$112+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Jul 19 — Jul 261
Round-trip
1 adult, Economy
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Find cheap flights from Pittsburgh to Caribbean with Cheapflights
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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 June 19, 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 June 19, 2026.
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/236:10 am
PIT
- STT
1 stop6h 43m
American Airlines
Thu 8/273:43 pm
STT
- PIT
1 stop7h 42m
American Airlines
Deal found 6/16![American Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 6/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:53 pm
PIT
- STT
2 stops20h 06m
American Airlines
Sun 8/303:43 pm
STT
- PIT
2 stops18h 37m
American Airlines
Deal found 6/17![American Airlines logo]()
$255
This Delta deal was found by Cheapflights users on 6/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:50 am
PIT
- STT
1 stop9h 12m
Delta
Sat 9/52:49 pm
STT
- PIT
1 stop8h 45m
Delta
Deal found 6/17![Delta logo]()
$260
This American Airlines deal was found by Cheapflights users on 6/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:39 pm
PIT
- STT
2 stops17h 14m
American Airlines
Sat 9/54:42 pm
STT
- PIT
2 stops18h 02m
American Airlines
Deal found 6/18![American Airlines logo]()
$285
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/215:42 pm
PIT
- STT
2 stops17h 36m
American Airlines
Mon 8/243:43 pm
STT
- PIT
2 stops18h 37m
American Airlines
Deal found 6/15![American Airlines logo]()
$290
This American Airlines deal was found by Cheapflights users on 6/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:33 pm
PIT
- STT
2 stops17h 07m
American Airlines
Thu 10/155:40 pm
STT
- PIT
2 stops16h 13m
American Airlines
Deal found 6/17![American Airlines logo]()
$295
This American Airlines deal was found by Cheapflights users on 6/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:10 am
PIT
- STT
1 stop9h 42m
American Airlines
Mon 8/243:43 pm
STT
- PIT
2 stops18h 37m
American Airlines
Deal found 6/17![American Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 6/19. 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.
Tue 10/277:45 pm
PIT
- STT
2 stops16h 55m
American Airlines
Tue 11/312:57 pm
STT
- PIT
1 stop11h 41m
American Airlines
Deal found 6/19![American Airlines logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 8/289:14 pm
PIT
- SJU
2 stops17h 15m
Multiple Airlines
Sun 8/307:00 am
SJU
- PIT
1 stop10h 58m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 6/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:09 pm
PIT
- SJU
1 stop5h 41m
American Airlines
Wed 10/148:30 am
SJU
- PIT
2 stops9h 27m
American Airlines
Deal found 6/17![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 6/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:18 am
PIT
- STT
1 stop30h 33m
American Airlines
Sat 9/191:41 pm
STT
- PIT
2 stops20h 47m
American Airlines
Deal found 6/18![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 6/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:00 am
PIT
- SJU
2 stops10h 34m
American Airlines
Wed 8/266:00 am
SJU
- PIT
2 stops9h 37m
American Airlines
Deal found 6/18![American Airlines 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 June 19, 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 June 19, 2026.
This Southwest deal was found by Cheapflights users on 6/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:10 am
PIT
- SJU
2 stops10h 45m
Southwest
Thu 8/205:00 am
SJU
- PIT
1 stop8h 25m
Southwest
Deal found 6/19![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 9/226:30 am
PIT
- NAS
1 stop7h 03m
United Airlines
Mon 9/282:53 pm
NAS
- PIT
1 stop7h 07m
United Airlines
Deal found 6/16![United Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 9/55:50 am
PIT
- NAS
1 stop10h 49m
Delta
Sat 9/121:16 pm
NAS
- PIT
1 stop5h 23m
Delta
Deal found 6/15![Delta logo]()
$350
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/208:00 am
PIT
- NAS
2 stops7h 13m
American Airlines
Fri 7/244:10 pm
NAS
- PIT
1 stop7h 38m
American Airlines
Deal found 6/14![American Airlines logo]()
$354
