$93+ Cheap flights from Pittsburgh (PIT) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SJU
Mar 14 — Mar 211
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 February 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 February 12, 2026.
This Priceline deal was found by Cheapflights users on 2/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:31 pm
PIT
- SJU
1 stop27h 23m
Frontier
Thu 2/263:53 am
SJU
- PIT
1 stop7h 41m
Frontier
Deal found 2/11![Frontier logo]()
$213
This Delta deal was found by Cheapflights users on 2/9. 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 5/36:30 am
PIT
- SJU
1 stop6h 22m
Delta
Mon 5/116:15 am
SJU
- PIT
1 stop9h 19m
Delta
Deal found 2/9![Delta logo]()
$216
This United Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/2412:24 pm
PIT
- SJU
2 stops8h 58m
United Airlines
Thu 2/262:05 am
SJU
- PIT
1 stop9h 08m
United Airlines
Deal found 2/10![United Airlines logo]()
$222
This United Airlines deal was found by Cheapflights users on 2/9. 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.
Fri 10/26:20 am
PIT
- SJU
2 stops14h 18m
United Airlines
Tue 10/64:55 pm
SJU
- PIT
1 stop6h 27m
United Airlines
Deal found 2/9![United Airlines logo]()
$223
This Delta deal was found by Cheapflights users on 2/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/92:11 pm
PIT
- SJU
1 stop8h 06m
Delta
Sat 5/165:15 pm
SJU
- PIT
1 stop7h 30m
Delta
Deal found 2/11![Delta logo]()
$226
This Priceline deal was found by Cheapflights users on 2/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:00 am
PIT
- SJU
1 stop6h 29m
Multiple Airlines
Sat 2/285:25 pm
SJU
- PIT
1 stop17h 16m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$227
This United Airlines deal was found by Cheapflights users on 2/11. 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.
Mon 4/137:20 am
PIT
- SJU
1 stop6h 25m
United Airlines
Thu 4/161:00 am
SJU
- PIT
2 stops8h 34m
United Airlines
Deal found 2/11![United Airlines logo]()
$231
This American Airlines deal was found by Cheapflights users on 2/9. 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 3/26:00 am
PIT
- SJU
1 stop16h 40m
American Airlines
Fri 3/65:02 pm
SJU
- PIT
1 stop6h 29m
American Airlines
Deal found 2/9![American Airlines logo]()
$232
This CheapOair deal was found by Cheapflights users on 2/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:40 pm
PIT
- SJU
1 stop6h 21m
Multiple Airlines
Mon 4/1311:59 pm
SJU
- PIT
1 stop9h 40m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$233
This Frontier deal was found by Cheapflights users on 2/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1812:44 pm
PIT
- SJU
1 stop13h 17m
Frontier
Fri 5/13:08 am
SJU
- PIT
1 stop8h 51m
Frontier
Deal found 2/11![Frontier logo]()
$234
This Cheapflightsfares deal was found by Cheapflights users on 2/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:00 am
PIT
- STT
1 stop9h 34m
Spirit Airlines
Wed 4/294:40 pm
STT
- PIT
1 stop7h 02m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$234
This American Airlines deal was found by Cheapflights users on 2/9. 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 2/166:00 am
PIT
- SJU
1 stop16h 40m
American Airlines
Wed 2/257:00 am
SJU
- PIT
1 stop12h 31m
American Airlines
Deal found 2/9![American Airlines logo]()
$237
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 February 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 February 12, 2026.
This Delta deal was found by Cheapflights users on 2/9. 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.
Sat 5/92:11 pm
PIT
- SJU
1 stop8h 06m
Delta
Sat 5/162:20 pm
SJU
- PIT
1 stop10h 25m
Delta
Deal found 2/9![Delta logo]()
$216
This United Airlines deal was found by Cheapflights users on 2/10. 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.
