$116+ Cheap flights from Pittsburgh (PIT) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Jun 22 — Jun 291
Round-trip
1 adult, Economy
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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 May 23, 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 May 23, 2026.
This United Airlines deal was found by Cheapflights users on 5/21. 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.
Sat 8/299:00 am
PIT
- STT
1 stop6h 43m
United Airlines
Sat 9/54:45 pm
STT
- PIT
1 stop6h 45m
United Airlines
Deal found 5/21![United Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 5/21. 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.
Sat 8/296:52 am
PIT
- STT
1 stop8h 09m
American Airlines
Sat 9/52:00 pm
STT
- PIT
1 stop9h 50m
American Airlines
Deal found 5/21![American Airlines logo]()
$275
This American Airlines deal was found by Cheapflights users on 5/20. 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.
Sat 8/226:14 am
PIT
- STT
1 stop6h 38m
American Airlines
Sat 8/291:49 pm
STT
- PIT
1 stop10h 05m
American Airlines
Deal found 5/20![American Airlines logo]()
$290
This American Airlines deal was found by Cheapflights users on 5/21. 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 8/195:40 pm
PIT
- STT
2 stops19h 12m
American Airlines
Mon 8/244:42 pm
STT
- PIT
2 stops17h 42m
American Airlines
Deal found 5/21![American Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/36:00 am
PIT
- SJU
1 stop8h 00m
Multiple Airlines
Thu 8/136:45 am
SJU
- PIT
1 stop16h 01m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$311
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 11/106:10 am
PIT
- GCM
1 stop10h 20m
United Airlines
Fri 11/205:45 pm
GCM
- PIT
2 stops16h 13m
United Airlines
Deal found 5/18![United Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 5/296:10 am
PIT
- GCM
1 stop7h 20m
United Airlines
Mon 6/11:35 pm
GCM
- PIT
1 stop9h 24m
United Airlines
Deal found 5/19![United Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/412:04 pm
PIT
- SJU
1 stop26h 29m
Multiple Airlines
Sat 6/67:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 5/20. 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.
Mon 8/247:41 am
PIT
- SJU
1 stop16h 18m
American Airlines
Tue 8/2510:33 am
SJU
- PIT
2 stops10h 27m
American Airlines
Deal found 5/20![American Airlines logo]()
$318
This American Airlines deal was found by Cheapflights users on 5/22. 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.
Tue 11/106:41 am
PIT
- GCM
1 stop5h 59m
American Airlines
Fri 11/201:00 pm
GCM
- PIT
1 stop10h 38m
American Airlines
Deal found 5/22![American Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/16:00 am
PIT
- SJU
1 stop8h 33m
Multiple Airlines
Wed 6/37:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$322
This JetBlue deal was found by Cheapflights users on 5/20. 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.
Mon 9/286:00 am
PIT
- PUJ
1 stop6h 45m
JetBlue
Wed 10/71:50 pm
PUJ
- PIT
1 stop7h 33m
JetBlue
Deal found 5/20![JetBlue logo]()
$322
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 May 23, 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 May 23, 2026.
This United Airlines deal was found by Cheapflights users on 5/21. 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 11/106:10 am
PIT
- GCM
1 stop10h 20m
United Airlines
Fri 11/205:45 pm
GCM
- PIT
2 stops16h 13m
United Airlines
Deal found 5/21![United Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/55:40 am
PIT
- GCM
1 stop7h 14m
Delta
Mon 6/812:59 pm
GCM
- PIT
1 stop10h 56m
Delta
Deal found 5/19![Delta logo]()
$317
This JetBlue deal was found by Cheapflights users on 5/20. 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.
Mon 8/246:00 am
PIT
- PUJ
1 stop6h 55m
JetBlue
Thu 8/272:05 pm
PUJ
- PIT
1 stop7h 21m
JetBlue
Deal found 5/20![JetBlue logo]()
$322
This American Airlines deal was found by Cheapflights users on 5/21. 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.
Thu 6/46:38 am
PIT
- GCM
1 stop5h 52m
American Airlines
Mon 6/85:12 pm
GCM
- PIT
2 stops17h 56m
American Airlines
Deal found 5/21![American Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 7/206:00 am
PIT
- SJU
1 stop8h 34m
Multiple Airlines
Tue 7/285:15 pm
SJU
- PIT
2 stops49h 54m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 5/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/164:15 pm
PIT
- SJU
2 stops8h 15m
Southwest
Sat 8/225:05 am
SJU
- PIT
2 stops9h 40m
Southwest
Deal found 5/21![Southwest logo]()
$432
This Delta deal was found by Cheapflights users on 5/21. 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.
