$87+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SDF
Feb 27 — Mar 61
1 adult, Economy
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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
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 January 28, 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 January 28, 2026.
This Priceline deal was found by Cheapflights users on 1/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/185:25 pm
SJU
- BNA
1 stop28h 41m
Frontier
Mon 2/2310:50 am
BNA
- SJU
1 stop14h 03m
Frontier
Deal found 1/26![Frontier logo]()
$178
This Frontier deal was found by Cheapflights users on 1/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
SJU
- CVG
1 stop11h 37m
Frontier
Mon 3/27:14 pm
CVG
- SJU
1 stop6h 39m
Frontier
Deal found 1/25![Frontier logo]()
$182
This Priceline deal was found by Cheapflights users on 1/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/253:53 am
SJU
- BNA
1 stop6h 22m
Frontier
Thu 3/59:00 am
BNA
- SJU
1 stop15h 53m
Frontier
Deal found 1/27![Frontier logo]()
$201
This CheapOair deal was found by Cheapflights users on 1/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/278:05 pm
SJU
- BNA
1 stop14h 24m
Spirit Airlines
Mon 3/28:52 pm
BNA
- SJU
1 stop20h 06m
Spirit Airlines
Deal found 1/26![Spirit Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/136:00 am
SJU
- CVG
1 stop14h 45m
Multiple Airlines
Mon 2/168:49 pm
CVG
- SJU
2 stops16h 33m
Multiple Airlines
Deal found 1/25![Multiple Airlines logo]()
$215
This Orbitz deal was found by Cheapflights users on 1/27. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/811:07 am
SJU
- CVG
1 stop12h 13m
Frontier
Wed 5/135:20 pm
CVG
- SJU
1 stop8h 41m
Frontier
Deal found 1/27![Frontier logo]()
$217
This CheapOair deal was found by Cheapflights users on 1/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/278:05 pm
SJU
- BNA
1 stop14h 24m
Spirit Airlines
Sun 3/16:15 am
BNA
- SJU
1 stop26h 02m
Spirit Airlines
Deal found 1/25![Spirit Airlines logo]()
$220
This CheapOair deal was found by Cheapflights users on 1/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/127:04 pm
SJU
- CVG
1 stop17h 58m
Frontier
Mon 2/166:05 am
CVG
- SJU
1 stop19h 20m
Frontier
Deal found 1/26![Frontier logo]()
$223
This Frontier deal was found by Cheapflights users on 1/27. 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.
Mon 3/93:08 am
SJU
- BNA
1 stop8h 33m
Frontier
Tue 3/1711:36 am
BNA
- SJU
1 stop10h 09m
Frontier
Deal found 1/27![Frontier logo]()
$228
This CheapOair deal was found by Cheapflights users on 1/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1111:07 am
SJU
- CVG
1 stop25h 05m
Frontier
Fri 2/209:27 pm
CVG
- SJU
1 stop28h 26m
Frontier
Deal found 1/25![Frontier logo]()
$229
This Priceline deal was found by Cheapflights users on 1/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:55 am
SJU
- BNA
1 stop10h 08m
Multiple Airlines
Tue 5/126:00 am
BNA
- SJU
1 stop7h 28m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$230
This CheapOair deal was found by Cheapflights users on 1/27. 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.
Fri 5/153:08 am
SJU
- BNA
1 stop15h 14m
Multiple Airlines
Wed 5/206:00 am
BNA
- SJU
1 stop15h 09m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$235
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 January 28, 2026.
Round-trip from | $178 (Priceline) |
|---|---|
One-way from | $87 (Frontier) |
Popular in | June |
Cheapest in | October |
Average price | $390 |
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 January 28, 2026.
Use the filters below to find and compare flights from Caribbean to Kentucky that are best for you.
Fly from
Caribbean
Fly to
Kentucky
Route
Depart
Return
Price
San JuanNashville
SJU - BNA
SJUBNA
San Juan Luis Munoz Marin Intl
Wed 2/18
5:25 pm-8:06 pm
1 stop28h 41m
Nashville Intl
Mon 2/23
10:50 am-2:53 am
1 stop14h 03m
$178
San JuanCincinnati
SJU - CVG
SJUCVG
San Juan Luis Munoz Marin Intl
Thu 2/26
6:00 am-4:37 pm
1 stop11h 37m
Cincinnati Cinci./N. Kentucky
Mon 3/2
7:14 pm-2:53 am
1 stop6h 39m
$182
San JuanNashville
SJU - BNA
SJUBNA
San Juan Luis Munoz Marin Intl
Wed 5/6
1:00 am-9:28 am
2 stops9h 28m
Nashville Intl
Tue 5/12
1:32 pm-9:24 pm
1 stop6h 52m
$236
San JuanNashville
SJU - BNA
SJUBNA
San Juan Luis Munoz Marin Intl
Thu 4/9
5:05 am-12:10 pm
1 stop8h 05m
Nashville Intl
Sun 4/12
10:10 pm-9:10 am
1 stop10h 00m
$236
San JuanNashville
SJU - BNA
SJUBNA
San Juan Luis Munoz Marin Intl
Mon 2/9
6:00 am-8:29 am
1 stop28h 29m
Nashville Intl
Mon 3/2
8:52 pm-6:58 pm
1 stop20h 06m
$239
San JuanNashville
SJU - BNA
SJUBNA
San Juan Luis Munoz Marin Intl
Wed 2/25
3:53 am-8:15 am
1 stop6h 22m
Nashville Intl
Thu 3/5
9:00 am-2:53 am
1 stop15h 53m
$240
San JuanCincinnati
SJU - CVG
SJUCVG
San Juan Luis Munoz Marin Intl
Wed 2/11
4:06 pm-5:32 pm
1 stop26h 26m
Cincinnati Cinci./N. Kentucky
Sun 2/15
5:20 am-2:53 am
1 stop20h 33m
$241
San JuanCincinnati
SJU - CVG
SJUCVG
San Juan Luis Munoz Marin Intl
Tue 2/24
6:37 pm-11:55 pm
1 stop6h 18m
Cincinnati Cinci./N. Kentucky
Wed 3/11
5:00 pm-11:59 pm
1 stop6h 59m
$246
San JuanLouisville
SJU - SDF
SJUSDF
San Juan Luis Munoz Marin Intl
Wed 3/4
7:00 am-11:59 pm
1 stop17h 59m
Louisville Intl
Mon 3/9
12:07 pm-4:24 am
1 stop16h 17m
$246
San JuanLouisville
SJU - SDF
SJUSDF
San Juan Luis Munoz Marin Intl
Wed 3/4
8:05 am-2:47 pm
1 stop7h 42m
Louisville Intl
Tue 3/10
1:47 pm-11:36 pm
1 stop9h 49m
$246
Showing 1-10 of 60 results
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.
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
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 January 28, 2026.
See what other customers who have flown with Southwest, Delta, and United 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
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
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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.
Top 4 airlines flying from Caribbean to Kentucky
Discover the top 4 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 January 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$138 | Average$375 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$175 | Average$335 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$226 | Average$499 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$232 | Average$494 | FlexibilityNo cancel fee | On-time69% |