$127+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Jun 9 — Jun 161
Round-trip
1 adult, Economy
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Find cheap flights from Pittsburgh to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 10, 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 10, 2026.
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 13m
American Airlines
Sat 9/53:43 pm
STT
- PIT
1 stop8h 09m
American Airlines
Deal found 5/6![American Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/189:14 pm
PIT
- SJU
1 stop12h 50m
Multiple Airlines
Thu 5/217:00 am
SJU
- PIT
1 stop27h 48m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$287
This American Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:14 am
PIT
- STT
1 stop9h 38m
American Airlines
Fri 8/214:42 pm
STT
- PIT
2 stops17h 42m
American Airlines
Deal found 5/9![American Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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
Sat 6/67:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$291
This CheapOair deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:59 pm
PIT
- SJU
1 stop12h 10m
Frontier
Wed 8/264:05 pm
SJU
- PIT
1 stop26h 59m
Frontier
Deal found 5/5![Frontier logo]()
$295
This Priceline deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/17:10 pm
PIT
- SJU
1 stop7h 01m
Frontier
Wed 8/56:31 pm
SJU
- PIT
1 stop23h 44m
Frontier
Deal found 5/8![Frontier logo]()
$301
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:20 am
PIT
- SJU
1 stop9h 18m
Delta
Tue 8/42:59 pm
SJU
- PIT
1 stop9h 37m
Delta
Deal found 5/8![Delta logo]()
$302
This Super.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com 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
Fri 8/282:05 pm
PUJ
- PIT
1 stop7h 21m
JetBlue
Deal found 5/9![JetBlue logo]()
$302
This Frontier deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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.
Sat 7/187:10 pm
PIT
- SJU
1 stop12h 47m
Frontier
Fri 7/246:00 am
SJU
- PIT
1 stop12h 15m
Frontier
Deal found 5/6![Frontier logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 34m
Multiple Airlines
Thu 8/67:00 am
SJU
- PIT
1 stop15h 46m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$306
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:07 am
PIT
- SJU
2 stops11h 03m
American Airlines
Tue 10/68:35 am
SJU
- PIT
2 stops9h 22m
American Airlines
Deal found 5/7![American Airlines logo]()
$307
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/126:56 pm
PIT
- STT
2 stops16h 39m
American Airlines
Thu 5/2111:43 am
STT
- PIT
1 stop9h 04m
American Airlines
Deal found 5/5![American Airlines logo]()
$315
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 10, 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 10, 2026.
This American Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:14 am
PIT
- STT
1 stop9h 38m
American Airlines
Fri 8/214:42 pm
STT
- PIT
2 stops17h 42m
American Airlines
Deal found 5/9![American Airlines logo]()
$290
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 9/196:30 am
PIT
- CUR
1 stop7h 10m
United Airlines
Sat 9/262:50 pm
CUR
- PIT
2 stops19h 08m
United Airlines
Deal found 5/5![United Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:30 am
PIT
- SJU
1 stop11h 03m
Delta
Wed 10/147:30 am
SJU
- PIT
1 stop9h 35m
Delta
Deal found 5/9![Delta logo]()
$353
This Cheapflightsfares deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:00 am
PIT
- AUA
1 stop7h 34m
JetBlue
Fri 9/42:39 pm
AUA
- PIT
1 stop6h 47m
JetBlue
Deal found 5/9![JetBlue logo]()
$383
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:00 am
PIT
- SJU
1 stop12h 15m
Southwest
Sat 8/225:05 am
SJU
- PIT
2 stops9h 40m
Southwest
Deal found 5/8![Southwest logo]()
$404
This Copa Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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.