This JetBlue deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 8/316:00 am
PIT
- SXM
1 stop6h 37m
JetBlue
Wed 9/21:42 pm
SXM
- PIT
1 stop7h 44m
JetBlue
Deal found 6/14![JetBlue logo]()
$367
This Expedia deal was found by Cheapflights users on 6/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
PIT
- AUA
1 stop8h 11m
Multiple Airlines
Sat 7/113:05 pm
AUA
- PIT
1 stop20h 28m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$377
This Gotogate deal was found by Cheapflights users on 6/17. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/103:35 pm
PIT
- UVF
2 stops22h 45m
Air Canada
Fri 8/143:15 pm
UVF
- PIT
2 stops23h 38m
Air Canada
Deal found 6/17![Air Canada logo]()
$588
This Southwest deal was found by Cheapflights users on 6/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1612:25 pm
PIT
- SJU
2 stops9h 55m
Southwest
Mon 10/199:45 pm
SJU
- PIT
1 stop12h 15m
Southwest
Deal found 6/19![Southwest logo]()
$322
This Copa Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/110:54 am
PIT
- CUR
2 stops31h 37m
Copa Airlines
Mon 7/63:39 pm
CUR
- PIT
2 stops29h 12m
Copa Airlines
Deal found 6/16![Copa Airlines logo]()
$665
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:05 am
PIT
- NAS
1 stop9h 34m
Delta
Thu 7/231:09 pm
NAS
- PIT
1 stop8h 30m
Delta
Deal found 6/16![Delta logo]()
$350
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/16:15 am
PIT
- NAS
1 stop7h 32m
United Airlines
Tue 7/72:53 pm
NAS
- PIT
1 stop9h 06m
United Airlines
Deal found 6/14![United Airlines logo]()
$350
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/16:14 am
PIT
- NAS
2 stops7h 03m
American Airlines
Tue 7/77:39 am
NAS
- PIT
2 stops7h 12m
American Airlines
Deal found 6/14![American Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/57:35 am
PIT
- SJU
1 stop11h 25m
Southwest
Wed 8/122:25 pm
SJU
- PIT
1 stop6h 25m
Southwest
Deal found 6/15![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 9/226:00 am
PIT
- NAS
1 stop5h 50m
Delta
Mon 9/283:14 pm
NAS
- PIT
1 stop5h 56m
Delta
Deal found 6/14![Delta logo]()
$350
This JetBlue deal was found by Cheapflights users on 6/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:00 am
PIT
- CUR
1 stop8h 06m
JetBlue
Wed 7/153:13 pm
CUR
- PIT
1 stop8h 33m
JetBlue
Deal found 6/17![JetBlue logo]()
$387
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 9/265:11 am
PIT
- PUJ
1 stop9h 16m
United Airlines
Fri 10/23:35 pm
PUJ
- PIT
1 stop18h 02m
United Airlines
Deal found 6/16![United Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 6/19. 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 7/28:00 am
PIT
- NAS
2 stops7h 09m
American Airlines
Tue 7/77:39 am
NAS
- PIT
2 stops7h 12m
American Airlines
Deal found 6/19![American Airlines logo]()
$364
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/44:05 pm
PIT
- SJU
1 stop5h 55m
Southwest
Wed 8/122:25 pm
SJU
- PIT
1 stop6h 25m
Southwest
Deal found 6/15![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 6/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:00 am
PIT
- CUR
1 stop7h 53m
Delta
Sun 9/133:10 pm
CUR
- PIT
1 stop9h 12m
Delta
Deal found 6/17![Delta logo]()
$355
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 9/96:30 am
PIT
- NAS
1 stop7h 03m
United Airlines
Sun 9/132:35 pm
NAS
- PIT
1 stop7h 55m
United Airlines
Deal found 6/16![United Airlines logo]()
$360
This JetBlue deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 11/26:00 am
PIT
- MBJ
1 stop8h 54m
JetBlue
Thu 11/52:00 pm
MBJ
- PIT
1 stop7h 22m
JetBlue
Deal found 6/14![JetBlue logo]()
$398
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/278:49 pm
PIT
- SXM
2 stops17h 02m
American Airlines
Fri 7/312:51 pm
SXM
- PIT
2 stops18h 39m
American Airlines
Deal found 6/14![American Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:30 pm
PIT
- SJU
1 stop9h 26m
Delta
Sat 11/77:00 am
SJU
- PIT
1 stop7h 32m
Delta
Deal found 6/15![Delta logo]()
$358
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:30 am
PIT
- NAS
1 stop6h 03m
United Airlines
Sun 9/272:53 pm
NAS
- PIT
1 stop7h 07m
United Airlines
Deal found 6/17![United Airlines logo]()
$360
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/187:45 pm
PIT
- SXM
2 stops18h 06m
American Airlines
