$86+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SDF
May 1 — May 81
Round-trip
1 adult, Economy
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Find cheap flights from Caribbean to Kentucky with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from 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 April 1, 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 April 1, 2026.
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Thu 4/163:19 pm
SJU
- CVG
1 stop8h 01m
Frontier
Wed 5/69:30 pm
CVG
- SJU
1 stop10h 34m
Frontier
Deal found 3/31![Frontier logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/1512:57 pm
SJU
- BNA
1 stop23h 59m
Multiple Airlines
Sun 4/196:30 am
BNA
- SJU
1 stop29h 03m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$187
This Trip.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/176:00 am
SJU
- CVG
1 stop15h 51m
Frontier
Mon 4/205:20 pm
CVG
- SJU
1 stop8h 41m
Frontier
Deal found 3/31![Frontier logo]()
$191
This Expedia deal was found by Cheapflights users on 3/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:59 am
SJU
- BNA
1 stop9h 53m
Frontier
Sat 4/255:53 pm
BNA
- SJU
1 stop7h 08m
Frontier
Deal found 3/29![Frontier logo]()
$194
This Frontier deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Fri 5/811:00 am
SJU
- CVG
1 stop9h 35m
Frontier
Sat 5/95:37 pm
CVG
- SJU
1 stop8h 31m
Frontier
Deal found 3/30![Frontier logo]()
$196
This Orbitz deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/173:19 pm
SJU
- BNA
1 stop26h 39m
Frontier
Sun 4/195:05 pm
BNA
- SJU
1 stop7h 56m
Frontier
Deal found 3/31![Frontier logo]()
$204
This CheapOair deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Sun 4/196:30 am
SJU
- BNA
1 stop10h 50m
Frontier
Thu 4/2311:13 am
BNA
- SJU
1 stop13h 48m
Frontier
Deal found 3/31![Frontier logo]()
$205
This OneTravel deal was found by Cheapflights users on 3/28. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2412:57 pm
SJU
- BNA
1 stop20h 38m
Spirit Airlines
Mon 4/276:25 am
BNA
- SJU
1 stop11h 57m
Spirit Airlines
Deal found 3/28![Spirit Airlines logo]()
$210
This Expedia deal was found by Cheapflights users on 3/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/303:21 am
SJU
- CVG
1 stop8h 34m
Frontier
Sun 5/310:00 am
CVG
- SJU
1 stop12h 56m
Frontier
Deal found 3/29![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/176:00 am
SJU
- CVG
1 stop15h 51m
Multiple Airlines
Mon 4/203:38 pm
CVG
- SJU
2 stops33h 16m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$212
This Travelocity deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Wed 4/293:21 am
SJU
- BNA
1 stop7h 57m
Frontier
Mon 5/111:56 pm
BNA
- SJU
1 stop11h 12m
Frontier
Deal found 3/31![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/216:30 am
SJU
- CVG
1 stop9h 22m
Multiple Airlines
Sat 4/257:46 pm
CVG
- SJU
2 stops40h 47m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$214
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 April 1, 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 April 1, 2026.
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Tue 4/216:30 am
SJU
- CVG
1 stop9h 22m
Frontier
Sat 4/254:26 pm
CVG
- SJU
1 stop9h 35m
Frontier
Deal found 3/31![Frontier logo]()
$186
This American Airlines deal was found by Cheapflights users on 3/27. 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 4/221:31 pm
SJU
- LEX
2 stops10h 21m
American Airlines
Sun 4/266:00 am
LEX
- SJU
2 stops12h 10m
American Airlines
Deal found 3/27![American Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 8/286:00 am
SJU
- CVG
1 stop8h 24m
Multiple Airlines
Sun 8/303:38 pm
CVG
- SJU
1 stop24h 20m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 3/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/245:05 am
SJU
- BNA
1 stop6h 50m
Southwest
Sat 4/252:10 pm
BNA
- SJU
Nonstop3h 55m
Southwest
Deal found 3/29![Southwest logo]()
$302
This United Airlines deal was found by Cheapflights users on 3/27. 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 5/63:56 pm
SJU
- LEX
1 stop7h 53m
United Airlines
Sat 5/97:00 am
LEX
- SJU
2 stops14h 24m
United Airlines
Deal found 3/27![United Airlines logo]()
$316
This CheapOair deal was found by Cheapflights users on 3/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/212:35 pm
SDQ
- BNA
1 stop19h 00m
Spirit Airlines
Mon 4/276:25 am
BNA
- SDQ
1 stop6h 04m