Sat 6/65:40 am
PIT
- GCM
1 stop7h 14m
Delta
Wed 6/1012:59 pm
GCM
- PIT
1 stop10h 56m
Delta
Deal found 5/21![Delta logo]()
$317
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/57:33 pm
PIT
- GCM
1 stop15h 49m
American Airlines
Mon 6/85:12 pm
GCM
- PIT
2 stops17h 56m
American Airlines
Deal found 5/19![American Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 8/276:10 am
PIT
- PUJ
1 stop6h 30m
United Airlines
Mon 8/313:35 pm
PUJ
- PIT
1 stop18h 01m
United Airlines
Deal found 5/19![United Airlines logo]()
$338
This JetBlue deal was found by Cheapflights users on 5/20. 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.
Tue 9/16:00 am
PIT
- NAS
1 stop7h 48m
JetBlue
Wed 9/23:02 pm
NAS
- PIT
1 stop6h 24m
JetBlue
Deal found 5/20![JetBlue logo]()
$340
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/36:37 am
PIT
- GCM
1 stop5h 53m
American Airlines
Tue 6/912:01 pm
GCM
- PIT
1 stop10h 57m
American Airlines
Deal found 5/19![American Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/26:06 am
PIT
- NAS
2 stops8h 51m
United Airlines
Fri 6/54:58 pm
NAS
- PIT
1 stop7h 01m
United Airlines
Deal found 5/19![United Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:50 pm
PIT
- SJU
1 stop8h 33m
Delta
Sat 9/123:10 pm
SJU
- PIT
1 stop7h 28m
Delta
Deal found 5/19![Delta logo]()
$353
This JetBlue deal was found by Cheapflights users on 5/21. 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 8/246:00 am
PIT
- SXM
1 stop6h 37m
JetBlue
Fri 8/281:42 pm
SXM
- PIT
1 stop7h 44m
JetBlue
Deal found 5/21![JetBlue logo]()
$357
This American Airlines deal was found by Cheapflights users on 5/21. 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.
Sat 6/67:59 pm
PIT
- GCM
1 stop16h 31m
American Airlines
Wed 6/105:12 pm
GCM
- PIT
2 stops16h 04m
American Airlines
Deal found 5/21![American Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 5/20. 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.
Fri 9/187:54 pm
PIT
- NAS
2 stops17h 39m
United Airlines
Fri 9/252:53 pm
NAS
- PIT
1 stop7h 08m
United Airlines
Deal found 5/20![United Airlines logo]()
$340
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 10/233:55 pm
PIT
- SJU
2 stops8h 40m
Southwest
Mon 10/265:30 am
SJU
- PIT
2 stops9h 45m
Southwest
Deal found 5/17![Southwest logo]()
$448
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 8/46:15 am
PIT
- NAS
1 stop7h 32m
United Airlines
Sat 8/81:15 pm
NAS
- PIT
1 stop10h 21m
United Airlines
Deal found 5/19![United Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 5/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/111:54 am
PIT
- SDQ
1 stop12h 47m
Delta
Tue 6/166:06 am
SDQ
- PIT
1 stop11h 00m
Delta
Deal found 5/22![Delta logo]()
$376
This American Airlines deal was found by Cheapflights users on 5/22. 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 10/177:33 pm
PIT
- MBJ
2 stops14h 32m
American Airlines
Sat 10/245:00 pm
MBJ
- PIT
2 stops15h 53m
American Airlines
Deal found 5/22![American Airlines logo]()
$357
This JetBlue deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 10/266:00 am
PIT
- MBJ
1 stop8h 48m
JetBlue
Thu 10/291:00 pm
MBJ
- PIT
1 stop7h 22m
JetBlue
Deal found 5/18![JetBlue logo]()
$423
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:30 am
PIT
- NAS
1 stop6h 18m
United Airlines
Mon 10/262:35 pm
NAS
- PIT
1 stop7h 45m
United Airlines
Deal found 5/19![United Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/205:19 pm
PIT
- SXM
2 stops19h 56m
American Airlines
Thu 9/242:50 pm
SXM
- PIT
2 stops23h 18m
American Airlines
Deal found 5/19![American Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 5/21. 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 6/3011:50 am
PIT
- SJU
1 stop10h 39m
Delta
Tue 7/72:21 pm
SJU
- PIT
1 stop9h 43m
Delta
Deal found 5/21![Delta logo]()
$403
This Southwest deal was found by Cheapflights users on 5/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2312:45 pm
PIT
- SJU
2 stops9h 15m
Southwest
Fri 6/268:15 pm
SJU
- PIT
1 stop12h 35m
Southwest
Deal found 5/21![Southwest logo]()
$526
This American Airlines deal was found by Cheapflights users on 5/22. 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.
