$98+ 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 12/30. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Dec 4 — Dec 111
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 November 4, 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 November 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:28 pm -
1 stop28h 01m
Sat 12/127:00 am -
1 stop11h 33m
Deal found 11/2![Frontier logo]()
$260
This Cheapflightsfares deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:59 pm -
1 stop14h 00m
Wed 12/24:07 pm -
1 stop26h 21m
Deal found 10/30![Frontier logo]()
$276
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:05 am -
1 stop7h 10m
Fri 12/113:15 pm -
2 stops9h 40m
Deal found 10/31![Southwest logo]()
$285
This Priceline deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:28 pm -
1 stop6h 45m
Sun 12/134:04 pm -
1 stop26h 29m
Deal found 10/31![Frontier logo]()
$294
This JetBlue deal was found by Cheapflights users on 11/2. 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.
Tue 12/86:20 am -
1 stop7h 51m
Fri 12/114:32 pm -
1 stop8h 24m
Deal found 11/2![JetBlue logo]()
$297
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:27 pm -
1 stop7h 19m
Wed 12/24:07 pm -
1 stop26h 21m
Deal found 11/1![Frontier logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/46:28 pm -
1 stop6h 43m
Sun 12/63:28 am -
2 stops17h 46m
Deal found 11/3![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Thu 12/36:28 pm -
1 stop6h 43m
Sun 12/63:28 am -
2 stops17h 46m
Deal found 11/3![Multiple Airlines logo]()
$303
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/308:00 am -
1 stop5h 41m
Tue 12/810:22 am -
1 stop12h 40m
Deal found 10/30![American Airlines logo]()
$306
This Cheapflightsfares deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:59 pm -
1 stop6h 25m
Thu 11/263:55 am -
1 stop15h 09m
Deal found 10/30![Frontier logo]()
$306
This JetBlue deal was found by Cheapflights users on 11/2. 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.
Wed 12/26:00 am -
1 stop6h 45m
Wed 12/912:25 pm -
1 stop9h 06m
Deal found 11/2![JetBlue logo]()
$307
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:28 pm -
1 stop15h 09m
Fri 12/183:55 am -
1 stop14h 28m
Deal found 11/1![Frontier logo]()
$307
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 November 4, 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 November 4, 2026.
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:05 am -
1 stop7h 10m
Fri 12/113:15 pm -
2 stops9h 40m
Deal found 10/31![Southwest logo]()
$285
This JetBlue deal was found by Cheapflights users on 11/2. 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.
Tue 12/86:20 am -
1 stop7h 51m
Fri 12/114:32 pm -
1 stop8h 24m
Deal found 11/2![JetBlue logo]()
$297
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/196:09 am -
2 stops8h 18m
Tue 1/2612:55 pm -
1 stop6h 09m
Deal found 10/31![United Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/36:00 am -
1 stop9h 15m
Tue 3/93:05 pm -
1 stop6h 44m
Deal found 11/1![Delta logo]()
$324
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/278:29 pm -
2 stops16h 28m
Wed 12/25:33 pm -
2 stops20h 30m
Deal found 11/1![American Airlines logo]()
$326
This Breeze Airways deal was found by Cheapflights users on 11/2. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/22:16 pm -
1 stop23h 14m
Tue 2/93:24 pm -
Nonstop4h 30m
Deal found 11/2![Breeze Airways logo]()
$460
This JetBlue deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/196:00 am -
1 stop6h 36m
Tue 1/261:50 pm -
1 stop9h 56m
Deal found 10/31![JetBlue logo]()
$302
This Southwest deal was found by Cheapflights users on 11/3. 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.
Sat 1/164:20 pm -
1 stop5h 55m
Sat 1/237:05 am -
1 stop9h 45m
Deal found 11/3![Southwest logo]()
$320
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/284:51 pm -
1 stop6h 45m
Thu 2/118:05 am -
1 stop7h 09m
Deal found 11/1![United Airlines logo]()
$320
This Air Canada deal was found by Cheapflights users on 11/4. 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.
Wed 12/97:20 pm -
1 stop19h 25m
Wed 12/234:45 pm -
1 stop26h 51m
Deal found 11/4![Air Canada logo]()
$652
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/162:58 pm -
2 stops20h 36m
Sat 1/231:50 pm -
1 stop8h 43m
Deal found 10/30![American Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 11/3. 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.
Tue 2/98:10 am -
1 stop5h 47m
Wed 2/103:07 pm -
1 stop9h 39m
Deal found 11/3![Delta logo]()
$336
This JetBlue deal was found by Cheapflights users on 11/2. 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.
