$93+ 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Sep 25 — Oct 21
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 August 26, 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 August 26, 2026.
This United Airlines deal was found by Cheapflights users on 8/24. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/273:15 pm -
1 stop6h 07m
Tue 11/38:25 am -
2 stops11h 10m
Deal found 8/24![United Airlines logo]()
$186
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Mon 10/58:18 pm -
1 stop15h 51m
Thu 10/812:41 pm -
1 stop11h 50m
Deal found 8/25![American Airlines logo]()
$190
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:00 am -
1 stop10h 01m
Wed 10/146:20 am -
1 stop17h 15m
Deal found 8/21![American Airlines logo]()
$191
This Frontier deal was found by Cheapflights users on 8/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/162:42 pm -
1 stop11h 10m
Thu 9/177:00 am -
1 stop6h 47m
Deal found 8/24![Frontier logo]()
$197
This American Airlines deal was found by Cheapflights users on 8/23. 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.
Wed 10/287:08 pm -
2 stops17h 33m
Mon 11/24:53 pm -
2 stops18h 21m
Deal found 8/23![American Airlines logo]()
$199
This Frontier deal was found by Cheapflights users on 8/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/262:32 pm -
1 stop6h 16m
Tue 9/292:57 am -
1 stop10h 50m
Deal found 8/25![Frontier logo]()
$202
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:00 am -
2 stops13h 38m
Sat 9/261:25 pm -
1 stop8h 11m
Deal found 8/22![United Airlines logo]()
$204
This FlightHub deal was found by Cheapflights users on 8/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:18 pm -
1 stop13h 00m
Mon 10/123:00 am -
1 stop15h 56m
Deal found 8/24![Frontier logo]()
$209
This CheapOair deal was found by Cheapflights users on 8/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/202:32 pm -
1 stop19h 03m
Thu 9/242:57 am -
1 stop10h 50m
Deal found 8/23![Frontier logo]()
$212
This Trip.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:32 pm -
1 stop23h 46m
Thu 9/177:00 am -
1 stop6h 47m
Deal found 8/21![Frontier logo]()
$219
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 9/247:40 pm -
2 stops13h 44m
Mon 9/2811:51 am -
2 stops11h 45m
Deal found 8/25![American Airlines logo]()
$221
This FlightHub deal was found by Cheapflights users on 8/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:51 pm -
1 stop18h 25m
Tue 10/137:00 am -
1 stop11h 56m
Deal found 8/24![Frontier logo]()
$222
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 August 26, 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 August 26, 2026.
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:00 am -
1 stop7h 44m
Tue 10/131:25 pm -
1 stop8h 11m
Deal found 8/22![United Airlines logo]()
$186
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 pm -
1 stop6h 05m
Sun 10/255:00 am -
1 stop6h 25m
Deal found 8/21![Southwest logo]()
$300
This American Airlines deal was found by Cheapflights users on 8/24. 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.
Tue 10/66:51 pm -
2 stops18h 07m
Mon 10/121:21 pm -
1 stop11h 10m
Deal found 8/24![American Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:50 am -
1 stop8h 04m
Sat 10/244:53 pm -
1 stop7h 53m
Deal found 8/22![Delta logo]()
$351
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Wed 9/306:30 am -
1 stop7h 15m
Tue 10/67:00 am -
1 stop8h 49m
Deal found 8/25![United Airlines logo]()
$186
This JetBlue deal was found by Cheapflights users on 8/24. 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 10/266:00 am -
1 stop7h 30m
Fri 10/301:10 pm -
1 stop8h 18m
Deal found 8/24![JetBlue logo]()
$391
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:00 am -
1 stop7h 44m
Tue 9/297:00 am -
2 stops13h 36m
Deal found 8/21![United Airlines logo]()
$186
This Air Canada deal was found by Cheapflights users on 8/25. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:20 pm -
2 stops17h 55m
Thu 10/291:20 pm -
1 stop29h 16m
Deal found 8/25![Air Canada logo]()
$440
This Priceline deal was found by Cheapflights users on 8/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:00 am -
1 stop11h 00m
Tue 10/131:43 pm -
1 stop7h 50m
Deal found 8/24![Multiple Airlines logo]()
$443
This Southwest deal was found by Cheapflights users on 8/24. 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 9/912:40 pm -
2 stops9h 25m
Sat 9/265:05 am -
2 stops9h 40m
Deal found 8/24![Southwest logo]()
$305
This United Airlines deal was found by Cheapflights users on 8/24. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:30 am -
1 stop7h 15m
Mon 10/193:56 pm -
1 stop8h 03m
Deal found 8/24![United Airlines logo]()
$257
This Copa Airlines deal was found by Cheapflights users on 8/24. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:26 am -
2 stops11h 54m
Thu 10/223:38 pm -
2 stops17h 00m
Deal found 8/24![Copa Airlines logo]()
$665
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:50 am -
1 stop8h 03m
Sat 10/101:06 pm -
1 stop8h 25m
Deal found 8/21![Delta logo]()
$351
This American Airlines deal was found by Cheapflights users on 8/25. 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 10/77:39 pm -
2 stops17h 02m
Tue 10/133:46 pm -
2 stops17h 44m
Deal found 8/25![American Airlines logo]()
$352
This Southwest deal was found by Cheapflights users on 8/25. 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.
