$90+ Cheap flights from Caribbean to Kentucky
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SDF
Sep 28 — Oct 51
Round-trip
1 adult, Economy
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Find cheap flights from Caribbean to Kentucky 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 Caribbean to Kentucky
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Cheapest flights from Caribbean to KentuckyExplore the most affordable flight options available from Caribbean to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 29, 2026.
Explore the most affordable flight options available from Caribbean to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 29, 2026.
This deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 11/196:15 am -
1 stop12h 03m
Tue 11/245:14 pm -
1 stop7h 19m
Deal found 8/26![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/212:57 am -
1 stop6h 51m
Tue 9/299:43 am -
1 stop7h 00m
Deal found 8/24![Frontier logo]()
$177
This deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 12/106:45 am -
1 stop10h 28m
Tue 12/155:45 am -
1 stop8h 21m
Deal found 8/26![Frontier logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/123:00 am -
1 stop17h 43m
Tue 10/208:29 pm -
1 stop11h 49m
Deal found 8/26![Frontier logo]()
$196
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2911:51 am -
1 stop10h 55m
Tue 10/64:35 pm -
1 stop16h 11m
Deal found 8/27![American Airlines logo]()
$204
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:45 pm -
1 stop9h 06m
Sun 11/155:24 am -
1 stop6h 15m
Deal found 8/24![American Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/212:57 am -
1 stop6h 51m
Fri 9/255:40 pm -
1 stop7h 12m
Deal found 8/24![Frontier logo]()
$208
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/216:00 am -
1 stop16h 46m
Mon 10/54:35 pm -
1 stop16h 11m
Deal found 8/26![American Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:55 pm -
1 stop17h 53m
Mon 9/285:40 pm -
1 stop7h 12m
Deal found 8/25![Frontier logo]()
$212
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:05 am -
1 stop7h 36m
Tue 12/19:45 am -
1 stop9h 15m
Deal found 8/25![United Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:33 am -
1 stop29h 05m
Fri 10/212:43 pm -
2 stops45h 30m
Deal found 8/28![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:42 am -
1 stop7h 03m
Thu 9/245:40 pm -
1 stop7h 12m
Deal found 8/26![Frontier logo]()
$228
Best flights from Caribbean to KentuckyDiscover carefully curated flight deals from Caribbean to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 29, 2026.
Discover carefully curated flight deals from Caribbean to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 29, 2026.
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/44:55 pm -
1 stop8h 25m
Sun 12/69:45 am -
1 stop9h 15m
Deal found 8/25![United Airlines logo]()
$224
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/25:59 pm -
1 stop6h 24m
Sun 10/46:00 am -
1 stop5h 45m
Deal found 8/26![Delta logo]()
$232
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/2112:21 pm -
2 stops11h 46m
Sun 10/258:18 pm -
1 stop15h 02m
Deal found 8/26![American Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:45 am -
1 stop25h 19m
Sat 9/263:51 pm -
1 stop10h 01m
Deal found 8/26![Multiple Airlines logo]()
$238
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:40 am -
2 stops9h 35m
Mon 12/78:35 pm -
1 stop11h 20m
Deal found 8/27![Southwest logo]()
$284
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Fri 10/166:30 pm -
1 stop24h 14m
Sun 10/258:00 am -
1 stop26h 30m
Deal found 8/27![Air Canada logo]()
$426
This JetBlue deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:10 pm -
1 stop6h 12m
Sun 10/257:25 am -
1 stop5h 21m
Deal found 8/24![JetBlue logo]()
$462
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/297:05 am -
2 stops11h 27m
Sun 11/16:00 am -
1 stop6h 15m
Deal found 8/26![United Airlines logo]()
$232
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 11/41:00 pm -
