$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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
May 18 — May 251
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 April 18, 2026.
Explore the most affordable flight options available from Pittsburgh to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:35 am
PIT
- SJU
2 stops42h 19m
Multiple Airlines
Sat 5/97:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$229
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1812:53 pm
PIT
- SJU
1 stop13h 08m
Frontier
Fri 5/13:08 am
SJU
- PIT
1 stop8h 41m
Frontier
Deal found 4/14![Frontier logo]()
$231
This Priceline deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:35 am
PIT
- SJU
1 stop12h 47m
Multiple Airlines
Tue 5/53:03 am
SJU
- PIT
1 stop16h 17m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$235
This CheapOair deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:35 am
PIT
- SJU
1 stop12h 47m
Multiple Airlines
Sat 5/96:00 am
SJU
- PIT
1 stop13h 20m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$242
This CheapOair deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/18:15 pm
PIT
- SJU
1 stop27h 07m
Frontier
Fri 6/53:03 am
SJU
- PIT
1 stop16h 17m
Frontier
Deal found 4/14![Frontier logo]()
$250
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:40 am
PIT
- STT
1 stop9h 37m
Delta
Thu 5/213:01 pm
STT
- PIT
1 stop9h 44m
Delta
Deal found 4/13![Delta logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:35 am
PIT
- SJU
2 stops30h 15m
Multiple Airlines
Sat 5/97:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$254
This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:45 pm
PIT
- STT
1 stop16h 50m
American Airlines
Wed 5/2012:25 pm
STT
- PIT
2 stops9h 50m
American Airlines
Deal found 4/15![American Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:35 am
PIT
- SJU
2 stops42h 19m
Multiple Airlines
Sun 5/107:00 am
SJU
- PIT
1 stop11h 37m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$258
This CheapOair deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:15 pm
PIT
- SJU
1 stop25h 07m
Spirit Airlines
Thu 4/3012:57 pm
SJU
- PIT
1 stop11h 02m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$262
This Mytrip deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:35 am
PIT
- SXM
1 stop7h 02m
Spirit Airlines
Sat 5/92:35 pm
SXM
- PIT
1 stop7h 32m
Spirit Airlines
Deal found 4/17![Spirit Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:05 am
PIT
- STT
1 stop6h 46m
Delta
Thu 4/301:22 pm
STT
- PIT
1 stop11h 13m
Delta
Deal found 4/13![Delta logo]()
$275
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 April 18, 2026.
Discover carefully curated flight deals from Pittsburgh to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 18, 2026.
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:46 am
PIT
- STT
1 stop8h 31m
Delta
Thu 5/213:01 pm
STT
- PIT
1 stop9h 44m
Delta
Deal found 4/15![Delta logo]()
$250
This Mytrip deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:35 am
PIT
- SXM
1 stop7h 02m
Spirit Airlines
Sat 5/92:35 pm
SXM
- PIT
1 stop7h 32m
Spirit Airlines
Deal found 4/17![Spirit Airlines logo]()
$269
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/510:55 am
PIT
- SJU
1 stop9h 39m
United Airlines
Wed 5/131:00 am
SJU
- PIT
2 stops8h 31m
United Airlines
Deal found 4/14![United Airlines logo]()
$282
This American Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:58 pm
PIT
- GCM
2 stops17h 57m
American Airlines
Tue 5/192:10 pm
GCM
- PIT
2 stops18h 33m
American Airlines
Deal found 4/17![American Airlines logo]()
$326
This Justfly.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:20 am
PIT
- GCM
1 stop6h 40m
Multiple Airlines
Sat 6/1310:55 am
GCM
- PIT
1 stop23h 38m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$341
This KAYAK deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:00 am
PIT
- GCM
1 stop8h 04m
JetBlue
Sat 5/232:20 pm
GCM
- PIT
1 stop8h 27m
JetBlue
Deal found 4/17![JetBlue logo]()
$372
This Air Canada deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/133:35 pm
PIT
- MBJ
2 stops44h 45m
Air Canada
Fri 6/1912:30 pm
MBJ
- PIT
2 stops49h 23m
Air Canada
Deal found 4/13![Air Canada logo]()
$465
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/273:00 pm
PIT
- SJU
1 stop6h 24m
United Airlines
