$94+ Cheap flights from Pittsburgh (PIT) to Caribbean Islands
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
May 3 — May 101
Round-trip
1 adult, Economy
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Find cheap flights from Pittsburgh to Caribbean Islands with Cheapflights
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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 Caribbean IslandsExplore the most affordable flight options available from Pittsburgh to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 3, 2026.
Explore the most affordable flight options available from Pittsburgh to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 3, 2026.
This Orbitz deal was found by Cheapflights users on 3/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:25 am
PIT
- SJU
1 stop12h 23m
Multiple Airlines
Wed 4/2212:57 pm
SJU
- PIT
1 stop11h 02m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$222
This CheapOair deal was found by Cheapflights users on 3/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/298:15 pm
PIT
- SJU
1 stop11h 49m
Frontier
Fri 6/53:03 am
SJU
- PIT
1 stop16h 17m
Frontier
Deal found 3/31![Frontier logo]()
$223
This Priceline deal was found by Cheapflights users on 3/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:00 pm
PIT
- SJU
1 stop27h 48m
Frontier
Thu 4/163:19 pm
SJU
- PIT
1 stop17h 10m
Frontier
Deal found 3/31![Frontier logo]()
$225
This CheapOair deal was found by Cheapflights users on 3/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:35 am
PIT
- SJU
1 stop12h 47m
Spirit Airlines
Tue 4/287:00 am
SJU
- PIT
1 stop16h 59m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$226
This CheapOair deal was found by Cheapflights users on 3/31. 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 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 3/31![Spirit Airlines logo]()
$227
This Priceline deal was found by Cheapflights users on 3/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:00 pm
PIT
- SJU
1 stop19h 31m
Multiple Airlines
Fri 4/1712:57 pm
SJU
- PIT
1 stop11h 02m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$229
This United Airlines deal was found by Cheapflights users on 3/30. 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.
Wed 4/157:00 am
PIT
- STT
1 stop8h 31m
United Airlines
Tue 4/211:22 pm
STT
- PIT
1 stop10h 04m
United Airlines
Deal found 3/30![United Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:15 pm
PIT
- SJU
1 stop18h 08m
Multiple Airlines
Wed 4/2912:57 pm
SJU
- PIT
1 stop11h 02m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$234
This Frontier deal was found by Cheapflights users on 3/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/37:40 pm
PIT
- SJU
1 stop6h 21m
Frontier
Fri 4/173:08 am
SJU
- PIT
1 stop8h 50m
Frontier
Deal found 3/29![Frontier logo]()
$239
This Mytrip deal was found by Cheapflights users on 3/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:15 pm
PIT
- SJU
2 stops30h 39m
Spirit Airlines
Wed 4/2912:57 pm
SJU
- PIT
1 stop11h 02m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$240
This CheapOair deal was found by Cheapflights users on 4/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:15 pm
PIT
- SJU
1 stop25h 07m
Spirit Airlines
Thu 4/3012:57 pm
SJU
- PIT
1 stop11h 02m
Spirit Airlines
Deal found 4/1![Spirit Airlines logo]()
$241
This United Airlines deal was found by Cheapflights users on 3/29. 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 4/186:00 am
PIT
- STT
1 stop9h 43m
United Airlines
Wed 4/221:22 pm
STT
- PIT
1 stop10h 04m
United Airlines
Deal found 3/29![United Airlines logo]()
$245
Best flights from Pittsburgh to Caribbean IslandsDiscover carefully curated flight deals from Pittsburgh to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 3, 2026.
Discover carefully curated flight deals from Pittsburgh to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 3, 2026.
This United Airlines deal was found by Cheapflights users on 3/30. 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.
Wed 4/156:10 am
PIT
- STT
1 stop6h 10m
United Airlines
Tue 4/211:22 pm
STT
- PIT
2 stops10h 31m
United Airlines
Deal found 3/30![United Airlines logo]()
$230
This Delta deal was found by Cheapflights users on 3/29. 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.
