$88+ 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 4/12. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Mar 26 — Apr 21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Pittsburgh to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Pittsburgh to Caribbean
Cheapest
Best
Last-minute
One-way
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 February 24, 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 February 24, 2026.
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/161:40 pm
PIT
- SJU
1 stop8h 37m
Delta
Thu 5/215:43 pm
SJU
- PIT
1 stop7h 02m
Delta
Deal found 2/24![Delta logo]()
$219
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/411:55 am
PIT
- SJU
1 stop8h 17m
Delta
Wed 3/115:30 pm
SJU
- PIT
1 stop6h 47m
Delta
Deal found 2/24![Delta logo]()
$222
This American Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:45 pm
PIT
- STT
2 stops15h 50m
American Airlines
Fri 4/1712:25 pm
STT
- PIT
2 stops10h 56m
American Airlines
Deal found 2/24![American Airlines logo]()
$230
This American Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:16 pm
PIT
- SJU
1 stop13h 55m
American Airlines
Mon 5/411:59 pm
SJU
- PIT
1 stop10h 45m
American Airlines
Deal found 2/21![American Airlines logo]()
$232
This American Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/87:45 pm
PIT
- STT
1 stop16h 50m
American Airlines
Thu 5/1412:25 pm
STT
- PIT
1 stop11h 34m
American Airlines
Deal found 2/24![American Airlines logo]()
$232
This Frontier deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:24 pm
PIT
- SJU
1 stop12h 37m
Frontier
Sun 5/173:08 am
SJU
- PIT
1 stop8h 51m
Frontier
Deal found 2/24![Frontier logo]()
$234
This American Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:16 pm
PIT
- SJU
1 stop13h 57m
American Airlines
Tue 4/215:45 am
SJU
- PIT
1 stop12h 43m
American Airlines
Deal found 2/24![American Airlines logo]()
$249
This Priceline deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:24 pm
PIT
- SJU
1 stop12h 37m
Frontier
Sun 5/173:19 pm
SJU
- PIT
1 stop20h 40m
Frontier
Deal found 2/24![Frontier logo]()
$252
This Priceline deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2512:44 pm
PIT
- SJU
1 stop13h 17m
Frontier
Sun 5/36:30 am
SJU
- PIT
1 stop27h 00m
Frontier
Deal found 2/23![Frontier logo]()
$254
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/41:43 pm
PIT
- SJU
1 stop6h 29m
Delta
Tue 3/105:30 pm
SJU
- PIT
1 stop6h 47m
Delta
Deal found 2/24![Delta logo]()
$255
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:09 am
PIT
- STT
1 stop6h 55m
Delta
Wed 3/111:55 pm
STT
- PIT
1 stop7h 29m
Delta
Deal found 2/24![Delta logo]()
$255
This Cheapflightsfares deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/712:15 pm
PIT
- SJU
1 stop9h 46m
JetBlue
Tue 4/1411:25 pm
SJU
- PIT
1 stop10h 14m
JetBlue
Deal found 2/21![JetBlue logo]()
$258
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 February 24, 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 February 24, 2026.
This Delta deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:00 pm
PIT
- SJU
1 stop6h 59m
Delta
Fri 4/1712:55 pm
SJU
- PIT
1 stop11h 40m
Delta
Deal found 2/22![Delta logo]()
$222
This United Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:10 am
PIT
- STT
1 stop6h 10m
United Airlines
Fri 5/11:22 pm
STT
- PIT
1 stop10h 22m
United Airlines
Deal found 2/20![United Airlines logo]()
$230
This American Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:37 am
PIT
- STT
1 stop9h 25m
American Airlines
Wed 3/2512:02 pm
STT
- PIT
2 stops11h 08m
American Airlines
Deal found 2/20![American Airlines logo]()
$230
This JetBlue deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/247:00 am
PIT
- GCM
1 stop6h 56m
JetBlue
Thu 3/262:25 pm
GCM
- PIT
1 stop7h 12m
JetBlue
Deal found 2/21![JetBlue logo]()
$355
This Southwest deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/124:40 pm
PIT
- SJU
1 stop7h 25m
Southwest
Wed 6/1712:20 pm
SJU
- PIT
2 stops10h 05m
Southwest
Deal found 2/21![Southwest logo]()
$396
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:00 am
PIT
- STT
1 stop8h 45m
Delta
Tue 3/2412:49 pm
STT
- PIT
1 stop8h 35m
Delta
Deal found 2/24![Delta logo]()
$230
This Delta deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/247:05 am
PIT
- STT
1 stop6h 42m
Delta
Tue 3/313:00 pm
STT
- PIT
1 stop9h 17m
Delta
Deal found 2/21![Delta logo]()
$230
This FlightHub deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:55 pm
PIT
- UVF
1 stop21h 15m
