$109+ 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Aug 17 — Aug 241
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 July 18, 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 July 18, 2026.
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 7/13![Delta logo]()
$250
This United Airlines deal was found by Cheapflights users on 7/16. 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 8/296:30 am
PIT
- STT
1 stop9h 13m
United Airlines
Sat 9/52:10 pm
STT
- PIT
2 stops9h 20m
United Airlines
Deal found 7/16![United Airlines logo]()
$270
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/296:19 am
PIT
- STT
2 stops9h 33m
American Airlines
Sat 9/54:42 pm
STT
- PIT
2 stops17h 37m
American Airlines
Deal found 7/13![American Airlines logo]()
$275
This United Airlines deal was found by Cheapflights users on 7/16. 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 9/57:00 am
PIT
- SJU
1 stop7h 44m
United Airlines
Sat 9/121:00 am
SJU
- PIT
2 stops8h 36m
United Airlines
Deal found 7/16![United Airlines logo]()
$282
This American Airlines deal was found by Cheapflights users on 7/14. 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 8/52:25 pm
PIT
- SJU
1 stop9h 34m
American Airlines
Wed 8/127:03 am
SJU
- PIT
1 stop16h 47m
American Airlines
Deal found 7/14![American Airlines logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 7/14. 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 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 8/136:26 am
SJU
- PIT
1 stop16h 20m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$284
This Delta deal was found by Cheapflights users on 7/17. 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.
Mon 8/1711:57 am
PIT
- SJU
1 stop10h 32m
Delta
Thu 8/275:49 pm
SJU
- PIT
1 stop6h 47m
Delta
Deal found 7/17![Delta logo]()
$286
This deal was found by Cheapflights users on 7/14. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:39 pm
PIT
- SJU
1 stop7h 11m
Frontier
Tue 11/2410:29 am
SJU
- PIT
1 stop9h 48m
Frontier
Deal found 7/14![Frontier logo]()
$287
This American Airlines deal was found by Cheapflights users on 7/17. 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 8/167:06 pm
PIT
- SJU
1 stop14h 37m
American Airlines
Thu 8/272:33 pm
SJU
- PIT
1 stop9h 17m
American Airlines
Deal found 7/17![American Airlines logo]()
$288
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/287:39 pm
PIT
- STT
2 stops17h 14m
American Airlines
Tue 9/11:49 pm
STT
- PIT
2 stops20h 31m
American Airlines
Deal found 7/13![American Airlines logo]()
$290
This Southwest deal was found by Cheapflights users on 7/17. 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.
Sat 8/153:30 pm
PIT
- SJU
1 stop6h 25m
Southwest
Wed 8/195:15 am
SJU
- PIT
1 stop9h 30m
Southwest
Deal found 7/17![Southwest logo]()
$291
This American Airlines deal was found by Cheapflights users on 7/17. 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 8/195:21 am
PIT
- SJU
1 stop17h 03m
American Airlines
Thu 8/272:33 pm
SJU
- PIT
1 stop6h 27m
American Airlines
Deal found 7/17![American Airlines logo]()
$293
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 July 18, 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 July 18, 2026.
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 7/13![Delta logo]()
$250
This United Airlines deal was found by Cheapflights users on 7/15. 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.
Sun 11/16:00 am
PIT
- STT
1 stop6h 56m
United Airlines
Wed 11/43:00 pm
STT
- PIT
1 stop8h 08m
United Airlines
Deal found 7/15![United Airlines logo]()
$270
This Southwest deal was found by Cheapflights users on 7/17. 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.
Thu 8/2711:20 am
PIT
- SJU
2 stops10h 50m
Southwest
Sat 8/296:25 am
SJU
- PIT
2 stops8h 20m
Southwest
Deal found 7/17![Southwest logo]()
$291
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 9/17:41 am
PIT
- NAS
1 stop5h 07m
American Airlines
Tue 9/83:34 pm
NAS
- PIT
1 stop7h 21m
American Airlines
Deal found 7/13![American Airlines logo]()
$394
This Breeze Airways deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 1/129:24 am
PIT
- PUJ
Nonstop4h 00m
Breeze Airways
Sun 1/173:24 pm
PUJ
- PIT
Nonstop4h 30m
Breeze Airways
Deal found 7/13![Breeze Airways logo]()
$397
This JetBlue deal was found by Cheapflights users on 7/14. 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.
Sat 8/296:15 am
PIT
- PUJ
1 stop6h 32m
JetBlue
Sat 9/51:52 pm
PUJ
- PIT
1 stop7h 36m
JetBlue
Deal found 7/14![JetBlue logo]()
$456
This Southwest deal was found by Cheapflights users on 7/17. 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.
