$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
maig 24 — maig 311
Round-trip
1 adult, Economy
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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 abril 24, 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 abril 24, 2026.
This United Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
dv. 5/86:00 am
PIT
- STT
1 stop9h 43m
United Airlines
dt. 5/121:22 pm
STT
- PIT
1 stop10h 22m
United Airlines
Deal found 4/21![United Airlines logo]()
$250
This Priceline deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dj. 4/306:35 am
PIT
- SJU
1 stop12h 47m
Multiple Airlines
dt. 5/193:33 pm
SJU
- PIT
1 stop27h 37m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$257
This Priceline deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
dv. 4/249:44 am
PIT
- SJU
1 stop13h 04m
Frontier
dv. 5/13:19 pm
SJU
- PIT
1 stop20h 30m
Frontier
Deal found 4/19![Frontier logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dg. 5/36:15 pm
PIT
- SJU
1 stop18h 08m
Multiple Airlines
ds. 5/97:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dl. 5/46:00 am
PIT
- SJU
2 stops32h 07m
Multiple Airlines
ds. 5/97:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
ds. 5/96:00 am
PIT
- SJU
2 stops17h 59m
Multiple Airlines
dc. 5/137:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$271
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
dt. 5/56:00 am
PIT
- STT
1 stop8h 48m
Delta
dc. 5/133:01 pm
STT
- PIT
1 stop9h 44m
Delta
Deal found 4/23![Delta logo]()
$275
This American Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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.
dj. 8/208:00 am
PIT
- SJU
1 stop14h 24m
American Airlines
dc. 8/267:05 am
SJU
- PIT
2 stops11h 21m
American Airlines
Deal found 4/22![American Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dg. 5/36:35 am
PIT
- SJU
1 stop29h 48m
Multiple Airlines
dv. 5/811:00 am
SJU
- PIT
1 stop11h 07m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$277
This Priceline deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
ds. 5/96:00 am
PIT
- SXM
1 stop7h 30m
Spirit Airlines
ds. 5/162:35 pm
SXM
- PIT
1 stop7h 32m
Spirit Airlines
Deal found 4/20![Spirit Airlines logo]()
$277
This CheapOair deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
ds. 7/257:59 pm
PIT
- SJU
1 stop12h 10m
Frontier
dj. 7/304:05 pm
SJU
- PIT
1 stop26h 59m
Frontier
Deal found 4/21![Frontier logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dl. 5/46:00 am
PIT
- SJU
2 stops32h 07m
Multiple Airlines
dv. 5/811:00 am
SJU
- PIT
1 stop11h 07m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$280
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 abril 24, 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 abril 24, 2026.
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
dv. 5/86:00 am
PIT
- STT
1 stop9h 43m
United Airlines
dt. 5/121:22 pm
STT
- PIT
1 stop10h 22m
United Airlines
Deal found 4/23![United Airlines logo]()
$250
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
dc. 9/21:50 pm
PIT
- SJU
1 stop8h 33m
Delta
ds. 9/123:10 pm
SJU
- PIT
1 stop7h 28m
Delta
Deal found 4/21![Delta logo]()
$276
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ds. 8/86:00 am
PIT
- SJU
1 stop12h 15m
Southwest
ds. 8/156:25 am
SJU
- PIT
1 stop6h 15m
Southwest
Deal found 4/19![Southwest logo]()
$312
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
dv. 5/87:16 pm
PIT
- SXM
1 stop16h 21m
American Airlines
dc. 5/132:21 pm
SXM
- PIT
1 stop9h 38m
American Airlines
Deal found 4/19![American Airlines logo]()
$367
This JetBlue deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dg. 5/246:00 am
PIT
- SXM
1 stop7h 54m
JetBlue
dj. 5/283:14 pm
SXM
- PIT
1 stop8h 41m
JetBlue
Deal found 4/20![JetBlue logo]()
$440
This Air Canada deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
dt. 7/146:00 am
PIT
- UVF
1 stop8h 20m
Air Canada
dt. 7/213:05 pm
UVF
- PIT
1 stop20h 28m
Air Canada
Deal found 4/19![Air Canada logo]()
$492
This FlightHub deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dl. 6/158:40 am
PIT
- MBJ
1 stop6h 54m
Multiple Airlines
dg. 6/2112:30 pm
MBJ
- PIT
1 stop22h 03m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$520
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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.
