$99+ Cheap flights from Pittsburgh (PIT) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Oct 27 — Nov 31
Round-trip
1 adult, Economy
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Find cheap flights from Pittsburgh to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Pittsburgh to CaribbeanExplore the most affordable flight options available from Pittsburgh to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 27, 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 September 27, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:27 pm -
1 stop14h 48m
Tue 11/311:20 am -
1 stop7h 12m
Deal found 9/22![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 9/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:27 pm -
1 stop7h 23m
Thu 10/2910:20 am -
1 stop7h 12m
Deal found 9/22![Frontier logo]()
$222
This FlightHub deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/197:51 pm -
1 stop13h 27m
Mon 10/267:44 pm -
1 stop21h 48m
Deal found 9/26![Frontier logo]()
$233
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
1 stop7h 27m
Wed 10/282:50 pm -
1 stop6h 38m
Deal found 9/26![JetBlue logo]()
$240
This JetBlue deal was found by Cheapflights users on 9/24. 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.
Sat 10/246:00 am -
1 stop7h 27m
Sat 10/312:50 pm -
1 stop6h 38m
Deal found 9/24![JetBlue logo]()
$241
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/216:00 am -
1 stop7h 27m
Wed 10/282:50 pm -
1 stop6h 38m
Deal found 9/26![JetBlue logo]()
$244
This deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/292:42 pm -
1 stop11h 10m
Mon 10/127:20 am -
1 stop11h 36m
Deal found 9/26![Frontier logo]()
$248
This Cheapflightsfares deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 11/16:27 pm -
1 stop14h 48m
Sat 11/77:23 am -
1 stop11h 09m
Deal found 9/25![Frontier logo]()
$255
This JetBlue deal was found by Cheapflights users on 9/24. 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.
Mon 12/76:00 am -
1 stop6h 49m
Fri 12/113:30 pm -
1 stop6h 59m
Deal found 9/24![JetBlue logo]()
$256
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
1 stop7h 27m
Sat 10/242:37 pm -
1 stop7h 03m
Deal found 9/26![JetBlue logo]()
$257
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/52:32 pm -
1 stop19h 03m
Thu 10/153:55 pm -
1 stop27h 01m
Deal found 9/23![Frontier logo]()
$259
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/216:00 am -
1 stop7h 27m
Sat 10/242:37 pm -
1 stop7h 03m
Deal found 9/26![JetBlue logo]()
$261
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 September 27, 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 September 27, 2026.
This United Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:15 pm -
1 stop6h 07m
Tue 11/38:05 am -
2 stops11h 14m
Deal found 9/26![United Airlines logo]()
$280
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
1 stop7h 20m
Sat 10/242:25 pm -
1 stop7h 15m
Deal found 9/26![JetBlue logo]()
$311
This Southwest deal was found by Cheapflights users on 9/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/73:45 pm -
2 stops8h 00m
Fri 12/116:35 am -
1 stop6h 15m
Deal found 9/24![Southwest logo]()
$317
This Orbitz deal was found by Cheapflights users on 9/22. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:20 pm -
1 stop16h 10m
Mon 11/309:25 pm -
1 stop21h 11m
Deal found 9/22![Air Canada logo]()
$338
This American Airlines deal was found by Cheapflights users on 9/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:34 pm -
2 stops18h 52m
Sun 11/83:26 pm -
1 stop9h 14m
Deal found 9/24![American Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 9/24. 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.
Sun 11/1511:07 am -
1 stop5h 50m
Sat 11/216:12 pm -
1 stop6h 34m
Deal found 9/24![Delta logo]()
$377
This United Airlines deal was found by Cheapflights users on 9/23. 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.
Thu 11/196:00 am -
1 stop7h 33m
Mon 11/2312:55 pm -
2 stops11h 04m
Deal found 9/23![United Airlines logo]()
$320
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 11/146:00 am -
1 stop7h 55m
Wed 11/183:50 pm -
1 stop8h 51m
Deal found 9/26![JetBlue logo]()
$336
This Southwest deal was found by Cheapflights users on 9/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/131:30 pm -
2 stops10h 25m
Thu 12/179:35 pm -
1 stop12h 55m
Deal found 9/23![Southwest logo]()
$356
This United deal was found by Cheapflights users on 9/24. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:30 am -
2 stops11h 50m
Tue 10/272:00 pm -
1 stop8h 09m
Deal found 9/24![Multiple Airlines logo]()
$734
This American Airlines deal was found by Cheapflights users on 9/22. 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.
Sat 10/36:33 pm -
1 stop19h 06m
Sat 10/1012:07 pm -
1 stop11h 28m
Deal found 9/22![American Airlines logo]()
$376
This JetBlue deal was found by Cheapflights users on 9/24. 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.
