$88+ Cheap flights from Pittsburgh (PIT) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Sep 11 — Sep 181
Round-trip
1 adult, Economy
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Find cheap flights from Pittsburgh to Caribbean with Cheapflights
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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 12, 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 12, 2026.
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 10/278:19 am -
2 stops13h 50m
Tue 11/38:00 am -
2 stops10h 04m
Deal found 8/11![American Airlines logo]()
$186
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/96:00 am -
1 stop8h 50m
Sat 9/122:58 pm -
1 stop8h 36m
Deal found 8/10![American Airlines logo]()
$191
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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
Tue 10/273:46 pm -
2 stops17h 44m
Deal found 8/10![American Airlines logo]()
$194
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/28:00 am -
1 stop14h 24m
Tue 9/86:00 am -
1 stop11h 00m
Deal found 8/10![American Airlines logo]()
$216
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:22 am -
2 stops8h 28m
Wed 9/306:00 am -
2 stops12h 16m
Deal found 8/7![American Airlines logo]()
$218
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/512:45 pm -
1 stop6h 40m
Sat 9/126:25 am -
2 stops8h 20m
Deal found 8/10![Southwest logo]()
$220
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:28 am -
2 stops9h 10m
Wed 10/146:30 am -
1 stop17h 05m
Deal found 8/7![American Airlines logo]()
$223
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/610:47 am -
1 stop11h 37m
Sun 9/1311:51 am -
2 stops11h 45m
Deal found 8/7![American Airlines logo]()
$227
This United Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/156:15 am -
1 stop8h 57m
Tue 9/151:00 am -
2 stops14h 07m
Deal found 8/9![United Airlines logo]()
$231
This United Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/236:30 am -
1 stop7h 23m
Sat 9/261:25 pm -
1 stop8h 11m
Deal found 8/9![United Airlines logo]()
$236
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/51:57 pm -
1 stop8h 32m
Wed 9/92:59 pm -
1 stop6h 40m
Deal found 8/8![Delta logo]()
$245
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/184:35 pm -
1 stop7h 20m
Tue 9/2210:30 am -
1 stop7h 40m
Deal found 8/7![Southwest logo]()
$248
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 12, 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 12, 2026.
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/1210:05 am -
1 stop8h 15m
Tue 9/158:20 am -
1 stop6h 25m
Deal found 8/11![Southwest logo]()
$186
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/51:57 pm -
1 stop8h 32m
Fri 9/112:59 pm -
1 stop9h 32m
Deal found 8/8![Delta logo]()
$245
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/206:10 am -
1 stop6h 44m
Fri 9/253:56 pm -
1 stop8h 03m
Deal found 8/8![United Airlines logo]()
$326
This Air Canada deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:20 pm -
1 stop19h 25m
Sun 11/84:45 pm -
1 stop26h 51m
Deal found 8/10![Air Canada logo]()
$344
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:00 am -
1 stop7h 38m
Mon 9/2810:32 am -
1 stop13h 02m
Deal found 8/7![American Airlines logo]()
$351
This JetBlue deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:15 am -
1 stop5h 05m
Wed 9/210:42 am -
1 stop10h 46m
Deal found 8/7![JetBlue logo]()
$404
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 1/196:00 am -
1 stop9h 15m
Thu 1/283:10 pm -
1 stop10h 09m
Deal found 8/10![Delta logo]()
$270
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 10/32:50 pm -
1 stop7h 29m
Sat 10/106:45 am -
1 stop10h 19m
Deal found 8/10![Delta logo]()
$294
This Copa Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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.