dt. 7/2810:13 am
PIT
- SJU
1 stop6h 32m
Delta
dt. 8/42:42 pm
SJU
- PIT
1 stop10h 00m
Delta
Deal found 4/22![Delta logo]()
$282
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
dc. 10/76:10 am
PIT
- SJU
1 stop6h 24m
United Airlines
dc. 10/147:00 am
SJU
- PIT
1 stop8h 49m
United Airlines
Deal found 4/19![United Airlines logo]()
$282
This Copa Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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.
ds. 6/137:44 pm
PIT
- AUA
2 stops19h 01m
Copa Airlines
dj. 6/183:40 pm
AUA
- PIT
2 stops18h 18m
Copa Airlines
Deal found 4/22![Copa Airlines logo]()
$595
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
dg. 9/136:10 am
PIT
- SJU
1 stop6h 44m
United Airlines
dv. 9/181:00 am
SJU
- PIT
2 stops12h 04m
United Airlines
Deal found 4/23![United Airlines logo]()
$301
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
dc. 7/227:20 am
PIT
- SJU
1 stop9h 18m
Delta
dj. 7/302:05 pm
SJU
- PIT
1 stop9h 59m
Delta
Deal found 4/24![Delta logo]()
$313
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
ds. 5/165:34 pm
PIT
- SXM
2 stops18h 03m
American Airlines
dc. 5/202:21 pm
SXM
- PIT
1 stop9h 38m
American Airlines
Deal found 4/19![American Airlines logo]()
$372
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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.
dv. 9/186:30 am
PIT
- SJU
1 stop7h 15m
United Airlines
dc. 9/232:20 pm
SJU
- PIT
1 stop9h 29m
United Airlines
Deal found 4/22![United Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dg. 9/206:00 am
PIT
- SJU
1 stop10h 31m
Delta
ds. 9/267:00 am
SJU
- PIT
1 stop9h 40m
Delta
Deal found 4/20![Delta logo]()
$346
This American Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
dl. 7/208:00 am
PIT
- PUJ
2 stops8h 56m
American Airlines
dj. 7/231:57 pm
PUJ
- PIT
1 stop10h 19m
American Airlines
Deal found 4/23![American Airlines logo]()
$385
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dl. 6/17:22 am
PIT
- SJU
1 stop9h 07m
Delta
ds. 6/66:15 am
SJU
- PIT
1 stop11h 29m
Delta
Deal found 4/20![Delta logo]()
$346
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
dg. 5/36:00 am
PIT
- MBJ
2 stops10h 10m
United Airlines
dj. 5/74:12 pm
MBJ
- PIT
1 stop16h 19m
United Airlines
Deal found 4/23![United Airlines logo]()
$350
This American Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
dg. 6/146:04 pm
PIT
- SXM
2 stops19h 18m
American Airlines
dv. 6/192:22 pm
SXM
- PIT
2 stops18h 48m
American Airlines
Deal found 4/23![American Airlines logo]()
$388
This JetBlue deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
dl. 6/86:00 am
PIT
- CUR
1 stop7h 53m
JetBlue
dl. 6/153:02 pm
CUR
- PIT
1 stop8h 19m
JetBlue
Deal found 4/24![JetBlue logo]()
$513
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
dt. 6/308:05 am
PIT
- AUA
2 stops8h 54m
American Airlines
dt. 7/74:51 pm
AUA
- PIT
1 stop7h 08m
American Airlines
Deal found 4/19![American Airlines logo]()
$392
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
ds. 5/96:00 am
PIT
- AUA
1 stop9h 40m
United Airlines
ds. 5/161:50 pm
AUA
- PIT
1 stop10h 09m
United Airlines
Deal found 4/20![United Airlines logo]()
$361
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dg. 5/106:46 am
PIT
- SXM
1 stop7h 05m
Delta
ds. 5/163:20 pm
SXM
- PIT
1 stop17h 42m
Delta
Deal found 4/20![Delta logo]()
$367
This Air Canada deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
ds. 6/136:00 am
PIT
- PUJ
2 stops34h 30m
Air Canada
dt. 6/165:25 pm
PUJ
- PIT
1 stop21h 28m
Air Canada
Deal found 4/23![Air Canada logo]()
$551
This American Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
dl. 7/208:00 am
PIT
- AUA
2 stops8h 59m
American Airlines
dl. 7/275:12 pm
AUA
- PIT
2 stops16h 55m
American Airlines
Deal found 4/23![American Airlines logo]()
$392
This JetBlue deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dl. 5/47:00 am
PIT
- PUJ
1 stop6h 21m
JetBlue
dj. 5/73:55 pm
PUJ
- PIT
1 stop8h 12m
JetBlue
Deal found 4/20![JetBlue logo]()
$537
This Copa Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
ds. 6/137:44 pm
PIT
- AUA
2 stops16h 27m
Copa Airlines
ds. 6/203:40 pm
AUA
- PIT
2 stops18h 18m
Copa Airlines
Deal found 4/23![Copa Airlines logo]()
$595
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dg. 7/199:40 am
PIT
- PUJ
1 stop6h 20m
Southwest
dg. 7/265:00 pm
PUJ
- PIT
1 stop7h 20m
Southwest
Deal found 4/19![Southwest logo]()
$602
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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.