Sat 10/37:00 am -
1 stop5h 01m
Mon 10/53:54 pm -
1 stop7h 26m
Deal found 9/24![JetBlue logo]()
$345
This United Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 12/66:00 am -
1 stop8h 39m
Thu 12/103:20 pm -
1 stop7h 07m
Deal found 9/25![United Airlines logo]()
$372
This Southwest deal was found by Cheapflights users on 9/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/114:00 pm -
2 stops7h 50m
Sun 11/159:40 pm -
1 stop12h 20m
Deal found 9/24![Southwest logo]()
$382
This JetBlue deal was found by Cheapflights users on 9/23. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
1 stop5h 20m
Mon 10/2612:21 pm -
1 stop9h 07m
Deal found 9/23![JetBlue logo]()
$349
This Orbitz deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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.
Wed 12/97:20 pm -
1 stop16h 50m
Wed 12/162:25 pm -
2 stops28h 11m
Deal found 9/25![Air Canada logo]()
$426
This United Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 1/253:00 pm -
1 stop6h 22m
Sat 2/138:05 am -
2 stops11h 19m
Deal found 9/25![United Airlines logo]()
$376
This American Airlines deal was found by Cheapflights users on 9/23. 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.
Fri 11/275:43 pm -
1 stop17h 35m
Wed 12/23:26 pm -
1 stop8h 31m
Deal found 9/23![American Airlines logo]()
$419
This JetBlue deal was found by Cheapflights users on 9/24. 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.
Tue 11/176:00 am -
1 stop8h 26m
Tue 11/244:04 pm -
1 stop8h 48m
Deal found 9/24![JetBlue logo]()
$354
This Delta deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 1/137:00 am -
1 stop7h 20m
Tue 1/194:30 pm -
1 stop8h 49m
Deal found 9/26![Delta logo]()
$474
This Air Canada deal was found by Cheapflights users on 9/24. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:20 pm -
1 stop17h 05m
Thu 10/291:20 pm -
1 stop29h 16m
Deal found 9/24![Air Canada logo]()
$433
This United Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/278:00 pm -
2 stops18h 14m
Sat 10/312:01 pm -
1 stop8h 58m
Deal found 9/25![United Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 9/23. 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.
Wed 1/137:00 am -
1 stop7h 20m
Sun 1/174:30 pm -
1 stop8h 49m
Deal found 9/23![Delta logo]()
$474
This American Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 12/96:11 am -
1 stop9h 11m
Wed 12/235:38 pm -
2 stops17h 39m
Deal found 9/25![American Airlines logo]()
$434
This JetBlue deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 12/186:00 am -
1 stop9h 56m
Mon 12/215:01 pm -
1 stop6h 41m
Deal found 9/27![JetBlue logo]()
$365
This Justfly.com deal was found by Cheapflights users on 9/22. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:20 pm -
2 stops42h 20m
Mon 11/24:45 pm -
1 stop26h 51m
Deal found 9/22![Air Canada logo]()
$453
This United Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/277:00 am -
1 stop6h 40m
Wed 10/281:05 am -
2 stops12h 01m
Deal found 9/26![United Airlines logo]()
$380
This Southwest deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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.
Fri 11/2712:30 pm -
2 stops9h 30m
Sat 12/55:40 am -
2 stops10h 20m
Deal found 9/25![Southwest logo]()
$465
This Delta deal was found by Cheapflights users on 9/24. 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.
Sun 3/217:55 pm -
1 stop18h 25m
Mon 3/293:30 pm -
1 stop17h 38m
Deal found 9/24![Delta logo]()
$474
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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.
Thu 12/176:00 am -
1 stop9h 56m
Mon 12/215:01 pm -
1 stop6h 41m
Deal found 9/26![JetBlue logo]()
$365
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated September 27, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated September 27, 2026 and is based on user searches.
This deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/292:42 pm -
1 stop11h 10m
Mon 10/127:20 am -
1 stop11h 36m
Deal found 9/26![Frontier logo]()
$248
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/52:32 pm -
1 stop19h 03m
Thu 10/153:55 pm -
1 stop27h 01m
Deal found 9/23![Frontier logo]()
$259
This Frontier deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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.
Tue 10/62:42 pm -
1 stop11h 10m
Tue 10/277:23 am -
1 stop10h 09m
Deal found 9/27![Frontier logo]()
$263
This FlightHub deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/197:51 pm -
1 stop13h 27m
Mon 10/267:44 pm -
1 stop21h 48m
Deal found 9/26![Frontier logo]()
$233
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
1 stop7h 27m
Wed 10/282:50 pm -
1 stop6h 38m
Deal found 9/26![JetBlue logo]()
$240
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
1 stop7h 27m
Sat 10/242:37 pm -
1 stop7h 03m
Deal found 9/26![JetBlue logo]()
$257
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/216:00 am -
1 stop7h 27m
Wed 10/282:50 pm -
1 stop6h 38m
Deal found 9/26![JetBlue logo]()
$244
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/216:00 am -
1 stop7h 27m
Sat 10/242:37 pm -
1 stop7h 03m
Deal found 9/26![JetBlue logo]()
$261
This JetBlue deal was found by Cheapflights users on 9/24. 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.