Multiple Airlines
Sat 4/184:15 pm
UVF
- PIT
1 stop17h 15m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$515
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:00 am
PIT
- STT
1 stop7h 47m
Delta
Thu 3/2612:49 pm
STT
- PIT
1 stop11h 28m
Delta
Deal found 2/24![Delta logo]()
$230
This United Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:59 pm
PIT
- SXM
2 stops16h 34m
United Airlines
Wed 4/153:50 pm
SXM
- PIT
2 stops17h 58m
United Airlines
Deal found 2/24![United Airlines logo]()
$280
This American Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:35 pm
PIT
- STT
2 stops16h 00m
American Airlines
Tue 5/512:47 pm
STT
- PIT
1 stop8h 48m
American Airlines
Deal found 2/21![American Airlines logo]()
$296
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1810:17 am
PIT
- GCM
1 stop5h 48m
United Airlines
Wed 4/221:50 pm
GCM
- PIT
1 stop18h 58m
United Airlines
Deal found 2/23![United Airlines logo]()
$300
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:09 am
PIT
- STT
1 stop6h 55m
Delta
Tue 3/1012:49 pm
STT
- PIT
1 stop11h 28m
Delta
Deal found 2/23![Delta logo]()
$255
This American Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:58 pm
PIT
- MBJ
1 stop16h 15m
American Airlines
Thu 4/234:37 pm
MBJ
- PIT
2 stops16h 06m
American Airlines
Deal found 2/22![American Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:10 am
PIT
- GCM
1 stop9h 55m
United Airlines
Tue 4/281:50 pm
GCM
- PIT
1 stop9h 03m
United Airlines
Deal found 2/21![United Airlines logo]()
$307
This American Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:00 am
PIT
- GCM
1 stop6h 05m
American Airlines
Tue 3/177:45 am
GCM
- PIT
1 stop14h 01m
American Airlines
Deal found 2/23![American Airlines logo]()
$323
This United Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1110:17 am
PIT
- GCM
1 stop5h 48m
United Airlines
Tue 4/141:50 pm
GCM
- PIT
1 stop9h 03m
United Airlines
Deal found 2/21![United Airlines logo]()
$307
This JetBlue deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:00 am
PIT
- MBJ
1 stop9h 40m
JetBlue
Tue 4/148:41 am
MBJ
- PIT
1 stop13h 04m
JetBlue
Deal found 2/20![JetBlue logo]()
$409
This Southwest deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/712:30 pm
PIT
- SJU
2 stops8h 35m
Southwest
Fri 4/106:50 am
SJU
- PIT
2 stops17h 15m
Southwest
Deal found 2/23![Southwest logo]()
$438
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:35 am
PIT
- GCM
1 stop5h 30m
United Airlines
Wed 5/201:35 pm
GCM
- PIT
1 stop9h 09m
United Airlines
Deal found 2/22![United Airlines logo]()
$307
This American Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:30 am
PIT
- AUA
2 stops9h 29m
American Airlines
Tue 3/101:46 pm
AUA
- PIT
1 stop7h 25m
American Airlines
Deal found 2/20![American Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
PIT
- AUA
1 stop8h 20m
Delta
Tue 3/101:10 pm
AUA
- PIT
1 stop11h 07m
Delta
Deal found 2/20![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/216:10 am
PIT
- GCM
1 stop10h 25m
United Airlines
Wed 3/254:45 pm
GCM
- PIT
1 stop17h 27m
United Airlines
Deal found 2/24![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/234:55 pm
PIT
- SJU
1 stop6h 20m
Southwest
Tue 5/2611:25 am
SJU
- PIT
2 stops10h 45m
Southwest
Deal found 2/24![Southwest logo]()
$455
This American Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:58 pm
PIT
- UVF
2 stops19h 47m
American Airlines
Thu 4/163:28 pm
UVF
- PIT
1 stop18h 15m
American Airlines
Deal found 2/24![American Airlines logo]()
$355
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/226:00 am
PIT
- AUA
1 stop6h 30m
Delta
Thu 3/263:35 pm
AUA
- PIT
1 stop17h 29m
Delta
Deal found 2/23![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
PIT
- SJU
1 stop9h 42m
United Airlines
Wed 4/291:00 am
SJU
- PIT
2 stops8h 31m
United Airlines
Deal found 2/21![United Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:30 am
PIT
- SJU
2 stops9h 55m
Southwest
Wed 9/28:20 am
SJU
- PIT
2 stops9h 20m
Southwest
Deal found 2/20![Southwest logo]()
$457
This JetBlue deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:30 am
PIT
- PUJ
1 stop6h 05m
JetBlue
Tue 4/1412:30 pm
PUJ
- PIT
1 stop9h 20m
JetBlue
Deal found 2/20![JetBlue logo]()
$504
This American Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/146:04 pm
PIT
- SXM
2 stops19h 22m
American Airlines
Fri 6/194:43 pm
SXM
- PIT
2 stops18h 28m
American Airlines
Deal found 2/20![American Airlines logo]()
$367
