$93+ Cheap flights from Pittsburgh (PIT) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Oct 9 — Oct 161
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Pittsburgh to Caribbean
Cheapest
Best
Last-minute
One-way
Cheapest flights from Pittsburgh to CaribbeanExplore the most affordable flight options available from Pittsburgh to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 9, 2026.
Explore the most affordable flight options available from Pittsburgh to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 9, 2026.
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Tue 10/276:00 am -
1 stop9h 23m
Tue 11/311:35 am -
1 stop12h 22m
Deal found 9/5![American Airlines logo]()
$186
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Sat 10/246:00 am -
1 stop16h 57m
Wed 10/286:20 am -
2 stops9h 45m
Deal found 9/5![American Airlines logo]()
$190
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Wed 10/145:00 am -
1 stop6h 20m
Wed 10/216:20 am -
1 stop17h 15m
Deal found 9/5![American Airlines logo]()
$191
This Priceline deal was found by Cheapflights users on 9/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/302:42 pm -
1 stop27h 01m
Mon 10/510:42 am -
1 stop27h 05m
Deal found 9/6![Frontier logo]()
$202
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Sat 9/266:22 am -
2 stops14h 25m
Wed 9/303:41 pm -
1 stop7h 13m
Deal found 9/5![American Airlines logo]()
$221
This American Airlines deal was found by Cheapflights users on 9/6. 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 10/136:00 am -
1 stop7h 37m
Sun 10/186:30 am -
1 stop17h 05m
Deal found 9/6![American Airlines logo]()
$223
This Priceline deal was found by Cheapflights users on 9/5. 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.
Wed 9/302:42 pm -
1 stop11h 10m
Fri 10/22:57 am -
1 stop10h 50m
Deal found 9/5![Frontier logo]()
$239
This deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:32 pm -
1 stop8h 41m
Sun 9/272:57 am -
1 stop10h 50m
Deal found 9/4![Frontier logo]()
$241
This Priceline deal was found by Cheapflights users on 9/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:51 pm -
1 stop18h 45m
Mon 10/267:44 pm -
1 stop21h 48m
Deal found 9/7![Frontier logo]()
$247
This Priceline deal was found by Cheapflights users on 9/5. 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 9/222:42 pm -
1 stop11h 10m
Fri 9/252:57 am -
1 stop10h 50m
Deal found 9/5![Frontier logo]()
$253
This United Airlines deal was found by Cheapflights users on 9/5. 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 9/264:15 pm -
1 stop7h 35m
Wed 9/301:25 pm -
1 stop8h 11m
Deal found 9/5![United Airlines logo]()
$256
This American Airlines deal was found by Cheapflights users on 9/8. 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 10/195:00 am -
1 stop6h 20m
Fri 10/236:26 pm -
1 stop5h 09m
Deal found 9/8![American Airlines logo]()
$306
Best flights from Pittsburgh to CaribbeanDiscover carefully curated flight deals from Pittsburgh to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 9, 2026.
Discover carefully curated flight deals from Pittsburgh to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 9, 2026.
This United Airlines deal was found by Cheapflights users on 9/5. 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 10/207:30 am -
1 stop6h 15m
Tue 11/172:35 pm -
2 stops9h 55m
Deal found 9/5![United Airlines logo]()
$260
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Tue 1/195:29 pm -
2 stops17h 44m
Thu 1/284:55 pm -
2 stops18h 25m
Deal found 9/9![American Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 9/9. 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 10/197:45 am -
1 stop6h 09m
Sat 10/244:53 pm -
1 stop7h 53m
Deal found 9/9![Delta logo]()
$343
This Air Canada deal was found by Cheapflights users on 9/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:20 pm -
1 stop20h 05m
Mon 11/235:25 pm -
1 stop26h 11m
Deal found 9/5![Air Canada logo]()
$357
This Southwest deal was found by Cheapflights users on 9/9. 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.
Wed 9/2310:10 am -
2 stops11h 00m
Sat 9/265:05 am -
1 stop7h 35m
Deal found 9/9![Southwest logo]()
$374
This JetBlue deal was found by Cheapflights users on 9/7. 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.