Tue 5/56:00 am
PIT
- SJU
1 stop10h 23m
Delta
Tue 5/125:43 pm
SJU
- PIT
1 stop7h 02m
Delta
Deal found 3/29![Delta logo]()
$282
This American Airlines deal was found by Cheapflights users on 4/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:38 pm
PIT
- CUR
2 stops18h 37m
American Airlines
Tue 9/153:00 pm
CUR
- PIT
2 stops20h 46m
American Airlines
Deal found 4/2![American Airlines logo]()
$323
This JetBlue deal was found by Cheapflights users on 3/29. 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 9/286:25 am
PIT
- PUJ
1 stop7h 15m
JetBlue
Thu 10/12:00 pm
PUJ
- PIT
1 stop8h 53m
JetBlue
Deal found 3/29![JetBlue logo]()
$369
This Expedia deal was found by Cheapflights users on 3/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/112:15 pm
PIT
- UVF
1 stop25h 55m
Air Canada
Fri 6/53:05 pm
UVF
- PIT
1 stop29h 33m
Air Canada
Deal found 3/29![Air Canada logo]()
$382
This Orbitz deal was found by Cheapflights users on 4/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
PIT
- MBJ
1 stop8h 03m
Multiple Airlines
Sun 6/1412:30 pm
MBJ
- PIT
1 stop22h 03m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$406
This United Airlines deal was found by Cheapflights users on 3/29. 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 4/156:10 am
PIT
- STT
1 stop6h 10m
United Airlines
Mon 4/204:45 pm
STT
- PIT
1 stop6h 35m
United Airlines
Deal found 3/29![United Airlines logo]()
$230
This United Airlines deal was found by Cheapflights users on 4/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1410:55 am
PIT
- SJU
2 stops10h 29m
United Airlines
Sat 4/187:20 am
SJU
- PIT
1 stop6h 38m
United Airlines
Deal found 4/2![United Airlines logo]()
$282
This Copa Airlines deal was found by Cheapflights users on 4/1. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:45 am
PIT
- CUR
2 stops27h 33m
Copa Airlines
Wed 8/193:39 pm
CUR
- PIT
2 stops17h 56m
Copa Airlines
Deal found 4/1![Copa Airlines logo]()
$625
This Delta deal was found by Cheapflights users on 3/29. 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.
Sun 9/206:00 am
PIT
- SJU
1 stop10h 31m
Delta
Sat 9/267:00 am
SJU
- PIT
1 stop9h 40m
Delta
Deal found 3/29![Delta logo]()
$346
This American Airlines deal was found by Cheapflights users on 3/28. 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.
Mon 5/47:12 pm
PIT
- SXM
2 stops18h 09m
American Airlines
Fri 5/82:21 pm
SXM
- PIT
2 stops19h 22m
American Airlines
Deal found 3/28![American Airlines logo]()
$368
This JetBlue deal was found by Cheapflights users on 3/30. 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.
Wed 5/66:00 am
PIT
- CUR
1 stop7h 37m
JetBlue
Thu 5/72:42 pm
CUR
- PIT
1 stop9h 25m
JetBlue
Deal found 3/30![JetBlue logo]()
$373
This United Airlines deal was found by Cheapflights users on 3/30. 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.
Mon 4/137:00 am
PIT
- STT
1 stop8h 31m
United Airlines
Wed 4/152:10 pm
STT
- PIT
1 stop9h 43m
United Airlines
Deal found 3/30![United Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 3/29. 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.
Sun 9/207:00 am
PIT
- SXM
1 stop6h 50m
Delta
Thu 9/243:20 pm
SXM
- PIT
1 stop9h 02m
Delta
Deal found 3/29![Delta logo]()
$363
This American Airlines deal was found by Cheapflights users on 3/29. 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.
Sun 6/146:04 pm
PIT
- SXM
2 stops19h 18m
American Airlines
Fri 6/192:53 pm
SXM
- PIT
2 stops19h 32m
American Airlines
Deal found 3/29![American Airlines logo]()
$368
This Air Canada deal was found by Cheapflights users on 3/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/146:00 am
PIT
- MBJ
1 stop6h 20m
Air Canada
Sat 6/2012:30 pm
MBJ
- PIT
2 stops25h 23m
Air Canada
Deal found 3/31![Air Canada logo]()
$411
This FlightHub deal was found by Cheapflights users on 3/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:55 pm
PIT
- NAS
1 stop19h 00m
Multiple Airlines
Fri 4/174:59 pm
NAS
- PIT
1 stop5h 46m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$424
This American Airlines deal was found by Cheapflights users on 3/29. 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.
