$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 10 — May 171
Round-trip
1 adult, Economy
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Find cheap flights from Pittsburgh to Caribbean with Cheapflights
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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 10, 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 10, 2026.
This CheapOair deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/5![Spirit Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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
Thu 4/3012:57 pm
SJU
- PIT
1 stop11h 02m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$227
This CheapOair deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/1812:53 pm
PIT
- SJU
1 stop13h 08m
Multiple Airlines
Sat 5/212:57 pm
SJU
- PIT
1 stop11h 02m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$228
This Mytrip deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Mon 4/206:35 am
PIT
- SJU
1 stop12h 47m
Spirit Airlines
Sat 4/255:45 am
SJU
- PIT
2 stops18h 14m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/105:40 am
PIT
- STT
1 stop9h 37m
Delta
Thu 5/213:01 pm
STT
- PIT
1 stop9h 44m
Delta
Deal found 4/6![Delta logo]()
$230
This CheapOair deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/7![Spirit Airlines logo]()
$231
This CheapOair deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/296:00 am
PIT
- SJU
1 stop12h 59m
Multiple Airlines
Sat 6/63:58 pm
SJU
- PIT
1 stop27h 22m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$235
This CheapOair deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/249:44 am
PIT
- SJU
1 stop13h 04m
Multiple Airlines
Wed 4/2912:57 pm
SJU
- PIT
1 stop11h 02m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 4/256:15 pm
PIT
- SJU
1 stop18h 08m
Multiple Airlines
Tue 4/287:01 pm
SJU
- PIT
2 stops28h 58m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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
Wed 5/203:01 pm
STT
- PIT
1 stop9h 44m
Delta
Deal found 4/9![Delta logo]()
$250
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/156:00 am
PIT
- STT
1 stop7h 51m
Delta
Mon 4/201:59 pm
STT
- PIT
1 stop7h 37m
Delta
Deal found 4/5![Delta logo]()
$255
This FlightHub deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:35 am
PIT
- SXM
1 stop7h 02m
Spirit Airlines
Sat 5/92:35 pm
SXM
- PIT
1 stop7h 32m
Spirit Airlines
Deal found 4/8![Spirit Airlines logo]()
$263
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 10, 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 10, 2026.
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/207:00 am
PIT
- STT
1 stop8h 31m
United Airlines
Fri 4/244:45 pm
STT
- PIT
1 stop6h 35m
United Airlines
Deal found 4/5![United Airlines logo]()
$230
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 7/77:20 am
PIT
- SJU
1 stop9h 18m
Delta
Fri 7/107:30 am
SJU
- PIT
1 stop8h 20m
Delta
Deal found 4/9![Delta logo]()
$282
This American Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:35 pm
PIT
- STT
2 stops16h 00m
American Airlines
Tue 5/53:30 pm
STT
- PIT
2 stops16h 30m
American Airlines
Deal found 4/5![American Airlines logo]()
$318
This JetBlue deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/6![JetBlue logo]()
$357
This Justfly.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Tue 6/26:00 am
PIT
- SXM
1 stop7h 54m
Multiple Airlines
Sat 6/66:00 pm
SXM
- PIT
1 stop17h 33m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$358
This Air Canada deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 8/2712:15 pm
PIT
- MBJ
1 stop24h 05m
Air Canada
Mon 8/3112:30 pm
MBJ
- PIT
2 stops25h 23m
Air Canada
Deal found 4/7![Air Canada logo]()
$413
This Priceline deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Thu 7/97:59 pm
PIT
- PUJ
1 stop20h 26m
Frontier
Sat 7/185:30 pm
PUJ
- PIT
1 stop25h 34m
Frontier
Deal found 4/5![Frontier logo]()
$490
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 7/2811:58 am
PIT
- SJU
1 stop11h 55m
Delta
Tue 8/42:42 pm
SJU
- PIT
1 stop10h 00m
Delta
Deal found 4/9![Delta logo]()
$282
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/115:40 am
PIT
- STT
1 stop9h 37m
Delta
Tue 5/193:01 pm
STT
- PIT
1 stop9h 44m
Delta
Deal found 4/6![Delta logo]()
$300
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/57:47 pm
PIT
- AUA
2 stops16h 53m
United Airlines
Tue 5/124:30 pm
AUA
- PIT
1 stop17h 01m
United Airlines
Deal found 4/5![United Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/76:00 am
PIT
- AUA
1 stop6h 55m
American Airlines
Mon 5/111:55 pm
AUA
- PIT
1 stop7h 40m
American Airlines
Deal found 4/9![American Airlines logo]()
$361
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/6![Delta logo]()
$313
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:44 pm
PIT
- SXM
2 stops16h 49m
United Airlines
Fri 6/51:35 pm
SXM
- PIT
1 stop9h 48m
United Airlines
Deal found 4/5![United Airlines logo]()
$363
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/77:39 pm
PIT
- AUA
2 stops17h 51m
American Airlines
Tue 5/125:25 pm
AUA
- PIT
2 stops16h 50m
American Airlines
Deal found 4/8![American Airlines logo]()
$366
This FlightHub deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/156:00 am
PIT
- MBJ
1 stop7h 45m
Multiple Airlines
Sun 6/2112:30 pm
MBJ
- PIT
