$107+ Cheap flights from Pittsburgh (PIT) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Jul 31 — Aug 71
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 July 1, 2026.
Explore the most affordable flight options available from Pittsburgh to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 1, 2026.
This United Airlines deal was found by Cheapflights users on 6/29. 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.
Sat 8/296:30 am
PIT
- STT
1 stop9h 13m
United Airlines
Sat 9/52:10 pm
STT
- PIT
2 stops9h 20m
United Airlines
Deal found 6/29![United Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 6/30. 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 8/297:41 am
PIT
- STT
1 stop7h 18m
American Airlines
Sat 9/54:42 pm
STT
- PIT
2 stops18h 02m
American Airlines
Deal found 6/30![American Airlines logo]()
$275
This American Airlines deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 8/225:21 am
PIT
- STT
1 stop8h 19m
American Airlines
Fri 8/283:43 pm
STT
- PIT
2 stops18h 37m
American Airlines
Deal found 6/27![American Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
Mon 8/36:00 am
PIT
- SJU
1 stop8h 00m
Multiple Airlines
Thu 8/136:26 am
SJU
- PIT
1 stop12h 43m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$314
This American Airlines deal was found by Cheapflights users on 6/28. 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 10/76:30 am
PIT
- SJU
2 stops9h 08m
American Airlines
Wed 10/146:20 am
SJU
- PIT
2 stops10h 26m
American Airlines
Deal found 6/28![American Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 9/75:21 am
PIT
- STT
2 stops10h 31m
American Airlines
Tue 9/291:41 pm
STT
- PIT
2 stops20h 42m
American Airlines
Deal found 6/27![American Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/142:15 pm
PIT
- SJU
1 stop10h 26m
Multiple Airlines
Thu 8/206:35 am
SJU
- PIT
2 stops12h 34m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$316
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:00 am
PIT
- MBJ
1 stop8h 48m
JetBlue
Thu 10/291:00 pm
MBJ
- PIT
1 stop7h 22m
JetBlue
Deal found 6/30![JetBlue logo]()
$316
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Sun 9/207:40 pm
PIT
- SJU
2 stops13h 44m
American Airlines
Sat 9/262:22 pm
SJU
- PIT
1 stop6h 39m
American Airlines
Deal found 6/28![American Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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.
Tue 8/1112:01 pm
PIT
- SJU
1 stop12h 40m
Multiple Airlines
Tue 8/185:37 pm
SJU
- PIT
2 stops24h 15m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2312:06 pm
PIT
- SJU
1 stop25h 54m
Multiple Airlines
Sun 8/307:00 am
SJU
- PIT
1 stop10h 58m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$321
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Fri 7/246:54 pm
PIT
- NAS
1 stop14h 46m
American Airlines
Fri 7/3112:29 pm
NAS
- PIT
1 stop7h 39m
American Airlines
Deal found 6/28![American Airlines logo]()
$322
Best flights from Pittsburgh to CaribbeanDiscover carefully curated flight deals from Pittsburgh to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 1, 2026.
Discover carefully curated flight deals from Pittsburgh to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 1, 2026.
This United Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 10/227:30 am
PIT
- SJU
1 stop6h 15m
United Airlines
Fri 10/301:05 am
SJU
- PIT
2 stops12h 01m
United Airlines
Deal found 6/26![United Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Fri 8/145:21 am
PIT
- NAS
1 stop8h 51m
American Airlines
Tue 8/183:34 pm
NAS
- PIT
1 stop7h 21m
American Airlines
Deal found 6/28![American Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 8/151:57 pm
PIT
- SJU
1 stop8h 32m
Delta
Wed 8/195:49 pm
SJU
- PIT
1 stop6h 47m
Delta
Deal found 6/27![Delta logo]()
$338
This Southwest deal was found by Cheapflights users on 6/28. 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.
Thu 9/311:20 am
PIT
- SJU
2 stops10h 50m
Southwest
Thu 9/1011:35 am
SJU
- PIT
1 stop7h 05m
Southwest
Deal found 6/28![Southwest logo]()
$343
This JetBlue deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 9/287:00 am
PIT
- SXM
1 stop7h 00m
JetBlue
Fri 10/23:05 pm
SXM
- PIT
1 stop8h 15m
JetBlue
Deal found 6/27![JetBlue logo]()
$381
This Air Canada deal was found by Cheapflights users on 6/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:30 pm
PIT
- NAS
1 stop21h 55m
Air Canada
Thu 10/16:30 pm
NAS
- PIT
2 stops20h 23m
Air Canada
Deal found 6/30![Air Canada logo]()
$412
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:15 am
PIT
- PUJ
1 stop9h 14m
Multiple Airlines
Tue 9/84:20 pm
PUJ
- PIT
2 stops22h 28m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$485
This American Airlines deal was found by Cheapflights users on 6/29. 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.
