$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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Sep 1 — Sep 81
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 August 2, 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 August 2, 2026.
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/235:21 am
PIT
- SJU
1 stop17h 03m
American Airlines
Fri 8/2810:33 am
SJU
- PIT
1 stop10h 52m
American Airlines
Deal found 7/31![American Airlines logo]()
$218
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/75:00 am
PIT
- SJU
1 stop6h 20m
American Airlines
Wed 10/143:51 pm
SJU
- PIT
1 stop16h 45m
American Airlines
Deal found 7/31![American Airlines logo]()
$223
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:29 am
PIT
- SJU
2 stops12h 18m
American Airlines
Wed 9/306:00 am
SJU
- PIT
2 stops12h 16m
American Airlines
Deal found 7/31![American Airlines logo]()
$227
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:10 am
PIT
- SJU
1 stop6h 44m
United Airlines
Wed 9/24:55 pm
SJU
- PIT
1 stop6h 35m
United Airlines
Deal found 7/29![United Airlines logo]()
$233
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:10 am
PIT
- SJU
1 stop15h 45m
American Airlines
Wed 8/266:00 am
SJU
- PIT
2 stops9h 37m
American Airlines
Deal found 7/30![American Airlines logo]()
$238
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 10/26:30 am
PIT
- SJU
1 stop7h 15m
United Airlines
Sat 10/31:00 am
SJU
- PIT
2 stops12h 09m
United Airlines
Deal found 8/1![United Airlines logo]()
$247
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 10/297:00 am
PIT
- SJU
1 stop6h 40m
United Airlines
Mon 11/28:25 am
SJU
- PIT
2 stops11h 10m
United Airlines
Deal found 7/29![United Airlines logo]()
$257
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:10 am
PIT
- SJU
1 stop6h 44m
United Airlines
Fri 9/114:55 pm
SJU
- PIT
1 stop6h 35m
United Airlines
Deal found 7/28![United Airlines logo]()
$262
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:45 am
PIT
- SJU
2 stops11h 53m
United Airlines
Mon 8/311:00 am
SJU
- PIT
2 stops8h 36m
United Airlines
Deal found 7/28![United Airlines logo]()
$263
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/308:18 pm
PIT
- SJU
1 stop15h 02m
American Airlines
Sat 11/76:28 am
SJU
- PIT
1 stop11h 27m
American Airlines
Deal found 7/31![American Airlines logo]()
$265
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/227:00 am
PIT
- SJU
2 stops13h 38m
United Airlines
Tue 9/81:00 am
SJU
- PIT
2 stops8h 36m
United Airlines
Deal found 7/28![United Airlines logo]()
$267
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 10/187:39 pm
PIT
- STT
2 stops17h 19m
American Airlines
Sat 10/243:46 pm
STT
- PIT
2 stops18h 18m
American Airlines
Deal found 7/30![American Airlines logo]()
$270
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 August 2, 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 August 2, 2026.
This American Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 10/187:39 pm
PIT
- STT
2 stops17h 19m
American Airlines
Sat 10/243:46 pm
STT
- PIT
2 stops18h 18m
American Airlines
Deal found 8/1![American Airlines logo]()
$270
This JetBlue deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:15 am
PIT
- SJU
1 stop6h 33m
JetBlue
Fri 9/41:48 pm
SJU
- PIT
1 stop7h 40m
JetBlue
Deal found 7/30![JetBlue logo]()
$294
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 stop7h 44m
Delta
Sat 9/54:13 pm
STT
- PIT
1 stop7h 21m
Delta
Deal found 7/30![Delta logo]()
$298
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 10/296:30 am
PIT
- SJU
1 stop8h 10m
United Airlines
Sat 10/312:05 am
SJU
- PIT
2 stops12h 01m
United Airlines
Deal found 8/1![United Airlines logo]()
$308
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 8/296:30 am
PIT
- STT
1 stop6h 50m
Southwest
Sat 9/52:05 pm
STT
- PIT
1 stop7h 35m
Southwest
Deal found 8/1![Southwest logo]()
$335
This Air Canada deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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.