Mon 1/256:00 am -
1 stop6h 36m
Sat 1/3012:00 pm -
1 stop9h 25m
Deal found 11/2![JetBlue logo]()
$308
This United Airlines deal was found by Cheapflights users on 11/2. 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 1/177:45 pm -
2 stops16h 04m
Thu 1/2112:55 pm -
2 stops10h 33m
Deal found 11/2![United Airlines logo]()
$321
This Southwest deal was found by Cheapflights users on 11/3. 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.
Sat 1/235:30 am -
1 stop7h 45m
Wed 1/273:15 pm -
1 stop7h 55m
Deal found 11/3![Southwest logo]()
$324
This Delta deal was found by Cheapflights users on 11/3. 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 1/171:00 pm -
1 stop9h 58m
Fri 1/226:30 am -
1 stop10h 09m
Deal found 11/3![Delta logo]()
$340
This JetBlue deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/156:20 am -
1 stop6h 25m
Tue 12/225:01 pm -
1 stop6h 41m
Deal found 10/31![JetBlue logo]()
$320
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/36:10 am -
2 stops9h 12m
Tue 3/95:20 pm -
1 stop5h 59m
Deal found 11/1![United Airlines logo]()
$328
This American Airlines deal was found by Cheapflights users on 11/3. 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 1/195:53 pm -
2 stops17h 31m
Thu 1/285:04 pm -
2 stops18h 18m
Deal found 11/3![American Airlines logo]()
$370
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/286:00 am -
1 stop6h 20m
Sat 2/63:20 pm -
1 stop8h 10m
Deal found 11/1![Southwest logo]()
$350
This JetBlue deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/87:30 am -
1 stop8h 12m
Thu 1/144:45 pm -
1 stop8h 01m
Deal found 11/1![JetBlue logo]()
$327
This United Airlines deal was found by Cheapflights users on 11/4. 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 2/68:40 am -
2 stops11h 44m
Fri 2/125:50 pm -
1 stop6h 30m
Deal found 11/4![United Airlines logo]()
$340
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/97:07 pm -
1 stop17h 17m
Tue 1/195:29 pm -
2 stops20h 47m
Deal found 11/1![American Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/235:55 am -
1 stop9h 29m
Mon 12/284:20 pm -
1 stop9h 21m
Deal found 10/30![Delta logo]()
$383
This Southwest deal was found by Cheapflights users on 11/3. 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 2/26:00 am -
1 stop6h 20m
Tue 2/92:10 pm -
1 stop9h 00m
Deal found 11/3![Southwest logo]()
$350
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/287:00 am -
1 stop8h 50m
Mon 2/15:50 pm -
1 stop6h 38m
Deal found 10/31![United Airlines logo]()
$342
This JetBlue deal was found by Cheapflights users on 11/2. 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 1/297:30 am -
1 stop8h 12m
Fri 2/52:10 pm -
1 stop10h 36m
Deal found 11/2![JetBlue logo]()
$360
This Southwest deal was found by Cheapflights users on 11/2. 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.
Mon 1/256:40 am -
1 stop6h 20m
Sat 1/302:20 pm -
1 stop6h 25m
Deal found 11/2![Southwest logo]()
$369
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:00 am -
2 stops8h 40m
Sat 12/512:21 pm -
2 stops8h 39m
Deal found 11/1![American Airlines logo]()
$416
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:25 pm -
2 stops17h 15m
Tue 12/155:35 pm -
2 stops17h 29m
Deal found 11/2![United Airlines logo]()
$346
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated November 4, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:27 pm -
1 stop7h 19m
Wed 12/24:07 pm -
1 stop26h 21m
Deal found 11/1![Frontier logo]()
$301
This Cheapflightsfares deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:59 pm -
1 stop6h 25m
Thu 11/263:55 am -
1 stop15h 09m
Deal found 10/30![Frontier logo]()
$306
This Cheapflightsfares deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:59 pm -
1 stop14h 00m
Wed 12/24:07 pm -
1 stop26h 21m
Deal found 10/30![Frontier logo]()
$276
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/308:00 am -
1 stop5h 41m
Tue 12/810:22 am -
1 stop12h 40m
Deal found 10/30![American Airlines logo]()
$306
This JetBlue deal was found by Cheapflights users on 11/2. 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.
Wed 12/26:00 am -
1 stop6h 45m
Wed 12/912:25 pm -
1 stop9h 06m
Deal found 11/2![JetBlue logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Thu 12/36:28 pm -
1 stop6h 43m
Sun 12/63:28 am -
2 stops17h 46m
Deal found 11/3![Multiple Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/46:28 pm -
1 stop6h 43m
Sun 12/63:28 am -
2 stops17h 46m
Deal found 11/3![Multiple Airlines logo]()
$302
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:28 pm -
1 stop15h 09m
Fri 12/183:55 am -
1 stop14h 28m
Deal found 11/1![Frontier logo]()
$307
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:28 pm -
1 stop28h 01m
Sat 12/127:00 am -
1 stop11h 33m
Deal found 11/2![Frontier logo]()
$260
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:05 am -
1 stop7h 10m
Fri 12/113:15 pm -
2 stops9h 40m
Deal found 10/31![Southwest logo]()
$285
This JetBlue deal was found by Cheapflights users on 11/2. 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.