Wed 4/291:00 am
SJU
- PIT
2 stops8h 31m
United Airlines
Deal found 4/16![United Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/37:05 am
PIT
- STT
1 stop7h 43m
Delta
Tue 5/123:01 pm
STT
- PIT
1 stop9h 44m
Delta
Deal found 4/15![Delta logo]()
$297
This American Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:39 pm
PIT
- GCM
2 stops16h 16m
American Airlines
Mon 5/182:10 pm
GCM
- PIT
2 stops19h 04m
American Airlines
Deal found 4/17![American Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:00 am
PIT
- MBJ
2 stops9h 10m
United Airlines
Fri 5/14:12 pm
MBJ
- PIT
1 stop16h 19m
United Airlines
Deal found 4/14![United Airlines logo]()
$324
This Cheapflightsfares deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
PIT
- STT
1 stop6h 47m
Spirit Airlines
Sun 5/311:52 pm
STT
- PIT
1 stop8h 15m
Spirit Airlines
Deal found 4/16![Spirit Airlines logo]()
$361
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:40 am
PIT
- GCM
1 stop7h 14m
Delta
Mon 5/181:19 pm
GCM
- PIT
1 stop10h 26m
Delta
Deal found 4/15![Delta logo]()
$341
This American Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:08 pm
PIT
- PUJ
2 stops16h 52m
American Airlines
Tue 10/65:20 pm
PUJ
- PIT
1 stop6h 29m
American Airlines
Deal found 4/13![American Airlines logo]()
$357
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:00 am
PIT
- STT
1 stop9h 43m
United Airlines
Tue 5/122:10 pm
STT
- PIT
2 stops9h 13m
United Airlines
Deal found 4/14![United Airlines logo]()
$340
This JetBlue deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:00 am
PIT
- PUJ
1 stop10h 24m
JetBlue
Wed 5/132:28 pm
PUJ
- PIT
1 stop8h 17m
JetBlue
Deal found 4/14![JetBlue logo]()
$414
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3011:54 am
PIT
- SJU
1 stop11h 41m
Delta
Sat 6/62:48 pm
SJU
- PIT
1 stop9h 57m
Delta
Deal found 4/13![Delta logo]()
$346
This American Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:03 am
PIT
- SXM
1 stop9h 19m
American Airlines
Sat 5/94:35 pm
SXM
- PIT
2 stops17h 08m
American Airlines
Deal found 4/17![American Airlines logo]()
$359
This FlightHub deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:45 am
PIT
- MBJ
1 stop8h 39m
Multiple Airlines
Mon 8/1012:30 pm
MBJ
- PIT
1 stop22h 03m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$455
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:24 pm
PIT
- GCM
2 stops18h 06m
United Airlines
Thu 5/281:35 pm
GCM
- PIT
1 stop9h 24m
United Airlines
Deal found 4/14![United Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
PIT
- AUA
1 stop8h 10m
Delta
Thu 5/73:25 pm
AUA
- PIT
1 stop17h 37m
Delta
Deal found 4/14![Delta logo]()
$350
This Air Canada deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:15 pm
PIT
- PUJ
2 stops25h 40m
Air Canada
Tue 6/25:25 pm
PUJ
- PIT
2 stops18h 08m
Air Canada
Deal found 4/16![Air Canada logo]()
$476
This American Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/15:00 am
PIT
- AUA
2 stops11h 59m
American Airlines
Wed 7/82:34 pm
AUA
- PIT
2 stops18h 56m
American Airlines
Deal found 4/17![American Airlines logo]()
$367
This JetBlue deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/197:00 am
PIT
- AUA
1 stop7h 05m
JetBlue
Thu 5/213:25 pm
AUA
- PIT
1 stop8h 22m
JetBlue
Deal found 4/14![JetBlue logo]()
$459
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:10 am
PIT
- AUA
1 stop6h 30m
United Airlines
Tue 5/124:30 pm
AUA
- PIT
1 stop6h 53m
United Airlines
Deal found 4/13![United Airlines logo]()
$357
This Air Canada deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:00 am
PIT
- PUJ
1 stop9h 25m
Air Canada
Mon 6/154:25 pm
PUJ
- PIT
1 stop19h 08m
Air Canada
Deal found 4/13![Air Canada logo]()
$480
This American Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:45 pm
PIT
- SXM
1 stop16h 55m
American Airlines
Thu 6/42:22 pm
SXM
- PIT
1 stop9h 37m
American Airlines
Deal found 4/13![American Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:00 am
PIT
- SXM
1 stop7h 50m
Delta
Thu 9/243:20 pm
SXM
- PIT
1 stop9h 02m
Delta
Deal found 4/13![Delta logo]()
$383
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:49 am
PIT
- AUA
1 stop8h 21m
United Airlines
Thu 6/44:30 pm
AUA
- PIT
1 stop7h 06m
United Airlines
Deal found 4/13![United Airlines logo]()
$357
This JetBlue deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/277:00 am
