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Kentucky

$81+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SDF
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap 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 December 15, 2025.

This Frontier deal was found by Cheapflights users on 12/14. 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 12/2510:33 amSJU - CVG
1 stop8h 11mFrontier
Sun 1/42:50 pmCVG - SJU
1 stop9h 47mFrontier
Deal found 12/14$227
This American Airlines deal was found by Cheapflights users on 12/13. 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 12/238:25 amSJU - CVG
1 stop16h 26mAmerican Airlines
Sat 1/37:53 amCVG - SJU
1 stop15h 06mAmerican Airlines
Deal found 12/13$235
This Priceline deal was found by Cheapflights users on 12/13. 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 12/293:55 amSJU - CVG
1 stop14h 49mFrontier
Wed 1/73:49 pmCVG - SJU
1 stop16h 19mFrontier
Deal found 12/13$247
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 12/256:28 pmSJU - BNA
1 stop5h 59mMultiple Airlines
Sat 1/178:12 pmBNA - SJU
1 stop14h 20mMultiple Airlines
Deal found 12/13$261
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 12/256:28 pmSJU - BNA
1 stop5h 59mMultiple Airlines
Mon 1/58:38 pmBNA - SJU
1 stop25h 06mMultiple Airlines
Deal found 12/13$262
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 12/246:28 pmSJU - BNA
1 stop5h 59mMultiple Airlines
Mon 1/58:38 pmBNA - SJU
1 stop25h 06mMultiple Airlines
Deal found 12/15$264
This eDestinos deal was found by Cheapflights users on 12/14. 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 12/254:55 pmSJU - BNA
1 stop8h 19mSpirit Airlines
Wed 12/315:23 pmBNA - SJU
1 stop15h 10mSpirit Airlines
Deal found 12/14$269
This United Airlines deal was found by Cheapflights users on 12/15. 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 12/228:30 amSJU - SDF
1 stop7h 14mUnited Airlines
Sun 1/118:29 amSDF - SJU
2 stops11h 57mUnited Airlines
Deal found 12/15$271
This eDestinos deal was found by Cheapflights users on 12/14. 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 12/256:28 pmSJU - BNA
1 stop5h 59mSpirit Airlines
Thu 1/111:14 amBNA - SJU
1 stop8h 51mSpirit Airlines
Deal found 12/14$271
This eDestinos deal was found by Cheapflights users on 12/13. 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.
Sat 12/206:28 pmSJU - BNA
1 stop5h 59mSpirit Airlines
Sat 1/36:10 amBNA - SJU
1 stop13h 55mSpirit Airlines
Deal found 12/13$273
This eDestinos deal was found by Cheapflights users on 12/13. 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.
Sun 12/214:55 pmSJU - BNA
1 stop8h 19mSpirit Airlines
Tue 12/3011:14 amBNA - SJU
1 stop8h 51mSpirit Airlines
Deal found 12/13$275
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/236:00 amSJU - BNA
1 stop19h 07mMultiple Airlines
Wed 12/318:38 pmBNA - SJU
1 stop23h 27mMultiple Airlines
Deal found 12/14$277

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 December 15, 2025.

Round-trip from

$161
(Trip.com)

One-way from

$81
(Trip.com)

Popular in

June

Cheapest in

October

Average price

$349
From Caribbean to Kentucky
Search Deals
One-way flight from Caribbean to Kentucky
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 15, 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 JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Thu 1/15

6:00 am-2:57 pm

1 stop9h 57m

Cincinnati Cinci./N. Kentucky

Mon 1/19

12:03 pm-2:48 am

1 stop13h 45m

$161

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Thu 1/15

6:00 am-2:57 pm

1 stop9h 57m

Cincinnati Cinci./N. Kentucky

Mon 1/19

7:45 pm-3:35 pm

2 stops18h 50m

$169

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Thu 1/29

8:00 am-4:29 pm

1 stop9h 29m

Cincinnati Cinci./N. Kentucky

Mon 2/2

4:21 pm-11:36 pm

1 stop6h 15m

$170

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Thu 1/22

8:00 am-4:29 pm

1 stop9h 29m

Cincinnati Cinci./N. Kentucky

Mon 1/26

10:30 am-6:40 pm

1 stop7h 10m

$170

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Mon 1/12

9:23 pm-5:48 pm

1 stop21h 25m

Cincinnati Cinci./N. Kentucky

Sat 1/17

4:13 pm-2:23 pm

1 stop21h 10m

$170

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Sun 3/1

2:54 am-2:50 pm

1 stop13h 56m

Nashville Intl

Mon 3/9

9:33 pm-9:45 am

1 stop11h 12m

$180

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Thu 1/22

4:36 pm-11:26 pm

1 stop7h 50m

Cincinnati Cinci./N. Kentucky

Tue 1/27

4:23 pm-11:59 pm

1 stop6h 36m

$196

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Sat 1/10

7:26 pm-8:31 pm

1 stop26h 05m

Cincinnati Cinci./N. Kentucky

Sat 1/17

4:13 pm-2:23 pm

1 stop21h 10m

$196

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Tue 1/27

4:49 pm-9:35 pm

1 stop6h 46m

Nashville Intl

Sun 2/1

5:00 am-3:59 pm

2 stops8h 59m

$215

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Tue 1/27

9:05 am-2:25 pm

1 stop7h 20m

Nashville Intl

Mon 2/2

4:05 pm-12:35 am

1 stop6h 30m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

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 $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.

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 December 15, 2025.

It’s typically best to fly out from Caribbean to Kentucky in the evening. Doing so could potentially save you 54% on the flight price compared to flying at noon, which is usually more expensive.

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 December 15, 2025.
See what other customers who have flown with Southwest, Delta, and American 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
7.9
Good
4,250 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

7.9

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

7.9

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,007 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

7.9

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,052 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

7.9

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Caribbean to Kentucky?

    Airlines like Frontier, American Airlines, and Southwest fly from Caribbean to Kentucky in about 6h 46m. The time it takes to get you to your destination can typically vary by up to 3h 11m. Caribbean and Kentucky are separated by a distance of 1753 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 ($81), Delta ($110), and American Airlines ($112).

  • 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 $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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$138Average$385FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$175Average$335FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$225Average$499FlexibilityNo cancel feeOn-time71%

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