dc. 9/96:10 am
PIT
- PUJ
1 stop6h 30m
United Airlines
dc. 9/163:35 pm
PUJ
- PIT
2 stops18h 19m
United Airlines
Deal found 4/22![United Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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.
dg. 9/206:00 am
PIT
- SXM
1 stop7h 50m
Delta
dj. 9/243:20 pm
SXM
- PIT
1 stop9h 02m
Delta
Deal found 4/22![Delta logo]()
$383
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated abril 24, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated abril 24, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
dv. 4/249:44 am
PIT
- SJU
1 stop13h 04m
Frontier
dv. 5/13:19 pm
SJU
- PIT
1 stop20h 30m
Frontier
Deal found 4/19![Frontier logo]()
$260
This Priceline deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dj. 4/306:35 am
PIT
- SJU
1 stop12h 47m
Multiple Airlines
dt. 5/193:33 pm
SJU
- PIT
1 stop27h 37m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dg. 5/36:15 pm
PIT
- SJU
1 stop18h 08m
Multiple Airlines
ds. 5/97:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dg. 5/36:35 am
PIT
- SJU
1 stop29h 48m
Multiple Airlines
dv. 5/811:00 am
SJU
- PIT
1 stop11h 07m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dl. 5/46:00 am
PIT
- SJU
2 stops32h 07m
Multiple Airlines
ds. 5/97:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dl. 5/46:00 am
PIT
- SJU
2 stops32h 07m
Multiple Airlines
dv. 5/811:00 am
SJU
- PIT
1 stop11h 07m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$280
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
dt. 5/56:00 am
PIT
- STT
1 stop8h 48m
Delta
dc. 5/133:01 pm
STT
- PIT
1 stop9h 44m
Delta
Deal found 4/23![Delta logo]()
$275
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dt. 5/52:08 pm
PIT
- SJU
1 stop9h 05m
Delta
ds. 5/95:43 pm
SJU
- PIT
1 stop7h 02m
Delta
Deal found 4/20![Delta logo]()
$282
This United Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
dv. 5/86:00 am
PIT
- STT
1 stop9h 43m
United Airlines
dt. 5/121:22 pm
STT
- PIT
1 stop10h 22m
United Airlines
Deal found 4/21![United Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
ds. 5/96:00 am
PIT
- SJU
2 stops17h 59m
Multiple Airlines
dc. 5/137:00 am
SJU
- PIT
1 stop28h 41m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$271
This Priceline deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
ds. 5/96:00 am
PIT
- SXM
1 stop7h 30m
Spirit Airlines
ds. 5/162:35 pm
SXM
- PIT
1 stop7h 32m
Spirit Airlines
Deal found 4/20![Spirit Airlines logo]()
$277
This Expedia deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dl. 5/256:00 am
PIT
- SJU
1 stop12h 59m
Multiple Airlines
dv. 5/299:09 am
SJU
- PIT
1 stop10h 11m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$286
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 abril 24, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated abril 24, 2026.
