$137+ Cheap flights from Caribbean to Kentucky
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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SDF
Nov 24 — Dec 11
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
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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 October 25, 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 October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/25:01 am -
2 stops12h 31m
Sat 12/55:12 pm -
1 stop29h 14m
Deal found 10/20![Multiple Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/67:00 am -
1 stop14h 04m
Mon 11/166:53 pm -
1 stop19h 26m
Deal found 10/22![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/103:55 pm -
2 stops24h 31m
Mon 11/166:53 pm -
1 stop19h 26m
Deal found 10/22![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/612:59 am -
2 stops15h 27m
Mon 11/166:53 pm -
1 stop19h 26m
Deal found 10/22![Multiple Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/43:59 pm -
2 stops29h 30m
Mon 11/166:53 pm -
1 stop19h 26m
Deal found 10/22![Multiple Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/67:00 am -
1 stop14h 04m
Wed 11/114:06 pm -
2 stops44h 19m
Deal found 10/22![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/67:00 am -
1 stop14h 04m
Sat 11/144:06 pm -
2 stops44h 19m
Deal found 10/22![Multiple Airlines logo]()
$365
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/312:30 pm -
2 stops10h 45m
Mon 12/73:50 pm -
2 stops8h 00m
Deal found 10/20![Southwest logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/512:50 pm -
1 stop8h 39m
Mon 11/166:53 pm -
1 stop19h 26m
Deal found 10/22![Multiple Airlines logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/67:00 am -
1 stop14h 04m
Thu 11/129:09 pm -
1 stop25h 50m
Deal found 10/22![Multiple Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/267:45 am -
1 stop15h 56m
Mon 11/306:16 am -
1 stop15h 20m
Deal found 10/20![American Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:05 am -
1 stop15h 41m
Sun 11/297:26 pm -
1 stop15h 59m
Deal found 10/21![American Airlines logo]()
$400
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 October 25, 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 October 25, 2026.
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 12/36:28 am -
1 stop12h 44m
Sun 12/65:00 am -
1 stop15h 33m
Deal found 10/21![American Airlines logo]()
$384
This Delta deal was found by Cheapflights users on 10/25. 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.
Wed 12/238:00 am -
1 stop7h 53m
Sat 1/28:15 am -
1 stop12h 55m
Deal found 10/25![Delta logo]()
$460
This United Airlines deal was found by Cheapflights users on 10/25. 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.
Wed 12/235:21 pm -
1 stop25h 59m
Sat 1/26:00 pm -
2 stops22h 19m
Deal found 10/25![United Airlines logo]()
$472
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/712:15 pm -
1 stop8h 50m
Wed 11/1112:55 pm -
1 stop10h 55m
Deal found 10/22![Southwest logo]()
$556
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/267:45 am -
1 stop15h 56m
Mon 11/306:16 am -
1 stop15h 20m
Deal found 10/20![American Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 10/24. 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.
Tue 2/235:49 pm -
1 stop17h 10m
Sat 2/2711:17 am -
1 stop13h 08m
Deal found 10/24![American Airlines logo]()
$426
This United Airlines deal was found by Cheapflights users on 10/24. 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.
Sat 11/213:45 pm -
2 stops27h 25m
Sat 11/289:00 am -
1 stop28h 48m
Deal found 10/24![United Airlines logo]()
$488
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/512:40 pm -
2 stops9h 25m
Mon 11/97:05 am -
2 stops9h 45m
Deal found 10/21![Southwest logo]()
$556
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 2/222:05 am -
2 stops15h 56m
Sat 2/2711:10 am -
2 stops12h 26m
Deal found 10/21![United Airlines logo]()
$511
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/17:05 am -
1 stop11h 21m
Mon 12/75:45 am -
1 stop6h 19m
Deal found 10/20![American Airlines logo]()
$467
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/24:55 pm -
1 stop8h 01m
Sun 12/67:00 am -
2 stops14h 22m
Deal found 10/22![United Airlines logo]()
$511
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/265:35 am -
2 stops11h 10m
Mon 11/305:40 am -
2 stops10h 35m
Deal found 10/20![Southwest logo]()
$590
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/222:53 pm -
1 stop6h 09m
Mon 12/2812:14 pm -
1 stop9h 32m
Deal found 10/22![Delta logo]()
$656
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/37:40 am -
2 stops14h 20m
Mon 12/710:25 am -
2 stops13h 11m
Deal found 10/20![United Airlines logo]()
$555
This American Airlines deal was found by Cheapflights users on 10/24. 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.