Sun 9/207:18 pm
PIT
- SXM
2 stops17h 57m
American Airlines
Thu 9/242:50 pm
SXM
- PIT
2 stops19h 56m
American Airlines
Deal found 3/29![American Airlines logo]()
$368
This United Airlines deal was found by Cheapflights users on 4/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
PIT
- STT
1 stop9h 43m
United Airlines
Wed 5/62:10 pm
STT
- PIT
2 stops9h 13m
United Airlines
Deal found 4/2![United Airlines logo]()
$345
This JetBlue deal was found by Cheapflights users on 3/30. 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 9/286:25 am
PIT
- NAS
1 stop10h 39m
JetBlue
Wed 9/301:30 pm
NAS
- PIT
1 stop9h 23m
JetBlue
Deal found 3/30![JetBlue logo]()
$420
This Delta deal was found by Cheapflights users on 3/30. 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.
Mon 5/185:40 am
PIT
- NAS
1 stop10h 55m
Delta
Fri 5/226:00 pm
NAS
- PIT
1 stop6h 45m
Delta
Deal found 3/30![Delta logo]()
$394
This Expedia deal was found by Cheapflights users on 3/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:00 am
PIT
- UVF
1 stop8h 20m
Multiple Airlines
Tue 6/301:50 pm
UVF
- PIT
1 stop9h 31m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$440
This United Airlines deal was found by Cheapflights users on 4/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/152:09 pm
PIT
- SJU
2 stops9h 41m
United Airlines
Wed 5/131:00 am
SJU
- PIT
2 stops8h 31m
United Airlines
Deal found 4/2![United Airlines logo]()
$346
This Air Canada deal was found by Cheapflights users on 4/1. 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.
Sat 6/133:35 pm
PIT
- MBJ
2 stops20h 45m
Air Canada
Fri 6/1912:30 pm
MBJ
- PIT
2 stops25h 23m
Air Canada
Deal found 4/1![Air Canada logo]()
$464
This JetBlue deal was found by Cheapflights users on 3/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:00 am
PIT
- AUA
1 stop7h 05m
JetBlue
Wed 5/133:55 pm
AUA
- PIT
1 stop8h 12m
JetBlue
Deal found 3/28![JetBlue logo]()
$430
This Delta deal was found by Cheapflights users on 4/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2411:50 am
PIT
- NAS
1 stop4h 47m
Delta
Tue 6/303:29 pm
NAS
- PIT
1 stop9h 15m
Delta
Deal found 4/2![Delta logo]()
$394
This American Airlines deal was found by Cheapflights users on 4/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:05 am
PIT
- AUA
2 stops11h 54m
American Airlines
Mon 7/205:12 pm
AUA
- PIT
2 stops16h 55m
American Airlines
Deal found 4/2![American Airlines logo]()
$397
This United Airlines deal was found by Cheapflights users on 3/31. 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 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
Tue 6/21:50 pm
AUA
- PIT
1 stop10h 09m
United Airlines
Deal found 3/31![United Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 3/31. 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.
Wed 5/67:05 am
PIT
- NAS
1 stop4h 43m
Delta
Thu 5/141:16 pm
NAS
- PIT
1 stop9h 06m
Delta
Deal found 3/31![Delta logo]()
$394
This Mytrip deal was found by Cheapflights users on 3/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1111:55 am
PIT
- UVF
3 stops26h 15m
Multiple Airlines
Tue 6/163:05 pm
UVF
- PIT
2 stops23h 48m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$489
Last-minute flights from Pittsburgh to Caribbean IslandsDiscover last-minute flight deals from Pittsburgh to Caribbean Islands. Data last updated April 3, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean Islands. Data last updated April 3, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 3/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/37:40 pm
PIT
- SJU
1 stop6h 21m
Frontier
Fri 4/173:08 am
SJU
- PIT
1 stop8h 50m
Frontier
Deal found 3/29![Frontier logo]()
$239
This Priceline deal was found by Cheapflights users on 3/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:00 pm
PIT
- SJU
1 stop27h 48m
Frontier
Thu 4/163:19 pm
SJU
- PIT
1 stop17h 10m
Frontier
Deal found 3/31![Frontier logo]()
$225
This Priceline deal was found by Cheapflights users on 3/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:00 pm
PIT
- SJU
1 stop19h 31m
Multiple Airlines
Fri 4/1712:57 pm
SJU
- PIT
1 stop11h 02m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$229
This United Airlines deal was found by Cheapflights users on 3/30. 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.