Sun 9/204:15 pm -
2 stops8h 20m
Sat 9/265:05 am -
2 stops9h 40m
Deal found 8/25![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:30 am -
1 stop7h 15m
Sat 10/317:05 am -
1 stop7h 13m
Deal found 8/22![United Airlines logo]()
$276
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:30 am -
1 stop7h 15m
Tue 10/274:50 pm -
1 stop6h 40m
Deal found 8/22![United Airlines logo]()
$276
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:11 am -
1 stop5h 44m
Mon 11/168:15 am -
1 stop15h 25m
Deal found 8/21![American Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 8/23. 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.
Sat 9/265:50 am -
1 stop6h 50m
Sun 9/271:00 pm -
1 stop10h 31m
Deal found 8/23![Delta logo]()
$371
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:24 pm -
1 stop15h 59m
Fri 11/208:15 am -
1 stop15h 26m
Deal found 8/21![American Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 8/24. 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.
Wed 9/98:00 am -
1 stop5h 53m
Tue 9/151:16 pm -
1 stop8h 23m
Deal found 8/24![Delta logo]()
$372
This United Airlines deal was found by Cheapflights users on 8/24. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:15 am -
1 stop8h 57m
Tue 9/221:00 am -
2 stops8h 36m
Deal found 8/24![United Airlines logo]()
$280
This Flysmarter deal was found by Cheapflights users on 8/25. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:30 am -
1 stop7h 03m
Sat 10/242:40 pm -
1 stop9h 04m
Deal found 8/25![JetBlue logo]()
$463
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:41 am -
1 stop7h 18m
Sat 9/54:42 pm -
2 stops18h 02m
Deal found 8/21![American Airlines logo]()
$375
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/65:50 am -
1 stop6h 49m
Thu 9/101:00 pm -
1 stop10h 31m
Deal found 8/22![Delta logo]()
$377
This JetBlue deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:10 am -
1 stop7h 00m
Wed 12/22:30 pm -
1 stop7h 54m
Deal found 8/21![JetBlue logo]()
$470
This United Airlines deal was found by Cheapflights users on 8/23. 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.
Sun 11/16:12 am -
1 stop6h 03m
Sun 11/88:05 am -
1 stop7h 09m
Deal found 8/23![United Airlines logo]()
$301
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Sun 10/116:00 am -
1 stop8h 10m
Thu 10/1512:00 pm -
2 stops11h 31m
Deal found 8/25![American Airlines logo]()
$376
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:00 am -
1 stop10h 35m
Sat 11/216:00 pm -
1 stop6h 36m
Deal found 8/21![Delta logo]()
$382
This JetBlue deal was found by Cheapflights users on 8/25. 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 10/316:00 am -
1 stop7h 55m
Wed 11/42:09 pm -
1 stop8h 19m
Deal found 8/25![JetBlue logo]()
$470
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated August 26, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated August 26, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:32 pm -
1 stop23h 46m
Thu 9/177:00 am -
1 stop6h 47m
Deal found 8/21![Frontier logo]()
$219
This Priceline deal was found by Cheapflights users on 8/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:32 pm -
1 stop11h 20m
Wed 9/1610:42 am -
1 stop27h 05m
Deal found 8/25![Frontier logo]()
$253
This Frontier deal was found by Cheapflights users on 8/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/152:42 pm -
1 stop11h 10m
Thu 9/172:57 am -
1 stop10h 50m
Deal found 8/24![Frontier logo]()
$247
This Frontier deal was found by Cheapflights users on 8/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/162:42 pm -
1 stop11h 10m
Thu 9/177:00 am -
1 stop6h 47m
Deal found 8/24![Frontier logo]()
$197
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:00 am -
2 stops9h 40m
Wed 9/303:41 pm -
1 stop7h 13m
Deal found 8/21![American Airlines logo]()
$252
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:00 am -
2 stops13h 38m
Sat 9/261:25 pm -
1 stop8h 11m
Deal found 8/22![United Airlines logo]()
$204
This Southwest deal was found by Cheapflights users on 8/25. 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.
Sun 9/204:15 pm -
1 stop7h 40m
Sat 9/265:05 am -
2 stops9h 40m
Deal found 8/25![Southwest logo]()
$186
This CheapOair deal was found by Cheapflights users on 8/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/202:32 pm -
1 stop19h 03m
Thu 9/242:57 am -
1 stop10h 50m
Deal found 8/23![Frontier logo]()
$212
This Delta deal was found by Cheapflights users on 8/24. 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.
