$111+ 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 6/23. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Jul 7 — Jul 141
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 June 7, 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 June 7, 2026.
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:21 am
PIT
- STT
2 stops10h 31m
American Airlines
Sun 8/303:43 pm
STT
- PIT
2 stops18h 37m
American Airlines
Deal found 6/7![American Airlines logo]()
$250
This Delta deal was found by Cheapflights users on 6/6. 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.
Sat 8/295:50 am
PIT
- STT
1 stop9h 12m
Delta
Sat 9/52:49 pm
STT
- PIT
1 stop8h 45m
Delta
Deal found 6/6![Delta logo]()
$260
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:39 pm
PIT
- STT
2 stops17h 14m
American Airlines
Thu 8/273:43 pm
STT
- PIT
2 stops18h 37m
American Airlines
Deal found 6/4![American Airlines logo]()
$290
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:42 pm
PIT
- STT
2 stops19h 11m
American Airlines
Sun 8/233:43 pm
STT
- PIT
2 stops18h 37m
American Airlines
Deal found 6/3![American Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 6/5. 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.
Thu 8/201:57 pm
PIT
- SJU
1 stop8h 32m
Delta
Wed 8/265:49 pm
SJU
- PIT
1 stop6h 47m
Delta
Deal found 6/5![Delta logo]()
$312
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/176:15 am
PIT
- GCM
1 stop7h 15m
United Airlines
Wed 6/241:35 pm
GCM
- PIT
1 stop9h 24m
United Airlines
Deal found 6/3![United Airlines logo]()
$314
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:10 am
PIT
- STT
1 stop9h 42m
American Airlines
Sat 9/512:08 pm
STT
- PIT
1 stop9h 17m
American Airlines
Deal found 6/4![American Airlines logo]()
$315
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:10 am
PIT
- GCM
1 stop10h 20m
United Airlines
Fri 11/205:45 pm
GCM
- PIT
2 stops16h 13m
United Airlines
Deal found 6/4![United Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/307:49 pm
PIT
- SJU
1 stop18h 40m
Multiple Airlines
Sat 9/56:41 pm
SJU
- PIT
2 stops21h 25m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:52 am
PIT
- GCM
1 stop6h 02m
Delta
Mon 6/812:59 pm
GCM
- PIT
1 stop10h 56m
Delta
Deal found 6/3![Delta logo]()
$317
This American Airlines deal was found by Cheapflights users on 6/6. 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 10/710:53 am
PIT
- SJU
2 stops9h 17m
American Airlines
Wed 10/148:35 am
SJU
- PIT
2 stops9h 22m
American Airlines
Deal found 6/6![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:01 am
PIT
- GCM
1 stop8h 34m
American Airlines
Mon 6/82:42 pm
GCM
- PIT
1 stop8h 15m
American Airlines
Deal found 6/4![American Airlines logo]()
$321
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 June 7, 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 June 7, 2026.
This Delta deal was found by Cheapflights users on 6/6. 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.
Sat 8/295:50 am
PIT
- STT
1 stop9h 12m
Delta
Sat 9/52:49 pm
STT
- PIT
1 stop8h 45m
Delta
Deal found 6/6![Delta logo]()
$260
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/176:15 am
PIT
- GCM
1 stop7h 15m
United Airlines
Wed 6/241:35 pm
GCM
- PIT
1 stop9h 24m
United Airlines
Deal found 6/3![United Airlines logo]()
$314
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 8/106:01 pm
PIT
- GCM
2 stops17h 59m
American Airlines
Sat 8/1511:55 am
GCM
- PIT
2 stops19h 36m
American Airlines
Deal found 6/3![American Airlines logo]()
$326
This JetBlue deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 9/16:00 am
PIT
- NAS
1 stop5h 15m
JetBlue
Wed 9/23:02 pm
NAS
- PIT
1 stop6h 24m
JetBlue
Deal found 6/3![JetBlue logo]()
$340
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2112:45 pm
PIT
- SJU
1 stop10h 05m
Southwest
Tue 7/288:35 pm
SJU
- PIT
1 stop13h 10m
Southwest
Deal found 6/3![Southwest logo]()
$420
This Air Canada deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 9/63:35 pm
PIT
- PUJ
1 stop24h 30m
Air Canada
Sat 9/125:05 pm
PUJ
- PIT
1 stop21h 48m
Air Canada
Deal found 6/4![Air Canada logo]()
$440
This Delta deal was found by Cheapflights users on 6/5. 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.
Thu 8/2011:57 am
PIT
- SJU
1 stop10h 32m
Delta
Tue 8/255:49 pm
SJU
- PIT
1 stop6h 47m
Delta
Deal found 6/5![Delta logo]()
$312
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:10 am
PIT
- GCM
1 stop10h 20m
United Airlines
Fri 11/205:45 pm
GCM
- PIT
2 stops16h 13m
United Airlines
Deal found 6/4![United Airlines logo]()
$316
This American Airlines deal was found by Cheapflights users on 6/2. 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.