Mon 2/233:00 pm
PIT
- SJU
1 stop6h 22m
United Airlines
Tue 2/242:05 am
SJU
- PIT
2 stops12h 04m
United Airlines
Deal found 2/10![United Airlines logo]()
$222
This JetBlue deal was found by Cheapflights users on 2/8. 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 3/26:00 am
PIT
- CUR
1 stop7h 47m
JetBlue
Wed 3/43:54 pm
CUR
- PIT
1 stop8h 55m
JetBlue
Deal found 2/8![JetBlue logo]()
$258
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Mon 4/137:57 pm
PIT
- CUR
2 stops17h 44m
American Airlines
Sat 4/183:48 pm
CUR
- PIT
2 stops18h 27m
American Airlines
Deal found 2/10![American Airlines logo]()
$283
This Mytrip deal was found by Cheapflights users on 2/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/95:45 am
PIT
- STT
1 stop7h 46m
Spirit Airlines
Tue 3/174:35 pm
STT
- PIT
3 stops30h 20m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$288
This Southwest deal was found by Cheapflights users on 2/11. 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.
Mon 5/115:45 am
PIT
- PUJ
1 stop6h 55m
Southwest
Fri 5/152:05 pm
PUJ
- PIT
1 stop9h 15m
Southwest
Deal found 2/11![Southwest logo]()
$329
This Air Canada deal was found by Cheapflights users on 2/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:55 pm
PIT
- NAS
1 stop19h 00m
Air Canada
Tue 4/149:10 pm
NAS
- PIT
1 stop20h 08m
Air Canada
Deal found 2/11![Air Canada logo]()
$352
This United Airlines deal was found by Cheapflights users on 2/10. 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.
Wed 5/1310:55 am
PIT
- SJU
1 stop9h 39m
United Airlines
Wed 5/207:20 am
SJU
- PIT
1 stop6h 42m
United Airlines
Deal found 2/10![United Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 2/10. 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.
Wed 5/1311:57 am
PIT
- SJU
1 stop10h 20m
Delta
Fri 5/222:20 pm
SJU
- PIT
1 stop10h 25m
Delta
Deal found 2/10![Delta logo]()
$226
This United Airlines deal was found by Cheapflights users on 2/9. 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 5/127:20 am
PIT
- SJU
1 stop6h 25m
United Airlines
Thu 5/141:00 am
SJU
- PIT
2 stops8h 31m
United Airlines
Deal found 2/9![United Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 2/10. 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 5/1211:57 am
PIT
- SJU
1 stop10h 20m
Delta
Thu 5/212:30 pm
SJU
- PIT
1 stop8h 08m
Delta
Deal found 2/10![Delta logo]()
$226
This United Airlines deal was found by Cheapflights users on 2/11. 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.
Wed 5/1310:55 am
PIT
- SJU
1 stop9h 39m
United Airlines
Sat 5/237:20 am
SJU
- PIT
1 stop6h 36m
United Airlines
Deal found 2/11![United Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 2/10. 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.
Wed 5/1311:57 am
PIT
- SJU
1 stop10h 20m
Delta
Thu 5/212:30 pm
SJU
- PIT
1 stop8h 08m
Delta
Deal found 2/10![Delta logo]()
$226
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Wed 3/116:22 am
PIT
- CUR
1 stop7h 41m
American Airlines
Mon 3/164:41 pm
CUR
- PIT
2 stops20h 18m
American Airlines
Deal found 2/9![American Airlines logo]()
$283
This United Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/2412:24 pm
PIT
- SJU
2 stops8h 58m
United Airlines
Wed 2/252:05 am
SJU
- PIT
1 stop9h 08m
United Airlines
Deal found 2/10![United Airlines logo]()
$222
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Sat 4/117:35 pm
PIT
- CUR
2 stops18h 57m
American Airlines
Fri 4/172:42 pm
CUR
- PIT
2 stops19h 01m
American Airlines
Deal found 2/9![American Airlines logo]()
$283
This United Airlines deal was found by Cheapflights users on 2/11. 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.
Sat 2/2112:30 pm
PIT
- SJU
2 stops8h 52m
United Airlines
Thu 2/262:05 am
SJU
- PIT
1 stop9h 08m
United Airlines
Deal found 2/11![United Airlines logo]()
$222
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Fri 3/205:10 pm
PIT
- CUR
2 stops20h 25m
American Airlines
Thu 3/262:35 pm
CUR
- PIT
1 stop8h 11m
American Airlines
Deal found 2/9![American Airlines logo]()
$283
This JetBlue deal was found by Cheapflights users on 2/8. 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 3/26:00 am
PIT
- PLS
1 stop8h 07m
JetBlue
Wed 3/43:12 pm
PLS
- PIT
1 stop8h 37m
JetBlue
Deal found 2/8![JetBlue logo]()
$345
This Air Canada deal was found by Cheapflights users on 2/10. 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.