Sun 8/163:15 pm
PIT
- SJU
1 stop7h 30m
Southwest
Wed 8/195:15 am
SJU
- PIT
1 stop9h 30m
Southwest
Deal found 7/17![Southwest logo]()
$291
This United Airlines deal was found by Cheapflights users on 7/17. 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 10/296:00 am
PIT
- SJU
1 stop6h 15m
United Airlines
Sat 10/312:05 am
SJU
- PIT
2 stops12h 01m
United Airlines
Deal found 7/17![United Airlines logo]()
$308
This Copa Airlines deal was found by Cheapflights users on 7/15. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:10 am
PIT
- CUR
2 stops12h 21m
Copa Airlines
Sun 9/207:31 pm
CUR
- PIT
2 stops38h 05m
Copa Airlines
Deal found 7/15![Copa Airlines logo]()
$652
This Delta deal was found by Cheapflights users on 7/16. 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 12/316:00 am
PIT
- STT
1 stop9h 25m
Delta
Thu 1/141:50 pm
STT
- PIT
1 stop11h 29m
Delta
Deal found 7/16![Delta logo]()
$360
This United Airlines deal was found by Cheapflights users on 7/16. 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.
Fri 10/3010:51 am
PIT
- SJU
1 stop9h 09m
United Airlines
Sat 11/75:50 pm
SJU
- PIT
1 stop6h 37m
United Airlines
Deal found 7/16![United Airlines logo]()
$348
This Delta deal was found by Cheapflights users on 7/16. 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.
Mon 10/196:00 am
PIT
- NAS
1 stop7h 49m
Delta
Sat 10/244:50 pm
NAS
- PIT
1 stop7h 46m
Delta
Deal found 7/16![Delta logo]()
$380
This United Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 9/197:50 pm
PIT
- NAS
2 stops17h 43m
United Airlines
Fri 9/252:35 pm
NAS
- PIT
1 stop8h 01m
United Airlines
Deal found 7/13![United Airlines logo]()
$360
This Southwest deal was found by Cheapflights users on 7/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
PIT
- SJU
1 stop12h 15m
Southwest
Mon 8/2411:35 am
SJU
- PIT
2 stops9h 30m
Southwest
Deal found 7/16![Southwest logo]()
$412
This American Airlines deal was found by Cheapflights users on 7/16. 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.
Thu 9/36:10 am
PIT
- UVF
1 stop7h 39m
American Airlines
Mon 9/74:12 pm
UVF
- PIT
2 stops21h 23m
American Airlines
Deal found 7/16![American Airlines logo]()
$455
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:50 am
PIT
- NAS
1 stop6h 01m
Delta
Wed 8/193:22 pm
NAS
- PIT
1 stop9h 14m
Delta
Deal found 7/13![Delta logo]()
$380
This JetBlue deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 10/276:00 am
PIT
- SXM
1 stop6h 35m
JetBlue
Fri 10/301:35 pm
SXM
- PIT
1 stop7h 47m
JetBlue
Deal found 7/13![JetBlue logo]()
$475
This Southwest deal was found by Cheapflights users on 7/17. 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 10/164:20 pm
PIT
- SJU
2 stops9h 00m
Southwest
Mon 10/196:30 am
SJU
- PIT
2 stops9h 10m
Southwest
Deal found 7/17![Southwest logo]()
$418
This United Airlines deal was found by Cheapflights users on 7/15. 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.
Tue 9/227:59 pm
PIT
- NAS
2 stops17h 34m
United Airlines
Mon 9/282:35 pm
NAS
- PIT
1 stop8h 01m
United Airlines
Deal found 7/15![United Airlines logo]()
$380
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 10/178:00 am
PIT
- NAS
1 stop7h 25m
Delta
Fri 10/233:15 pm
NAS
- PIT
1 stop9h 21m
Delta
Deal found 7/13![Delta logo]()
$380
This American Airlines deal was found by Cheapflights users on 7/17. 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 8/165:00 am
PIT
- UVF
1 stop9h 29m
American Airlines
Sun 8/232:49 pm
UVF
- PIT
2 stops18h 15m
American Airlines
Deal found 7/17![American Airlines logo]()
$460
This JetBlue deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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.
Thu 8/276:00 am
PIT
- SXM
1 stop7h 54m
JetBlue
Thu 9/31:42 pm
SXM
- PIT
1 stop7h 46m
JetBlue
Deal found 7/13![JetBlue logo]()
$481
This United Airlines deal was found by Cheapflights users on 7/15. 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.
Thu 9/107:50 pm
PIT
- NAS
2 stops17h 43m
United Airlines
Mon 9/142:35 pm
NAS
- PIT
1 stop7h 55m
United Airlines
Deal found 7/15![United Airlines logo]()
$380
This Delta deal was found by Cheapflights users on 7/17. 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.