Sat 8/226:19 am
PIT
- NAS
1 stop5h 01m
American Airlines
Wed 8/261:50 pm
NAS
- PIT
1 stop4h 55m
American Airlines
Deal found 6/29![American Airlines logo]()
$322
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Fri 11/136:05 am
PIT
- GCM
1 stop10h 25m
United Airlines
Sat 11/215:30 pm
GCM
- PIT
1 stop16h 09m
United Airlines
Deal found 6/30![United Airlines logo]()
$331
This Copa Airlines deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 9/156:10 am
PIT
- CUR
2 stops36h 21m
Copa Airlines
Tue 9/221:23 pm
CUR
- PIT
2 stops43h 15m
Copa Airlines
Deal found 6/27![Copa Airlines logo]()
$668
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 11/312:20 pm
PIT
- SJU
2 stops8h 55m
Southwest
Mon 11/96:35 am
SJU
- PIT
1 stop6h 15m
Southwest
Deal found 6/27![Southwest logo]()
$343
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:30 pm
PIT
- SJU
1 stop9h 26m
Delta
Sat 11/147:15 am
SJU
- PIT
1 stop7h 17m
Delta
Deal found 6/26![Delta logo]()
$343
This American Airlines deal was found by Cheapflights users on 6/29. 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.
Sat 12/56:16 am
PIT
- GCM
1 stop6h 40m
American Airlines
Sat 12/122:00 pm
GCM
- PIT
1 stop9h 22m
American Airlines
Deal found 6/29![American Airlines logo]()
$331
This United Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 11/106:00 am
PIT
- GCM
2 stops10h 30m
United Airlines
Fri 11/205:45 pm
GCM
- PIT
2 stops16h 08m
United Airlines
Deal found 6/26![United Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 8/126:10 am
PIT
- GCM
1 stop5h 50m
American Airlines
Wed 8/1912:00 pm
GCM
- PIT
1 stop8h 25m
American Airlines
Deal found 6/27![American Airlines logo]()
$336
This United Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/147:25 am
PIT
- NAS
1 stop6h 04m
United Airlines
Tue 7/214:58 pm
NAS
- PIT
1 stop7h 01m
United Airlines
Deal found 6/26![United Airlines logo]()
$341
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:30 pm
PIT
- SJU
1 stop9h 26m
Delta
Sat 11/77:00 am
SJU
- PIT
1 stop7h 32m
Delta
Deal found 6/28![Delta logo]()
$381
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 10/223:55 pm
PIT
- SJU
2 stops8h 40m
Southwest
Mon 10/266:30 am
SJU
- PIT
2 stops8h 45m
Southwest
Deal found 6/27![Southwest logo]()
$383
This JetBlue deal was found by Cheapflights users on 6/29. 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 9/287:00 am
PIT
- MBJ
1 stop6h 03m
JetBlue
Thu 10/13:00 pm
MBJ
- PIT
1 stop7h 20m
JetBlue
Deal found 6/29![JetBlue logo]()
$444
This Air Canada deal was found by Cheapflights users on 6/28. 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.
Sat 7/256:00 am
PIT
- AUA
1 stop8h 15m
Air Canada
Sat 8/13:05 pm
AUA
- PIT
2 stops23h 43m
Air Canada
Deal found 6/28![Air Canada logo]()
$450
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Tue 9/16:30 am
PIT
- NAS
1 stop7h 03m
United Airlines
Tue 9/82:35 pm
NAS
- PIT
1 stop6h 22m
United Airlines
Deal found 6/30![United Airlines logo]()
$341
This American Airlines deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/278:01 pm
PIT
- SXM
1 stop17h 50m
American Airlines
Fri 7/312:46 pm
SXM
- PIT
1 stop9h 10m
American Airlines
Deal found 6/27![American Airlines logo]()
$351
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:50 pm
PIT
- SJU
2 stops10h 00m
Southwest
Sun 9/205:00 am
SJU
- PIT
2 stops10h 20m
Southwest
Deal found 6/30![Southwest logo]()
$395
This JetBlue deal was found by Cheapflights users on 6/29. 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 7/276:00 am
PIT
- AUA
1 stop7h 32m
JetBlue
Tue 8/44:17 pm
AUA
- PIT
1 stop7h 29m
JetBlue
Deal found 6/29![JetBlue logo]()
$451
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/2911:58 am
PIT
- SJU
1 stop11h 55m
Delta
Mon 8/37:30 am
SJU
- PIT
1 stop9h 45m
Delta
Deal found 6/27![Delta logo]()
$412
This United Airlines deal was found by Cheapflights users on 6/30. 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 11/86:00 am
PIT
- SJU
1 stop7h 40m
United Airlines
Sat 11/142:05 am
SJU
- PIT
1 stop7h 26m
United Airlines
Deal found 6/30![United Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 6/30. 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 7/125:35 am
PIT
- NAS
2 stops7h 43m
American Airlines
Wed 7/1512:03 pm
NAS
- PIT
1 stop6h 11m
American Airlines
Deal found 6/30![American Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Sat 8/87:00 am
PIT
- MBJ
2 stops9h 10m
United Airlines
Sat 8/222:40 pm
MBJ
- PIT
2 stops18h 09m
United Airlines
Deal found 7/1![United Airlines logo]()
$348
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/125:45 am
PIT
- NAS
1 stop10h 54m
Delta
Mon 7/136:04 pm
NAS
- PIT
1 stop6h 46m
Delta
Deal found 6/27![Delta logo]()
$423
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/206:00 am
PIT
- AUA
1 stop7h 32m
JetBlue
Mon 7/276:00 pm
AUA
- PIT
1 stop17h 03m
JetBlue
Deal found 6/30![JetBlue logo]()
$483
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated July 1, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated July 1, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/29. 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.
