airways deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/199:24 am -
Nonstop4h 00m
Thu 2/43:24 pm -
Nonstop4h 30m
Deal found 10/20![Breeze Airways logo]()
$357
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 2/269:00 pm -
1 stop11h 50m
Sat 3/65:40 am -
1 stop7h 15m
Deal found 10/20![Southwest logo]()
$388
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 1/196:00 am -
1 stop7h 15m
Thu 2/42:32 pm -
1 stop9h 46m
Deal found 10/21![Delta logo]()
$450
This Air Canada deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/67:20 pm -
2 stops19h 00m
Thu 12/104:45 pm -
1 stop26h 51m
Deal found 10/24![Air Canada logo]()
$525
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 1/177:45 pm -
1 stop17h 05m
Fri 1/224:25 pm -
1 stop7h 49m
Deal found 10/23![United Airlines logo]()
$302
This JetBlue deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Sat 12/56:00 am -
1 stop6h 55m
Sat 12/1212:25 pm -
1 stop9h 06m
Deal found 10/21![JetBlue logo]()
$303
This American Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 10/318:36 pm -
2 stops19h 55m
Wed 11/43:26 pm -
2 stops19h 52m
Deal found 10/24![American Airlines logo]()
$332
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 12/27:00 am -
1 stop6h 48m
Wed 12/92:55 pm -
1 stop6h 02m
Deal found 10/21![United Airlines logo]()
$306
This JetBlue deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 1/106:00 am -
1 stop6h 35m
Thu 1/1412:00 pm -
1 stop9h 30m
Deal found 10/22![JetBlue logo]()
$306
This American Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/278:29 pm -
2 stops16h 28m
Wed 12/25:33 pm -
2 stops20h 07m
Deal found 10/24![American Airlines logo]()
$332
This JetBlue deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 1/36:20 am -
1 stop9h 36m
Wed 1/612:00 pm -
1 stop9h 30m
Deal found 10/24![JetBlue logo]()
$306
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 1/37:18 am -
1 stop6h 30m
Wed 1/64:30 pm -
1 stop6h 44m
Deal found 10/23![United Airlines logo]()
$313
This JetBlue deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/137:53 am -
1 stop7h 47m
Fri 12/181:20 pm -
1 stop10h 28m
Deal found 10/20![JetBlue logo]()
$306
This American Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/195:30 am -
1 stop7h 40m
Thu 1/281:58 pm -
1 stop10h 25m
Deal found 10/25![American Airlines logo]()
$350
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 1/127:00 am -
1 stop6h 40m
Fri 1/158:05 am -
1 stop7h 08m
Deal found 10/22![United Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 4/69:55 am -
2 stops9h 45m
Mon 4/127:15 am -
2 stops9h 40m
Deal found 10/23![Southwest logo]()
$448
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 1/66:00 am -
1 stop5h 49m
Mon 1/113:35 pm -
1 stop8h 24m
Deal found 10/23![United Airlines logo]()
$321
This American Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 2/246:00 pm -
2 stops17h 13m
Tue 3/22:19 pm -
1 stop8h 21m
Deal found 10/24![American Airlines logo]()
$355
This JetBlue deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Wed 11/46:00 am -
1 stop7h 51m
Sat 11/1412:21 pm -
1 stop9h 07m
Deal found 10/21![JetBlue logo]()
$330
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 2/167:00 am -
1 stop5h 45m
Tue 2/233:50 pm -
1 stop8h 29m
Deal found 10/25![Delta logo]()
$514
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 12/26:00 am -
1 stop7h 48m
Mon 12/712:55 pm -
1 stop9h 32m
Deal found 10/21![United Airlines logo]()
$323
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 3/316:55 am -
2 stops11h 30m
Sat 4/107:20 pm -
1 stop13h 15m
Deal found 10/23![Southwest logo]()
$477
This JetBlue deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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.
Tue 12/16:00 am -
1 stop8h 11m
Tue 12/84:32 pm -
1 stop8h 24m
Deal found 10/22![JetBlue logo]()
$341
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/176:46 pm -
2 stops18h 43m
Wed 12/233:23 pm -
1 stop9h 34m
Deal found 10/22![American Airlines logo]()
$386
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 2/216:00 am -
1 stop9h 15m
Sun 2/284:15 pm -
1 stop9h 04m
Deal found 10/24![Delta logo]()
$515
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 1/97:07 pm -
1 stop17h 17m
Tue 1/195:29 pm -
2 stops20h 48m
Deal found 10/22![American Airlines logo]()
$397
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 2/167:00 am -
1 stop8h 15m
Fri 2/264:15 pm -
1 stop9h 04m
Deal found 10/23![Delta logo]()
$529
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated October 25, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 10/318:36 pm -
2 stops19h 55m
Wed 11/43:26 pm -
2 stops19h 52m
Deal found 10/24![American Airlines logo]()
$332
This Cheapflightsfares deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:27 pm -
1 stop14h 48m
Wed 11/117:23 am -
1 stop11h 09m
Deal found 10/20![Frontier logo]()
$301
This JetBlue deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Wed 11/46:00 am -
1 stop7h 51m
Sat 11/1412:21 pm -
1 stop9h 07m
Deal found 10/21![JetBlue logo]()
$330
This deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:27 pm -
1 stop7h 19m
Sun 11/811:20 am -
1 stop7h 12m
Deal found 10/22![Frontier logo]()
$283
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/96:11 am -
1 stop15h 05m
Fri 11/1311:51 am -
2 stops8h 58m
Deal found 10/22![American Airlines logo]()
$324
This Cheapflightsfares deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:27 pm -
1 stop7h 19m
Wed 12/24:07 pm -
1 stop26h 21m
Deal found 10/20![Frontier logo]()
$287
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:45 am -
2 stops10h 54m
Wed 12/212:59 pm -
2 stops9h 18m
Deal found 10/20![American Airlines logo]()
$320
This Frontier deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:27 pm -
1 stop7h 19m
Thu 11/127:23 am -
1 stop11h 09m
Deal found 10/21![Frontier logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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.