1 stop22h 03m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$411
This JetBlue deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/5![JetBlue logo]()
$413
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 7/247:20 am
PIT
- SJU
1 stop9h 18m
Delta
Sun 8/25:56 pm
SJU
- PIT
1 stop6h 54m
Delta
Deal found 4/9![Delta logo]()
$313
This American Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:35 pm
PIT
- SXM
2 stops17h 45m
American Airlines
Sat 5/93:32 pm
SXM
- PIT
2 stops18h 43m
American Airlines
Deal found 4/5![American Airlines logo]()
$368
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 10/76:10 am
PIT
- SJU
1 stop9h 32m
United Airlines
Tue 10/131:05 am
SJU
- PIT
2 stops12h 04m
United Airlines
Deal found 4/5![United Airlines logo]()
$372
This American Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 7/195:44 pm
PIT
- SXM
2 stops20h 07m
American Airlines
Mon 7/272:51 pm
SXM
- PIT
2 stops19h 16m
American Airlines
Deal found 4/5![American Airlines logo]()
$368
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/276:10 am
PIT
- SJU
1 stop6h 24m
United Airlines
Wed 4/291:00 am
SJU
- PIT
2 stops14h 21m
United Airlines
Deal found 4/5![United Airlines logo]()
$372
This Cheapflightsfares deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Sat 6/136:45 am
PIT
- MBJ
1 stop8h 49m
JetBlue
Fri 6/1910:50 am
MBJ
- PIT
1 stop11h 31m
JetBlue
Deal found 4/5![JetBlue logo]()
$459
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/7![Delta logo]()
$363
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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
- SXM
2 stops10h 42m
American Airlines
Wed 7/84:46 pm
SXM
- PIT
2 stops19h 39m
American Airlines
Deal found 4/6![American Airlines logo]()
$373
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/137:20 pm
PIT
- AUA
2 stops17h 20m
United Airlines
Sat 4/183:10 pm
AUA
- PIT
1 stop8h 34m
United Airlines
Deal found 4/6![United Airlines logo]()
$379
This Air Canada deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:00 am
PIT
- UVF
1 stop8h 20m
Air Canada
Tue 7/213:05 pm
UVF
- PIT
1 stop20h 28m
Air Canada
Deal found 4/6![Air Canada logo]()
$556
This American Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/146:57 pm
PIT
- SXM
1 stop20h 45m
American Airlines
Fri 6/191:40 pm
SXM
- PIT
1 stop27h 17m
American Airlines
Deal found 4/5![American Airlines logo]()
$378
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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
- AUA
2 stops10h 30m
United Airlines
Mon 4/201:50 pm
AUA
- PIT
1 stop10h 03m
United Airlines
Deal found 4/6![United Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/187:05 am
PIT
- AUA
1 stop7h 05m
Delta
Sat 4/253:25 pm
AUA
- PIT
1 stop9h 10m
Delta
Deal found 4/7![Delta logo]()
$379
This United Airlines deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/37:50 pm
PIT
- PUJ
2 stops16h 50m
United Airlines
Wed 5/62:20 pm
PUJ
- PIT
1 stop9h 24m
United Airlines
Deal found 4/9![United Airlines logo]()
$390
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated April 10, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated April 10, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/156:00 am
PIT
- STT
1 stop7h 51m
Delta
Mon 4/201:59 pm
STT
- PIT
1 stop7h 37m
Delta
Deal found 4/5![Delta logo]()
$255
This CheapOair deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/1812:53 pm
PIT
- SJU
1 stop13h 08m
Multiple Airlines
Sat 5/212:57 pm
SJU
- PIT
1 stop11h 02m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$228
This Mytrip deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Mon 4/206:35 am
PIT
- SJU
1 stop12h 47m
Spirit Airlines
Sat 4/255:45 am
SJU
- PIT
2 stops18h 14m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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
Thu 4/3012:57 pm
SJU
- PIT
1 stop11h 02m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$227
This CheapOair deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/7![Spirit Airlines logo]()
$231
This CheapOair deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/249:44 am
PIT
- SJU
1 stop13h 04m
Multiple Airlines
Wed 4/2912:57 pm
SJU
- PIT
1 stop11h 02m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 4/256:15 pm
PIT
- SJU
1 stop18h 08m
Multiple Airlines
Tue 4/287:01 pm
SJU
- PIT
2 stops28h 58m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$239
This CheapOair deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/5![Spirit Airlines logo]()
$226
This FlightHub deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:35 am
PIT
- SXM
1 stop7h 02m
Spirit Airlines
Sat 5/92:35 pm
SXM
- PIT
1 stop7h 32m
Spirit Airlines
Deal found 4/8![Spirit Airlines logo]()
$263
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/105:40 am
PIT
- STT
1 stop9h 37m
Delta
Wed 5/203:01 pm
STT
- PIT
1 stop9h 44m
Delta
Deal found 4/6![Delta logo]()
$230
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/211:16 pm
STT
- PIT
1 stop11h 29m
Delta
Deal found 4/9![Delta logo]()
$250
This CheapOair deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/296:00 am
PIT
- SJU
1 stop12h 59m
Multiple Airlines
Sat 6/63:58 pm
SJU
- PIT
1 stop27h 22m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$235
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 10, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 10, 2026.