Spirit Airlines
Deal found 3/27![Spirit Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 3/28. 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 9/231:15 pm
NAS
- BNA
1 stop4h 26m
Delta
Sat 9/266:25 am
BNA
- NAS
1 stop8h 15m
Delta
Deal found 3/28![Delta logo]()
$367
This Faresmojo deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/146:00 am
SJU
- SDF
1 stop5h 53m
JetBlue
Thu 7/161:02 pm
SDF
- SJU
1 stop7h 43m
JetBlue
Deal found 4/1![JetBlue logo]()
$376
This CheapOair deal was found by Cheapflights users on 3/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:00 am
SJU
- CVG
1 stop15h 54m
Frontier
Sun 5/310:00 am
CVG
- SJU
1 stop12h 56m
Frontier
Deal found 3/27![Frontier logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Thu 4/303:21 am
SJU
- CVG
1 stop8h 34m
Frontier
Sun 5/33:29 pm
CVG
- SJU
2 stops31h 00m
Frontier
Deal found 3/28![Frontier logo]()
$248
This CheapOair deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Thu 5/711:35 am
KIN
- BNA
2 stops33h 21m
Air Canada
Thu 5/148:15 am
BNA
- KIN
2 stops29h 40m
Air Canada
Deal found 3/31![Air Canada logo]()
$578
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/14:25 pm
SJU
- SDF
1 stop7h 20m
Southwest
Tue 5/55:50 pm
SDF
- SJU
1 stop5h 50m
Southwest
Deal found 3/31![Southwest logo]()
$316
This American Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 8/2710:32 am
SJU
- SDF
2 stops12h 15m
American Airlines
Fri 9/44:49 pm
SDF
- SJU
1 stop6h 52m
American Airlines
Deal found 4/1![American Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 3/27. 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 7/36:00 am
SJU
- BNA
1 stop7h 55m
Southwest
Fri 7/171:55 pm
BNA
- SJU
1 stop9h 30m
Southwest
Deal found 3/27![Southwest logo]()
$322
This CheapOair deal was found by Cheapflights users on 3/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/243:18 pm
KIN
- BNA
2 stops23h 00m
Spirit Airlines
Mon 4/276:25 am
BNA
- KIN
1 stop7h 47m
Spirit Airlines
Deal found 3/28![Spirit Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 3/27. 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.
Mon 5/112:53 pm
NAS
- BNA
1 stop28h 32m
United Airlines
Mon 5/186:00 am
BNA
- NAS
1 stop7h 57m
United Airlines
Deal found 3/27![United Airlines logo]()
$367
This eDestinos deal was found by Cheapflights users on 3/29. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/49:00 am
SJU
- TYS
2 stops38h 39m
Multiple Airlines
Fri 7/317:20 pm
TYS
- SJU
2 stops32h 37m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$372
This CheapOair deal was found by Cheapflights users on 3/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/63:33 pm
SJU
- CVG
1 stop8h 07m
Frontier
Mon 5/119:30 pm
CVG
- SJU
1 stop28h 38m
Frontier
Deal found 3/29![Frontier logo]()
$309
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 4/185:58 pm
NAS
- BNA
1 stop5h 58m
Delta
Mon 4/207:30 am
BNA
- NAS
1 stop8h 03m
Delta
Deal found 3/30![Delta logo]()
$400
This United Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/62:53 pm
NAS
- BNA
1 stop25h 26m
United Airlines
Sun 5/106:02 pm
BNA
- NAS
1 stop18h 45m
United Airlines
Deal found 3/31![United Airlines logo]()
$367
This Southwest deal was found by Cheapflights users on 3/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:05 am
SJU
- BNA
2 stops9h 35m
Southwest
Tue 5/191:20 pm
BNA
- SJU
1 stop8h 20m
Southwest
Deal found 3/28![Southwest logo]()
$335
This American Airlines deal was found by Cheapflights users on 3/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/301:31 pm
SJU
- CVG
2 stops10h 25m
American Airlines
Sun 5/35:00 am
CVG
- SJU
2 stops7h 29m
American Airlines
Deal found 3/28![American Airlines logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Fri 4/242:35 pm
SDQ
- TYS
1 stop21h 31m
Multiple Airlines
Fri 5/17:30 am
TYS
- SDQ
1 stop5h 59m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/162:35 pm
SDQ
- BNA
1 stop19h 00m
Spirit Airlines
Mon 4/203:27 pm
BNA
- SDQ
1 stop21h 02m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$396
This Delta deal was found by Cheapflights users on 3/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:15 pm
NAS
- BNA
1 stop10h 34m
Delta
Sun 9/275:25 am
BNA
- NAS
1 stop5h 25m
Delta
Deal found 3/27![Delta logo]()
$400
This American Airlines deal was found by Cheapflights users on 3/29. 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.