Wed 4/156:10 am
PIT
- STT
1 stop6h 10m
United Airlines
Tue 4/211:22 pm
STT
- PIT
2 stops10h 31m
United Airlines
Deal found 3/30![United Airlines logo]()
$230
This United Airlines deal was found by Cheapflights users on 3/29. 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 4/186:00 am
PIT
- STT
1 stop9h 43m
United Airlines
Wed 4/221:22 pm
STT
- PIT
1 stop10h 04m
United Airlines
Deal found 3/29![United Airlines logo]()
$245
This Orbitz deal was found by Cheapflights users on 3/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:25 am
PIT
- SJU
1 stop12h 23m
Multiple Airlines
Wed 4/2212:57 pm
SJU
- PIT
1 stop11h 02m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$222
This CheapOair deal was found by Cheapflights users on 3/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:35 am
PIT
- SJU
1 stop12h 47m
Spirit Airlines
Tue 4/287:00 am
SJU
- PIT
1 stop16h 59m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:15 pm
PIT
- SJU
1 stop18h 08m
Multiple Airlines
Wed 4/2912:57 pm
SJU
- PIT
1 stop11h 02m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$234
This CheapOair deal was found by Cheapflights users on 4/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:15 pm
PIT
- SJU
1 stop25h 07m
Spirit Airlines
Thu 4/3012:57 pm
SJU
- PIT
1 stop11h 02m
Spirit Airlines
Deal found 4/1![Spirit Airlines logo]()
$241
This Mytrip deal was found by Cheapflights users on 3/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:15 pm
PIT
- SJU
2 stops30h 39m
Spirit Airlines
Wed 4/2912:57 pm
SJU
- PIT
1 stop11h 02m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$240
This CheapOair deal was found by Cheapflights users on 3/31. 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 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 3/31![Spirit Airlines logo]()
$227
This CheapOair deal was found by Cheapflights users on 3/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/298:15 pm
PIT
- SJU
1 stop11h 49m
Frontier
Fri 6/53:03 am
SJU
- PIT
1 stop16h 17m
Frontier
Deal found 3/31![Frontier logo]()
$223
One-way flights from Pittsburgh to Caribbean IslandsSearch for one-way flight options from Pittsburgh to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated April 3, 2026.
Search for one-way flight options from Pittsburgh to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated April 3, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1510:45 am
PIT
- SJU
1 stop8h 37m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$94
This Frontier deal was found by Cheapflights users on 3/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:15 pm
PIT
- SJU
1 stop11h 49m
Frontier
Deal found 3/31![Frontier logo]()
$106
This United Airlines deal was found by Cheapflights users on 3/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:10 am
PIT
- STT
1 stop6h 10m
United Airlines
Deal found 3/31![United Airlines logo]()
$113
This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:35 am
PIT
- SJU
1 stop12h 47m
Spirit Airlines
Deal found 4/1![Spirit Airlines logo]()
$117
This Orbitz deal was found by Cheapflights users on 4/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/195:55 pm
PIT
- NAS
1 stop26h 10m
Air Canada
Deal found 4/2![Air Canada logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:15 pm
PIT
- SJU
1 stop25h 07m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$121
This CheapOair deal was found by Cheapflights users on 3/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:45 am
PIT
- SJU
1 stop16h 14m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$122
This United Airlines deal was found by Cheapflights users on 3/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/257:00 am
PIT
- STT
2 stops10h 00m
United Airlines
Deal found 3/31![United Airlines logo]()
$123
This Priceline deal was found by Cheapflights users on 4/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/159:44 am
PIT
- PUJ
1 stop23h 34m
Frontier
Deal found 4/2![Frontier logo]()
$125
This Priceline deal was found by Cheapflights users on 3/30. 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.
Sat 4/118:53 pm
PIT
- SJU
1 stop11h 03m
Frontier
Deal found 3/30![Frontier logo]()
$127
This Travelocity deal was found by Cheapflights users on 3/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:55 pm
PIT
- NAS
2 stops42h 30m
Air Canada
Deal found 3/29![Air Canada logo]()
$133
This American Airlines deal was found by Cheapflights users on 3/31. 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 9/57:13 pm
PIT
- CUR
2 stops18h 02m
American Airlines
Deal found 3/31![American Airlines logo]()
$134
Find flight deals from Pittsburgh to Caribbean Islands
Keep the following information in mind while searching for Pittsburgh to Caribbean Islands flight deals. Data was last updated April 3, 2026.