Mon 8/105:50 am
PIT
- NAS
1 stop6h 01m
Delta
Thu 8/131:09 pm
NAS
- PIT
1 stop8h 28m
Delta
Deal found 7/17![Delta logo]()
$380
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 9/26:01 pm
PIT
- UVF
2 stops19h 48m
American Airlines
Mon 9/74:12 pm
UVF
- PIT
2 stops21h 23m
American Airlines
Deal found 7/13![American Airlines logo]()
$460
This JetBlue deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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.
Thu 8/276:15 am
PIT
- MBJ
1 stop10h 53m
JetBlue
Thu 9/312:04 pm
MBJ
- PIT
1 stop8h 24m
JetBlue
Deal found 7/13![JetBlue logo]()
$483
This Southwest deal was found by Cheapflights users on 7/17. 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 10/165:50 am
PIT
- SJU
2 stops9h 30m
Southwest
Fri 10/1610:50 pm
SJU
- PIT
1 stop11h 00m
Southwest
Deal found 7/17![Southwest logo]()
$445
This American Airlines deal was found by Cheapflights users on 7/16. 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.
Mon 8/247:06 pm
PIT
- UVF
1 stop18h 43m
American Airlines
Thu 8/273:19 pm
UVF
- PIT
1 stop8h 06m
American Airlines
Deal found 7/16![American Airlines logo]()
$460
This United Airlines deal was found by Cheapflights users on 7/18. 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 9/196:15 am
PIT
- PUJ
1 stop9h 15m
United Airlines
Sat 9/266:45 pm
PUJ
- PIT
2 stops14h 52m
United Airlines
Deal found 7/18![United Airlines logo]()
$395
This Copa Airlines deal was found by Cheapflights users on 7/16. 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.
Mon 1/1110:50 am
PIT
- AUA
2 stops26h 49m
Copa Airlines
Sun 1/311:12 pm
AUA
- PIT
2 stops32h 39m
Copa Airlines
Deal found 7/16![Copa Airlines logo]()
$661
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated July 18, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated July 18, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/14. 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 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 8/136:26 am
SJU
- PIT
1 stop16h 20m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 7/14. 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 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
Sat 8/155:22 pm
SJU
- PIT
1 stop16h 11m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$302
This American Airlines deal was found by Cheapflights users on 7/14. 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 8/52:25 pm
PIT
- SJU
1 stop9h 34m
American Airlines
Wed 8/127:03 am
SJU
- PIT
1 stop16h 47m
American Airlines
Deal found 7/14![American Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 7/17. 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.
Sat 8/153:30 pm
PIT
- SJU
1 stop6h 25m
Southwest
Wed 8/195:15 am
SJU
- PIT
1 stop9h 30m
Southwest
Deal found 7/17![Southwest logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 7/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:32 pm
PIT
- SJU
2 stops30h 09m
Multiple Airlines
Thu 8/207:00 am
SJU
- PIT
1 stop12h 09m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 7/17. 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 8/167:06 pm
PIT
- SJU
1 stop14h 37m
American Airlines
Thu 8/272:33 pm
SJU
- PIT
1 stop9h 17m
American Airlines
Deal found 7/17![American Airlines logo]()
$288
This Delta deal was found by Cheapflights users on 7/17. 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.
Mon 8/1711:57 am
PIT
- SJU
1 stop10h 32m
Delta
Thu 8/275:49 pm
SJU
- PIT
1 stop6h 47m
Delta
Deal found 7/17![Delta logo]()
$286
This American Airlines deal was found by Cheapflights users on 7/17. 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 8/195:21 am
PIT
- SJU
1 stop17h 03m
American Airlines
Thu 8/272:33 pm
SJU
- PIT
1 stop6h 27m
American Airlines
Deal found 7/17![American Airlines logo]()
$293
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/287:39 pm
PIT
- STT
2 stops17h 14m
American Airlines
Tue 9/11:49 pm
STT
- PIT
2 stops20h 31m
American Airlines
Deal found 7/13![American Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 7/13![Delta logo]()
$250
This United Airlines deal was found by Cheapflights users on 7/16. 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 8/296:30 am
PIT
- STT
1 stop9h 13m
United Airlines
Sat 9/52:10 pm
STT
- PIT
2 stops9h 20m
United Airlines
Deal found 7/16![United Airlines logo]()
$270
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/296:19 am
PIT
- STT
2 stops9h 33m
American Airlines
Sat 9/54:42 pm
STT
- PIT
2 stops17h 37m
American Airlines
Deal found 7/13![American Airlines logo]()
$275
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 July 18, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 18, 2026.