1 stop8h 39m
Mon 11/95:10 am -
1 stop9h 30m
Deal found 8/27![United Airlines logo]()
$232
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 11/136:55 pm -
1 stop6h 04m
Tue 11/172:40 pm -
1 stop7h 35m
Deal found 8/26![Delta logo]()
$310
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/216:20 am -
1 stop16h 39m
Tue 10/276:20 am -
2 stops9h 18m
Deal found 8/27![American Airlines logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:00 am -
1 stop10h 50m
Thu 10/19:11 pm -
1 stop16h 31m
Deal found 8/26![Multiple Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:50 pm -
1 stop7h 00m
Sun 11/152:30 pm -
2 stops8h 35m
Deal found 8/25![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/155:00 am -
2 stops9h 10m
Wed 11/42:00 pm -
2 stops8h 45m
Deal found 8/26![Southwest logo]()
$326
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 12/44:55 pm -
1 stop8h 01m
Mon 12/75:00 am -
1 stop9h 40m
Deal found 8/28![United Airlines logo]()
$316
This American Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/22:22 pm -
1 stop7h 34m
Sun 10/46:00 am -
2 stops9h 40m
Deal found 8/29![American Airlines logo]()
$356
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:25 am -
1 stop7h 59m
Sat 11/148:55 am -
2 stops12h 27m
Deal found 8/25![United Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:16 am -
2 stops13h 35m
Mon 10/58:03 pm -
2 stops15h 28m
Deal found 8/24![American Airlines logo]()
$366
This Air Canada deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/116:30 pm -
1 stop15h 59m
Sun 10/186:35 pm -
1 stop21h 55m
Deal found 8/28![Air Canada logo]()
$469
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:25 pm -
1 stop9h 54m
Sun 10/256:00 am -
1 stop6h 15m
Deal found 8/25![United Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/212:59 pm -
1 stop7h 23m
Sat 10/244:11 pm -
1 stop6h 07m
Deal found 8/28![Delta logo]()
$436
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:25 pm -
1 stop6h 45m
Sun 11/295:35 am -
1 stop13h 05m
Deal found 8/25![Southwest logo]()
$399
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:41 pm -
1 stop8h 59m
Sun 11/18:11 pm -
1 stop15h 52m
Deal found 8/25![American Airlines logo]()
$374
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:40 am -
2 stops14h 12m
Mon 11/210:27 am -
1 stop9h 33m
Deal found 8/24![United Airlines logo]()
$322
This Travelocity deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:30 pm -
2 stops51h 24m
Wed 9/166:35 pm -
2 stops17h 50m
Deal found 8/27![Air Canada logo]()
$488
This Expedia deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Fri 10/23:59 pm -
1 stop6h 39m
Thu 10/152:27 pm -
1 stop10h 37m
Deal found 8/27![JetBlue logo]()
$546
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/122:50 pm -
1 stop7h 37m
Sat 9/197:50 am -
1 stop8h 59m
Deal found 8/25![Delta logo]()
$453
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/162:34 pm -
1 stop8h 12m
Sat 9/196:28 pm -
2 stops16h 12m
Deal found 8/25![American Airlines logo]()
$378
This eDestinos deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:44 am -
2 stops16h 12m
Mon 9/79:00 am -
1 stop24h 19m
Deal found 8/24![Multiple Airlines logo]()
$511
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:40 am -
2 stops8h 25m
Wed 11/1812:25 pm -
2 stops8h 55m
Deal found 8/24![Southwest logo]()
$424
Last-minute flights from Caribbean to KentuckyDiscover last-minute flight deals from Caribbean to Kentucky. Data last updated August 29, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to Kentucky. Data last updated August 29, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:42 am -
1 stop7h 03m
Thu 9/1710:52 am -
1 stop11h 21m
Deal found 8/27![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/212:57 am -
1 stop6h 51m
Tue 9/299:43 am -
1 stop7h 00m
Deal found 8/24![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/212:57 am -
1 stop6h 51m
Fri 9/255:40 pm -
1 stop7h 12m
Deal found 8/24![Frontier logo]()
$208