Round-trip from | $222 (Orbitz) |
|---|---|
One-way from | $94 (Cheapflightsfares) |
Popular in | December |
Cheapest in | October |
Average price | $363 |
Cheapflights Fare Finder
Customize your flight search to find flights from Pittsburgh to Caribbean Islands 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 3, 2026.
Use the filters below to find and compare flights from Pittsburgh to Caribbean Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Wed 4/15
6:10 am-12:20 pm
1 stop6h 10m
Saint Thomas Island Cyril E King
Tue 4/21
1:22 pm-11:53 pm
2 stops10h 31m
$230
Quickest round-trip
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Wed 4/15
6:10 am-12:20 pm
1 stop6h 10m
Saint Thomas Island Cyril E King
Mon 4/20
4:45 pm-11:20 pm
1 stop6h 35m
$230
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Tue 5/5
6:00 am-4:23 pm
1 stop10h 23m
San Juan Luis Munoz Marin Intl
Tue 5/12
5:43 pm-12:45 am
1 stop7h 02m
$282
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Tue 4/14
10:55 am-9:24 pm
2 stops10h 29m
San Juan Luis Munoz Marin Intl
Sat 4/18
7:20 am-1:58 pm
1 stop6h 38m
$282
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Mon 4/13
7:00 am-3:31 pm
1 stop8h 31m
Saint Thomas Island Cyril E King
Wed 4/15
2:10 pm-11:53 pm
1 stop9h 43m
$320
PittsburghWillemstad
PIT - CUR
PITCUR
Pittsburgh
Sat 9/5
8:38 pm-3:15 pm
2 stops18h 37m
Willemstad Hato Int.
Tue 9/15
3:00 pm-11:46 am
2 stops20h 46m
$323
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Fri 5/1
6:00 am-3:43 pm
1 stop9h 43m
Saint Thomas Island Cyril E King
Wed 5/6
2:10 pm-11:23 pm
2 stops9h 13m
$345
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Sun 9/20
6:00 am-4:31 pm
1 stop10h 31m
San Juan Luis Munoz Marin Intl
Sat 9/26
7:00 am-4:40 pm
1 stop9h 40m
$346
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Wed 4/15
2:09 pm-11:50 pm
2 stops9h 41m
San Juan Luis Munoz Marin Intl
Wed 5/13
1:00 am-9:31 am
2 stops8h 31m
$346
PittsburghOranjestad
PIT - AUA
PITAUA
Pittsburgh
Thu 5/28
6:49 am-3:10 pm
1 stop8h 21m
Oranjestad Reina Beatrix
Tue 6/2
1:50 pm-11:59 pm
1 stop10h 09m
$357
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Pittsburgh to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Pittsburgh with our price prediction graph.
PIT-SJU
PIT-STT
PIT-NAS
PIT-PUJ
PIT-CUR
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 Islands
PIT-zzEPX
PIT-SJU
PIT-STT
PIT-NAS
PIT-PUJ
What is the cheapest month to book a flight from Pittsburgh to Caribbean Islands?
Currently, March is the cheapest month in which you can book a flight from Pittsburgh to Caribbean Islands (average of $148). Flying from Pittsburgh to Caribbean Islands in July is currently the most expensive (average of $255). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Caribbean Islands
Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated April 3, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andJetBlue from Pittsburgh to Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.9
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.9
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.9
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.9
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.9
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.9
Food
7.2
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 Islands. 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 Islands
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Pittsburgh to Caribbean Islands by cabin class
Find flights from Pittsburgh to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Pittsburgh and Caribbean Islands flights
Browse other Pittsburgh and Caribbean Islands flight options. Last updated on April 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Pittsburgh to Caribbean Islands flights
Consider these flights traveling from Pittsburgh to Caribbean Islands.
Top 8 airlines flying from Pittsburgh to Caribbean Islands
Discover the top 8 airlines that operate flights from Pittsburgh to Caribbean Islands. 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 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$315 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$141 | Average$462 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$152 | Average$491 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$153 | Average$416 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$222 | Average$490 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$225 | Average$629 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$232 | Average$563 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$406 | Average$494 | FlexibilityNo cancel fee | On-time67% |