Thu 9/176:25 pm
PIT
- STT
2 stops18h 26m
American Airlines
Tue 9/221:41 pm
STT
- PIT
2 stops20h 42m
American Airlines
Deal found 6/2![American Airlines logo]()
$330
This JetBlue deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 9/16:00 am
PIT
- SXM
1 stop6h 37m
JetBlue
Wed 9/21:42 pm
SXM
- PIT
1 stop7h 44m
JetBlue
Deal found 6/3![JetBlue logo]()
$357
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/246:00 am
PIT
- MBJ
1 stop10h 34m
Delta
Thu 8/271:09 pm
MBJ
- PIT
1 stop10h 27m
Delta
Deal found 6/4![Delta logo]()
$344
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 9/166:30 am
PIT
- PUJ
1 stop9h 00m
United Airlines
Fri 9/183:35 pm
PUJ
- PIT
1 stop18h 01m
United Airlines
Deal found 6/4![United Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 6/5. 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 7/198:01 pm
PIT
- SXM
1 stop17h 50m
American Airlines
Mon 7/274:45 pm
SXM
- PIT
2 stops19h 20m
American Airlines
Deal found 6/5![American Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 6/6. 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.
Fri 7/105:45 am
PIT
- NAS
1 stop10h 54m
Delta
Fri 7/173:26 pm
NAS
- PIT
1 stop9h 24m
Delta
Deal found 6/6![Delta logo]()
$350
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/206:15 am
PIT
- GCM
1 stop10h 20m
United Airlines
Sat 6/274:45 pm
GCM
- PIT
2 stops16h 13m
United Airlines
Deal found 6/3![United Airlines logo]()
$353
This Orbitz deal was found by Cheapflights users on 6/6. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/194:15 pm
PIT
- PUJ
1 stop18h 55m
Air Canada
Tue 11/2410:40 pm
PUJ
- PIT
1 stop17h 51m
Air Canada
Deal found 6/6![Air Canada logo]()
$450
This American Airlines deal was found by Cheapflights users on 6/6. 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.
Sun 9/206:25 pm
PIT
- SXM
2 stops18h 57m
American Airlines
Thu 9/242:22 pm
SXM
- PIT
2 stops19h 26m
American Airlines
Deal found 6/6![American Airlines logo]()
$372
This Southwest deal was found by Cheapflights users on 6/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/83:30 pm
PIT
- SJU
1 stop6h 25m
Southwest
Sun 8/165:00 am
SJU
- PIT
2 stops10h 20m
Southwest
Deal found 6/5![Southwest logo]()
$464
This Delta deal was found by Cheapflights users on 6/6. 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 7/277:05 am
PIT
- NAS
1 stop9h 34m
Delta
Fri 7/313:26 pm
NAS
- PIT
1 stop9h 24m
Delta
Deal found 6/6![Delta logo]()
$350
This United Airlines deal was found by Cheapflights users on 6/2. 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.
Sun 7/197:00 am
PIT
- PUJ
1 stop7h 27m
United Airlines
Thu 7/233:35 pm
PUJ
- PIT
2 stops18h 23m
United Airlines
Deal found 6/2![United Airlines logo]()
$373
This American Airlines deal was found by Cheapflights users on 6/5. 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.
Tue 6/238:05 am
PIT
- AUA
2 stops8h 54m
American Airlines
Tue 6/302:33 pm
AUA
- PIT
2 stops18h 06m
American Airlines
Deal found 6/5![American Airlines logo]()
$382
This JetBlue deal was found by Cheapflights users on 6/6. 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.
Fri 7/246:10 am
PIT
- CUR
1 stop7h 56m
JetBlue
Tue 7/283:13 pm
CUR
- PIT
1 stop8h 33m
JetBlue
Deal found 6/6![JetBlue logo]()
$463
This Delta deal was found by Cheapflights users on 6/7. 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 7/116:00 am
PIT
- NAS
1 stop6h 58m
Delta
Thu 7/163:26 pm
NAS
- PIT
1 stop7h 34m
Delta
Deal found 6/7![Delta logo]()
$350
This Southwest deal was found by Cheapflights users on 6/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:00 am
PIT
- SXM
1 stop9h 40m
Southwest
Sun 11/84:40 pm
SXM
- PIT
1 stop8h 15m
Southwest
Deal found 6/5![Southwest logo]()
$477
This Air Canada deal was found by Cheapflights users on 6/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:00 am
PIT
- SXM
1 stop11h 00m
Air Canada
Sat 10/176:00 pm
SXM
- PIT
1 stop17h 32m
Air Canada
Deal found 6/5![Air Canada logo]()
$491
This United Airlines deal was found by Cheapflights users on 6/5. 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 6/309:12 am
PIT
- AUA
1 stop7h 28m
United Airlines
Tue 7/73:10 pm
AUA
- PIT
2 stops18h 30m
United Airlines
Deal found 6/5![United Airlines logo]()
$382
This Delta deal was found by Cheapflights users on 6/6. 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.