Mon 10/267:20 pm
PIT
- MBJ
1 stop17h 30m
Air Canada
Fri 10/3012:50 pm
MBJ
- PIT
1 stop28h 46m
Air Canada
Deal found 8/1![Air Canada logo]()
$431
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 10/2710:49 am
PIT
- SJU
2 stops10h 33m
United Airlines
Mon 11/22:05 am
SJU
- PIT
2 stops12h 01m
United Airlines
Deal found 8/1![United Airlines logo]()
$308
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 10/3010:49 am
PIT
- SJU
1 stop9h 11m
United Airlines
Sat 11/78:05 am
SJU
- PIT
2 stops11h 14m
United Airlines
Deal found 8/1![United Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/267:05 am
PIT
- GCM
1 stop5h 34m
Delta
Wed 9/21:04 pm
GCM
- PIT
1 stop10h 32m
Delta
Deal found 7/29![Delta logo]()
$351
This American Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 8/297:41 am
PIT
- GCM
1 stop8h 19m
American Airlines
Sat 9/52:10 pm
GCM
- PIT
1 stop6h 15m
American Airlines
Deal found 8/1![American Airlines logo]()
$351
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/411:20 am
PIT
- SJU
2 stops10h 55m
Southwest
Sat 9/1210:25 am
SJU
- PIT
1 stop8h 15m
Southwest
Deal found 7/28![Southwest logo]()
$361
This Priceline deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/316:15 am
PIT
- SXM
1 stop6h 22m
JetBlue
Sat 9/51:42 pm
SXM
- PIT
1 stop7h 46m
JetBlue
Deal found 7/28![JetBlue logo]()
$385
This American Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/227:04 am
PIT
- GCM
1 stop8h 13m
American Airlines
Sat 8/2911:55 am
GCM
- PIT
1 stop8h 30m
American Airlines
Deal found 7/28![American Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/215:50 am
PIT
- GCM
1 stop6h 50m
Delta
Fri 9/251:00 pm
GCM
- PIT
1 stop10h 31m
Delta
Deal found 7/31![Delta logo]()
$351
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:15 am
PIT
- SJU
1 stop9h 27m
United Airlines
Tue 9/13:56 pm
SJU
- PIT
1 stop8h 14m
United Airlines
Deal found 7/28![United Airlines logo]()
$328
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:53 am
PIT
- GCM
1 stop5h 37m
American Airlines
Thu 9/1012:36 pm
GCM
- PIT
1 stop7h 09m
American Airlines
Deal found 7/30![American Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/65:50 am
PIT
- GCM
1 stop6h 49m
Delta
Thu 9/101:00 pm
GCM
- PIT
1 stop10h 31m
Delta
Deal found 7/31![Delta logo]()
$351
This JetBlue deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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.
Sun 9/66:00 am
PIT
- SXM
1 stop6h 37m
JetBlue
Thu 9/103:05 pm
SXM
- PIT
1 stop8h 15m
JetBlue
Deal found 8/1![JetBlue logo]()
$391
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 12/66:20 am
PIT
- NAS
2 stops7h 28m
United Airlines
Fri 12/1112:55 pm
NAS
- PIT
1 stop10h 24m
United Airlines
Deal found 8/1![United Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 8/246:21 am
PIT
- SXM
2 stops9h 18m
American Airlines
Wed 9/22:22 pm
SXM
- PIT
2 stops18h 24m
American Airlines
Deal found 8/1![American Airlines logo]()
$367
This JetBlue deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Sun 8/306:15 am
PIT
- NAS
1 stop7h 35m
JetBlue
Thu 9/312:20 pm
NAS
- PIT
1 stop9h 08m
JetBlue
Deal found 7/31![JetBlue logo]()
$404
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:00 am
PIT
- NAS
1 stop8h 39m
Delta
Wed 9/93:18 pm
NAS
- PIT
1 stop6h 21m
Delta
Deal found 8/1![Delta logo]()
$374
This Air Canada deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/63:35 pm
PIT
- PLS
2 stops21h 10m
Air Canada
Sat 9/121:40 pm
PLS
- PIT
2 stops25h 08m
Air Canada
Deal found 7/28![Air Canada logo]()
$507
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 11/110:49 am
PIT
- SJU
1 stop9h 11m
United Airlines
Sat 11/75:50 pm
SJU
- PIT
1 stop6h 40m
United Airlines
Deal found 7/29![United Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/316:10 am
PIT
- SXM
1 stop7h 12m
American Airlines
Sat 9/52:33 pm
SXM
- PIT
1 stop7h 24m
American Airlines
Deal found 7/31![American Airlines logo]()
$380
This Air Canada deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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.