Tue 7/214:45 pm
SXM
- PIT
2 stops19h 20m
American Airlines
Deal found 6/14![American Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/12:30 pm
PIT
- SJU
1 stop9h 26m
Delta
Sat 11/77:00 am
SJU
- PIT
1 stop7h 32m
Delta
Deal found 6/16![Delta logo]()
$358
This Southwest deal was found by Cheapflights users on 6/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/66:55 pm
PIT
- SJU
1 stop6h 30m
Southwest
Tue 7/75:30 am
SJU
- PIT
1 stop8h 30m
Southwest
Deal found 6/19![Southwest logo]()
$397
This United Airlines deal was found by Cheapflights users on 6/18. 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 9/226:10 am
PIT
- PUJ
1 stop6h 30m
United Airlines
Sat 9/266:45 pm
PUJ
- PIT
1 stop18h 17m
United Airlines
Deal found 6/18![United Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/87:30 pm
PIT
- SXM
1 stop17h 30m
American Airlines
Fri 11/135:24 pm
SXM
- PIT
2 stops20h 36m
American Airlines
Deal found 6/14![American Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 6/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/710:00 am
PIT
- SJU
1 stop6h 38m
Delta
Fri 8/147:30 am
SJU
- PIT
1 stop9h 45m
Delta
Deal found 6/17![Delta logo]()
$358
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated June 19, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated June 19, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 6/258:42 pm
PIT
- NAS
1 stop14h 54m
American Airlines
Sun 6/288:00 am
NAS
- PIT
1 stop15h 58m
American Airlines
Deal found 6/15![American Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/16:15 am
PIT
- NAS
1 stop7h 32m
United Airlines
Tue 7/72:53 pm
NAS
- PIT
1 stop9h 06m
United Airlines
Deal found 6/15![United Airlines logo]()
$350
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/18:05 am
PIT
- NAS
2 stops9h 45m
American Airlines
Tue 7/712:29 pm
NAS
- PIT
1 stop9h 01m
American Airlines
Deal found 6/15![American Airlines logo]()
$359
This Frontier deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/812:49 pm
PIT
- SJU
1 stop13h 26m
Frontier
Thu 7/99:02 am
SJU
- PIT
1 stop9h 13m
Frontier
Deal found 6/15![Frontier logo]()
$350
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/146:38 am
PIT
- SJU
1 stop16h 21m
American Airlines
Tue 8/186:00 am
SJU
- PIT
1 stop15h 25m
American Airlines
Deal found 6/16![American Airlines logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Thu 7/167:49 pm
PIT
- SJU
1 stop18h 06m
Multiple Airlines
Thu 7/236:30 am
SJU
- PIT
1 stop16h 09m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Sun 7/197:49 pm
PIT
- SJU
1 stop18h 06m
Multiple Airlines
Thu 7/236:30 am
SJU
- PIT
1 stop28h 13m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 stop7h 55m
Multiple Airlines
Thu 7/236:30 am
SJU
- PIT
1 stop28h 13m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$327
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/208:00 am
PIT
- NAS
2 stops7h 13m
American Airlines
Fri 7/244:10 pm
NAS
- PIT
1 stop7h 38m
American Airlines
Deal found 6/14![American Airlines logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Fri 7/246:00 am
PIT
- SJU
1 stop8h 00m
Multiple Airlines
Thu 7/306:45 am
SJU
- PIT
1 stop27h 58m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/252:00 pm
PIT
- SJU
1 stop8h 33m
American Airlines
Thu 7/307:25 am
SJU
- PIT
1 stop16h 51m
American Airlines
Deal found 6/15![American Airlines logo]()
$357
This Priceline deal was found by Cheapflights users on 6/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/307:13 pm
PIT
- SJU
1 stop7h 02m
Frontier
Wed 8/58:37 pm
SJU
- PIT
1 stop21h 38m
Frontier
Deal found 6/17![Frontier logo]()
$355
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 June 19, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 19, 2026.
This American Airlines deal was found by Cheapflights users on 6/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:00 am
PIT
- SJU
2 stops9h 40m
American Airlines
Deal found 6/18![American Airlines logo]()
$112
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/305:50 am
PIT
- NAS
1 stop6h 01m
Delta
Deal found 6/16![Delta logo]()
$121
This American Airlines deal was found by Cheapflights users on 6/19. 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.