Tue 8/410:54 am
PIT
- CUR
2 stops31h 37m
Copa Airlines
Tue 8/113:39 pm
CUR
- PIT
2 stops29h 18m
Copa Airlines
Deal found 5/5![Copa Airlines logo]()
$673
This United Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:49 am
PIT
- NAS
1 stop8h 08m
United Airlines
Fri 6/263:59 pm
NAS
- PIT
1 stop8h 00m
United Airlines
Deal found 5/8![United Airlines logo]()
$376
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 9/207:00 am
PIT
- SXM
1 stop6h 50m
Delta
Thu 9/243:20 pm
SXM
- PIT
1 stop9h 02m
Delta
Deal found 5/5![Delta logo]()
$383
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/307:59 pm
PIT
- SXM
2 stops19h 43m
American Airlines
Fri 6/54:43 pm
SXM
- PIT
2 stops16h 11m
American Airlines
Deal found 5/6![American Airlines logo]()
$388
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/288:36 am
PIT
- NAS
1 stop6h 21m
United Airlines
Fri 7/32:53 pm
NAS
- PIT
1 stop9h 06m
United Airlines
Deal found 5/7![United Airlines logo]()
$376
This JetBlue deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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
- SDQ
1 stop6h 22m
JetBlue
Thu 10/11:32 pm
SDQ
- PIT
1 stop7h 51m
JetBlue
Deal found 5/6![JetBlue logo]()
$418
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/6![Delta logo]()
$386
This American Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:19 pm
PIT
- SXM
2 stops18h 46m
American Airlines
Sat 10/174:30 pm
SXM
- PIT
2 stops20h 02m
American Airlines
Deal found 5/8![American Airlines logo]()
$388
This JetBlue deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Fri 10/301:00 pm
MBJ
- PIT
1 stop7h 22m
JetBlue
Deal found 5/9![JetBlue logo]()
$423
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/245:50 pm
PIT
- SJU
1 stop6h 25m
Southwest
Sat 7/258:15 pm
SJU
- PIT
1 stop12h 30m
Southwest
Deal found 5/8![Southwest logo]()
$469
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 9/286:10 am
PIT
- SJU
1 stop6h 24m
United Airlines
Fri 10/21:00 am
SJU
- PIT
2 stops12h 09m
United Airlines
Deal found 5/5![United Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/145:11 pm
PIT
- SXM
1 stop19h 29m
American Airlines
Fri 6/194:43 pm
SXM
- PIT
2 stops18h 36m
American Airlines
Deal found 5/9![American Airlines logo]()
$394
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:20 am
PIT
- SJU
2 stops10h 20m
Southwest
Sat 8/296:25 am
SJU
- PIT
2 stops8h 20m
Southwest
Deal found 5/8![Southwest logo]()
$469
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:00 am
PIT
- MBJ
1 stop10h 34m
Delta
Wed 8/121:09 pm
MBJ
- PIT
1 stop10h 27m
Delta
Deal found 5/8![Delta logo]()
$429
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:25 am
PIT
- MBJ
2 stops8h 45m
United Airlines
Thu 6/44:12 pm
MBJ
- PIT
1 stop16h 28m
United Airlines
Deal found 5/7![United Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:09 pm
PIT
- MBJ
1 stop15h 56m
American Airlines
Sat 10/2410:50 am
MBJ
- PIT
1 stop5h 54m
American Airlines
Deal found 5/9![American Airlines logo]()
$406
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:00 am
PIT
- PLS
1 stop6h 45m
Delta
Tue 11/32:05 pm
PLS
- PIT
1 stop10h 14m
Delta
Deal found 5/8![Delta logo]()
$435
This United Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:15 am
PIT
- NAS
1 stop9h 41m
United Airlines
Mon 6/83:59 pm
NAS
- PIT
1 stop8h 00m
United Airlines
Deal found 5/9![United Airlines logo]()
$402
This JetBlue deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:00 am
PIT
- NAS
1 stop10h 04m
JetBlue
Sat 6/2012:08 pm
NAS
- PIT
1 stop11h 49m
JetBlue
Deal found 5/7![JetBlue logo]()
$490
This American Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/195:01 am
PIT
- NAS
1 stop5h 01m
American Airlines
Tue 6/2312:39 pm
NAS
- PIT
1 stop11h 10m
American Airlines
Deal found 5/9![American Airlines logo]()
$408
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/25:10 am
PIT
- MBJ
1 stop9h 10m
Southwest
Tue 7/711:45 am
MBJ
- PIT
1 stop7h 55m
Southwest
Deal found 5/9![Southwest logo]()
$495
This JetBlue deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/16:00 am
PIT
- NAS
1 stop7h 29m
JetBlue
Wed 6/32:04 pm
NAS
- PIT
1 stop9h 43m
JetBlue
Deal found 5/6![JetBlue logo]()
$495
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:00 am
PIT
- SJU
1 stop7h 16m
Delta
Tue 9/227:00 am
SJU
- PIT
1 stop9h 40m
Delta
Deal found 5/9![Delta logo]()
$454
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/126:15 am
PIT
- PLS
1 stop8h 10m