Sun 6/147:59 pm
PIT
- SXM
1 stop17h 51m
American Airlines
Fri 6/194:43 pm
SXM
- PIT
2 stops18h 36m
American Airlines
Deal found 5/22![American Airlines logo]()
$362
This United Airlines deal was found by Cheapflights users on 5/20. 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.
Thu 7/167:40 pm
PIT
- SXM
2 stops16h 53m
United Airlines
Tue 7/213:50 pm
SXM
- PIT
2 stops18h 08m
United Airlines
Deal found 5/20![United Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 8/186:00 am
PIT
- STT
1 stop7h 34m
Delta
Tue 8/252:49 pm
STT
- PIT
1 stop9h 47m
Delta
Deal found 5/19![Delta logo]()
$420
This American Airlines deal was found by Cheapflights users on 5/21. 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 8/128:59 pm
PIT
- SXM
2 stops18h 40m
American Airlines
Wed 8/194:39 pm
SXM
- PIT
1 stop24h 21m
American Airlines
Deal found 5/21![American Airlines logo]()
$375
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 7/201:45 pm
PIT
- SJU
2 stops9h 50m
Southwest
Tue 7/285:00 am
SJU
- PIT
2 stops10h 15m
Southwest
Deal found 5/17![Southwest logo]()
$554
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated May 23, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated May 23, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 5/296:10 am
PIT
- GCM
1 stop7h 20m
United Airlines
Mon 6/11:35 pm
GCM
- PIT
1 stop9h 24m
United Airlines
Deal found 5/19![United Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 5/22. 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.
Fri 5/298:05 am
PIT
- SJU
1 stop14h 56m
American Airlines
Sat 6/65:30 am
SJU
- PIT
1 stop13h 11m
American Airlines
Deal found 5/22![American Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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.
Fri 5/299:14 pm
PIT
- SJU
1 stop20h 38m
Multiple Airlines
Sat 6/67:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/16:00 am
PIT
- SJU
1 stop8h 33m
Multiple Airlines
Wed 6/37:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/16:00 am
PIT
- SJU
1 stop8h 33m
Multiple Airlines
Sun 6/77:00 am
SJU
- PIT
1 stop16h 27m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/36:14 am
PIT
- GCM
2 stops10h 57m
American Airlines
Tue 6/95:12 pm
GCM
- PIT
2 stops14h 27m
American Airlines
Deal found 5/19![American Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/412:04 pm
PIT
- SJU
1 stop26h 29m
Multiple Airlines
Sat 6/67:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 5/22. 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 6/46:38 am
PIT
- GCM
1 stop5h 52m
American Airlines
Mon 6/82:42 pm
GCM
- PIT
1 stop8h 15m
American Airlines
Deal found 5/22![American Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/412:04 pm
PIT
- SJU
1 stop26h 29m
Multiple Airlines
Thu 6/117:00 am
SJU
- PIT
1 stop15h 26m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/188:05 am
PIT
- NAS
2 stops9h 45m
American Airlines
Mon 6/2212:36 pm
NAS
- PIT
1 stop11h 23m
American Airlines
Deal found 5/19![American Airlines logo]()
$344
This American Airlines deal was found by Cheapflights users on 5/22. 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.
Sun 6/218:42 pm
PIT
- NAS
1 stop14h 54m
American Airlines
Thu 6/2510:17 am
NAS
- PIT
1 stop13h 41m
American Airlines
Deal found 5/22![American Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 5/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/3011:50 am
PIT
- SJU
1 stop10h 39m
Delta
Mon 7/65:56 pm
SJU
- PIT
1 stop6h 59m
Delta
Deal found 5/20![Delta logo]()
$326
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 May 23, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated May 23, 2026.
This American Airlines deal was found by Cheapflights users on 5/22. 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.
Sun 8/307:06 pm
PIT
- NAS
1 stop14h 30m
American Airlines
Deal found 5/22![American Airlines logo]()
$116
This American Airlines deal was found by Cheapflights users on 5/21. 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.
Tue 6/307:59 pm
PIT
- STT
1 stop15h 04m
American Airlines
Deal found 5/21![American Airlines logo]()
$123
This American Airlines deal was found by Cheapflights users on 5/22. 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.
Sun 7/198:01 pm
PIT
- SXM
1 stop17h 50m
American Airlines
Deal found 5/22![American Airlines logo]()
$134
This American Airlines deal was found by Cheapflights users on 5/21. 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.