Wed 7/295:45 am
PIT
- MBJ
1 stop10h 49m
Delta
Wed 8/52:26 pm
MBJ
- PIT
1 stop9h 10m
Delta
Deal found 6/6![Delta logo]()
$354
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/258:01 pm
PIT
- SXM
2 stops17h 18m
American Airlines
Sat 8/11:34 pm
SXM
- PIT
2 stops19h 56m
American Airlines
Deal found 6/7![American Airlines logo]()
$398
This Southwest deal was found by Cheapflights users on 6/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/131:45 pm
PIT
- SJU
2 stops10h 05m
Southwest
Mon 8/175:00 am
SJU
- PIT
2 stops10h 30m
Southwest
Deal found 6/2![Southwest logo]()
$493
This JetBlue deal was found by Cheapflights users on 6/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:10 am
PIT
- SJU
1 stop9h 49m
JetBlue
Mon 8/33:17 pm
SJU
- PIT
1 stop8h 29m
JetBlue
Deal found 6/2![JetBlue logo]()
$514
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated June 7, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated June 7, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:01 am
PIT
- GCM
1 stop8h 34m
American Airlines
Mon 6/82:42 pm
GCM
- PIT
1 stop8h 15m
American Airlines
Deal found 6/4![American Airlines logo]()
$321
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/176:15 am
PIT
- GCM
1 stop7h 15m
United Airlines
Wed 6/241:35 pm
GCM
- PIT
1 stop9h 24m
United Airlines
Deal found 6/3![United Airlines logo]()
$314
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/178:05 am
PIT
- GCM
2 stops9h 06m
American Airlines
Wed 6/245:12 pm
GCM
- PIT
2 stops17h 45m
American Airlines
Deal found 6/3![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:16 am
PIT
- GCM
1 stop10h 55m
American Airlines
Tue 7/75:10 pm
GCM
- PIT
1 stop22h 51m
American Airlines
Deal found 6/3![American Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:00 am
PIT
- SJU
1 stop8h 29m
Multiple Airlines
Sun 7/196:30 am
SJU
- PIT
1 stop17h 08m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 6/2. 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.
Sat 7/116:00 am
PIT
- NAS
1 stop6h 58m
Delta
Fri 7/173:26 pm
NAS
- PIT
1 stop9h 24m
Delta
Deal found 6/2![Delta logo]()
$340
This Southwest deal was found by Cheapflights users on 6/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/275:50 pm
PIT
- SJU
1 stop6h 30m
Southwest
Wed 8/58:20 am
SJU
- PIT
1 stop6h 25m
Southwest
Deal found 6/7![Southwest logo]()
$333
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/2810:48 am
PIT
- SJU
1 stop12h 09m
American Airlines
Tue 8/47:00 am
SJU
- PIT
1 stop9h 25m
American Airlines
Deal found 6/3![American Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 6/2. 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.
Tue 7/287:20 am
PIT
- SJU
1 stop9h 18m
Delta
Wed 8/55:49 pm
SJU
- PIT
1 stop6h 47m
Delta
Deal found 6/2![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 6/6. 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.
Wed 7/291:57 pm
PIT
- SJU
1 stop8h 33m
Delta
Wed 8/55:49 pm
SJU
- PIT
1 stop6h 47m
Delta
Deal found 6/6![Delta logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:00 am
PIT
- SJU
1 stop8h 00m
Multiple Airlines
Sun 8/26:45 am
SJU
- PIT
1 stop16h 53m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 6/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:00 am
PIT
- SJU
1 stop8h 00m
Multiple Airlines
Wed 8/58:37 pm
SJU
- PIT
1 stop21h 38m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$341
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 June 7, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 7, 2026.
This Delta deal was found by Cheapflights users on 6/6. 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 6/235:30 am
PIT
- GCM
1 stop7h 04m
Delta
Deal found 6/6![Delta logo]()
$111
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:00 am
PIT
- NAS
1 stop7h 57m
Delta
Deal found 6/3![Delta logo]()
$116
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:15 am
PIT
- NAS
1 stop7h 32m
United Airlines
Deal found 6/4![United Airlines logo]()
$121
This American Airlines deal was found by Cheapflights users on 6/5. 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.