Sun 12/67:40 am -
1 stop8h 01m
Sat 12/122:00 pm -
1 stop10h 59m
Deal found 9/7![JetBlue logo]()
$374
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3110:49 am -
2 stops10h 33m
Mon 11/22:35 pm -
1 stop7h 12m
Deal found 9/4![United Airlines logo]()
$260
This Flysmarter deal was found by Cheapflights users on 9/8. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:00 am -
2 stops9h 12m
Thu 11/55:46 pm -
2 stops17h 32m
Deal found 9/8![British Airways logo]()
$584
This Breeze Airways deal was found by Cheapflights users on 9/5. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/79:24 am -
Nonstop4h 00m
Sun 3/142:24 pm -
Nonstop4h 30m
Deal found 9/5![Breeze Airways logo]()
$607
This American Airlines deal was found by Cheapflights users on 9/7. 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 10/286:00 am -
2 stops10h 02m
Wed 11/45:16 pm -
1 stop6h 44m
Deal found 9/7![American Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 9/6. 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.
Fri 10/305:50 am -
1 stop8h 04m
Tue 11/104:58 pm -
1 stop7h 48m
Deal found 9/6![Delta logo]()
$346
This JetBlue deal was found by Cheapflights users on 9/9. 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.
Sun 10/186:30 am -
1 stop6h 53m
Tue 10/271:10 pm -
1 stop8h 18m
Deal found 9/9![JetBlue logo]()
$374
This United Airlines deal was found by Cheapflights users on 9/7. 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 10/276:12 am -
2 stops14h 12m
Tue 11/38:05 am -
2 stops11h 14m
Deal found 9/7![United Airlines logo]()
$350
This American Airlines deal was found by Cheapflights users on 9/6. 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 9/196:33 pm -
2 stops15h 09m
Fri 9/252:34 pm -
2 stops9h 02m
Deal found 9/6![American Airlines logo]()
$353
This Air Canada deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:20 pm -
1 stop17h 05m
Thu 10/291:20 pm -
1 stop29h 16m
Deal found 9/4![Air Canada logo]()
$391
This Southwest deal was found by Cheapflights users on 9/9. 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.
Wed 3/311:30 am -
2 stops9h 30m
Mon 3/86:45 am -
1 stop11h 15m
Deal found 9/9![Southwest logo]()
$403
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:00 am -
1 stop8h 03m
Wed 11/186:12 pm -
1 stop6h 34m
Deal found 9/4![Delta logo]()
$382
This United Airlines deal was found by Cheapflights users on 9/6. 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.
Sun 12/66:10 am -
2 stops14h 14m
Wed 12/92:05 am -
2 stops13h 58m
Deal found 9/6![United Airlines logo]()
$350
This JetBlue deal was found by Cheapflights users on 9/6. 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.
Mon 10/266:00 am -
1 stop7h 30m
Fri 10/301:10 pm -
1 stop8h 18m
Deal found 9/6![JetBlue logo]()
$391
This American Airlines deal was found by Cheapflights users on 9/8. 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.
Sat 10/36:33 pm -
1 stop19h 06m
Sat 10/1012:18 pm -
1 stop6h 58m
Deal found 9/8![American Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 9/7. 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.
Thu 10/84:20 pm -
2 stops9h 05m
Wed 10/146:35 am -
2 stops10h 10m
Deal found 9/7![Southwest logo]()
$413
This Delta deal was found by Cheapflights users on 9/8. 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 11/156:00 am -
1 stop10h 57m
Sat 11/216:12 pm -
1 stop6h 34m
Deal found 9/8![Delta logo]()
$382
This United Airlines deal was found by Cheapflights users on 9/6. 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.
Fri 10/308:00 pm -
2 stops15h 49m
Tue 11/1012:55 pm -
1 stop6h 07m
Deal found 9/6![United Airlines logo]()
$360
This American Airlines deal was found by Cheapflights users on 9/8. 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.