Wed 10/215:11 am -
2 stops33h 25m
Sun 10/257:21 pm -
2 stops14h 18m
Deal found 8/11![Copa Airlines logo]()
$675
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 10/318:00 am -
1 stop5h 48m
Sat 11/142:40 pm -
1 stop9h 17m
Deal found 8/10![United Airlines logo]()
$352
This Air Canada deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:20 pm -
1 stop20h 25m
Wed 11/44:45 pm -
1 stop26h 51m
Deal found 8/12![Air Canada logo]()
$352
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:19 am -
2 stops9h 36m
Fri 10/232:08 pm -
2 stops10h 23m
Deal found 8/7![American Airlines logo]()
$354
This Travelocity deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2212:15 pm -
2 stops49h 10m
Mon 9/286:30 pm -
1 stop17h 02m
Deal found 8/7![Air Canada logo]()
$354
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:00 am -
2 stops11h 55m
Wed 9/302:39 pm -
2 stops8h 51m
Deal found 8/7![American Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 1/296:00 am -
1 stop5h 53m
Tue 2/212:55 pm -
1 stop7h 39m
Deal found 8/8![United Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/46:00 am -
1 stop9h 15m
Thu 2/113:10 pm -
1 stop10h 09m
Deal found 8/8![Delta logo]()
$376
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:30 am -
1 stop7h 15m
Fri 10/231:00 am -
2 stops12h 09m
Deal found 8/7![United Airlines logo]()
$379
This Orbitz deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:20 pm -
1 stop19h 25m
Sat 11/73:45 pm -
2 stops27h 51m
Deal found 8/7![Air Canada logo]()
$379
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 10/318:36 pm -
2 stops17h 54m
Wed 11/43:26 pm -
2 stops19h 22m
Deal found 8/12![American Airlines logo]()
$380
This JetBlue deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/306:00 am -
1 stop7h 18m
Wed 2/33:37 pm -
1 stop9h 18m
Deal found 8/7![JetBlue logo]()
$469
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:05 am -
1 stop6h 48m
Sat 9/53:18 pm -
1 stop8h 16m
Deal found 8/9![Delta logo]()
$380
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:16 am -
2 stops9h 23m
Tue 9/152:23 pm -
2 stops22h 09m
Deal found 8/7![American Airlines logo]()
$380
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 11/278:00 pm -
2 stops17h 48m
Wed 12/23:36 pm -
1 stop7h 43m
Deal found 8/8![United Airlines logo]()
$383
This JetBlue deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 2/56:00 am -
1 stop7h 48m
Wed 2/102:30 pm -
1 stop9h 25m
Deal found 8/9![JetBlue logo]()
$476
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/266:30 am -
1 stop6h 50m
Mon 10/52:50 pm -
2 stops8h 40m
Deal found 8/10![Southwest logo]()
$540
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 10/3010:49 am -
1 stop9h 11m
Sat 11/78:05 am -
2 stops11h 14m
Deal found 8/11![United Airlines logo]()
$384
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 10/105:37 pm -
2 stops19h 46m
Sat 10/174:39 pm -
2 stops17h 25m
Deal found 8/10![American Airlines logo]()
$385
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 11/118:00 am -
1 stop7h 30m
Sun 11/154:55 pm -
1 stop7h 41m
Deal found 8/8![Delta logo]()
$396
This Air Canada deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:20 pm -
2 stops22h 25m
Sat 11/217:45 pm -
2 stops23h 51m
Deal found 8/8![Air Canada logo]()
$436
This JetBlue deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/296:00 am -
1 stop7h 48m
Fri 2/53:00 pm -
1 stop6h 28m
Deal found 8/7![JetBlue logo]()
$494
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated August 12, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated August 12, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 8/285:42 pm -
2 stops17h 36m
Wed 9/211:49 am -
2 stops20h 57m
Deal found 8/8![American Airlines logo]()
$310
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 8/297:39 pm -
2 stops17h 14m
Sat 9/54:42 pm -
2 stops18h 02m
Deal found 8/10![American Airlines logo]()
$295
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/28:00 am -
1 stop14h 24m
Tue 9/86:00 am -
1 stop11h 00m
Deal found 8/10![American Airlines logo]()
$216
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/512:45 pm -
1 stop6h 40m
Sat 9/126:25 am -
2 stops8h 20m
Deal found 8/10![Southwest logo]()
$220
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/51:57 pm -
1 stop8h 32m
Thu 9/105:59 pm -
1 stop6h 32m
Deal found 8/8![Delta logo]()
$245
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/610:47 am -
1 stop11h 37m
Sun 9/1311:51 am -
2 stops11h 45m
Deal found 8/7![American Airlines logo]()
$227
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/66:30 am -
1 stop7h 15m
Fri 9/111:25 pm -
2 stops10h 05m
Deal found 8/12![United Airlines logo]()
$256
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/96:00 am -
1 stop8h 50m
Sat 9/122:58 pm -
1 stop8h 36m
Deal found 8/10![American Airlines logo]()
$191
This United Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/156:15 am -
1 stop8h 57m
Tue 9/151:00 am -
2 stops14h 07m
Deal found 8/9![United Airlines logo]()
$231
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/184:35 pm -
1 stop7h 20m
Tue 9/2210:30 am -
1 stop7h 40m
Deal found 8/7![Southwest logo]()
$248
This United Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/237:00 am -
2 stops13h 38m
Sat 9/263:56 pm -
1 stop8h 03m
Deal found 8/9![United Airlines logo]()
$236
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/268:29 am -
2 stops12h 18m
Wed 9/306:00 am -
2 stops12h 16m
Deal found 8/11![American Airlines logo]()
$186
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 12, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
This Faresmojo deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/108:55 pm -
1 stop12h 15m
Deal found 8/12![JetBlue logo]()
$88
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 10/319:26 am -
2 stops13h 31m
Deal found 8/12![American Airlines logo]()
$93
This Faresmojo deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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.