This Frontier deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
dg. 5/108:05 pm
PIT
- SJU
1 stop11h 59m
Frontier
Deal found 4/19![Frontier logo]()
$88
This Priceline deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
dl. 5/118:15 pm
PIT
- SJU
1 stop26h 28m
Frontier
Deal found 4/19![Frontier logo]()
$94
This Priceline deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
ds. 5/98:15 pm
PIT
- SJU
1 stop11h 49m
Frontier
Deal found 4/20![Frontier logo]()
$98
This Orbitz deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dv. 5/88:15 pm
PIT
- SJU
1 stop26h 28m
Frontier
Deal found 4/20![Frontier logo]()
$104
This Frontier deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dc. 5/138:15 pm
PIT
- SJU
1 stop11h 49m
Frontier
Deal found 4/20![Frontier logo]()
$106
This CheapOair deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dl. 5/188:15 pm
PIT
- SJU
1 stop17h 00m
Frontier
Deal found 4/20![Frontier logo]()
$112
This Orbitz deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
ds. 6/137:09 pm
PIT
- SJU
1 stop7h 00m
Frontier
Deal found 4/19![Frontier logo]()
$120
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dl. 5/186:00 am
PIT
- STT
1 stop9h 43m
United Airlines
Deal found 4/20![United Airlines logo]()
$123
This CheapOair deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
dc. 5/208:05 pm
PIT
- SJU
1 stop21h 07m
Frontier
Deal found 4/21![Frontier logo]()
$126
This Priceline deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
dv. 5/19:59 am
PIT
- SJU
1 stop12h 49m
Frontier
Deal found 4/21![Frontier logo]()
$127
This Cheapflightsfares deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
dl. 5/186:00 am
PIT
- AUA
1 stop8h 36m
Spirit Airlines
Deal found 4/21![Spirit Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
dv. 5/89:14 pm
PIT
- SJU
1 stop12h 50m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$134
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 abril 24, 2026.
Round-trip from | $250 (United Airlines) |
|---|---|
One-way from | $88 (Frontier) |
Popular in | December |
Cheapest in | October |
Average price | $366 |
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 abril 24, 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
dv. 5/8
6:00 am-3:43 pm
1 stop9h 43m
Saint Thomas Island Cyril E King
dt. 5/12
1:22 pm-11:44 pm
1 stop10h 22m
$250
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
dc. 9/2
1:50 pm-10:23 pm
1 stop8h 33m
San Juan Luis Munoz Marin Intl
ds. 9/12
3:10 pm-10:38 pm
1 stop7h 28m
$276
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
dt. 7/28
10:13 am-4:45 pm
1 stop6h 32m
San Juan Luis Munoz Marin Intl
dt. 8/4
2:42 pm-12:42 am
1 stop10h 00m
$282
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
dc. 10/7
6:10 am-12:34 pm
1 stop6h 24m
San Juan Luis Munoz Marin Intl
dc. 10/14
7:00 am-3:49 pm
1 stop8h 49m
$282
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
dg. 9/13
6:10 am-12:54 pm
1 stop6h 44m
San Juan Luis Munoz Marin Intl
dv. 9/18
1:00 am-1:04 pm
2 stops12h 04m
$301
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
ds. 8/8
6:00 am-6:15 pm
1 stop12h 15m
San Juan Luis Munoz Marin Intl
ds. 8/15
6:25 am-12:40 pm
1 stop6h 15m
$312
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
dc. 7/22
7:20 am-4:38 pm
1 stop9h 18m
San Juan Luis Munoz Marin Intl
dj. 7/30
2:05 pm-12:04 am
1 stop9h 59m
$313
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
dv. 9/18
6:30 am-1:45 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
dc. 9/23
2:20 pm-11:49 pm
1 stop9h 29m
$343
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
dg. 9/20
6:00 am-4:31 pm
1 stop10h 31m
San Juan Luis Munoz Marin Intl
ds. 9/26
7:00 am-4:40 pm
1 stop9h 40m
$346
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
dl. 6/1
7:22 am-4:29 pm
1 stop9h 07m
San Juan Luis Munoz Marin Intl
ds. 6/6
6:15 am-5:44 pm
1 stop11h 29m
$346
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-STT
PIT-SJU
PIT-SXM
PIT-AUA
PIT-UVF
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-STT
PIT-SJU
PIT-SXM
PIT-AUA
How far ahead should I book a flight from Pittsburgh to Caribbean?
Booking 67 days in advance of your planned departure date is, on average, the best time to get cheap flights from Pittsburgh to Caribbean. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
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 abril 24, 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.
Food
7.2
Overall
7.9
Comfort
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Overall
7.9
Comfort
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Overall
7.9
Comfort
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Overall
7.9
Comfort
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Overall
7.9
Comfort
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Overall
7.9
Comfort
7.9
Entertainment
7.8
Boarding
8.1
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 abril 24, 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 abril 24, 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$464 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$153 | Average$430 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$225 | Average$615 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$225 | Average$480 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$232 | Average$548 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$406 | Average$494 | FlexibilityNo cancel fee | On-time67% |