PIT
- PUJ
1 stop6h 23m
JetBlue
Thu 4/3012:45 pm
PUJ
- PIT
1 stop11h 14m
JetBlue
Deal found 4/15![JetBlue logo]()
$486
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated April 18, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated April 18, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1812:53 pm
PIT
- SJU
1 stop13h 08m
Frontier
Fri 5/13:08 am
SJU
- PIT
1 stop8h 41m
Frontier
Deal found 4/14![Frontier logo]()
$231
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:05 am
PIT
- STT
1 stop6h 46m
Delta
Thu 4/301:22 pm
STT
- PIT
1 stop11h 13m
Delta
Deal found 4/13![Delta logo]()
$275
This CheapOair deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:35 am
PIT
- SJU
1 stop12h 47m
Multiple Airlines
Sat 5/96:00 am
SJU
- PIT
1 stop13h 20m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$242
This CheapOair deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:15 pm
PIT
- SJU
1 stop25h 07m
Spirit Airlines
Thu 4/3012:57 pm
SJU
- PIT
1 stop11h 02m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:35 am
PIT
- SJU
2 stops42h 19m
Multiple Airlines
Sat 5/97:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:35 am
PIT
- SJU
2 stops42h 19m
Multiple Airlines
Sun 5/107:00 am
SJU
- PIT
1 stop11h 37m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:35 am
PIT
- SJU
2 stops30h 15m
Multiple Airlines
Sat 5/97:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$254
This Priceline deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:35 am
PIT
- SJU
1 stop12h 47m
Multiple Airlines
Tue 5/53:03 am
SJU
- PIT
1 stop16h 17m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:35 am
PIT
- SJU
2 stops17h 24m
Multiple Airlines
Sat 5/97:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$263
This Mytrip deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:35 am
PIT
- SXM
1 stop7h 02m
Spirit Airlines
Sat 5/92:35 pm
SXM
- PIT
1 stop7h 32m
Spirit Airlines
Deal found 4/17![Spirit Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:40 am
PIT
- STT
1 stop9h 37m
Delta
Thu 5/213:01 pm
STT
- PIT
1 stop9h 44m
Delta
Deal found 4/13![Delta logo]()
$250
This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:45 pm
PIT
- STT
1 stop16h 50m
American Airlines
Wed 5/2012:25 pm
STT
- PIT
2 stops9h 50m
American Airlines
Deal found 4/15![American Airlines logo]()
$255
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 April 18, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 18, 2026.
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/108:05 pm
PIT
- SJU
1 stop11h 59m
Frontier
Deal found 4/14![Frontier logo]()
$88
This Priceline deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 5/88:15 pm
PIT
- SJU
1 stop26h 28m
Frontier
Deal found 4/12![Frontier logo]()
$94
This Super.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/19:59 am
PIT
- SJU
1 stop16h 02m
Frontier
Deal found 4/16![Frontier logo]()
$97
This Justfly.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:00 am
PIT
- GCM
1 stop6h 19m
JetBlue
Deal found 4/16![JetBlue logo]()
$104
This CheapOair deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/188:15 pm
PIT
- SJU
1 stop17h 00m
Frontier
Deal found 4/17![Frontier logo]()
$104
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:15 pm
PIT
- SJU
1 stop11h 49m
Frontier
Deal found 4/14![Frontier logo]()
$106
This American Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:15 am
PIT
- GCM
1 stop10h 56m
American Airlines
Deal found 4/16![American Airlines logo]()
$108
This Mytrip deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:15 pm
PIT
- SJU
2 stops30h 39m
Spirit Airlines
Deal found 4/16![Spirit Airlines logo]()
$116
This CheapOair deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:05 pm
PIT
- SJU
1 stop21h 07m
Frontier
Deal found 4/17![Frontier logo]()
$117
This Travelocity deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/137:09 pm
PIT
- SJU
1 stop7h 00m
Frontier
Deal found 4/16![Frontier logo]()
$120
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:46 am
PIT
- STT
1 stop8h 31m
Delta
Deal found 4/14![Delta logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:35 am
PIT
- SJU
2 stops34h 56m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$124
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 April 18, 2026.