Sat 7/188:01 pm
PIT
- STT
1 stop15h 02m
American Airlines
Deal found 6/19![American Airlines logo]()
$123
This Delta deal was found by Cheapflights users on 6/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/278:00 am
PIT
- NAS
1 stop8h 37m
Delta
Deal found 6/17![Delta logo]()
$126
This United Airlines deal was found by Cheapflights users on 6/19. 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 11/137:59 pm
PIT
- NAS
2 stops15h 50m
United Airlines
Deal found 6/19![United Airlines logo]()
$132
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/137:59 pm
PIT
- SXM
1 stop16h 34m
United Airlines
Deal found 6/15![United Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Sun 7/267:49 pm
PIT
- SJU
1 stop18h 11m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$140
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/198:49 pm
PIT
- SXM
2 stops17h 02m
American Airlines
Deal found 6/15![American Airlines logo]()
$145
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/67:25 pm
PIT
- SXM
1 stop18h 17m
American Airlines
Deal found 6/15![American Airlines logo]()
$152
This JetBlue deal was found by Cheapflights users on 6/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:00 am
PIT
- CUR
1 stop8h 06m
JetBlue
Deal found 6/17![JetBlue logo]()
$154
This American Airlines deal was found by Cheapflights users on 6/19. 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.
Tue 6/306:04 pm
PIT
- STT
2 stops16h 59m
American Airlines
Deal found 6/19![American Airlines logo]()
$154
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 10/312:30 pm
PIT
- SJU
1 stop9h 26m
Delta
Deal found 6/16![Delta logo]()
$156
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 June 19, 2026.
Round-trip from | $250 (American Airlines) |
|---|---|
One-way from | $112 (American Airlines) |
Popular in | June |
Cheapest in | October |
Average price | $489 |
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 June 19, 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
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Mon 8/17
6:10 am-4:55 pm
2 stops10h 45m
San Juan Luis Munoz Marin Intl
Thu 8/20
5:00 am-1:25 pm
1 stop8h 25m
$317
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Fri 10/16
12:25 pm-10:20 pm
2 stops9h 55m
San Juan Luis Munoz Marin Intl
Mon 10/19
9:45 pm-10:00 am
1 stop12h 15m
$322
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Wed 8/5
7:35 am-7:00 pm
1 stop11h 25m
San Juan Luis Munoz Marin Intl
Wed 8/12
2:25 pm-8:50 pm
1 stop6h 25m
$332
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Tue 8/4
4:05 pm-10:00 pm
1 stop5h 55m
San Juan Luis Munoz Marin Intl
Wed 8/12
2:25 pm-8:50 pm
1 stop6h 25m
$332
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Tue 9/22
6:30 am-1:33 pm
1 stop7h 03m
Nassau Intl
Mon 9/28
2:53 pm-10:00 pm
1 stop7h 07m
$350
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Sat 9/5
5:50 am-4:39 pm
1 stop10h 49m
Nassau Intl
Sat 9/12
1:16 pm-6:39 pm
1 stop5h 23m
$350
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Thu 7/16
7:05 am-4:39 pm
1 stop9h 34m
Nassau Intl
Thu 7/23
1:09 pm-9:39 pm
1 stop8h 30m
$350
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Wed 7/1
6:15 am-1:47 pm
1 stop7h 32m
Nassau Intl
Tue 7/7
2:53 pm-11:59 pm
1 stop9h 06m
$350
Quickest round-trip
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Tue 9/22
6:00 am-11:50 am
1 stop5h 50m
Nassau Intl
Mon 9/28
3:14 pm-9:10 pm
1 stop5h 56m
$350
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Mon 7/20
8:00 am-3:13 pm
2 stops7h 13m
Nassau Intl
Fri 7/24
4:10 pm-11:48 pm
1 stop7h 38m
$354
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-SJU
PIT-NAS
PIT-STT
PIT-SXM
PIT-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 Pittsburgh to Caribbean
PIT-0CB
PIT-SJU
PIT-NAS
PIT-STT
PIT-SXM
What is the cheapest month to book a flight from Pittsburgh to Caribbean?
Currently, September is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $123). Flying from Pittsburgh to Caribbean in October is currently the most expensive (average of $1,574). 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 60 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 June 19, 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.
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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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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 June 19, 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 7 airlines flying from Pittsburgh to Caribbean
Discover the top 7 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 June 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$339 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$152 | Average$506 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$184 | Average$501 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$619 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$225 | Average$460 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$232 | Average$572 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$406 | Average$492 | FlexibilityNo cancel fee | On-time67% |