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 10/318:18 pm
PIT
- SJU
1 stop16h 46m
American Airlines
Deal found 7/13![American Airlines logo]()
$109
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/108:00 am
PIT
- SJU
2 stops10h 33m
American Airlines
Deal found 7/13![American Airlines logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 7/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:32 pm
PIT
- SJU
2 stops30h 02m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$118
This American Airlines deal was found by Cheapflights users on 7/15. 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 10/218:18 pm
PIT
- SJU
1 stop15h 02m
American Airlines
Deal found 7/15![American Airlines logo]()
$124
This United Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 9/16:30 am
PIT
- NAS
1 stop7h 03m
United Airlines
Deal found 7/13![United Airlines logo]()
$126
This Delta deal was found by Cheapflights users on 7/15. 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.
Thu 9/173:41 pm
PIT
- SJU
1 stop6h 38m
Delta
Deal found 7/15![Delta logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 7/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/127:29 pm
PIT
- SJU
1 stop28h 09m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$130
This Air Canada deal was found by Cheapflights users on 7/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:15 pm
PIT
- NAS
2 stops25h 20m
Air Canada
Deal found 7/17![Air Canada logo]()
$133
This United Airlines deal was found by Cheapflights users on 7/14. 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.
Thu 1/77:00 am
PIT
- STT
2 stops9h 50m
United Airlines
Deal found 7/14![United Airlines logo]()
$133
This Air Canada deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/303:35 pm
PIT
- NAS
2 stops25h 55m
Air Canada
Deal found 7/13![Air Canada logo]()
$140
This United Airlines deal was found by Cheapflights users on 7/15. 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 8/317:52 pm
PIT
- NAS
2 stops17h 41m
United Airlines
Deal found 7/15![United Airlines logo]()
$142
This Delta deal was found by Cheapflights users on 7/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/22:30 pm
PIT
- SJU
1 stop9h 26m
Delta
Deal found 7/18![Delta logo]()
$143
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 July 18, 2026.
Round-trip from | $250 (Delta) |
|---|---|
One-way from | $109 (American Airlines) |
Popular in | June |
Cheapest in | October |
Average price | $458 |
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 July 18, 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
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Sat 8/29
5:50 am-3:02 pm
1 stop9h 12m
Saint Thomas Island Cyril E King
Sat 9/5
2:49 pm-11:34 pm
1 stop8h 45m
$250
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Sun 11/1
6:00 am-1:56 pm
1 stop6h 56m
Saint Thomas Island Cyril E King
Wed 11/4
3:00 pm-10:08 pm
1 stop8h 08m
$270
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Thu 8/27
11:20 am-10:10 pm
2 stops10h 50m
San Juan Luis Munoz Marin Intl
Sat 8/29
6:25 am-2:45 pm
2 stops8h 20m
$291
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Sun 8/16
3:15 pm-10:45 pm
1 stop7h 30m
San Juan Luis Munoz Marin Intl
Wed 8/19
5:15 am-2:45 pm
1 stop9h 30m
$291
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Thu 10/29
6:00 am-12:15 pm
1 stop6h 15m
San Juan Luis Munoz Marin Intl
Sat 10/31
2:05 am-1:06 pm
2 stops12h 01m
$308
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Fri 10/30
10:51 am-8:00 pm
1 stop9h 09m
San Juan Luis Munoz Marin Intl
Sat 11/7
5:50 pm-11:27 pm
1 stop6h 37m
$348
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Thu 12/31
6:00 am-4:25 pm
1 stop9h 25m
Saint Thomas Island Cyril E King
Thu 1/14
1:50 pm-12:19 am
1 stop11h 29m
$360
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Sat 9/19
7:50 pm-1:33 pm
2 stops17h 43m
Nassau Intl
Fri 9/25
2:35 pm-10:36 pm
1 stop8h 01m
$360
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Mon 10/19
6:00 am-1:49 pm
1 stop7h 49m
Nassau Intl
Sat 10/24
4:50 pm-12:36 am
1 stop7h 46m
$380
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Wed 8/12
5:50 am-11:51 am
1 stop6h 01m
Nassau Intl
Wed 8/19
3:22 pm-12:36 am
1 stop9h 14m
$380
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-STT
PIT-SJU
PIT-NAS
PIT-MBJ
PIT-CUR
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-STT
PIT-SJU
PIT-NAS
PIT-MBJ
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 $420). Flying from Pittsburgh to Caribbean in December is currently the most expensive (average of $599). 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 64 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 July 18, 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.
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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 July 18, 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 July 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$339 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$499 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$184 | Average$481 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$630 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$225 | Average$460 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$233 | Average$570 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$406 | Average$492 | FlexibilityNo cancel fee | On-time67% |