United Airlines
Fri 7/175:15 pm
PLS
- PIT
1 stop6h 21m
United Airlines
Deal found 5/5![United Airlines logo]()
$414
This American Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:00 am
PIT
- PLS
1 stop6h 39m
American Airlines
Mon 7/201:11 pm
PLS
- PIT
1 stop10h 36m
American Airlines
Deal found 5/9![American Airlines logo]()
$435
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated May 10, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated May 10, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/910:35 am
PIT
- MBJ
1 stop5h 35m
United Airlines
Mon 5/112:40 pm
MBJ
- PIT
1 stop8h 04m
United Airlines
Deal found 5/5![United Airlines logo]()
$344
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/127:55 pm
PIT
- STT
1 stop17h 40m
American Airlines
Thu 5/2111:43 am
STT
- PIT
1 stop9h 04m
American Airlines
Deal found 5/5![American Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/1610:33 am
PIT
- SJU
1 stop10h 22m
American Airlines
Thu 5/216:20 am
SJU
- PIT
1 stop10h 09m
American Airlines
Deal found 5/5![American Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/189:14 pm
PIT
- SJU
1 stop12h 50m
Multiple Airlines
Thu 5/217:00 am
SJU
- PIT
1 stop27h 48m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$287
This American Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1810:55 am
PIT
- SJU
1 stop11h 10m
American Airlines
Wed 5/201:25 pm
SJU
- PIT
2 stops8h 50m
American Airlines
Deal found 5/9![American Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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
Wed 6/36:20 am
SJU
- PIT
1 stop14h 40m
American Airlines
Deal found 5/6![American Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/6![Multiple Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/3112:08 pm
PIT
- SJU
1 stop26h 25m
Multiple Airlines
Sat 6/67:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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
Sat 6/67:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/210:55 am
PIT
- SJU
1 stop12h 06m
American Airlines
Tue 6/96:21 am
SJU
- PIT
1 stop14h 39m
American Airlines
Deal found 5/5![American Airlines logo]()
$344
This American Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:45 pm
PIT
- STT
2 stops18h 02m
American Airlines
Tue 6/1611:44 am
STT
- PIT
1 stop9h 03m
American Airlines
Deal found 5/8![American Airlines logo]()
$331
This Priceline deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/257:09 pm
PIT
- SJU
1 stop18h 07m
Frontier
Sat 7/44:05 pm
SJU
- PIT
1 stop26h 10m
Frontier
Deal found 5/5![Frontier logo]()
$321
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 10, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated May 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Deal found 5/7![Multiple Airlines logo]()
$127
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:00 am
PIT
- NAS
1 stop5h 51m
Delta
Deal found 5/9![Delta logo]()
$134
This Priceline deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/177:10 pm
PIT
- SJU
1 stop7h 01m
Frontier
Deal found 5/7![Frontier logo]()
$138
This Super.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:00 am
PIT
- PUJ
1 stop9h 27m
JetBlue
Deal found 5/9![JetBlue logo]()
$139
This Super.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/257:09 pm
PIT
- SJU
1 stop22h 12m
Frontier
Deal found 5/7![Frontier logo]()
$142
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/195:30 am
PIT
- SXM
1 stop8h 25m
Delta
Deal found 5/8![Delta logo]()
$147
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/48:00 am
PIT
- MBJ
1 stop8h 34m
Delta
Deal found 5/9![Delta logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/3112:08 pm
PIT
- SJU
1 stop26h 25m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$149
This American Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:37 am
PIT
- AUA
2 stops10h 22m
American Airlines
Deal found 5/9![American Airlines logo]()
$149
This Justfly.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/36:00 am
PIT
- PUJ
1 stop6h 55m
JetBlue
Deal found 5/9![JetBlue logo]()
$149
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1611:54 am
PIT
- SJU
1 stop11h 41m
Delta
Deal found 5/8![Delta logo]()
$151
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1510:55 am
PIT
- SJU
1 stop11h 10m
American Airlines
Deal found 5/7![American Airlines logo]()
$153
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 10, 2026.