Mon 7/68:00 am
PIT
- SJU
1 stop14h 57m
American Airlines
Wed 7/87:00 am
SJU
- PIT
1 stop9h 25m
American Airlines
Deal found 6/29![American Airlines logo]()
$337
This United Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/147:25 am
PIT
- NAS
1 stop6h 04m
United Airlines
Tue 7/214:58 pm
NAS
- PIT
1 stop7h 01m
United Airlines
Deal found 6/26![United Airlines logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2312:06 pm
PIT
- SJU
1 stop25h 54m
Multiple Airlines
Sun 8/307:00 am
SJU
- PIT
1 stop10h 58m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$321
This American Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/238:00 am
PIT
- GCM
2 stops9h 10m
American Airlines
Mon 7/275:10 pm
GCM
- PIT
2 stops15h 57m
American Airlines
Deal found 6/26![American Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Fri 7/246:54 pm
PIT
- NAS
1 stop14h 46m
American Airlines
Fri 7/3112:29 pm
NAS
- PIT
1 stop7h 39m
American Airlines
Deal found 6/28![American Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 6/29. 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.
Sat 7/258:00 am
PIT
- NAS
2 stops7h 13m
American Airlines
Fri 7/3112:29 pm
NAS
- PIT
1 stop7h 39m
American Airlines
Deal found 6/29![American Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Sun 7/265:03 am
PIT
- NAS
1 stop8h 15m
American Airlines
Sun 8/212:29 pm
NAS
- PIT
1 stop11h 23m
American Airlines
Deal found 6/28![American Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/267:49 pm
PIT
- SJU
1 stop18h 11m
Multiple Airlines
Thu 7/306:00 am
SJU
- PIT
2 stops13h 09m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:00 am
PIT
- SJU
1 stop8h 00m
Multiple Airlines
Thu 7/306:00 am
SJU
- PIT
2 stops13h 09m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 6/29. 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 7/2911:58 am
PIT
- SJU
1 stop11h 55m
Delta
Thu 8/137:30 am
SJU
- PIT
1 stop9h 45m
Delta
Deal found 6/29![Delta logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
Fri 7/316:00 am
PIT
- SJU
1 stop8h 00m
Multiple Airlines
Mon 8/175:22 pm
SJU
- PIT
1 stop17h 59m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
Fri 7/316:00 am
PIT
- SJU
1 stop8h 00m
Multiple Airlines
Tue 8/113:10 am
SJU
- PIT
1 stop8h 54m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$330
One-way flights from Pittsburgh to CaribbeanSearch for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 1, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 1, 2026.
This Delta deal was found by Cheapflights users on 6/30. 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.
Sun 8/305:50 am
PIT
- NAS
1 stop6h 01m
Delta
Deal found 6/30![Delta logo]()
$107
This American Airlines deal was found by Cheapflights users on 7/1. 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 10/318:18 pm
PIT
- SJU
1 stop16h 46m
American Airlines
Deal found 7/1![American Airlines logo]()
$109
This American Airlines deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 8/238:00 am
PIT
- SJU
2 stops8h 57m
American Airlines
Deal found 6/27![American Airlines logo]()
$111
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:05 am
PIT
- GCM
1 stop5h 34m
Delta
Deal found 6/28![Delta logo]()
$113
This American Airlines deal was found by Cheapflights users on 6/28. 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 9/166:00 am
PIT
- SJU
2 stops9h 40m
American Airlines
Deal found 6/28![American Airlines logo]()
$116
This American Airlines deal was found by Cheapflights users on 6/30. 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 7/186:01 am
PIT
- STT
1 stop8h 55m
American Airlines
Deal found 6/30![American Airlines logo]()
$123
This American Airlines deal was found by Cheapflights users on 6/30. 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 9/247:40 pm
PIT
- STT
2 stops17h 11m
American Airlines
Deal found 6/30![American Airlines logo]()
$129
This American Airlines deal was found by Cheapflights users on 6/30. 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 7/198:01 pm
PIT
- SXM
1 stop17h 50m
American Airlines
Deal found 6/30![American Airlines logo]()
$131
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/265:05 am
PIT
- MBJ
1 stop6h 50m
Southwest
Deal found 6/26![Southwest logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:57 pm
PIT
- SJU
1 stop27h 41m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$140
This American Airlines deal was found by Cheapflights users on 6/30. 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.