Tue 9/18:00 am
SJU
- CVG
2 stops10h 20m
American Airlines
Tue 9/226:49 am
CVG
- SJU
2 stops11h 21m
American Airlines
Deal found 3/29![American Airlines logo]()
$375
This JetBlue deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/108:32 pm
SDQ
- BNA
1 stop12h 27m
JetBlue
Wed 5/138:49 am
BNA
- SDQ
1 stop9h 28m
JetBlue
Deal found 3/30![JetBlue logo]()
$460
This Southwest deal was found by Cheapflights users on 3/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/33:15 pm
SJU
- SDF
1 stop7h 40m
Southwest
Mon 6/86:05 pm
SDF
- SJU
2 stops7h 15m
Southwest
Deal found 3/29![Southwest logo]()
$356
This Priceline deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/293:18 pm
KIN
- BNA
1 stop8h 06m
Multiple Airlines
Wed 5/68:15 am
BNA
- KIN
2 stops26h 10m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$403
This United Airlines deal was found by Cheapflights users on 3/27. 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.
Thu 5/73:56 pm
SJU
- SDF
1 stop8h 00m
United Airlines
Mon 5/115:50 am
SDF
- SJU
1 stop6h 44m
United Airlines
Deal found 3/27![United Airlines logo]()
$406
Last-minute flights from Caribbean to KentuckyDiscover last-minute flight deals from Caribbean to Kentucky. Data last updated April 1, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to Kentucky. Data last updated April 1, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/1512:57 pm
SJU
- BNA
1 stop23h 59m
Multiple Airlines
Sun 4/196:30 am
BNA
- SJU
1 stop29h 03m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$187
This CheapOair deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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.
Wed 4/1512:57 pm
SJU
- BNA
1 stop11h 27m
Multiple Airlines
Sat 4/185:53 pm
BNA
- SJU
1 stop7h 08m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$214
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Thu 4/163:19 pm
SJU
- CVG
1 stop8h 01m
Frontier
Wed 5/69:30 pm
CVG
- SJU
1 stop10h 34m
Frontier
Deal found 3/31![Frontier logo]()
$186
This Trip.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/176:00 am
SJU
- CVG
1 stop15h 51m
Frontier
Mon 4/205:20 pm
CVG
- SJU
1 stop8h 41m
Frontier
Deal found 3/31![Frontier logo]()
$191
This Orbitz deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/173:19 pm
SJU
- BNA
1 stop26h 39m
Frontier
Sun 4/195:05 pm
BNA
- SJU
1 stop7h 56m
Frontier
Deal found 3/31![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/176:00 am
SJU
- CVG
1 stop15h 51m
Multiple Airlines
Mon 4/203:38 pm
CVG
- SJU
2 stops33h 16m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$212
This CheapOair deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Sun 4/196:30 am
SJU
- BNA
1 stop10h 50m
Frontier
Thu 4/2311:13 am
BNA
- SJU
1 stop13h 48m
Frontier
Deal found 3/31![Frontier logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/216:30 am
SJU
- CVG
1 stop9h 22m
Multiple Airlines
Sat 4/257:46 pm
CVG
- SJU
2 stops40h 47m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$214
This Expedia deal was found by Cheapflights users on 3/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:59 am
SJU
- BNA
1 stop9h 53m
Frontier
Sat 4/255:53 pm
BNA
- SJU
1 stop7h 08m
Frontier
Deal found 3/29![Frontier logo]()
$194
This OneTravel deal was found by Cheapflights users on 3/28. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2412:57 pm
SJU
- BNA
1 stop20h 38m
Spirit Airlines
Mon 4/276:25 am
BNA
- SJU
1 stop11h 57m
Spirit Airlines
Deal found 3/28![Spirit Airlines logo]()
$210
This Priceline deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Mon 4/273:08 am
SJU
- CVG
1 stop20h 12m
Frontier
Tue 5/57:00 am
CVG
- SJU
1 stop19h 08m
Frontier
Deal found 3/31![Frontier logo]()
$211
This Travelocity deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Wed 4/293:21 am
SJU
- BNA
1 stop7h 57m
Frontier
Mon 5/111:56 pm
BNA
- SJU
1 stop11h 12m
Frontier
Deal found 3/31![Frontier logo]()
$212
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 April 1, 2026.
