$89+ 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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Nov 9 — Nov 161
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 October 10, 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 October 10, 2026.
This JetBlue deal was found by Cheapflights users on 10/7. 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.
Tue 11/106:00 am -
1 stop7h 05m
Wed 12/23:50 pm -
1 stop6h 40m
Deal found 10/7![JetBlue logo]()
$150
This JetBlue deal was found by Cheapflights users on 10/7. 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.
Tue 11/106:00 am -
1 stop7h 05m
Fri 12/43:50 pm -
1 stop6h 40m
Deal found 10/7![JetBlue logo]()
$152
This JetBlue deal was found by Cheapflights users on 10/7. 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.
Mon 11/166:30 am -
1 stop7h 10m
Wed 12/23:50 pm -
1 stop6h 40m
Deal found 10/7![JetBlue logo]()
$164
This JetBlue deal was found by Cheapflights users on 10/7. 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.
Mon 11/166:30 am -
1 stop7h 10m
Fri 12/43:50 pm -
1 stop6h 40m
Deal found 10/7![JetBlue logo]()
$166
This JetBlue deal was found by Cheapflights users on 10/7. 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.
Tue 11/106:00 am -
1 stop7h 05m
Mon 12/73:30 pm -
1 stop6h 59m
Deal found 10/7![JetBlue logo]()
$169
This JetBlue deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:00 am -
1 stop7h 05m
Thu 12/33:50 pm -
1 stop6h 40m
Deal found 10/6![JetBlue logo]()
$175
This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:27 pm -
1 stop7h 23m
Fri 11/63:55 am -
1 stop14h 37m
Deal found 10/8![Frontier logo]()
$178
This Frontier deal was found by Cheapflights users on 10/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:27 pm -
1 stop7h 19m
Fri 12/47:17 am -
1 stop11h 11m
Deal found 10/7![Frontier logo]()
$180
This FlightHub deal was found by Cheapflights users on 10/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:27 pm -
1 stop14h 48m
Wed 12/23:43 am -
1 stop14h 45m
Deal found 10/8![Frontier logo]()
$183
This FlightHub deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:27 pm -
1 stop7h 19m
Mon 11/167:26 pm -
1 stop23h 06m
Deal found 10/6![Frontier logo]()
$190
This JetBlue deal was found by Cheapflights users on 10/7. 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.
Tue 11/106:00 am -
1 stop7h 05m
Sat 12/55:22 pm -
1 stop7h 34m
Deal found 10/7![JetBlue logo]()
$196
This American Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:45 am -
2 stops10h 54m
Wed 12/212:59 pm -
2 stops9h 18m
Deal found 10/6![American Airlines logo]()
$198
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 October 10, 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 October 10, 2026.
This United Airlines deal was found by Cheapflights users on 10/8. 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 11/136:00 am -
1 stop6h 32m
Fri 12/41:00 pm -
1 stop8h 57m
Deal found 10/8![United Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 10/8. 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.
Mon 11/167:20 am -
1 stop8h 36m
Mon 12/77:00 am -
1 stop11h 01m
Deal found 10/8![Delta logo]()
$256
This JetBlue deal was found by Cheapflights users on 10/9. 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.
Tue 11/106:00 am -
1 stop7h 05m
Mon 12/73:30 pm -
1 stop6h 59m
Deal found 10/9![JetBlue logo]()
$291
This Southwest deal was found by Cheapflights users on 10/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:50 pm -
1 stop6h 20m
Thu 11/1910:45 am -
2 stops9h 05m
Deal found 10/9![Southwest logo]()
$326
This Breeze Airways deal was found by Cheapflights users on 10/7. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/199:24 am -
Nonstop4h 00m
Thu 2/43:24 pm -
Nonstop4h 30m
Deal found 10/7![Breeze Airways logo]()
$347
This American Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/97:07 pm -
1 stop17h 17m
Tue 1/195:29 pm -
2 stops20h 48m
Deal found 10/6![American Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 10/8. 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.
Tue 11/107:20 am -
1 stop8h 36m
Wed 12/27:00 am -
1 stop11h 01m
Deal found 10/8![Delta logo]()
$256
This Air Canada deal was found by Cheapflights users on 10/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/67:20 pm -
2 stops19h 00m
Thu 12/104:45 pm -
1 stop26h 51m
Deal found 10/9![Air Canada logo]()
$543
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/276:00 am -
1 stop6h 32m
Tue 2/27:40 am -
2 stops16h 34m
Deal found 10/6![United Airlines logo]()
$298
This JetBlue deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
1 stop5h 20m
Fri 10/232:25 pm -
1 stop7h 37m
Deal found 10/5![JetBlue logo]()
$316
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:30 am -
2 stops13h 54m
Mon 11/22:05 am -
2 stops14h 14m
Deal found 10/5![United Airlines logo]()
$298
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/155:50 am -
1 stop7h 25m
Sun 11/223:15 pm -
2 stops9h 50m
Deal found 10/5![Southwest logo]()
$331
This Delta deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:45 am -
1 stop6h 09m
Fri 10/233:19 pm -
1 stop6h 49m
Deal found 10/6![Delta logo]()
$316
This JetBlue deal was found by Cheapflights users on 10/7. 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.