Wed 2/255:55 pm
PIT
- NAS
1 stop26h 15m
Air Canada
Wed 3/49:10 pm
NAS
- PIT
1 stop20h 04m
Air Canada
Deal found 2/10![Air Canada logo]()
$354
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Sun 5/107:39 pm
PIT
- CUR
2 stops18h 02m
American Airlines
Wed 5/202:42 pm
CUR
- PIT
1 stop9h 14m
American Airlines
Deal found 2/11![American Airlines logo]()
$283
This Delta deal was found by Cheapflights users on 2/9. 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.
Wed 5/66:00 am
PIT
- STT
1 stop8h 48m
Delta
Wed 5/133:00 pm
STT
- PIT
1 stop9h 45m
Delta
Deal found 2/9![Delta logo]()
$286
This Air Canada deal was found by Cheapflights users on 2/9. 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.
Mon 3/25:55 pm
PIT
- NAS
1 stop26h 15m
Air Canada
Wed 3/49:10 pm
NAS
- PIT
1 stop20h 04m
Air Canada
Deal found 2/9![Air Canada logo]()
$362
This American Airlines deal was found by Cheapflights users on 2/10. 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 4/117:12 pm
PIT
- CUR
2 stops19h 20m
American Airlines
Sat 4/183:48 pm
CUR
- PIT
2 stops19h 16m
American Airlines
Deal found 2/10![American Airlines logo]()
$283
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 5/57:05 am
PIT
- STT
1 stop7h 43m
Delta
Wed 5/133:00 pm
STT
- PIT
1 stop9h 45m
Delta
Deal found 2/9![Delta logo]()
$286
This Air Canada deal was found by Cheapflights users on 2/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/165:55 pm
PIT
- PLS
2 stops23h 45m
Air Canada
Mon 2/236:40 pm
PLS
- PIT
2 stops22h 34m
Air Canada
Deal found 2/11![Air Canada logo]()
$362
This United Airlines deal was found by Cheapflights users on 2/9. 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.
Fri 4/107:00 am
PIT
- STT
1 stop8h 31m
United Airlines
Fri 4/171:22 pm
STT
- PIT
1 stop10h 04m
United Airlines
Deal found 2/9![United Airlines logo]()
$286
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Wed 3/116:00 am
PIT
- STT
2 stops8h 54m
American Airlines
Wed 3/1812:02 pm
STT
- PIT
1 stop11h 57m
American Airlines
Deal found 2/9![American Airlines logo]()
$286
This Delta deal was found by Cheapflights users on 2/10. 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.
Thu 3/196:00 am
PIT
- STT
1 stop8h 45m
Delta
Wed 3/2512:49 pm
STT
- PIT
1 stop11h 28m
Delta
Deal found 2/10![Delta logo]()
$296
This Air Canada deal was found by Cheapflights users on 2/9. 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.