This Frontier deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/6![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/196:35 am
PIT
- SJU
1 stop29h 58m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$93
This Cheapflightsfares deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Sun 5/36:35 am
PIT
- SJU
1 stop12h 47m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$95
This Priceline deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/212:44 pm
PIT
- SJU
1 stop10h 04m
Frontier
Deal found 4/8![Frontier logo]()
$98
This Cheapflightsfares deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 4/226:35 am
PIT
- SJU
1 stop12h 47m
Spirit Airlines
Deal found 4/8![Spirit Airlines logo]()
$101
This Priceline deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Thu 5/147:00 pm
PIT
- SJU
1 stop18h 15m
Frontier
Deal found 4/6![Frontier logo]()
$104
This Frontier deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/6![Frontier logo]()
$106
This TravelUp deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure TravelUp 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 4/8![Frontier logo]()
$109
This Cheapflightsfares deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/186:00 am
PIT
- SJU
1 stop12h 59m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$110
This CheapOair deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 stop17h 10m
Frontier
Deal found 4/6![Frontier logo]()
$112
This Frontier deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/88:15 pm
PIT
- PUJ
1 stop13h 03m
Frontier
Deal found 4/6![Frontier logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Sun 4/196:35 am
PIT
- SJU
1 stop12h 47m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$116
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 10, 2026.
Round-trip from | $226 (CheapOair) |
|---|---|
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 10, 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
Mon 4/20
7:00 am-3:31 pm
1 stop8h 31m
Saint Thomas Island Cyril E King
Fri 4/24
4:45 pm-11:20 pm
1 stop6h 35m
$230
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Tue 7/7
7:20 am-4:38 pm
1 stop9h 18m
San Juan Luis Munoz Marin Intl
Fri 7/10
7:30 am-3:50 pm
1 stop8h 20m
$282
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Tue 7/28
11:58 am-11:53 pm
1 stop11h 55m
San Juan Luis Munoz Marin Intl
Tue 8/4
2:42 pm-12:42 am
1 stop10h 00m
$282
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Mon 5/11
5:40 am-3:17 pm
1 stop9h 37m
Saint Thomas Island Cyril E King
Tue 5/19
3:01 pm-12:45 am
1 stop9h 44m
$300
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
$313
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Fri 7/24
7:20 am-4:38 pm
1 stop9h 18m
San Juan Luis Munoz Marin Intl
Sun 8/2
5:56 pm-12:50 am
1 stop6h 54m
$313
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Sat 5/2
7:35 pm-11:35 am
2 stops16h 00m
Saint Thomas Island Cyril E King
Tue 5/5
3:30 pm-8:00 am
2 stops16h 30m
$318
PittsburghWillemstad
PIT - CUR
PITCUR
Pittsburgh
Wed 5/6
6:00 am-1:37 pm
1 stop7h 37m
Willemstad Hato Int.
Thu 5/7
2:42 pm-12:07 am
1 stop9h 25m
$357
PittsburghOranjestad
PIT - AUA
PITAUA
Pittsburgh
Tue 5/5
7:47 pm-12:40 pm
2 stops16h 53m
Oranjestad Reina Beatrix
Tue 5/12
4:30 pm-9:31 am
1 stop17h 01m
$357
PittsburghSimpson Bay
PIT - SXM
PITSXM
Pittsburgh
Tue 6/2
6:00 am-1:54 pm
1 stop7h 54m
Simpson Bay Princess Juliana
Sat 6/6
6:00 pm-11:33 am
1 stop17h 33m
$358
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-UVF
PIT-PUJ
PIT-SXM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Pittsburgh to Caribbean
PIT-0CB
PIT-SJU
PIT-STT
PIT-UVF
PIT-PUJ
What is the cheapest month to book a flight from Pittsburgh to Caribbean?
Currently, April is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $145). Flying from Pittsburgh to Caribbean in July is currently the most expensive (average of $251). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from PIT to CB?
Find hourly flight availability from Pittsburgh to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 10, 2026.
When flying from Pittsburgh to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated April 10, 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.
Crew
8.5
Food
7.2
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Food
7.2
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Food
7.2
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Food
7.2
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Food
7.2
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Food
7.2
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Overall
7.9
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 10, 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 10, 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$488 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$153 | Average$408 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$225 | Average$629 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$225 | Average$489 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$232 | Average$563 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$406 | Average$494 | FlexibilityNo cancel fee | On-time67% |