Mon 10/196:00 am -
1 stop5h 20m
Sat 10/241:55 pm -
1 stop9h 49m
Deal found 10/7![JetBlue logo]()
$316
This United Airlines deal was found by Cheapflights users on 10/9. 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.
Sun 11/83:15 pm -
1 stop6h 07m
Fri 11/132:05 am -
2 stops11h 56m
Deal found 10/9![United Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/45:20 am -
1 stop8h 55m
Thu 1/75:13 pm -
2 stops17h 35m
Deal found 10/9![American Airlines logo]()
$371
This JetBlue deal was found by Cheapflights users on 10/7. 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 10/246:00 am -
1 stop7h 20m
Tue 11/312:21 pm -
1 stop9h 07m
Deal found 10/7![JetBlue logo]()
$316
This Delta deal was found by Cheapflights users on 10/8. 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.
Tue 12/156:00 am -
1 stop9h 36m
Wed 12/305:29 pm -
1 stop4h 57m
Deal found 10/8![Delta logo]()
$336
This American Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/56:11 am -
1 stop7h 02m
Wed 2/106:05 pm -
2 stops16h 14m
Deal found 10/6![American Airlines logo]()
$393
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/86:00 am -
1 stop7h 40m
Fri 2/128:05 am -
2 stops9h 52m
Deal found 10/5![United Airlines logo]()
$326
This JetBlue deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:00 am -
1 stop7h 51m
Sat 11/1412:21 pm -
1 stop9h 07m
Deal found 10/5![JetBlue logo]()
$333
This Delta deal was found by Cheapflights users on 10/8. 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.
Sun 12/207:05 am -
1 stop6h 23m
Wed 12/302:53 pm -
1 stop7h 33m
Deal found 10/8![Delta logo]()
$336
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:35 am -
1 stop6h 25m
Wed 11/113:25 pm -
1 stop6h 15m
Deal found 10/6![Southwest logo]()
$408
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/56:16 am -
1 stop9h 24m
Tue 1/125:35 pm -
1 stop17h 03m
Deal found 10/5![United Airlines logo]()
$328
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Tue 2/167:30 pm -
2 stops17h 06m
Tue 2/234:14 pm -
2 stops18h 05m
Deal found 10/8![American Airlines logo]()
$402
This Delta deal was found by Cheapflights users on 10/8. 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 11/146:00 am -
1 stop7h 47m
Wed 11/184:05 pm -
1 stop9h 41m
Deal found 10/8![Delta logo]()
$356
This JetBlue deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:00 am -
1 stop8h 11m
Wed 12/24:32 pm -
1 stop8h 24m
Deal found 10/5![JetBlue logo]()
$359
This American Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:49 pm -
2 stops19h 37m
Sun 11/85:33 pm -
2 stops20h 40m
Deal found 10/7![American Airlines logo]()
$413
This United Airlines deal was found by Cheapflights users on 10/8. 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.
Thu 1/77:00 am -
1 stop8h 50m
Mon 1/115:50 pm -
1 stop6h 38m
Deal found 10/8![United Airlines logo]()
$348
This Delta deal was found by Cheapflights users on 10/9. 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.
Fri 11/137:20 am -
1 stop8h 36m
Mon 12/76:59 pm -
1 stop6h 47m
Deal found 10/9![Delta logo]()
$363
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated October 10, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated October 10, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:27 pm -
1 stop7h 23m
Fri 11/63:55 am -
1 stop14h 37m
Deal found 10/8![Frontier logo]()
$178
This JetBlue deal was found by Cheapflights users on 10/7. 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.
Tue 11/106:00 am -
1 stop7h 05m
Wed 12/23:50 pm -
1 stop6h 40m
Deal found 10/7![JetBlue logo]()
$150
This JetBlue deal was found by Cheapflights users on 10/7. 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.
Tue 11/106:00 am -
1 stop7h 05m
Fri 12/43:50 pm -
1 stop6h 40m
Deal found 10/7![JetBlue logo]()
$152
This JetBlue deal was found by Cheapflights users on 10/7. 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.
Tue 11/106:00 am -
1 stop7h 05m
Mon 12/73:30 pm -
1 stop6h 59m
Deal found 10/7![JetBlue logo]()
$169
This JetBlue deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:00 am -
1 stop7h 05m
Thu 12/33:50 pm -
1 stop6h 40m
Deal found 10/6![JetBlue logo]()
$175
This JetBlue deal was found by Cheapflights users on 10/7. 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.