Mon 5/116:00 am
PIT
- NAS
1 stop11h 30m
Air Canada
Thu 5/141:35 pm
NAS
- PIT
1 stop25h 13m
Air Canada
Deal found 2/9![Air Canada logo]()
$364
Last-minute flights from Pittsburgh to CaribbeanDiscover last-minute flight deals from Pittsburgh to Caribbean. Data last updated February 12, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Caribbean. Data last updated February 12, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/9. 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 2/166:00 am
PIT
- SJU
1 stop16h 40m
American Airlines
Wed 2/257:00 am
SJU
- PIT
1 stop12h 31m
American Airlines
Deal found 2/9![American Airlines logo]()
$237
This Priceline deal was found by Cheapflights users on 2/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:31 pm
PIT
- SJU
1 stop27h 23m
Frontier
Thu 2/263:53 am
SJU
- PIT
1 stop7h 41m
Frontier
Deal found 2/11![Frontier logo]()
$213
This CheapOair deal was found by Cheapflights users on 2/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
PIT
- SJU
1 stop8h 31m
Multiple Airlines
Sat 2/285:25 pm
SJU
- PIT
1 stop17h 16m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$216
This Cheapflightsfares deal was found by Cheapflights users on 2/9. 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 2/236:00 am
PIT
- STT
1 stop9h 34m
Spirit Airlines
Fri 2/275:40 pm
STT
- PIT
1 stop7h 19m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$238
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/232:19 pm
PIT
- SJU
1 stop11h 34m
Frontier
Sat 2/285:25 pm
SJU
- PIT
1 stop17h 16m
Frontier
Deal found 2/10![Frontier logo]()
$245
This United Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 2/2412:24 pm
PIT
- SJU
2 stops8h 58m
United Airlines
Thu 2/262:05 am
SJU
- PIT
1 stop9h 08m
United Airlines
Deal found 2/10![United Airlines logo]()
$222
This Priceline deal was found by Cheapflights users on 2/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:00 am
PIT
- SJU
1 stop6h 29m
Multiple Airlines
Sat 2/285:25 pm
SJU
- PIT
1 stop17h 16m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$227
This Mytrip deal was found by Cheapflights users on 2/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:00 am
PIT
- SJU
3 stops27h 17m
Spirit Airlines
Thu 2/264:36 pm
SJU
- PIT
1 stop8h 23m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$243
This American Airlines deal was found by Cheapflights users on 2/9. 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 3/26:00 am
PIT
- SJU
1 stop16h 40m
American Airlines
Fri 3/65:02 pm
SJU
- PIT
1 stop6h 29m
American Airlines
Deal found 2/9![American Airlines logo]()
$232
This Delta deal was found by Cheapflights users on 2/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/311:20 am
PIT
- SJU
1 stop11h 36m
Delta
Tue 3/106:15 am
SJU
- PIT
1 stop6h 22m
Delta
Deal found 2/11![Delta logo]()
$226
This American Airlines deal was found by Cheapflights users on 2/11. 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 3/39:57 am
PIT
- SJU
2 stops9h 42m
American Airlines
Tue 3/107:11 am
SJU
- PIT
1 stop15h 35m
American Airlines
Deal found 2/11![American Airlines logo]()
$242
This WAYA deal was found by Cheapflights users on 2/10. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:45 am
PIT
- STT
1 stop7h 46m
Spirit Airlines
Wed 3/182:36 pm
STT
- PIT
1 stop8h 19m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$244
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 February 12, 2026.
Search for one-way flight options from Pittsburgh to Caribbean. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
This Super.com deal was found by Cheapflights users on 2/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
PIT
- SJU
1 stop8h 31m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$93
This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:00 am
PIT
- SJU
1 stop8h 31m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$95
This United Airlines deal was found by Cheapflights users on 2/9. 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.
Mon 4/137:59 pm
PIT
- GCM
2 stops17h 46m
United Airlines
Deal found 2/9![United Airlines logo]()
$96
This American Airlines deal was found by Cheapflights users on 2/9. 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 4/137:57 pm
PIT
- GCM
1 stop16h 38m
American Airlines
Deal found 2/9![American Airlines logo]()
$101
This United Airlines deal was found by Cheapflights users on 2/9. 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 3/108:51 am
PIT
- SJU
2 stops14h 45m
United Airlines
Deal found 2/9![United Airlines logo]()
$106
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Wed 4/295:58 pm
PIT
- GCM
2 stops18h 02m
American Airlines
Deal found 2/9![American Airlines logo]()
$107
This Delta deal was found by Cheapflights users on 2/9. 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.
Wed 4/296:00 am
PIT
- GCM
1 stop7h 00m
Delta
Deal found 2/9![Delta logo]()
$108
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 5/1211:57 am
PIT
- SJU
1 stop10h 20m
Delta
Deal found 2/9![Delta logo]()
$108
This United Airlines deal was found by Cheapflights users on 2/11. 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.
Tue 3/248:51 am
PIT
- SJU
2 stops14h 45m
United Airlines
Deal found 2/11![United Airlines logo]()
$111
This United Airlines deal was found by Cheapflights users on 2/9. 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 2/258:06 pm
PIT
- GCM
2 stops17h 39m
United Airlines
Deal found 2/9![United Airlines logo]()
$112
This Delta deal was found by Cheapflights users on 2/10. 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.