Wed 8/57:25 pm
PIT
- SXM
2 stops20h 14m
American Airlines
Deal found 6/30![American Airlines logo]()
$142
This American Airlines deal was found by Cheapflights users on 6/30. 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 8/67:25 pm
PIT
- SXM
1 stop18h 17m
American Airlines
Deal found 6/30![American Airlines logo]()
$144
Find flight deals from Pittsburgh to Caribbean
Keep the following information in mind while searching for Pittsburgh to Caribbean flight deals. Data was last updated July 1, 2026.
Round-trip from | $250 (United Airlines) |
|---|---|
One-way from | $107 (Delta) |
Popular in | June |
Cheapest in | October |
Average price | $446 |
Cheapflights Fare Finder
Customize your flight search to find flights from Pittsburgh to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 1, 2026.
Use the filters below to find and compare flights from Pittsburgh to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Thu 10/22
7:30 am-1:45 pm
1 stop6h 15m
San Juan Luis Munoz Marin Intl
Fri 10/30
1:05 am-1:06 pm
2 stops12h 01m
$317
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Fri 8/14
5:21 am-2:12 pm
1 stop8h 51m
Nassau Intl
Tue 8/18
3:34 pm-10:55 pm
1 stop7h 21m
$322
Quickest round-trip
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Sat 8/22
6:19 am-11:20 am
1 stop5h 01m
Nassau Intl
Wed 8/26
1:50 pm-6:45 pm
1 stop4h 55m
$322
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Fri 11/13
6:05 am-4:30 pm
1 stop10h 25m
George Town Owen Roberts Intl
Sat 11/21
5:30 pm-9:39 am
1 stop16h 09m
$331
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Sat 12/5
6:16 am-12:56 pm
1 stop6h 40m
George Town Owen Roberts Intl
Sat 12/12
2:00 pm-11:22 pm
1 stop9h 22m
$331
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Tue 11/10
6:00 am-4:30 pm
2 stops10h 30m
George Town Owen Roberts Intl
Fri 11/20
5:45 pm-9:53 am
2 stops16h 08m
$336
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Wed 8/12
6:10 am-11:00 am
1 stop5h 50m
George Town Owen Roberts Intl
Wed 8/19
12:00 pm-9:25 pm
1 stop8h 25m
$336
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Sat 8/15
1:57 pm-10:29 pm
1 stop8h 32m
San Juan Luis Munoz Marin Intl
Wed 8/19
5:49 pm-12:36 am
1 stop6h 47m
$338
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Tue 7/14
7:25 am-1:29 pm
1 stop6h 04m
Nassau Intl
Tue 7/21
4:58 pm-11:59 pm
1 stop7h 01m
$341
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Tue 9/1
6:30 am-1:33 pm
1 stop7h 03m
Nassau Intl
Tue 9/8
2:35 pm-8:57 pm
1 stop6h 22m
$341
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Pittsburgh to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Pittsburgh with our price prediction graph.
PIT-SJU
PIT-NAS
PIT-GCM
PIT-PUJ
PIT-MBJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Pittsburgh to Caribbean
PIT-0CB
PIT-SJU
PIT-NAS
PIT-GCM
PIT-PUJ
What is the cheapest month to book a flight from Pittsburgh to Caribbean?
Currently, September is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $123). Flying from Pittsburgh to Caribbean in December is currently the most expensive (average of $1,446). 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 July 1, 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.
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Pittsburgh to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Pittsburgh to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Pittsburgh to Caribbean by cabin class
Find flights from Pittsburgh to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Pittsburgh and Caribbean flights
Browse other Pittsburgh and Caribbean flight options. Last updated on July 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Pittsburgh to Caribbean flights
Consider these flights traveling from Pittsburgh to Caribbean.
Top 7 airlines flying from Pittsburgh to Caribbean
Discover the top 7 airlines that operate flights from Pittsburgh to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$339 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$152 | Average$502 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$184 | Average$481 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$628 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$225 | Average$460 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$232 | Average$569 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$406 | Average$492 | FlexibilityNo cancel fee | On-time67% |