Tue 9/812:10 pm -
1 stop11h 39m
Deal found 8/12![JetBlue logo]()
$94
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 8/10![American Airlines logo]()
$101
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 11/1711:01 am -
1 stop11h 12m
Deal found 8/10![Delta logo]()
$108
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/128:18 pm -
1 stop15h 51m
Deal found 8/7![American Airlines logo]()
$109
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:00 am -
2 stops13h 38m
Deal found 8/7![United Airlines logo]()
$118
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/17:05 am -
1 stop4h 46m
Deal found 8/10![Delta logo]()
$121
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/86:21 am -
2 stops9h 50m
Deal found 8/11![American Airlines logo]()
$121
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:50 am -
1 stop6h 01m
Deal found 8/9![Delta logo]()
$122
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/96:25 pm -
2 stops14h 59m
Deal found 8/12![American Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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.
Tue 9/1510:17 am -
2 stops29h 00m
Deal found 8/11![Multiple Airlines logo]()
$127
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 12, 2026.
Round-trip from | $186 (American Airlines) |
|---|---|
One-way from | $88 (Faresmojo) |
Popular in | June |
Cheapest in | October |
Average price | $363 |
Good round-trip deal | $456 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 2,558,603 searches. Data last updated August 12, 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
Sat 9/12
10:05 am-6:20 pm
1 stop8h 15m
San Juan Luis Munoz Marin Intl
Tue 9/15
8:20 am-2:45 pm
1 stop6h 25m
$186
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Sat 9/5
1:57 pm-10:29 pm
1 stop8h 32m
San Juan Luis Munoz Marin Intl
Fri 9/11
2:59 pm-12:31 am
1 stop9h 32m
$245
PittsburghSaint Thomas Island
PIT Pittsburgh - STT Saint Thomas Island Cyril E King
PITSTT
Pittsburgh
Tue 1/19
6:00 am-4:15 pm
1 stop9h 15m
Saint Thomas Island Cyril E King
Thu 1/28
3:10 pm-12:19 am
1 stop10h 09m
$270
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Sat 10/3
2:50 pm-10:19 pm
1 stop7h 29m
San Juan Luis Munoz Marin Intl
Sat 10/10
6:45 am-5:04 pm
1 stop10h 19m
$294
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Sun 9/20
6:10 am-12:54 pm
1 stop6h 44m
San Juan Luis Munoz Marin Intl
Fri 9/25
3:56 pm-11:59 pm
1 stop8h 03m
$326
PittsburghSimpson Bay
PIT Pittsburgh - SXM Simpson Bay Princess Juliana
PITSXM
Pittsburgh
Sun 11/1
7:20 pm-3:45 pm
1 stop19h 25m
Simpson Bay Princess Juliana
Sun 11/8
4:45 pm-6:36 pm
1 stop26h 51m
$344
PittsburghNassau
PIT Pittsburgh - NAS Nassau Intl
PITNAS
Pittsburgh
Tue 9/22
6:00 am-1:38 pm
1 stop7h 38m
Nassau Intl
Mon 9/28
10:32 am-11:34 pm
1 stop13h 02m
$351
PittsburghNassau
PIT Pittsburgh - NAS Nassau Intl
PITNAS
Pittsburgh
Sat 10/31
8:00 am-1:48 pm
1 stop5h 48m
Nassau Intl
Sat 11/14
2:40 pm-11:57 pm
1 stop9h 17m
$352
PittsburghSimpson Bay
PIT Pittsburgh - SXM Simpson Bay Princess Juliana
PITSXM
Pittsburgh
Sat 10/31
7:20 pm-3:45 pm
1 stop20h 25m
Simpson Bay Princess Juliana
Wed 11/4
4:45 pm-6:36 pm
1 stop26h 51m
$352
PittsburghNassau
PIT Pittsburgh - NAS Nassau Intl
PITNAS
Pittsburgh
Mon 10/19
8:19 am-5:55 pm
2 stops9h 36m
Nassau Intl
Fri 10/23
2:08 pm-12:31 am
2 stops10h 23m
$354
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-SXM
PIT-NAS
PIT-STT
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-SJU
PIT-SXM
PIT-NAS
PIT-STT
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 $596). 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 August 12, 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.
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
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 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Pittsburgh to Caribbean flights
Consider these flights traveling from Pittsburgh to Caribbean.
Top 7 airlines flying from Pittsburgh to Caribbean
Discover the top 7 airlines that operate flights from Pittsburgh to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$321 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$141 | Average$488 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$168 | Average$510 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$221 | Average$461 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$225 | Average$561 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$231 | Average$640 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$406 | Average$494 | FlexibilityNo cancel fee | On-time67% |