Sat 6/277:45 pm
PIT
- AUA
1 stop17h 14m
American Airlines
Deal found 5/21![American Airlines logo]()
$140
This American Airlines deal was found by Cheapflights users on 5/23. 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 11/17:30 pm
PIT
- SXM
2 stops19h 50m
American Airlines
Deal found 5/23![American Airlines logo]()
$140
This Super.com deal was found by Cheapflights users on 5/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:00 am
PIT
- PUJ
1 stop6h 55m
JetBlue
Deal found 5/21![JetBlue logo]()
$140
This United Airlines deal was found by Cheapflights users on 5/22. 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.
Sun 11/17:00 am
PIT
- SXM
1 stop7h 57m
United Airlines
Deal found 5/22![United Airlines logo]()
$147
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/216:15 am
PIT
- MBJ
1 stop10h 11m
United Airlines
Deal found 5/19![United Airlines logo]()
$148
This Cheapflightsfares deal was found by Cheapflights users on 5/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
PIT
- PUJ
1 stop9h 27m
JetBlue
Deal found 5/22![JetBlue logo]()
$148
This JetBlue deal was found by Cheapflights users on 5/20. 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.
Sat 8/156:00 am
PIT
- PUJ
1 stop6h 55m
JetBlue
Deal found 5/20![JetBlue logo]()
$149
This American Airlines deal was found by Cheapflights users on 5/22. 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 11/210:03 am
PIT
- SJU
1 stop12h 44m
American Airlines
Deal found 5/22![American Airlines logo]()
$151
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/66:15 am
PIT
- AUA
1 stop9h 05m
United Airlines
Deal found 5/18![United Airlines logo]()
$151
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 May 23, 2026.
Round-trip from | $250 (United Airlines) |
|---|---|
One-way from | $116 (American Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $366 |
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 2,558,603 searches. Data last updated May 23, 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
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Tue 11/10
6:10 am-4:30 pm
1 stop10h 20m
George Town Owen Roberts Intl
Fri 11/20
5:45 pm-9:58 am
2 stops16h 13m
$316
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Fri 6/5
5:40 am-11:54 am
1 stop7h 14m
George Town Owen Roberts Intl
Mon 6/8
12:59 pm-12:55 am
1 stop10h 56m
$317
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Sat 6/6
5:40 am-11:54 am
1 stop7h 14m
George Town Owen Roberts Intl
Wed 6/10
12:59 pm-12:55 am
1 stop10h 56m
$317
PittsburghPunta Cana
PIT - PUJ
PITPUJ
Pittsburgh
Mon 8/24
6:00 am-12:55 pm
1 stop6h 55m
Punta Cana
Thu 8/27
2:05 pm-9:26 pm
1 stop7h 21m
$322
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Thu 6/4
6:38 am-11:30 am
1 stop5h 52m
George Town Owen Roberts Intl
Mon 6/8
5:12 pm-12:08 pm
2 stops17h 56m
$326
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Fri 6/5
7:33 pm-10:22 am
1 stop15h 49m
George Town Owen Roberts Intl
Mon 6/8
5:12 pm-12:08 pm
2 stops17h 56m
$326
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Wed 6/3
6:37 am-11:30 am
1 stop5h 53m
George Town Owen Roberts Intl
Tue 6/9
12:01 pm-11:58 pm
1 stop10h 57m
$326
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Sat 6/6
7:59 pm-11:30 am
1 stop16h 31m
George Town Owen Roberts Intl
Wed 6/10
5:12 pm-10:16 am
2 stops16h 04m
$326
PittsburghPunta Cana
PIT - PUJ
PITPUJ
Pittsburgh
Thu 8/27
6:10 am-12:40 pm
1 stop6h 30m
Punta Cana
Mon 8/31
3:35 pm-9:36 am
1 stop18h 01m
$338
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Tue 9/1
6:00 am-1:48 pm
1 stop7h 48m
Nassau Intl
Wed 9/2
3:02 pm-9:26 pm
1 stop6h 24m
$340
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-GCM
PIT-SJU
PIT-NAS
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-GCM
PIT-SJU
PIT-NAS
PIT-PUJ
What is the cheapest month to book a flight from Pittsburgh to Caribbean?
Currently, August is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $109). Flying from Pittsburgh to Caribbean in October is currently the most expensive (average of $1,350). 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 4 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 May 23, 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
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for 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 May 23, 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 2,558,603 searches. Data last updated May 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$123 | Average$428 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$135 | Average$319 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$141 | Average$443 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$141 | Average$487 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$614 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$225 | Average$483 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$232 | Average$551 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$406 | Average$492 | FlexibilityNo cancel fee | On-time67% |