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated February 24, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated February 24, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/15:40 pm
PIT
- SJU
1 stop6h 25m
Southwest
Wed 3/45:40 am
SJU
- PIT
2 stops11h 00m
Southwest
Deal found 2/22![Southwest logo]()
$265
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:09 am
PIT
- STT
1 stop6h 55m
Delta
Thu 3/51:50 pm
STT
- PIT
1 stop10h 21m
Delta
Deal found 2/23![Delta logo]()
$280
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/24:54 pm
PIT
- SJU
1 stop6h 04m
Delta
Sat 3/76:15 am
SJU
- PIT
1 stop10h 42m
Delta
Deal found 2/23![Delta logo]()
$290
This American Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/311:34 am
PIT
- SJU
1 stop10h 57m
American Airlines
Tue 3/107:11 am
SJU
- PIT
1 stop15h 35m
American Airlines
Deal found 2/23![American Airlines logo]()
$271
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/411:55 am
PIT
- SJU
1 stop8h 17m
Delta
Wed 3/115:30 pm
SJU
- PIT
1 stop6h 47m
Delta
Deal found 2/24![Delta logo]()
$222
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/41:43 pm
PIT
- SJU
1 stop6h 29m
Delta
Tue 3/105:30 pm
SJU
- PIT
1 stop6h 47m
Delta
Deal found 2/24![Delta logo]()
$255
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:09 am
PIT
- STT
1 stop6h 55m
Delta
Wed 3/111:55 pm
STT
- PIT
1 stop7h 29m
Delta
Deal found 2/24![Delta logo]()
$255
This American Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:37 am
PIT
- STT
1 stop9h 25m
American Airlines
Tue 3/1712:02 pm
STT
- PIT
2 stops11h 08m
American Airlines
Deal found 2/20![American Airlines logo]()
$291
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:00 am
PIT
- STT
1 stop8h 18m
United Airlines
Mon 3/162:05 pm
STT
- PIT
1 stop9h 46m
United Airlines
Deal found 2/22![United Airlines logo]()
$284
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/156:00 am
PIT
- STT
1 stop8h 45m
Delta
Thu 3/2612:49 pm
STT
- PIT
1 stop11h 28m
Delta
Deal found 2/24![Delta logo]()
$281
This American Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:37 am
PIT
- STT
1 stop9h 25m
American Airlines
Wed 3/251:53 pm
STT
- PIT
1 stop10h 06m
American Airlines
Deal found 2/24![American Airlines logo]()
$230
This Delta deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/236:00 am
PIT
- SJU
1 stop10h 18m
Delta
Thu 3/261:00 pm
SJU
- PIT
1 stop11h 17m
Delta
Deal found 2/22![Delta logo]()
$288
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 February 24, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated February 24, 2026.
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:00 am
PIT
- GCM
1 stop7h 30m
United Airlines
Deal found 2/23![United Airlines logo]()
$88
This American Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:16 pm
PIT
- SJU
1 stop15h 37m
American Airlines
Deal found 2/24![American Airlines logo]()
$91
This American Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:58 pm
PIT
- GCM
2 stops18h 02m
American Airlines
Deal found 2/23![American Airlines logo]()
$94
This United Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:00 am
PIT
- GCM
1 stop7h 30m
United Airlines
Deal found 2/21![United Airlines logo]()
$101
This American Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:35 pm
PIT
- GCM
2 stops16h 56m
American Airlines
Deal found 2/23![American Airlines logo]()
$107
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/41:43 pm
PIT
- SJU
1 stop6h 29m
Delta
Deal found 2/24![Delta logo]()
$111
This American Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/77:17 pm
PIT
- STT
1 stop14h 55m
American Airlines
Deal found 2/21![American Airlines logo]()
$113
This American Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:55 am
PIT
- SJU
1 stop11h 10m
American Airlines
Deal found 2/21![American Airlines logo]()
$114
This United Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:00 am
PIT
- GCM
1 stop7h 15m
United Airlines
Deal found 2/24![United Airlines logo]()
$117
This Priceline deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/249:44 am
PIT
- SJU
1 stop13h 04m
Frontier
Deal found 2/23![Frontier logo]()
$117
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/206:10 am
PIT
- SXM
1 stop6h 40m
United Airlines
Deal found 2/23![United Airlines logo]()
$117
This American Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:57 pm
PIT
- AUA
1 stop16h 23m
American Airlines
Deal found 2/24![American Airlines logo]()
$118
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 February 24, 2026.