Wed 3/47:09 am
PIT
- SJU
1 stop9h 18m
Delta
Deal found 2/10![Delta logo]()
$113
This United Airlines deal was found by Cheapflights users on 2/8. 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 3/86:10 am
PIT
- PLS
1 stop9h 50m
United Airlines
Deal found 2/8![United Airlines logo]()
$116
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 February 12, 2026.
Round-trip from | $213 (Priceline) |
|---|---|
One-way from | $93 (Super.com) |
Popular in | August |
Cheapest in | September |
Average price | $437 |
Good round-trip deal | $334 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 February 12, 2026.
Use the filters below to find and compare flights from Pittsburgh to Caribbean that are best for you.
Fly from
Pittsburgh
Fly to
Caribbean
Route
Depart
Return
Price
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Sat 5/9
2:11 pm-10:17 pm
1 stop8h 06m
San Juan Luis Munoz Marin Intl
Sat 5/16
2:20 pm-12:45 am
1 stop10h 25m
$216
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Mon 2/23
3:00 pm-10:22 pm
1 stop6h 22m
San Juan Luis Munoz Marin Intl
Tue 2/24
2:05 am-1:09 pm
2 stops12h 04m
$222
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Wed 5/13
10:55 am-8:34 pm
1 stop9h 39m
San Juan Luis Munoz Marin Intl
Wed 5/20
7:20 am-2:02 pm
1 stop6h 42m
$222
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Tue 5/12
7:20 am-1:45 pm
1 stop6h 25m
San Juan Luis Munoz Marin Intl
Thu 5/14
1:00 am-9:31 am
2 stops8h 31m
$222
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Wed 5/13
10:55 am-8:34 pm
1 stop9h 39m
San Juan Luis Munoz Marin Intl
Sat 5/23
7:20 am-1:56 pm
1 stop6h 36m
$222
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Tue 2/24
12:24 pm-10:22 pm
2 stops8h 58m
San Juan Luis Munoz Marin Intl
Wed 2/25
2:05 am-10:13 am
1 stop9h 08m
$222
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Sat 2/21
12:30 pm-10:22 pm
2 stops8h 52m
San Juan Luis Munoz Marin Intl
Thu 2/26
2:05 am-10:13 am
1 stop9h 08m
$222
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Wed 5/13
11:57 am-10:17 pm
1 stop10h 20m
San Juan Luis Munoz Marin Intl
Fri 5/22
2:20 pm-12:45 am
1 stop10h 25m
$226
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Tue 5/12
11:57 am-10:17 pm
1 stop10h 20m
San Juan Luis Munoz Marin Intl
Thu 5/21
2:30 pm-10:38 pm
1 stop8h 08m
$226
PittsburghSan Juan
PIT - SJU
PITSJU
Pittsburgh
Wed 5/13
11:57 am-10:17 pm
1 stop10h 20m
San Juan Luis Munoz Marin Intl
Thu 5/21
2:30 pm-10:38 pm
1 stop8h 08m
$226
Showing 1-10 of 60 results
Best time to book a flight from Pittsburgh to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Pittsburgh with our price prediction graph.
PIT-SJU
PIT-STT
PIT-GCM
PIT-PLS
PIT-NAS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Pittsburgh to Caribbean
PIT-0CB
PIT-SJU
PIT-STT
PIT-GCM
PIT-PLS
What is the cheapest month to book a flight from Pittsburgh to Caribbean?
Currently, April is the cheapest month in which you can book a flight from Pittsburgh to Caribbean (average of $145). Flying from Pittsburgh to Caribbean in July is currently the most expensive (average of $255). 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.
What is the cheapest time of day to fly from PIT to CB?
Find hourly flight availability from Pittsburgh to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 12, 2026.
When flying from Pittsburgh to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
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 February 12, 2026.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American 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.
Entertainment
7.8
Overall
7.9
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Overall
7.9
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Overall
7.9
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Overall
7.9
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Overall
7.9
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Overall
7.9
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
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 February 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 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 2,558,603 searches. Data last updated February 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$135 | Average$314 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$141 | Average$470 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$158 | Average$483 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$164 | Average$399 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$225 | Average$617 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$225 | Average$503 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$232 | Average$545 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$381 | Average$508 | FlexibilityNo cancel fee | On-time67% |