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Kentucky

$80+ Cheap flights from Caribbean to Kentucky

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SDF
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Caribbean to Kentucky

Keep the following information in mind while searching for Caribbean to Kentucky flight deals. Data was last updated July 31, 2025.

Round-trip from

$195
(American Airlines)

One-way from

$80
(Booking.com)

Popular in

May

Cheapest in

January

Average price

$468
From Caribbean to Kentucky
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One-way flight from Caribbean to Kentucky
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Highest demand for flights based on searches. 4% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Caribbean to Kentucky

Cheapest flights from Caribbean to Kentucky
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 July 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/217:05 pmSJU - BNA
1 stop16h 24mAmerican Airlines
Tue 8/267:28 amBNA - SJU
1 stop15h 31mAmerican Airlines
Deal found 7/30$195
This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/281:36 pmSJU - SDF
1 stop10h 49mAmerican Airlines
Sun 8/3110:49 amSDF - SJU
1 stop12h 00mAmerican Airlines
Deal found 7/31$205
This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/23:55 pmSJU - CVG
2 stops8h 34mAmerican Airlines
Tue 10/71:05 pmCVG - SJU
2 stops9h 05mAmerican Airlines
Deal found 7/31$205
This Delta deal was found by Cheapflights users on 7/30. 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.
Fri 9/125:41 pmSJU - BNA
1 stop6h 16mDelta
Mon 9/152:18 pmBNA - SJU
1 stop6h 42mDelta
Deal found 7/30$205
This Booking.com deal was found by Cheapflights users on 7/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/173:19 pmSJU - BNA
1 stop9h 04mSpirit Airlines
Wed 9/245:05 amBNA - SJU
1 stop8h 06mSpirit Airlines
Deal found 7/29$207
This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/226:00 amSJU - LEX
2 stops14h 53mAmerican Airlines
Sat 8/304:04 pmLEX - SJU
1 stop6h 45mAmerican Airlines
Deal found 7/31$215
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1412:50 pmSJU - CVG
1 stop11h 05mDelta
Fri 8/222:30 pmCVG - SJU
1 stop7h 37mDelta
Deal found 7/31$225
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/292:40 pmSJU - BNA
1 stop6h 55mSouthwest
Mon 9/16:05 amBNA - SJU
1 stop7h 35mSouthwest
Deal found 7/30$235
This Frontier deal was found by Cheapflights users on 7/31. 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.
Fri 8/83:34 amSJU - CVG
1 stop10h 00mFrontier
Tue 8/198:00 amCVG - SJU
1 stop11h 08mFrontier
Deal found 7/31$238
This OneTravel deal was found by Cheapflights users on 7/31. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1811:59 amSJU - BNA
1 stop5h 36mMultiple Airlines
Sun 9/216:56 pmBNA - SJU
1 stop12h 06mMultiple Airlines
Deal found 7/31$251
This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/225:05 pmSDQ - BNA
1 stop6h 04mSpirit Airlines
Tue 9/26:05 amBNA - SDQ
1 stop8h 55mSpirit Airlines
Deal found 7/31$257
This Frontier deal was found by Cheapflights users on 7/31. 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 8/213:59 amSJU - BNA
1 stop7h 43mFrontier
Mon 8/2511:37 amBNA - SJU
1 stop6h 31mFrontier
Deal found 7/31$258

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 July 31, 2025.
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

Thu 8/21

7:05 pm-10:29 am

1 stop16h 24m

Nashville Intl

Tue 8/26

7:28 am-11:59 pm

1 stop15h 31m

$195

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Fri 9/12

5:41 pm-10:57 pm

1 stop6h 16m

Nashville Intl

Mon 9/15

2:18 pm-10:00 pm

1 stop6h 42m

$205

San JuanLouisville

SJU - SDF

SJUSDF

San Juan Luis Munoz Marin Intl

Thu 8/28

1:36 pm-12:25 am

1 stop10h 49m

Louisville Intl

Sun 8/31

10:49 am-10:49 pm

1 stop12h 00m

$205

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Thu 10/2

3:55 pm-12:29 am

2 stops8h 34m

Cincinnati Cinci./N. Kentucky

Tue 10/7

1:05 pm-10:10 pm

2 stops9h 05m

$205

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Wed 9/17

3:19 pm-11:23 pm

1 stop9h 04m

Nashville Intl

Wed 9/24

5:05 am-2:11 pm

1 stop8h 06m

$207

San JuanLexington

SJU - LEX

SJULEX

San Juan Luis Munoz Marin Intl

Fri 8/22

6:00 am-8:53 pm

2 stops14h 53m

Lexington Blue Grass

Sat 8/30

4:04 pm-10:49 pm

1 stop6h 45m

$215

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Thu 8/14

12:50 pm-11:55 pm

1 stop11h 05m

Cincinnati Cinci./N. Kentucky

Fri 8/22

2:30 pm-10:07 pm

1 stop7h 37m

$225

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Fri 8/29

2:40 pm-8:35 pm

1 stop6h 55m

Nashville Intl

Mon 9/1

6:05 am-2:40 pm

1 stop7h 35m

$235

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Tue 8/12

3:40 am-3:09 pm

1 stop11h 29m

Cincinnati Cinci./N. Kentucky

Sat 8/16

8:00 am-3:54 pm

1 stop7h 54m

$238

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Thu 9/18

11:59 am-4:35 pm

1 stop5h 36m

Nashville Intl

Sun 9/21

6:56 pm-8:02 am

1 stop12h 06m

$251

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 60 results
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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 $299). Flying from Caribbean to Kentucky in April is currently the most expensive (average of $369). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CB to KY?

Find hourly flight availability from Caribbean to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

When flying from Caribbean to Kentucky, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing 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 July 31, 2025.
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.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,914 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • What are the cheapest airlines to fly from Caribbean to Kentucky one-way?

    The cheapest airlines for a one-way flight from Caribbean to Kentucky are Spirit Airlines ($80), United Airlines ($98), and Delta ($103).

  • Can I find deals for flights from Caribbean to Kentucky that include hotel bookings?

    Yes. In addition to deals on Caribbean to Kentucky flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean to Kentucky?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean to Kentucky.

  • Can I find deals for business class flights from Caribbean to Kentucky?

    Yes. Cheapflights offers flight deals from Caribbean to Kentucky by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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 $299). Flying from Caribbean to Kentucky in April is currently the most expensive (average of $369). 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.

See more FAQs

Browse thousands of different 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.
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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$205Average$335FlexibilityNo cancel feeOn-time63%
DeltaCheapest$215Average$520FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$305Average$489FlexibilityNo cancel feeOn-time71%

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