Round-trip from | $219 (Delta) |
|---|---|
One-way from | $88 (United Airlines) |
Popular in | August |
Cheapest in | October |
Average price | $437 |
Good round-trip deal | $498 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Pittsburgh to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 24, 2026.
Use the filters below to find and compare flights from Pittsburgh to Caribbean that are best for you.
Fly from
Pittsburgh
Fly to
Caribbean
Route
Depart
Return
Price
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Mon 4/13
5:00 pm-11:59 pm
1 stop6h 59m
San Juan Luis Munoz Marin Intl
Fri 4/17
12:55 pm-12:35 am
1 stop11h 40m
$222
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Tue 4/28
6:10 am-12:20 pm
1 stop6h 10m
Saint Thomas Island Cyril E King
Fri 5/1
1:22 pm-11:44 pm
1 stop10h 22m
$230
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Thu 3/19
6:37 am-4:02 pm
1 stop9h 25m
Saint Thomas Island Cyril E King
Wed 3/25
12:02 pm-11:10 pm
2 stops11h 08m
$230
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Tue 3/17
6:00 am-2:45 pm
1 stop8h 45m
Saint Thomas Island Cyril E King
Tue 3/24
12:49 pm-9:24 pm
1 stop8h 35m
$230
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Tue 3/24
7:05 am-1:47 pm
1 stop6h 42m
Saint Thomas Island Cyril E King
Tue 3/31
3:00 pm-12:17 am
1 stop9h 17m
$230
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Tue 3/17
6:00 am-1:47 pm
1 stop7h 47m
Saint Thomas Island Cyril E King
Thu 3/26
12:49 pm-12:17 am
1 stop11h 28m
$230
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Wed 3/4
7:09 am-3:04 pm
1 stop6h 55m
Saint Thomas Island Cyril E King
Tue 3/10
12:49 pm-12:17 am
1 stop11h 28m
$255
PittsburghSimpson Bay
PIT - SXM
PITSXM
Pittsburgh
Wed 4/8
7:59 pm-12:33 pm
2 stops16h 34m
Simpson Bay Princess Juliana
Wed 4/15
3:50 pm-9:48 am
2 stops17h 58m
$280
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Sat 5/2
7:35 pm-11:35 am
2 stops16h 00m
Saint Thomas Island Cyril E King
Tue 5/5
12:47 pm-9:35 pm
1 stop8h 48m
$296
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Sat 4/18
10:17 am-3:05 pm
1 stop5h 48m
George Town Owen Roberts Intl
Wed 4/22
1:50 pm-9:48 am
1 stop18h 58m
$300
Showing 1-10 of 60 results
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-STT
PIT-GCM
PIT-PUJ
PIT-SXM
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-STT
PIT-GCM
PIT-PUJ
What is the cheapest month to book a flight from Pittsburgh to Caribbean?
Currently, March is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $148). Flying from Pittsburgh to Caribbean in July is currently the most expensive (average of $255). 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.
What is the cheapest time of day to fly from PIT to CB?
Find hourly flight availability from Pittsburgh to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 24, 2026.
When flying from Pittsburgh to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
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 February 24, 2026.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American 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.
Crew
8.5
Overall
7.9
Comfort
7.9
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Overall
7.9
Comfort
7.9
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Overall
7.9
Comfort
7.9
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Overall
7.9
Comfort
7.9
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Overall
7.9
Comfort
7.9
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Overall
7.9
Comfort
7.9
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
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.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top countries
Top destinations
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 February 24, 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 February 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$315 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$141 | Average$464 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$153 | Average$406 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$158 | Average$498 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$225 | Average$640 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$225 | Average$506 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$225 | Average$568 | FlexibilityNo cancel fee | On-time71% |