Thu 10/226:00 am -
1 stop9h 23m
Thu 10/292:50 pm -
1 stop6h 38m
Deal found 9/24![JetBlue logo]()
$264
This JetBlue deal was found by Cheapflights users on 9/24. 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.
Sat 10/246:00 am -
1 stop7h 27m
Sat 10/312:50 pm -
1 stop6h 38m
Deal found 9/24![JetBlue logo]()
$241
This Cheapflightsfares deal was found by Cheapflights users on 9/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:27 pm -
1 stop14h 48m
Tue 11/311:20 am -
1 stop7h 12m
Deal found 9/22![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 9/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:27 pm -
1 stop7h 23m
Thu 10/2910:20 am -
1 stop7h 12m
Deal found 9/22![Frontier logo]()
$222
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 September 27, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 27, 2026.
This JetBlue deal was found by Cheapflights users on 9/24. 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.
Tue 10/206:00 am -
1 stop5h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![JetBlue logo]()
$99
This JetBlue deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/216:00 am -
1 stop5h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![JetBlue logo]()
$104
This American Airlines deal was found by Cheapflights users on 9/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:11 am -
1 stop9h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![American Airlines logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:27 pm -
1 stop7h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$109
This JetBlue deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/37:00 am -
1 stop9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![JetBlue logo]()
$111
This Priceline deal was found by Cheapflights users on 9/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:51 pm -
1 stop13h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$111
This American Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 11/15:49 pm -
2 stops19h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![American Airlines logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 9/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:51 pm -
1 stop27h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$115
This Priceline deal was found by Cheapflights users on 9/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/187:51 pm -
1 stop27h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$117
This Travelocity deal was found by Cheapflights users on 9/22. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:20 pm -
2 stops17h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Air Canada logo]()
$121
This Expedia deal was found by Cheapflights users on 9/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:00 am -
1 stop11h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Air Canada logo]()
$125
This Travelocity deal was found by Cheapflights users on 9/22. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:20 pm -
1 stop19h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Air Canada logo]()
$125
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 September 27, 2026.
Round-trip from | $220 (Cheapflightsfares) |
|---|---|
One-way from | $99 (JetBlue) |
Popular in | June |
Cheapest in | September |
Average price | $308 |
Good round-trip deal | $591 or less |
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 7,457,451 searches. Data last updated September 27, 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
PittsburghNassau
PIT Pittsburgh - NAS Nassau Intl
PITNAS
Pittsburgh
Sat 10/17
6:30 am-12:50 pm
1 stop6h 20m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$99
PittsburghNassau
PIT Pittsburgh - NAS Nassau Intl
PITNAS
Pittsburgh
Wed 9/30
6:30 am-1:33 pm
1 stop7h 03m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$99
PittsburghNassau
PIT Pittsburgh - NAS Nassau Intl
PITNAS
Pittsburgh
Mon 10/19
8:18 pm-11:05 am
1 stop14h 47m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$99
PittsburghNassau
PIT Pittsburgh - NAS Nassau Intl
PITNAS
Pittsburgh
Mon 10/26
6:00 am-11:21 am
1 stop5h 21m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$99
PittsburghNassau
PIT Pittsburgh - NAS Nassau Intl
PITNAS
Pittsburgh
Sun 10/4
6:30 am-1:33 pm
1 stop7h 03m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$99
PittsburghNassau
PIT Pittsburgh - NAS Nassau Intl
PITNAS
Pittsburgh
Tue 10/13
6:30 am-12:50 pm
1 stop6h 20m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$99
PittsburghNassau
PIT Pittsburgh - NAS Nassau Intl
PITNAS
Pittsburgh
Tue 10/13
6:30 am-1:33 pm
1 stop7h 03m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$99
PittsburghNassau
PIT Pittsburgh - NAS Nassau Intl
PITNAS
Pittsburgh
Tue 10/20
6:00 am-11:20 am
1 stop5h 20m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$99
PittsburghSimpson Bay
PIT Pittsburgh - SXM Simpson Bay Princess Juliana
PITSXM
Pittsburgh
Sun 11/15
6:11 am-4:31 pm
1 stop9h 20m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$108
PittsburghSimpson Bay
PIT Pittsburgh - SXM Simpson Bay Princess Juliana
PITSXM
Pittsburgh
Mon 11/2
7:16 pm-4:31 pm
2 stops20h 15m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$114
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-NAS
PIT-SXM
PIT-MBJ
PIT-STT
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-NAS
PIT-SXM
PIT-MBJ
What is the cheapest month to book a flight from Pittsburgh to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $410). Flying from Pittsburgh to Caribbean in November is currently the most expensive (average of $624). 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 9 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 September 27, 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.
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
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 September 27, 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 7,457,451 searches. Data last updated September 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$321 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$533 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$184 | Average$515 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$218 | Average$478 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$222 | Average$579 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$255 | Average$647 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$404 | Average$494 | FlexibilityNo cancel fee | On-time67% |