Sat 11/2112:12 pm -
1 stop12h 11m
Sat 11/287:21 pm -
1 stop14h 06m
Deal found 10/24![American Airlines logo]()
$588
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/221:05 pm -
1 stop6h 15m
Mon 12/288:45 am -
2 stops28h 48m
Deal found 10/22![United Airlines logo]()
$569
This Mytrip deal was found by Cheapflights users on 10/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:50 pm -
3 stops23h 42m
Sat 11/281:45 pm -
2 stops21h 40m
Deal found 10/24![Multiple Airlines logo]()
$1,766
This WestJet deal was found by Cheapflights users on 10/24. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:35 pm -
2 stops22h 30m
Sat 11/2810:23 am -
2 stops51h 12m
Deal found 10/24![WestJet logo]()
$1,807
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/58:25 am -
1 stop9h 37m
Tue 11/177:00 am -
2 stops14h 22m
Deal found 10/22![United Airlines logo]()
$570
This Mytrip deal was found by Cheapflights users on 10/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/212:05 pm -
3 stops26h 57m
Sat 11/281:45 pm -
3 stops23h 30m
Deal found 10/24![Air Canada logo]()
$1,947
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/312:56 pm -
1 stop7h 39m
Sun 12/69:55 am -
1 stop6h 33m
Deal found 10/22![United Airlines logo]()
$587
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/45:10 pm -
1 stop22h 41m
Tue 12/89:55 am -
1 stop6h 33m
Deal found 10/22![United Airlines logo]()
$587
This American Airlines deal was found by Cheapflights users on 10/24. 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.
Sat 11/215:08 pm -
1 stop8h 15m
Sat 11/287:11 pm -
2 stops19h 55m
Deal found 10/24![American Airlines logo]()
$793
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 1/235:10 pm -
1 stop22h 34m
Thu 1/285:43 pm -
2 stops18h 25m
Deal found 10/22![United Airlines logo]()
$587
This American Airlines deal was found by Cheapflights users on 10/24. 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.
Sat 11/213:56 pm -
1 stop9h 27m
Sat 11/285:02 am -
1 stop9h 28m
Deal found 10/24![American Airlines logo]()
$829
This United Airlines deal was found by Cheapflights users on 10/24. 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.
Sat 11/211:05 pm -
2 stops9h 25m
Sat 11/289:02 am -
2 stops28h 31m
Deal found 10/24![United Airlines logo]()
$609
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 2/256:00 am -
1 stop18h 30m
Mon 3/16:00 am -
1 stop7h 53m
Deal found 10/23![United Airlines logo]()
$741
This United Airlines deal was found by Cheapflights users on 10/24. 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.
Sat 11/212:58 pm -
2 stops27h 34m
Sat 11/287:00 am -
2 stops30h 52m
Deal found 10/24![United Airlines logo]()
$1,070
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/262:55 pm -
1 stop8h 44m
Sun 12/278:45 am -
1 stop28h 30m
Deal found 10/22![United Airlines logo]()
$1,237
Last-minute flights from Caribbean to KentuckyDiscover last-minute flight deals from Caribbean to Kentucky. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to Kentucky. Data last updated October 25, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/43:59 pm -
2 stops29h 30m
Mon 11/166:53 pm -
1 stop19h 26m
Deal found 10/22![Multiple Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/512:50 pm -
1 stop8h 39m
Mon 11/166:53 pm -
1 stop19h 26m
Deal found 10/22![Multiple Airlines logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/67:00 am -
1 stop14h 04m
Mon 11/166:53 pm -
1 stop19h 26m
Deal found 10/22![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/612:59 am -
2 stops15h 27m
Mon 11/166:53 pm -
1 stop19h 26m
Deal found 10/22![Multiple Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/67:00 am -
1 stop14h 04m
Wed 11/114:06 pm -
2 stops44h 19m
Deal found 10/22![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/67:00 am -
1 stop14h 04m
Sat 11/144:06 pm -
2 stops44h 19m
Deal found 10/22![Multiple Airlines logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/67:00 am -
1 stop14h 04m
Thu 11/129:09 pm -
1 stop25h 50m
Deal found 10/22![Multiple Airlines logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/103:55 pm -
2 stops24h 31m
Mon 11/166:53 pm -
1 stop19h 26m
Deal found 10/22![Multiple Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:05 am -
1 stop15h 41m
Sun 11/297:26 pm -
1 stop15h 59m
Deal found 10/21![American Airlines logo]()
$400
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/257:05 am -
1 stop11h 20m
Sun 11/298:10 pm -
2 stops13h 31m
Deal found 10/21![American Airlines logo]()
$426
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/267:45 am -
1 stop15h 56m
Mon 11/306:16 am -
1 stop15h 20m
Deal found 10/20![American Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/267:05 am -
1 stop7h 20m
Wed 12/99:44 am -
1 stop10h 28m
Deal found 10/21![American Airlines logo]()
$405
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 October 25, 2026.