Sun 9/136:00 am -
1 stop5h 40m
Thu 9/1710:32 am -
1 stop13h 02m
Deal found 9/8![American Airlines logo]()
$365
This JetBlue deal was found by Cheapflights users on 9/8. 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.
Mon 11/166:30 am -
1 stop7h 13m
Tue 11/244:05 pm -
1 stop8h 47m
Deal found 9/8![JetBlue logo]()
$429
This Southwest deal was found by Cheapflights users on 9/5. 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.
Thu 1/712:55 pm -
1 stop8h 05m
Sat 1/166:10 am -
2 stops10h 15m
Deal found 9/5![Southwest logo]()
$432
This United Airlines deal was found by Cheapflights users on 9/7. 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 11/278:00 pm -
2 stops15h 49m
Wed 12/22:55 pm -
2 stops8h 27m
Deal found 9/7![United Airlines logo]()
$364
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Wed 10/216:00 am -
1 stop7h 23m
Wed 10/284:39 pm -
2 stops17h 25m
Deal found 9/6![American Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 9/7. 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.
Mon 2/87:20 am -
1 stop8h 00m
Fri 2/126:06 pm -
1 stop7h 13m
Deal found 9/7![Delta logo]()
$410
This JetBlue deal was found by Cheapflights users on 9/9. 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.
Sat 10/249:07 am -
1 stop7h 33m
Mon 11/23:40 pm -
1 stop6h 48m
Deal found 9/9![JetBlue logo]()
$438
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated September 9, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated September 9, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 9/5. 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 9/222:42 pm -
1 stop11h 10m
Fri 9/252:57 am -
1 stop10h 50m
Deal found 9/5![Frontier logo]()
$253
This deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:32 pm -
1 stop8h 41m
Sun 9/272:57 am -
1 stop10h 50m
Deal found 9/4![Frontier logo]()
$241
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Sat 9/266:22 am -
2 stops14h 25m
Wed 9/303:41 pm -
1 stop7h 13m
Deal found 9/5![American Airlines logo]()
$221
This United Airlines deal was found by Cheapflights users on 9/5. 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 9/264:15 pm -
1 stop7h 35m
Wed 9/301:25 pm -
1 stop8h 11m
Deal found 9/5![United Airlines logo]()
$256
This Priceline deal was found by Cheapflights users on 9/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/302:42 pm -
1 stop27h 01m
Mon 10/510:42 am -
1 stop27h 05m
Deal found 9/6![Frontier logo]()
$202
This Priceline deal was found by Cheapflights users on 9/5. 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.
Wed 9/302:42 pm -
1 stop11h 10m
Fri 10/22:57 am -
1 stop10h 50m
Deal found 9/5![Frontier logo]()
$239
This American Airlines deal was found by Cheapflights users on 9/6. 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 10/136:00 am -
1 stop7h 37m
Sun 10/186:30 am -
1 stop17h 05m
Deal found 9/6![American Airlines logo]()
$223
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Wed 10/145:00 am -
1 stop6h 20m
Wed 10/216:20 am -
1 stop17h 15m
Deal found 9/5![American Airlines logo]()
$191
This American Airlines deal was found by Cheapflights users on 9/8. 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 10/195:00 am -
1 stop6h 20m
Fri 10/236:26 pm -
1 stop5h 09m
Deal found 9/8![American Airlines logo]()
$306
This Priceline deal was found by Cheapflights users on 9/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:51 pm -
1 stop18h 45m
Mon 10/267:44 pm -
1 stop21h 48m
Deal found 9/7![Frontier logo]()
$247
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Sat 10/246:00 am -
1 stop16h 57m
Wed 10/286:20 am -
2 stops9h 45m
Deal found 9/5![American Airlines logo]()
$190
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Tue 10/276:00 am -
1 stop9h 23m
Tue 11/311:35 am -
1 stop12h 22m
Deal found 9/5![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 September 9, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 9, 2026.