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/216:00 am -
1 stop16h 46m
Mon 10/54:35 pm -
1 stop16h 11m
Deal found 8/26![American Airlines logo]()
$209
This Frontier deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:42 am -
1 stop7h 03m
Thu 9/245:40 pm -
1 stop7h 12m
Deal found 8/26![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:11 pm -
1 stop18h 27m
Thu 10/112:43 pm -
1 stop26h 36m
Deal found 8/27![Frontier logo]()
$231
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:59 pm -
1 stop9h 24m
Sun 9/276:00 am -
1 stop5h 45m
Deal found 8/25![Delta logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:55 pm -
1 stop17h 53m
Mon 9/285:40 pm -
1 stop7h 12m
Deal found 8/25![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:33 am -
1 stop29h 05m
Fri 10/212:43 pm -
2 stops45h 30m
Deal found 8/28![Frontier logo]()
$228
This FlightHub deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:42 pm -
1 stop15h 06m
Sun 9/279:59 pm -
1 stop11h 14m
Deal found 8/28![Frontier logo]()
$231
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2510:16 am -
2 stops12h 41m
Fri 10/26:21 pm -
2 stops15h 03m
Deal found 8/26![American Airlines logo]()
$237
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2911:51 am -
1 stop10h 55m
Tue 10/64:35 pm -
1 stop16h 11m
Deal found 8/27![American Airlines logo]()
$204
One-way flights from Caribbean to KentuckySearch for one-way flight options from Caribbean to Kentucky. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
Search for one-way flight options from Caribbean to Kentucky. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
This Trip.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:55 pm -
1 stop17h 53m
Deal found 8/26![Frontier logo]()
$90
This Trip.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:23 am -
1 stop13h 18m
Deal found 8/28![Frontier logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:42 am -
1 stop7h 03m
Deal found 8/26![Frontier logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/232:57 am -
1 stop6h 51m
Deal found 8/26![Frontier logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:00 am -
1 stop27h 35m
Deal found 8/24![Frontier logo]()
$102
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/292:58 pm -
1 stop7h 48m
Deal found 8/27![American Airlines logo]()
$102
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/93:51 pm -
1 stop17h 04m
Deal found 8/27![American Airlines logo]()
$104
This Trip.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:00 am -
1 stop9h 16m
Deal found 8/27![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/302:57 am -
1 stop6h 51m
Deal found 8/28![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2910:42 am -
1 stop23h 06m
Deal found 8/28![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/252:57 am -
1 stop6h 51m
Deal found 8/28![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:00 am -
1 stop26h 42m
Deal found 8/28![Frontier logo]()
$111
Find flight deals from Caribbean to Kentucky
Keep the following information in mind while searching for Caribbean to Kentucky flight deals. Data was last updated August 29, 2026.
Round-trip from | $170 |
|---|---|
One-way from | $90 (Trip.com) |
Popular in | June |
Cheapest in | February |
Average price | $350 |
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean to Kentucky that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 29, 2026.
Use the filters below to find and compare flights from Caribbean to Kentucky that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JuanNashville
SJU San Juan Luis Munoz Marin Intl - BNA Nashville Intl
SJUBNA
San Juan Luis Munoz Marin Intl
Fri 12/4
4:55 pm-11:20 pm
1 stop8h 25m
Nashville Intl
Sun 12/6
9:45 am-9:00 pm
1 stop9h 15m
$224
San JuanCincinnati
SJU San Juan Luis Munoz Marin Intl - CVG Cincinnati Cinci./N. Kentucky
SJUCVG
San Juan Luis Munoz Marin Intl
Fri 10/2
5:59 pm-12:23 am
1 stop6h 24m
Cincinnati Cinci./N. Kentucky
Sun 10/4
6:00 am-11:45 am
1 stop5h 45m
$232