Round-trip from | $229 (Kiwi.com) |
|---|---|
One-way from | $88 (Frontier) |
Popular in | December |
Cheapest in | October |
Average price | $363 |
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 April 18, 2026.
Use the filters below to find and compare flights from Pittsburgh to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Sun 5/17
6:46 am-3:17 pm
1 stop8h 31m
Saint Thomas Island Cyril E King
Thu 5/21
3:01 pm-12:45 am
1 stop9h 44m
$250
PittsburghSimpson Bay
PIT - SXM
PITSXM
Pittsburgh
Sun 5/3
6:35 am-1:37 pm
1 stop7h 02m
Simpson Bay Princess Juliana
Sat 5/9
2:35 pm-10:07 pm
1 stop7h 32m
$269
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Tue 5/5
10:55 am-8:34 pm
1 stop9h 39m
San Juan Luis Munoz Marin Intl
Wed 5/13
1:00 am-9:31 am
2 stops8h 31m
$282
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Mon 4/27
3:00 pm-9:24 pm
1 stop6h 24m
San Juan Luis Munoz Marin Intl
Wed 4/29
1:00 am-9:31 am
2 stops8h 31m
$282
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Sun 5/3
7:05 am-2:48 pm
1 stop7h 43m
Saint Thomas Island Cyril E King
Tue 5/12
3:01 pm-12:45 am
1 stop9h 44m
$297
PittsburghMontego Bay
PIT - MBJ
PITMBJ
Pittsburgh
Tue 4/28
7:00 am-3:10 pm
2 stops9h 10m
Montego Bay Sangster Intl
Fri 5/1
4:12 pm-9:31 am
1 stop16h 19m
$324
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Fri 5/15
5:58 pm-10:55 am
2 stops17h 57m
George Town Owen Roberts Intl
Tue 5/19
2:10 pm-9:43 am
2 stops18h 33m
$326
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Fri 5/15
7:39 pm-10:55 am
2 stops16h 16m
George Town Owen Roberts Intl
Mon 5/18
2:10 pm-10:14 am
2 stops19h 04m
$326
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Wed 5/6
6:00 am-3:43 pm
1 stop9h 43m
Saint Thomas Island Cyril E King
Tue 5/12
2:10 pm-11:23 pm
2 stops9h 13m
$340
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Sat 6/6
7:20 am-1:00 pm
1 stop6h 40m
George Town Owen Roberts Intl
Sat 6/13
10:55 am-11:33 am
1 stop23h 38m
$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-STT
PIT-SXM
PIT-GCM
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-STT
PIT-SXM
PIT-GCM
What is the cheapest month to book a flight from Pittsburgh to Caribbean?
Currently, August is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $109). Flying from Pittsburgh to Caribbean in October is currently the most expensive (average of $1,414). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated April 18, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andJetBlue 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
Entertainment
7.8
Food
7.2
Overall
7.9
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Entertainment
7.8
Food
7.2
Overall
7.9
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Entertainment
7.8
Food
7.2
Overall
7.9
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Entertainment
7.8
Food
7.2
Overall
7.9
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Entertainment
7.8
Food
7.2
Overall
7.9
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Entertainment
7.8
Food
7.2
Overall
7.9
Comfort
7.9
Crew
8.5
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.
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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 April 18, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Pittsburgh to Caribbean flights
Consider these flights traveling from Pittsburgh to Caribbean.
Top 8 airlines flying from Pittsburgh to Caribbean
Discover the top 8 airlines that operate flights from Pittsburgh to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$315 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$141 | Average$489 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$150 | Average$453 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$153 | Average$428 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$225 | Average$608 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$225 | Average$481 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$232 | Average$555 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$406 | Average$494 | FlexibilityNo cancel fee | On-time67% |