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Sat 10/315:00 am -
1 stop6h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$93
This American Airlines deal was found by Cheapflights users on 9/7. 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 11/1810:45 am -
2 stops10h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$100
This CheapOair deal was found by Cheapflights users on 9/7. 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 CheapOair 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 9/7![Frontier logo]()
$102
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/308:00 am -
1 stop5h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![American Airlines logo]()
$107
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Sun 11/85:00 am -
1 stop6h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![American Airlines logo]()
$118
This United Airlines deal was found by Cheapflights users on 9/8. 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.
Sat 11/148:49 am -
2 stops12h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![United Airlines logo]()
$130
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Sat 1/96:04 pm -
2 stops17h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$134
This American Airlines deal was found by Cheapflights users on 9/5. 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 11/18:19 pm -
1 stop16h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$134
This American Airlines deal was found by Cheapflights users on 9/7. 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 11/46:00 am -
2 stops9h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$136
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Mon 11/308:29 pm -
2 stops17h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$137
This American Airlines deal was found by Cheapflights users on 9/5. 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 11/295:43 pm -
1 stop19h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$143
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Sat 2/66:04 pm -
2 stops17h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$143
Find flight deals from Pittsburgh to Caribbean
Keep the following information in mind while searching for Pittsburgh to Caribbean flight deals. Data was last updated September 9, 2026.
Round-trip from | $186 (American Airlines) |
|---|---|
One-way from | $93 (American Airlines) |
Popular in | June |
Cheapest in | September |
Average price | $309 |
Good round-trip deal | $690 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Pittsburgh to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 9, 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
PittsburghGeorge Town
PIT Pittsburgh - GCM George Town Owen Roberts Intl
PITGCM
Pittsburgh
Sun 11/8
5:00 am-11:23 am
1 stop6h 23m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$118
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Sat 11/14
8:49 am-10:22 pm
2 stops12h 33m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Sun 1/24
6:04 pm-6:15 am
2 stops11h 11m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
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
$134
PittsburghOranjestad
PIT Pittsburgh - AUA Oranjestad Reina Beatrix
PITAUA
Pittsburgh
Mon 11/30
8:29 pm-3:13 pm
2 stops17h 44m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$137
PittsburghOranjestad
PIT Pittsburgh - AUA Oranjestad Reina Beatrix
PITAUA
Pittsburgh
Sun 11/29
5:43 pm-2:33 pm
1 stop19h 50m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$143
PittsburghSaint Thomas Island
PIT Pittsburgh - STT Saint Thomas Island Cyril E King
PITSTT
Pittsburgh
Sat 2/6
6:04 pm-12:13 pm
2 stops17h 09m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$143
PittsburghNassau
PIT Pittsburgh - NAS Nassau Intl
PITNAS
Pittsburgh
Sun 11/29
7:20 pm-11:30 am
1 stop16h 10m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$151
PittsburghSan Juan
PIT Pittsburgh - SJU San Juan Luis Munoz Marin Intl
PITSJU
Pittsburgh
Thu 9/17
2:32 pm-1:52 am
1 stop11h 20m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$152
PittsburghOranjestad
PIT Pittsburgh - AUA Oranjestad Reina Beatrix
PITAUA
Pittsburgh
Wed 12/2
7:20 pm-4:30 pm
1 stop20h 10m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$152
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-GCM
PIT-SXM
PIT-AUA
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-GCM
PIT-SXM
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 $612). 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 September 9, 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.
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Related info for your journey
Find useful and relevant information for your journey from Pittsburgh to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top countries
Top destinations
Alternative routes for Pittsburgh to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Pittsburgh to Caribbean by cabin class
Find flights from Pittsburgh to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Pittsburgh and Caribbean flights
Browse other Pittsburgh and Caribbean flight options. Last updated on September 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Pittsburgh to Caribbean flights
Consider these flights traveling from Pittsburgh to Caribbean.
Top 7 airlines flying from Pittsburgh to Caribbean
Discover the top 7 airlines that operate flights from Pittsburgh to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$321 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$528 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$184 | Average$513 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$218 | Average$463 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$222 | Average$574 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$240 | Average$643 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$404 | Average$494 | FlexibilityNo cancel fee | On-time67% |