Tue 12/86:20 am -
1 stop7h 51m
Fri 12/114:32 pm -
1 stop8h 24m
Deal found 11/2![JetBlue logo]()
$297
This Priceline deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:28 pm -
1 stop6h 45m
Sun 12/134:04 pm -
1 stop26h 29m
Deal found 10/31![Frontier logo]()
$294
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 November 4, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/305:20 am -
1 stop7h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Southwest logo]()
$98
This JetBlue deal was found by Cheapflights users on 11/3. 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.
Wed 1/136:00 am -
1 stop7h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![JetBlue logo]()
$108
This JetBlue deal was found by Cheapflights users on 11/3. 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 1/126:00 am -
1 stop7h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![JetBlue logo]()
$113
This JetBlue deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/147:53 am -
1 stop7h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![JetBlue logo]()
$118
This American Airlines deal was found by Cheapflights users on 11/3. 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 1/125:53 pm -
2 stops17h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![American Airlines logo]()
$123
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/148:21 pm -
2 stops18h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![American Airlines logo]()
$124
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/306:46 pm -
2 stops17h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![American Airlines logo]()
$124
This Super.com deal was found by Cheapflights users on 11/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:28 pm -
1 stop6h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$129
This JetBlue deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/136:00 am -
1 stop7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![JetBlue logo]()
$130
This American Airlines deal was found by Cheapflights users on 11/3. 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 1/135:20 pm -
2 stops18h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![American Airlines logo]()
$134
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/306:09 pm -
1 stop26h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$135
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Mon 12/147:25 pm -
2 stops17h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![United Airlines logo]()
$138
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 November 4, 2026.
Round-trip from | $260 (Cheapflightsfares) |
|---|---|
One-way from | $98 (Southwest) |
Popular in | June |
Cheapest in | September |
Average price | $407 |
Good round-trip deal | $418 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 November 4, 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
PittsburghSimpson Bay
PIT Pittsburgh - SXM Simpson Bay Princess Juliana
PITSXM
Pittsburgh
Wed 12/30
5:20 am-2:15 pm
1 stop7h 55m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$98
PittsburghSimpson Bay
PIT Pittsburgh - SXM Simpson Bay Princess Juliana
PITSXM
Pittsburgh
Wed 1/13
6:00 am-2:15 pm
1 stop7h 15m
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
Tue 1/12
6:00 am-2:15 pm
1 stop7h 15m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$113
PittsburghOranjestad
PIT Pittsburgh - AUA Oranjestad Reina Beatrix
PITAUA
Pittsburgh
Mon 12/14
7:53 am-4:40 pm
1 stop7h 47m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
PittsburghOranjestad
PIT Pittsburgh - AUA Oranjestad Reina Beatrix
PITAUA
Pittsburgh
Mon 12/14
8:21 pm-4:16 pm
2 stops18h 55m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$124
PittsburghSimpson Bay
PIT Pittsburgh - SXM Simpson Bay Princess Juliana
PITSXM
Pittsburgh
Wed 12/30
6:46 pm-1:05 pm
2 stops17h 19m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$124
PittsburghOranjestad
PIT Pittsburgh - AUA Oranjestad Reina Beatrix
PITAUA
Pittsburgh
Sun 12/13
6:46 pm-1:59 pm
1 stop18h 13m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
PittsburghOranjestad
PIT Pittsburgh - AUA Oranjestad Reina Beatrix
PITAUA
Pittsburgh
Sun 12/13
6:00 am-2:35 pm
1 stop7h 35m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
PittsburghSimpson Bay
PIT Pittsburgh - SXM Simpson Bay Princess Juliana
PITSXM
Pittsburgh
Wed 1/13
5:20 pm-12:34 pm
2 stops18h 14m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$134
PittsburghOranjestad
PIT Pittsburgh - AUA Oranjestad Reina Beatrix
PITAUA
Pittsburgh
Mon 12/14
8:04 pm-1:40 pm
1 stop16h 36m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
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-SXM
PIT-NAS
PIT-PUJ
PIT-SJU
PIT-CUR
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Pittsburgh to Caribbean
PIT-0CB
PIT-SXM
PIT-NAS
PIT-PUJ
PIT-SJU
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 $407). Flying from Pittsburgh to Caribbean in November is currently the most expensive (average of $618). 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 November 4, 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.
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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 November 4, 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 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$355 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$506 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$211 | Average$502 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$218 | Average$460 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$221 | Average$552 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$275 | Average$669 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$382 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$404 | Average$494 | FlexibilityNo cancel fee | On-time67% |