Fri 7/38:01 pm
PIT
- STT
1 stop14h 58m
American Airlines
Deal found 6/5![American Airlines logo]()
$123
This Orbitz deal was found by Cheapflights users on 6/6. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/233:35 pm
PIT
- GCM
2 stops44h 50m
Air Canada
Deal found 6/6![Air Canada logo]()
$126
This Southwest deal was found by Cheapflights users on 6/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/245:50 am
PIT
- GCM
1 stop7h 05m
Southwest
Deal found 6/6![Southwest logo]()
$131
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/198:01 pm
PIT
- SXM
1 stop17h 50m
American Airlines
Deal found 6/4![American Airlines logo]()
$134
This Super.com deal was found by Cheapflights users on 6/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:00 am
PIT
- PUJ
1 stop6h 55m
JetBlue
Deal found 6/2![JetBlue logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/197:49 pm
PIT
- SJU
1 stop18h 06m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$139
This Super.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am
PIT
- PUJ
1 stop9h 27m
JetBlue
Deal found 6/4![JetBlue logo]()
$143
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:36 pm
PIT
- SXM
2 stops18h 24m
American Airlines
Deal found 6/7![American Airlines logo]()
$145
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:39 pm
PIT
- CUR
2 stops20h 00m
American Airlines
Deal found 6/4![American Airlines logo]()
$147
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 June 7, 2026.
Round-trip from | $250 (American Airlines) |
|---|---|
One-way from | $111 (Delta) |
Popular in | December |
Cheapest in | October |
Average price | $456 |
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 June 7, 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
Sat 8/29
5:50 am-3:02 pm
1 stop9h 12m
Saint Thomas Island Cyril E King
Sat 9/5
2:49 pm-11:34 pm
1 stop8h 45m
$260
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Thu 8/20
11:57 am-10:29 pm
1 stop10h 32m
San Juan Luis Munoz Marin Intl
Tue 8/25
5:49 pm-12:36 am
1 stop6h 47m
$312
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Wed 6/17
6:15 am-12:30 pm
1 stop7h 15m
George Town Owen Roberts Intl
Wed 6/24
1:35 pm-11:59 pm
1 stop9h 24m
$314
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Tue 11/10
6:10 am-4:30 pm
1 stop10h 20m
George Town Owen Roberts Intl
Fri 11/20
5:45 pm-9:58 am
2 stops16h 13m
$316
PittsburghGeorge Town
PIT - GCM
PITGCM
Pittsburgh
Mon 8/10
6:01 pm-11:00 am
2 stops17h 59m
George Town Owen Roberts Intl
Sat 8/15
11:55 am-8:31 am
2 stops19h 36m
$326
PittsburghSaint Thomas Island
PIT - STT
PITSTT
Pittsburgh
Thu 9/17
6:25 pm-12:51 pm
2 stops18h 26m
Saint Thomas Island Cyril E King
Tue 9/22
1:41 pm-10:23 am
2 stops20h 42m
$330
Quickest round-trip
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Tue 9/1
6:00 am-11:15 am
1 stop5h 15m
Nassau Intl
Wed 9/2
3:02 pm-9:26 pm
1 stop6h 24m
$340
PittsburghMontego Bay
PIT - MBJ
PITMBJ
Pittsburgh
Mon 8/24
6:00 am-3:34 pm
1 stop10h 34m
Montego Bay Sangster Intl
Thu 8/27
1:09 pm-12:36 am
1 stop10h 27m
$344
PittsburghPunta Cana
PIT - PUJ
PITPUJ
Pittsburgh
Wed 9/16
6:30 am-3:30 pm
1 stop9h 00m
Punta Cana
Fri 9/18
3:35 pm-9:36 am
1 stop18h 01m
$346
PittsburghNassau
PIT - NAS
PITNAS
Pittsburgh
Fri 7/10
5:45 am-4:39 pm
1 stop10h 54m
Nassau Intl
Fri 7/17
3:26 pm-12:50 am
1 stop9h 24m
$350
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-GCM
PIT-NAS
PIT-PUJ
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-GCM
PIT-NAS
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 December is currently the most expensive (average of $1,294). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How far ahead should I book a flight from Pittsburgh to Caribbean?
Booking 60 days in advance of your planned departure date is, on average, the best time to get cheap flights from Pittsburgh to Caribbean. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated June 7, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Pittsburgh to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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 June 7, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Pittsburgh to Caribbean flights
Consider these flights traveling from Pittsburgh to Caribbean.
Top 7 airlines flying from Pittsburgh to Caribbean
Discover the top 7 airlines that operate flights from Pittsburgh to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$319 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$152 | Average$504 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$184 | Average$496 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$621 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$225 | Average$459 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$232 | Average$573 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$406 | Average$492 | FlexibilityNo cancel fee | On-time67% |