Tue 11/106:00 am -
1 stop7h 05m
Sat 12/55:22 pm -
1 stop7h 34m
Deal found 10/7![JetBlue logo]()
$196
This American Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:45 am -
2 stops10h 54m
Wed 12/212:59 pm -
2 stops9h 18m
Deal found 10/6![American Airlines logo]()
$198
This Frontier deal was found by Cheapflights users on 10/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:27 pm -
1 stop7h 19m
Fri 12/47:17 am -
1 stop11h 11m
Deal found 10/7![Frontier logo]()
$180
This FlightHub deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:27 pm -
1 stop7h 19m
Mon 11/167:26 pm -
1 stop23h 06m
Deal found 10/6![Frontier logo]()
$190
This FlightHub deal was found by Cheapflights users on 10/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:27 pm -
1 stop14h 48m
Wed 12/23:43 am -
1 stop14h 45m
Deal found 10/8![Frontier logo]()
$183
This JetBlue deal was found by Cheapflights users on 10/7. 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.
Mon 11/166:30 am -
1 stop7h 10m
Wed 12/23:50 pm -
1 stop6h 40m
Deal found 10/7![JetBlue logo]()
$164
This JetBlue deal was found by Cheapflights users on 10/7. 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.
Mon 11/166:30 am -
1 stop7h 10m
Fri 12/43:50 pm -
1 stop6h 40m
Deal found 10/7![JetBlue logo]()
$166
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 October 10, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.
This Super.com deal was found by Cheapflights users on 10/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:27 pm -
1 stop7h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Frontier logo]()
$89
This Cheapflightsfares deal was found by Cheapflights users on 10/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:27 pm -
1 stop14h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$90
This United Airlines deal was found by Cheapflights users on 10/9. 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 11/246:00 am -
1 stop5h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![United Airlines logo]()
$99
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:00 am -
1 stop9h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![United Airlines logo]()
$99
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/77:10 am -
1 stop15h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![American Airlines logo]()
$103
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Mon 2/87:01 pm -
1 stop13h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![American Airlines logo]()
$109
This Priceline deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:27 pm -
1 stop14h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Frontier logo]()
$111
This United Airlines deal was found by Cheapflights users on 10/8. 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.
Wed 1/66:16 am -
2 stops10h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![United Airlines logo]()
$117
This American Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/18:19 pm -
1 stop16h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![American Airlines logo]()
$118
This Expedia deal was found by Cheapflights users on 10/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:27 pm -
1 stop7h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$121
This JetBlue deal was found by Cheapflights users on 10/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/156:00 am -
1 stop7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![JetBlue logo]()
$124
This Delta deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/131:35 pm -
1 stop8h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Delta logo]()
$128
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 October 10, 2026.
Round-trip from | $150 (JetBlue) |
|---|---|
One-way from | $89 (Super.com) |
Popular in | June |
Cheapest in | September |
Average price | $370 |
Good round-trip deal | $543 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 October 10, 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 11/7
6:27 pm-2:46 am
1 stop7h 19m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$90
PittsburghNassau
PIT Pittsburgh - NAS Nassau Intl
PITNAS
Pittsburgh
Tue 11/24
6:00 am-11:49 am
1 stop5h 49m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$99
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Sat 10/31
6:00 am-3:36 pm
1 stop9h 36m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$99
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Thu 10/29
8:49 am-9:22 pm
2 stops12h 33m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$99
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
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$99
PittsburghSaint Thomas Island
PIT Pittsburgh - STT Saint Thomas Island Cyril E King
PITSTT
Pittsburgh
Wed 1/6
10:19 am-5:50 pm
1 stop6h 31m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$117
PittsburghSimpson Bay
PIT Pittsburgh - SXM Simpson Bay Princess Juliana
PITSXM
Pittsburgh
Sun 11/1
8:19 pm-1:26 pm
1 stop16h 07m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
PittsburghOranjestad
PIT Pittsburgh - AUA Oranjestad Reina Beatrix
PITAUA
Pittsburgh
Tue 12/15
6:00 am-2:35 pm
1 stop7h 35m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$124
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Sun 12/13
1:35 pm-11:13 pm
1 stop8h 38m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$128
PittsburghPunta Cana
PIT Pittsburgh - PUJ Punta Cana
PITPUJ
Pittsburgh
Sun 11/8
6:00 am-3:26 pm
1 stop8h 26m
Punta Cana
Wed 12/31
12:00 am-11:30 pm
Nonstop0h 00m
$134
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Pittsburgh to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Pittsburgh with our price prediction graph.
PIT-SJU
PIT-NAS
PIT-SXM
PIT-AUA
PIT-PUJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Pittsburgh to Caribbean
PIT-0CB
PIT-SJU
PIT-NAS
PIT-SXM
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 $407). Flying from Pittsburgh to Caribbean in November is currently the most expensive (average of $631). 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 October 10, 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
Entertainment
7.4
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Entertainment
7.4
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Entertainment
7.4
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Entertainment
7.4
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Entertainment
7.4
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Entertainment
7.4
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
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.
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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 October 10, 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 October 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$321 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$141 | Average$491 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$506 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$218 | Average$474 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$222 | Average$556 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$255 | Average$647 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$386 | Average$456 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$404 | Average$494 | FlexibilityNo cancel fee | On-time67% |