Mon 9/146:00 am
PIT
- PUJ
1 stop9h 25m
Air Canada
Fri 9/185:05 pm
PUJ
- PIT
1 stop21h 43m
Air Canada
Deal found 8/2![Air Canada logo]()
$513
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/206:30 am
PIT
- SJU
1 stop7h 15m
United Airlines
Fri 9/251:00 am
SJU
- PIT
2 stops14h 25m
United Airlines
Deal found 7/30![United Airlines logo]()
$357
This JetBlue deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/127:00 am
PIT
- SDQ
1 stop6h 19m
JetBlue
Sat 9/192:29 pm
SDQ
- PIT
1 stop8h 51m
JetBlue
Deal found 7/29![JetBlue logo]()
$438
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/186:35 pm
PIT
- STT
2 stops18h 45m
Southwest
Fri 9/252:35 pm
STT
- PIT
1 stop7h 00m
Southwest
Deal found 7/29![Southwest logo]()
$545
This American Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 10/186:00 am
PIT
- SXM
1 stop7h 23m
American Airlines
Tue 10/272:23 pm
SXM
- PIT
2 stops19h 07m
American Airlines
Deal found 8/1![American Airlines logo]()
$380
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated August 2, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated August 2, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:15 am
PIT
- SJU
1 stop8h 33m
JetBlue
Fri 8/211:48 pm
SJU
- PIT
1 stop7h 40m
JetBlue
Deal found 7/28![JetBlue logo]()
$295
This American Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 stop8h 03m
American Airlines
Tue 9/17:03 am
SJU
- PIT
1 stop14h 54m
American Airlines
Deal found 7/28![American Airlines logo]()
$243
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/197:00 am
PIT
- SJU
2 stops13h 38m
United Airlines
Tue 9/81:00 am
SJU
- PIT
2 stops8h 36m
United Airlines
Deal found 7/28![United Airlines logo]()
$265
This American Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/197:41 am
PIT
- SJU
1 stop16h 18m
American Airlines
Wed 9/96:00 am
SJU
- PIT
2 stops13h 03m
American Airlines
Deal found 7/28![American Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:10 am
PIT
- SJU
1 stop15h 45m
American Airlines
Wed 8/266:00 am
SJU
- PIT
2 stops9h 37m
American Airlines
Deal found 7/30![American Airlines logo]()
$238
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/227:00 am
PIT
- SJU
2 stops13h 38m
United Airlines
Tue 9/81:00 am
SJU
- PIT
2 stops8h 36m
United Airlines
Deal found 7/28![United Airlines logo]()
$267
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/235:21 am
PIT
- SJU
1 stop17h 03m
American Airlines
Fri 8/2810:33 am
SJU
- PIT
1 stop10h 52m
American Airlines
Deal found 7/31![American Airlines logo]()
$218
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:45 am
PIT
- SJU
2 stops11h 53m
United Airlines
Mon 8/311:00 am
SJU
- PIT
2 stops8h 36m
United Airlines
Deal found 7/28![United Airlines logo]()
$263
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/2610:45 am
PIT
- SJU
2 stops13h 05m
United Airlines
Tue 9/11:00 am
SJU
- PIT
2 stops8h 36m
United Airlines
Deal found 7/28![United Airlines logo]()
$273
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:39 pm
PIT
- STT
2 stops17h 14m
American Airlines
Sat 9/54:42 pm
STT
- PIT
2 stops18h 02m
American Airlines
Deal found 7/30![American Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 stop7h 44m
Delta
Sat 9/54:13 pm
STT
- PIT
1 stop7h 21m
Delta
Deal found 7/30![Delta logo]()
$298
This JetBlue deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:15 am
PIT
- SJU
1 stop6h 33m
JetBlue
Fri 9/41:48 pm
SJU
- PIT
1 stop7h 40m
JetBlue
Deal found 7/29![JetBlue logo]()
$294
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 August 2, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:30 am
PIT
- SJU
1 stop7h 15m
United Airlines
Deal found 8/1![United Airlines logo]()
$109
This American Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/236:10 am
PIT
- SJU
1 stop15h 45m
American Airlines
Deal found 8/1![American Airlines logo]()
$111
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/512:45 pm
PIT
- SJU
1 stop6h 40m
Southwest
Deal found 7/28![Southwest logo]()
$114
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 10/205:11 am
PIT
- SJU
2 stops15h 27m
United Airlines
Deal found 7/29![United Airlines logo]()
$119
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:50 am
PIT
- NAS
1 stop6h 01m
Delta
Deal found 8/1![Delta logo]()
$122
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 1/168:45 pm
PIT
- GCM
1 stop17h 00m