Thu 11/126:30 am -
2 stops41h 29m
Wed 11/187:23 am -
1 stop11h 09m
Deal found 10/24![Multiple Airlines logo]()
$323
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:27 pm -
1 stop14h 48m
Tue 11/173:55 am -
1 stop14h 37m
Deal found 10/21![Frontier logo]()
$276
This American Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/158:19 pm -
1 stop16h 58m
Tue 11/245:29 pm -
1 stop20h 14m
Deal found 10/23![American Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/308:00 am -
1 stop5h 41m
Tue 12/810:22 am -
1 stop12h 40m
Deal found 10/21![American Airlines logo]()
$306
One-way flights from Pittsburgh to CaribbeanSearch for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/246:00 am -
1 stop7h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![United Airlines logo]()
$99
This JetBlue deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 12/147:53 am -
1 stop7h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![JetBlue logo]()
$107
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 2/157:10 pm -
1 stop16h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![American Airlines logo]()
$114
This American Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/308:00 am -
1 stop7h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![American Airlines logo]()
$118
This American Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/18:19 pm -
1 stop16h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![American Airlines logo]()
$119
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 12/147:25 pm -
2 stops17h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![United Airlines logo]()
$120
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/306:00 am -
1 stop6h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![United Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 2/87:57 pm -
1 stop15h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$139
This deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:28 pm -
1 stop6h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/307:45 am -
3 stops41h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$151
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/258:02 am -
2 stops9h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$154
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 2/84:25 pm -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$160
Find flight deals from Pittsburgh to Caribbean
Keep the following information in mind while searching for Pittsburgh to Caribbean flight deals. Data was last updated October 25, 2026.
Round-trip from | $260 (Cheapflightsfares) |
|---|---|
One-way from | $99 (United Airlines) |
Popular in | June |
Cheapest in | September |
Average price | $388 |
Good round-trip deal | $418 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Pittsburgh 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 25, 2026.
Use the filters below to find and compare flights from Pittsburgh to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PittsburghNassau
PIT Pittsburgh - NAS Nassau Intl
PITNAS
Pittsburgh
Tue 11/24
6:00 am-1:48 pm
1 stop7h 48m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$99
PittsburghOranjestad
PIT Pittsburgh - AUA Oranjestad Reina Beatrix
PITAUA
Pittsburgh
Mon 12/14
7:53 am-4:40 pm
1 stop7h 47m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$107
PittsburghNassau
PIT Pittsburgh - NAS Nassau Intl
PITNAS
Pittsburgh
Mon 2/15
7:10 pm-11:21 am
1 stop16h 11m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$114
PittsburghSimpson Bay
PIT Pittsburgh - SXM Simpson Bay Princess Juliana
PITSXM
Pittsburgh
Fri 12/4
7:55 pm-1:27 pm
1 stop16h 32m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$119
PittsburghOranjestad
PIT Pittsburgh - AUA Oranjestad Reina Beatrix
PITAUA
Pittsburgh
Mon 12/14
8:04 pm-1:40 pm
1 stop16h 36m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$120
PittsburghSimpson Bay
PIT Pittsburgh - SXM Simpson Bay Princess Juliana
PITSXM
Pittsburgh
Wed 12/30
7:57 pm-1:07 pm
2 stops16h 10m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$123
PittsburghSimpson Bay
PIT Pittsburgh - SXM Simpson Bay Princess Juliana
PITSXM
Pittsburgh
Sun 11/1
5:34 pm-1:26 pm
2 stops18h 52m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$125
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Mon 11/30
7:45 am-1:58 am
3 stops41h 13m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$151
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Mon 2/8
6:00 am-2:05 pm
1 stop7h 05m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$160
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Sun 2/7
6:05 am-1:45 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$160
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Pittsburgh to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Pittsburgh with our price prediction graph.
PIT-NAS
PIT-AUA
PIT-SJU
PIT-PUJ
PIT-STT
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 Pittsburgh to Caribbean
PIT-0CB
PIT-NAS
PIT-AUA
PIT-SJU
PIT-PUJ
What is the cheapest month to book a flight from Pittsburgh to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $407). Flying from Pittsburgh to Caribbean in November is currently the most expensive (average of $615). 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 Pittsburgh to Caribbean?
Booking 9 days in advance of your planned departure date is, on average, the best time to get cheap flights from Pittsburgh 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 25, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Pittsburgh to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.4
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Related info for your journey
Find useful and relevant information for your journey from Pittsburgh 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 Pittsburgh 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 Pittsburgh to Caribbean by cabin class
Find flights from Pittsburgh to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Pittsburgh and Caribbean flights
Browse other Pittsburgh and Caribbean flight options. Last updated on October 25, 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.
Pittsburgh to Caribbean flights
Consider these flights traveling from Pittsburgh to Caribbean.
Top 8 airlines flying from Pittsburgh to Caribbean
Discover the top 8 airlines that operate flights from Pittsburgh 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 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$355 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$141 | Average$508 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$506 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$218 | Average$459 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$221 | Average$552 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$258 | Average$665 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$382 | Average$456 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$404 | Average$494 | FlexibilityNo cancel fee | On-time67% |