Search for one-way flight options from Caribbean to Kentucky. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 1/146:00 am -
1 stop12h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$137
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/183:20 pm -
1 stop6h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$192
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/153:35 pm -
1 stop9h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Delta logo]()
$198
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/187:30 am -
2 stops10h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/108:45 am -
3 stops31h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$210
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/252:29 pm -
1 stop8h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/27:00 am -
3 stops28h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$231
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/142:05 am -
2 stops16h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![United Airlines logo]()
$248
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 1/212:10 pm -
1 stop7h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$251
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/211:25 pm -
2 stops27h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![United Airlines logo]()
$257
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/194:31 pm -
1 stop6h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![American Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/211:20 am -
1 stop6h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$278
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 October 25, 2026.
Round-trip from | $330 (Kiwi.com) |
|---|---|
One-way from | $137 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $398 |
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 October 25, 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 JuanLouisville
SJU San Juan Luis Munoz Marin Intl - SDF Louisville Intl
SJUSDF
San Juan Luis Munoz Marin Intl
Thu 1/14
6:00 am-5:58 pm
1 stop12h 58m
Louisville Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$137
San JuanLexington
SJU San Juan Luis Munoz Marin Intl - LEX Lexington Blue Grass
SJULEX
San Juan Luis Munoz Marin Intl
Tue 12/15
3:35 pm-12:04 am
1 stop9h 29m
Lexington Blue Grass
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$198
San JuanLexington
SJU San Juan Luis Munoz Marin Intl - LEX Lexington Blue Grass
SJULEX
San Juan Luis Munoz Marin Intl
Fri 12/18
3:35 pm-12:04 am
1 stop9h 29m
Lexington Blue Grass
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$198
San JuanLexington
SJU San Juan Luis Munoz Marin Intl - LEX Lexington Blue Grass
SJULEX
San Juan Luis Munoz Marin Intl
Thu 12/24
3:00 pm-9:17 pm
1 stop7h 17m
Lexington Blue Grass
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$198
San JuanLouisville
SJU San Juan Luis Munoz Marin Intl - SDF Louisville Intl
SJUSDF
San Juan Luis Munoz Marin Intl
Wed 11/18
7:30 am-5:12 pm
2 stops10h 42m
Louisville Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$200
San JuanLouisville
SJU San Juan Luis Munoz Marin Intl - SDF Louisville Intl
SJUSDF
San Juan Luis Munoz Marin Intl
Wed 11/18
3:20 pm-9:13 pm
1 stop6h 53m
Louisville Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$208
San JuanLouisville
SJU San Juan Luis Munoz Marin Intl - SDF Louisville Intl
SJUSDF
San Juan Luis Munoz Marin Intl
Tue 11/10
11:20 am-3:26 pm
2 stops29h 06m
Louisville Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$243
San JuanLexington
SJU San Juan Luis Munoz Marin Intl - LEX Lexington Blue Grass
SJULEX
San Juan Luis Munoz Marin Intl
Mon 12/14
2:05 am-5:15 pm
2 stops16h 10m
Lexington Blue Grass
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$248
Montego BayLexington
MBJ Montego Bay Sangster Intl - LEX Lexington Blue Grass
MBJLEX
Montego Bay Sangster Intl
Thu 1/21
2:10 pm-9:35 pm
1 stop7h 25m
Lexington Blue Grass
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$251
Montego BayLexington
MBJ Montego Bay Sangster Intl - LEX Lexington Blue Grass
MBJLEX
Montego Bay Sangster Intl
Thu 1/21
1:25 pm-5:22 pm
2 stops27h 57m
Lexington Blue Grass
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$257
Showing 1-10 of 58 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-SDF
MBJ-SDF
SJU-LEX
MBJ-LEX
NAS-SDF
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-SDF
MBJ-SDF
SJU-LEX
MBJ-LEX
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 $355). 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.
How far ahead should I book a flight from Caribbean to Kentucky?
The best time to book flights from Caribbean to Kentucky is 76 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
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 October 25, 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.
Entertainment
7.4
Crew
8.6
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Crew
8.6
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Crew
8.6
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Crew
8.6
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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.
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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 October 25, 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 October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$199 | Average$389 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$250 | Average$507 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$318 | Average$446 | FlexibilityNo cancel fee | On-time63% |