United Airlines
Deal found 7/28![United Airlines logo]()
$123
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 9/75:50 am
PIT
- STT
1 stop7h 44m
Delta
Deal found 8/1![Delta logo]()
$133
This Air Canada deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/306:00 am
PIT
- NAS
1 stop11h 30m
Air Canada
Deal found 7/28![Air Canada logo]()
$135
This Air Canada deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 7/28![Air Canada logo]()
$138
This American Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:51 pm
PIT
- STT
2 stops18h 07m
American Airlines
Deal found 7/29![American Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 10/47:30 am
PIT
- SJU
2 stops30h 04m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$143
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/18:19 pm
PIT
- SXM
1 stop16h 07m
American Airlines
Deal found 7/30![American Airlines 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 August 2, 2026.
Round-trip from | $218 (American Airlines) |
|---|---|
One-way from | $109 (United Airlines) |
Popular in | June |
Cheapest in | October |
Average price | $382 |
Good round-trip deal | $456 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 August 2, 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 10/18
7:39 pm-12:58 pm
2 stops17h 19m
Saint Thomas Island Cyril E King
Sat 10/24
3:46 pm-10:04 am
2 stops18h 18m
$270
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Mon 8/31
6:15 am-12:48 pm
1 stop6h 33m
San Juan Luis Munoz Marin Intl
Fri 9/4
1:48 pm-9:28 pm
1 stop7h 40m
$294
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Sat 8/29
5:50 am-1:34 pm
1 stop7h 44m
Saint Thomas Island Cyril E King
Sat 9/5
4:13 pm-11:34 pm
1 stop7h 21m
$298
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Thu 10/29
6:30 am-2:40 pm
1 stop8h 10m
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
Tue 10/27
10:49 am-9:22 pm
2 stops10h 33m
San Juan Luis Munoz Marin Intl
Mon 11/2
2:05 am-1:06 pm
2 stops12h 01m
$308
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Fri 10/30
10:49 am-8:00 pm
1 stop9h 11m
San Juan Luis Munoz Marin Intl
Sat 11/7
8:05 am-6:19 pm
2 stops11h 14m
$308
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Tue 8/25
6:15 am-3:42 pm
1 stop9h 27m
San Juan Luis Munoz Marin Intl
Tue 9/1
3:56 pm-12:10 am
1 stop8h 14m
$328
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Sat 8/29
6:30 am-1:20 pm
1 stop6h 50m
Saint Thomas Island Cyril E King
Sat 9/5
2:05 pm-9:40 pm
1 stop7h 35m
$335
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Wed 8/26
7:05 am-11:39 am
1 stop5h 34m
George Town Owen Roberts Intl
Wed 9/2
1:04 pm-12:36 am
1 stop10h 32m
$351
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Sat 8/29
7:41 am-3:00 pm
1 stop8h 19m
George Town Owen Roberts Intl
Sat 9/5
2:10 pm-9:25 pm
1 stop6h 15m
$351
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Pittsburgh to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Pittsburgh with our price prediction graph.
PIT-SJU
PIT-STT
PIT-NAS
PIT-GCM
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-NAS
PIT-GCM
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 $418). Flying from Pittsburgh to Caribbean in December is currently the most expensive (average of $591). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How far ahead should I book a flight from Pittsburgh to Caribbean?
Booking 60 days in advance of your planned departure date is, on average, the best time to get cheap flights from Pittsburgh to Caribbean. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated August 2, 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.
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
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 August 2, 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 August 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$321 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$172 | Average$509 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$184 | Average$485 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$222 | Average$461 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$225 | Average$559 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$231 | Average$643 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$406 | Average$494 | FlexibilityNo cancel fee | On-time67% |