Tue 9/225:50 am -
1 stop6h 01m
Tue 9/291:16 pm -
1 stop8h 23m
Deal found 8/24![Delta logo]()
$350
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 9/247:40 pm -
2 stops13h 44m
Mon 9/2811:51 am -
2 stops11h 45m
Deal found 8/25![American Airlines logo]()
$221
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 9/247:40 pm -
2 stops13h 44m
Thu 10/12:22 pm -
1 stop9h 14m
Deal found 8/25![American Airlines logo]()
$256
This Frontier deal was found by Cheapflights users on 8/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/262:32 pm -
1 stop6h 16m
Tue 9/292:57 am -
1 stop10h 50m
Deal found 8/25![Frontier logo]()
$202
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 August 26, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
This United Airlines deal was found by Cheapflights users on 8/23. 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.
Sat 10/318:49 am -
2 stops12h 33m
Deal found 8/23![United Airlines logo]()
$93
This Frontier deal was found by Cheapflights users on 8/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:27 pm -
1 stop7h 23m
Deal found 8/25![Frontier logo]()
$101
This American Airlines deal was found by Cheapflights users on 8/24. 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.
Tue 10/136:51 pm -
2 stops18h 07m
Deal found 8/24![American Airlines logo]()
$101
This Delta deal was found by Cheapflights users on 8/23. 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 9/308:00 am -
1 stop5h 53m
Deal found 8/23![Delta logo]()
$121
This United Airlines deal was found by Cheapflights users on 8/23. 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.
Sat 10/37:30 am -
1 stop6h 03m
Deal found 8/23![United Airlines logo]()
$122
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Fri 11/68:00 pm -
2 stops15h 49m
Deal found 8/25![United Airlines logo]()
$128
This Faresmojo deal was found by Cheapflights users on 8/22. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:55 pm -
1 stop12h 15m
Deal found 8/22![JetBlue logo]()
$130
This American Airlines deal was found by Cheapflights users on 8/24. 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.
Tue 10/136:00 am -
1 stop10h 02m
Deal found 8/24![American Airlines logo]()
$131
This Delta deal was found by Cheapflights users on 8/23. 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.
Mon 9/215:50 am -
1 stop6h 50m
Deal found 8/23![Delta logo]()
$133
This American Airlines deal was found by Cheapflights users on 8/23. 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.
Thu 9/245:16 pm -
2 stops19h 11m
Deal found 8/23![American Airlines logo]()
$139
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Sun 11/18:19 pm -
1 stop16h 07m
Deal found 8/25![American Airlines logo]()
$143
This JetBlue deal was found by Cheapflights users on 8/23. 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.
Fri 10/27:00 am -
1 stop9h 00m
Deal found 8/23![JetBlue logo]()
$148
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 August 26, 2026.
Round-trip from | $186 (United Airlines) |
|---|---|
One-way from | $93 (United Airlines) |
Popular in | June |
Cheapest in | September |
Average price | $360 |
Good round-trip deal | $766 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 August 26, 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
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Tue 10/6
7:00 am-2:44 pm
1 stop7h 44m
San Juan Luis Munoz Marin Intl
Tue 10/13
1:25 pm-9:36 pm
1 stop8h 11m
$186
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Wed 9/30
6:30 am-1:45 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Tue 10/6
7:00 am-3:49 pm
1 stop8h 49m
$186
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Tue 9/15
7:00 am-2:44 pm
1 stop7h 44m
San Juan Luis Munoz Marin Intl
Tue 9/29
7:00 am-8:36 pm
2 stops13h 36m
$186
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Fri 10/16
6:30 am-1:45 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Mon 10/19
3:56 pm-11:59 pm
1 stop8h 03m
$257
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Fri 10/16
6:30 am-1:45 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Sat 10/31
7:05 am-2:18 pm
1 stop7h 13m
$276
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Fri 10/16
6:30 am-1:45 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Tue 10/27
4:50 pm-11:30 pm
1 stop6h 40m
$276
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Wed 9/9
6:15 am-3:12 pm
1 stop8h 57m
San Juan Luis Munoz Marin Intl
Tue 9/22
1:00 am-9:36 am
2 stops8h 36m
$280
Quickest round-trip
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Thu 10/22
6:00 pm-12:05 am
1 stop6h 05m
San Juan Luis Munoz Marin Intl
Sun 10/25
5:00 am-11:25 am
1 stop6h 25m
$300
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Sun 11/1
6:12 am-1:15 pm
1 stop6h 03m
San Juan Luis Munoz Marin Intl
Sun 11/8
8:05 am-2:14 pm
1 stop7h 09m
$301
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Wed 9/9
12:40 pm-10:05 pm
2 stops9h 25m
San Juan Luis Munoz Marin Intl
Sat 9/26
5:05 am-2:45 pm
2 stops9h 40m
$305
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Pittsburgh to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Pittsburgh with our price prediction graph.
PIT-SJU
PIT-STT
PIT-NAS
PIT-AUA
PIT-GCM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Pittsburgh to Caribbean
PIT-0CB
PIT-SJU
PIT-STT
PIT-NAS
PIT-AUA
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 $412). Flying from Pittsburgh to Caribbean in November is currently the most expensive (average of $610). 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 71 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 August 26, 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
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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.
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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 August 26, 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 August 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$321 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$141 | Average$516 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$537 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$221 | Average$463 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$225 | Average$578 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$231 | Average$646 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$406 | Average$494 | FlexibilityNo cancel fee | On-time67% |