Search for one-way flight options from Caribbean to Kentucky. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 4/246:00 am
SJU
- CVG
1 stop15h 36m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/226:30 am
SJU
- CVG
1 stop9h 22m
Frontier
Deal found 3/31![Frontier logo]()
$87
This Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:00 am
SJU
- BNA
1 stop9h 58m
Frontier
Deal found 3/27![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/246:00 am
SJU
- BNA
1 stop27h 35m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$89
This Priceline deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2210:59 am
SJU
- BNA
1 stop24h 19m
Frontier
Deal found 3/31![Frontier logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2311:30 am
SJU
- CVG
1 stop26h 56m
Frontier
Deal found 3/31![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Wed 4/2912:57 pm
SJU
- BNA
1 stop11h 27m
Spirit Airlines
Deal found 3/27![Spirit Airlines logo]()
$96
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Thu 4/163:19 pm
SJU
- CVG
1 stop8h 01m
Frontier
Deal found 3/31![Frontier logo]()
$98
This Frontier deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Mon 5/116:00 am
SJU
- BNA
1 stop8h 11m
Frontier
Deal found 3/30![Frontier logo]()
$98
This CheapOair deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 4/176:00 am
SJU
- CVG
1 stop15h 51m
Frontier
Deal found 3/30![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” 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 5/106:41 pm
SJU
- CVG
1 stop23h 25m
Frontier
Deal found 4/1![Frontier logo]()
$106
This Frontier deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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 4/293:21 am
SJU
- BNA
1 stop7h 57m
Frontier
Deal found 3/30![Frontier logo]()
$106
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 April 1, 2026.
Round-trip from | $186 (Frontier) |
|---|---|
One-way from | $87 (Kiwi.com) |
Popular in | June |
Cheapest in | October |
Average price | $365 |
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 2,558,603 searches. Data last updated April 1, 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 JuanCincinnati
SJU - CVG
SJUCVG
San Juan Luis Munoz Marin Intl
Tue 4/21
6:30 am-3:52 pm
1 stop9h 22m
Cincinnati Cinci./N. Kentucky
Sat 4/25
4:26 pm-2:01 am
1 stop9h 35m
$186
San JuanLexington
SJU - LEX
SJULEX
San Juan Luis Munoz Marin Intl
Wed 4/22
1:31 pm-11:52 pm
2 stops10h 21m
Lexington Blue Grass
Sun 4/26
6:00 am-6:10 pm
2 stops12h 10m
$226
San JuanCincinnati
SJU - CVG
SJUCVG
San Juan Luis Munoz Marin Intl
Thu 4/30
6:00 am-9:54 pm
1 stop15h 54m
Cincinnati Cinci./N. Kentucky
Sun 5/3
10:00 am-10:56 pm
1 stop12h 56m
$241
San JuanCincinnati
SJU - CVG
SJUCVG
San Juan Luis Munoz Marin Intl
Thu 4/30
3:21 am-11:55 am
1 stop8h 34m
Cincinnati Cinci./N. Kentucky
Sun 5/3
3:29 pm-10:29 pm
2 stops31h 00m
$248
San JuanCincinnati
SJU - CVG
SJUCVG
San Juan Luis Munoz Marin Intl
Fri 8/28
6:00 am-2:24 pm
1 stop8h 24m
Cincinnati Cinci./N. Kentucky
Sun 8/30
3:38 pm-3:58 pm
1 stop24h 20m
$277
Quickest round-trip
San JuanNashville
SJU - BNA
SJUBNA
San Juan Luis Munoz Marin Intl
Fri 4/24
5:05 am-10:55 am
1 stop6h 50m
Nashville Intl
Sat 4/25
2:10 pm-7:05 pm
Nonstop3h 55m
$302
San JuanCincinnati
SJU - CVG
SJUCVG
San Juan Luis Munoz Marin Intl
Wed 5/6
3:33 pm-11:40 pm
1 stop8h 07m
Cincinnati Cinci./N. Kentucky
Mon 5/11
9:30 pm-2:08 am
1 stop28h 38m
$309
San JuanLexington
SJU - LEX
SJULEX
San Juan Luis Munoz Marin Intl
Wed 5/6
3:56 pm-11:49 pm
1 stop7h 53m
Lexington Blue Grass
Sat 5/9
7:00 am-9:24 pm
2 stops14h 24m
$316
San JuanLouisville
SJU - SDF
SJUSDF
San Juan Luis Munoz Marin Intl
Fri 5/1
4:25 pm-11:45 pm
1 stop7h 20m
Louisville Intl
Tue 5/5
5:50 pm-11:40 pm
1 stop5h 50m
$316
San JuanNashville
SJU - BNA
SJUBNA
San Juan Luis Munoz Marin Intl
Fri 7/3
6:00 am-12:55 pm
1 stop7h 55m
Nashville Intl
Fri 7/17
1:55 pm-12:25 am
1 stop9h 30m
$322
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-CVG
SJU-BNA
SDQ-BNA
SJU-SDF
SJU-TYS
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-CVG
SJU-BNA
SDQ-BNA
SJU-SDF
What is the cheapest month to book a flight from Caribbean to Kentucky?
Currently, January is the cheapest month in which you can book a flight from Caribbean to Kentucky (average of $113). Flying from Caribbean to Kentucky in June is currently the most expensive (average of $251). 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 April 1, 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
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 April 1, 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 2,558,603 searches. Data last updated April 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$199 | Average$389 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$205 | Average$405 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$226 | Average$498 | FlexibilityNo cancel fee | On-time71% |