San JuanLouisville
SJU San Juan Luis Munoz Marin Intl - SDF Louisville Intl
SJUSDF
San Juan Luis Munoz Marin Intl
Wed 10/21
12:21 pm-12:07 am
2 stops11h 46m
Louisville Intl
Sun 10/25
8:18 pm-11:20 am
1 stop15h 02m
$232
San JuanLouisville
SJU San Juan Luis Munoz Marin Intl - SDF Louisville Intl
SJUSDF
San Juan Luis Munoz Marin Intl
Thu 10/29
7:05 am-6:32 pm
2 stops11h 27m
Louisville Intl
Sun 11/1
6:00 am-1:15 pm
1 stop6h 15m
$232
San JuanLouisville
SJU San Juan Luis Munoz Marin Intl - SDF Louisville Intl
SJUSDF
San Juan Luis Munoz Marin Intl
Wed 11/4
1:00 pm-8:39 pm
1 stop8h 39m
Louisville Intl
Mon 11/9
5:10 am-3:40 pm
1 stop9h 30m
$232
San JuanKnoxville
SJU San Juan Luis Munoz Marin Intl - TYS Knoxville McGhee Tyson
SJUTYS
San Juan Luis Munoz Marin Intl
Wed 9/23
8:45 am-10:04 am
1 stop25h 19m
Knoxville McGhee Tyson
Sat 9/26
3:51 pm-1:52 am
1 stop10h 01m
$238
San JuanNashville
SJU San Juan Luis Munoz Marin Intl - BNA Nashville Intl
SJUBNA
San Juan Luis Munoz Marin Intl
Fri 12/4
5:40 am-1:15 pm
2 stops9h 35m
Nashville Intl
Mon 12/7
8:35 pm-9:55 am
1 stop11h 20m
$284
San JuanKnoxville
SJU San Juan Luis Munoz Marin Intl - TYS Knoxville McGhee Tyson
SJUTYS
San Juan Luis Munoz Marin Intl
Fri 11/13
6:55 pm-11:59 pm
1 stop6h 04m
Knoxville McGhee Tyson
Tue 11/17
2:40 pm-11:15 pm
1 stop7h 35m
$310
San JuanKnoxville
SJU San Juan Luis Munoz Marin Intl - TYS Knoxville McGhee Tyson
SJUTYS
San Juan Luis Munoz Marin Intl
Wed 10/21
6:20 am-10:59 pm
1 stop16h 39m
Knoxville McGhee Tyson
Tue 10/27
6:20 am-3:38 pm
2 stops9h 18m
$310
San JuanLexington
SJU San Juan Luis Munoz Marin Intl - LEX Lexington Blue Grass
SJULEX
San Juan Luis Munoz Marin Intl
Thu 9/24
7:00 am-5:50 pm
1 stop10h 50m
Lexington Blue Grass
Thu 10/1
9:11 pm-1:42 pm
1 stop16h 31m
$312
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Caribbean to Kentucky
Have a flexible travel schedule? Discover the best time to fly to Kentucky from Caribbean with our price prediction graph.
SJU-BNA
SJU-CVG
SJU-SDF
SJU-TYS
NAS-BNA
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 Caribbean to Kentucky
0CB-USKY
SJU-BNA
SJU-CVG
SJU-SDF
SJU-TYS
What is the cheapest month to book a flight from Caribbean to Kentucky?
Currently, September is the cheapest month in which you can book a flight from Caribbean to Kentucky (average of $331). Flying from Caribbean to Kentucky in April is currently the most expensive (average of $621). 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.
Reviews of airlines servicing Kentucky
Get insights into the airlines that provide service to Kentucky. 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 Kentucky. Reviews last updated August 29, 2026.
See what other customers who have flown with Southwest,Delta, andAmerican Airlines from Caribbean to Kentucky have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Caribbean to Kentucky. 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
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Alternative routes for Caribbean to Kentucky
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Kentucky by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Caribbean to Kentucky by cabin class
Find flights from Caribbean to Kentucky, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Caribbean and Kentucky flights
Browse other Caribbean and Kentucky flight options. Last updated on August 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Kentucky
Find the right flight back to Caribbean after your stay in Kentucky
Caribbean to Kentucky flights
Consider these flights traveling from Caribbean to Kentucky.
Top 3 airlines flying from Caribbean to Kentucky
Discover the top 3 airlines that operate flights from Caribbean to Kentucky. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$199 | Average$389 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$250 | Average$532 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$318 | Average$474 | FlexibilityNo cancel fee | On-time63% |