Round-trip from | $250 (American Airlines) |
|---|---|
One-way from | $127 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $367 |
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 10, 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
Sun 8/16
6:14 am-3:52 pm
1 stop9h 38m
Saint Thomas Island Cyril E King
Fri 8/21
4:42 pm-10:24 am
2 stops17h 42m
$290
PittsburghWillemstad
PIT - CUR
PITCUR
Pittsburgh
Sat 9/19
6:30 am-1:40 pm
1 stop7h 10m
Willemstad Hato Int.
Sat 9/26
2:50 pm-9:58 am
2 stops19h 08m
$343
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Wed 10/7
5:30 am-4:33 pm
1 stop11h 03m
San Juan Luis Munoz Marin Intl
Wed 10/14
7:30 am-5:05 pm
1 stop9h 35m
$353
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Tue 6/23
6:49 am-2:57 pm
1 stop8h 08m
Nassau Intl
Fri 6/26
3:59 pm-11:59 pm
1 stop8h 00m
$376
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Sun 6/28
8:36 am-2:57 pm
1 stop6h 21m
Nassau Intl
Fri 7/3
2:53 pm-11:59 pm
1 stop9h 06m
$376
PittsburghOranjestad
PIT - AUA
PITAUA
Pittsburgh
Fri 8/28
6:00 am-1:34 pm
1 stop7h 34m
Oranjestad Reina Beatrix
Fri 9/4
2:39 pm-9:26 pm
1 stop6h 47m
$383
PittsburghSimpson Bay
PIT - SXM
PITSXM
Pittsburgh
Sun 9/20
7:00 am-1:50 pm
1 stop6h 50m
Simpson Bay Princess Juliana
Thu 9/24
3:20 pm-12:22 am
1 stop9h 02m
$383
PittsburghSanto Domingo
PIT - SDQ
PITSDQ
Pittsburgh
Mon 6/1
11:54 am-12:41 am
1 stop12h 47m
Santo Domingo Las Americas
Tue 6/16
6:06 am-5:06 pm
1 stop11h 00m
$386
PittsburghSimpson Bay
PIT - SXM
PITSXM
Pittsburgh
Sat 5/30
7:59 pm-3:42 pm
2 stops19h 43m
Simpson Bay Princess Juliana
Fri 6/5
4:43 pm-8:54 am
2 stops16h 11m
$388
PittsburghSimpson Bay
PIT - SXM
PITSXM
Pittsburgh
Sat 10/10
8:19 pm-3:05 pm
2 stops18h 46m
Simpson Bay Princess Juliana
Sat 10/17
4:30 pm-12:32 pm
2 stops20h 02m
$388
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Pittsburgh to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Pittsburgh with our price prediction graph.
PIT-NAS
PIT-SJU
PIT-PUJ
PIT-AUA
PIT-SDQ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Pittsburgh to Caribbean
PIT-0CB
PIT-NAS
PIT-SJU
PIT-PUJ
PIT-AUA
How far ahead should I book a flight from Pittsburgh to Caribbean?
Booking 67 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.
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 $1,414). 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.
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 10, 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
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
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 10, 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 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$123 | Average$446 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$135 | Average$318 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$141 | Average$492 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$144 | Average$441 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$225 | Average$613 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$225 | Average$484 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$232 | Average$544 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$406 | Average$492 | FlexibilityNo cancel fee | On-time67% |