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Kentucky

$108+ 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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SDF
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$215
(Southwest)

One-way from

$108
(Delta)

Popular in

June

Cheapest in

January

Average price

$421
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. 7% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/10. 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 10/224:45 pmSJU - BNA
1 stop6h 40mAmerican Airlines
Sun 10/267:17 amBNA - SJU
1 stop15h 37mAmerican Airlines
Deal found 9/10$215
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/117:10 amSJU - CVG
1 stop17h 20mAmerican Airlines
Sat 10/181:05 pmCVG - SJU
2 stops10h 49mAmerican Airlines
Deal found 9/11$225
This United Airlines deal was found by Cheapflights users on 9/10. 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 9/301:05 amSJU - SDF
2 stops12h 16mUnited Airlines
Tue 10/146:15 amSDF - SJU
1 stop7h 30mUnited Airlines
Deal found 9/10$225
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/243:00 pmSJU - CVG
1 stop8h 59mAmerican Airlines
Mon 11/36:00 amCVG - SJU
1 stop16h 52mAmerican Airlines
Deal found 9/11$230
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/235:30 amSJU - SDF
1 stop9h 32mAmerican Airlines
Sun 10/266:45 amSDF - SJU
1 stop7h 23mAmerican Airlines
Deal found 9/10$230
This American Airlines deal was found by Cheapflights users on 9/10. 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 11/114:43 pmSJU - CVG
1 stop7h 26mAmerican Airlines
Sun 11/166:00 amCVG - SJU
1 stop8h 53mAmerican Airlines
Deal found 9/10$231
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/215:30 amSJU - CVG
1 stop7h 05mAmerican Airlines
Thu 10/3012:24 pmCVG - SJU
2 stops9h 46mAmerican Airlines
Deal found 9/11$235
This American Airlines deal was found by Cheapflights users on 9/10. 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 11/134:44 pmSJU - LEX
1 stop8h 15mAmerican Airlines
Sun 11/168:10 pmLEX - SJU
1 stop16h 28mAmerican Airlines
Deal found 9/10$235
This Frontier deal was found by Cheapflights users on 9/11. 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 10/29:26 pmSJU - CVG
2 stops20h 12mFrontier
Tue 10/73:10 pmCVG - SJU
1 stop11h 20mFrontier
Deal found 9/11$240
This American Airlines deal was found by Cheapflights users on 9/10. 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 11/116:25 amSJU - CVG
1 stop17h 44mAmerican Airlines
Mon 11/1711:16 amCVG - SJU
1 stop8h 32mAmerican Airlines
Deal found 9/10$241
This Frontier deal was found by Cheapflights users on 9/11. 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 9/259:26 pmSJU - CVG
2 stops20h 12mFrontier
Tue 9/303:32 pmCVG - SJU
1 stop11h 02mFrontier
Deal found 9/11$246
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/14:43 pmSJU - SDF
1 stop6h 32mAmerican Airlines
Tue 10/148:18 amSDF - SJU
1 stop13h 52mAmerican Airlines
Deal found 9/10$246

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 September 11, 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 JuanLouisville

SJU - SDF

SJUSDF

San Juan Luis Munoz Marin Intl

Tue 9/30

1:05 am-11:33 am

1 stop10h 28m

Louisville Intl

Tue 10/14

6:15 am-1:45 pm

1 stop7h 30m

$225

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Sat 10/11

7:10 am-12:30 am

1 stop17h 20m

Cincinnati Cinci./N. Kentucky

Sat 10/18

1:05 pm-11:54 pm

2 stops10h 49m

$225

San JuanLouisville

SJU - SDF

SJUSDF

San Juan Luis Munoz Marin Intl

Thu 10/23

5:30 am-3:02 pm

1 stop9h 32m

Louisville Intl

Sun 10/26

6:45 am-2:08 pm

1 stop7h 23m

$230

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Tue 11/11

4:43 pm-11:09 pm

1 stop7h 26m

Cincinnati Cinci./N. Kentucky

Sat 11/15

8:00 am-11:52 pm

1 stop14h 52m

$231

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Tue 11/11

4:43 pm-11:09 pm

1 stop7h 26m

Cincinnati Cinci./N. Kentucky

Sun 11/16

6:00 am-3:53 pm

1 stop8h 53m

$231

San JuanLexington

SJU - LEX

SJULEX

San Juan Luis Munoz Marin Intl

Thu 11/13

4:44 pm-11:59 pm

1 stop8h 15m

Lexington Blue Grass

Sun 11/16

8:10 pm-1:38 pm

1 stop16h 28m

$235

San JuanLouisville

SJU - SDF

SJUSDF

San Juan Luis Munoz Marin Intl

Thu 10/16

5:30 am-3:02 pm

1 stop9h 32m

Louisville Intl

Sun 10/19

7:33 am-11:59 pm

1 stop16h 26m

$251

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Thu 12/11

2:05 pm-7:55 pm

1 stop7h 50m

Nashville Intl

Mon 12/15

6:55 am-3:30 pm

1 stop6h 35m

$255

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Thu 1/15

5:35 am-11:40 am

2 stops8h 05m

Nashville Intl

Mon 1/19

12:55 pm-9:50 pm

1 stop6h 55m

$255

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Fri 12/12

2:10 pm-8:45 pm

1 stop8h 35m

Nashville Intl

Mon 12/15

6:55 am-3:30 pm

1 stop6h 35m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

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 September 11, 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 September 11, 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
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 United Airlines, American Airlines, and Southwest fly from Caribbean to Kentucky in about 7h 50m. The time it takes to get you to your destination can typically vary by up to 9h 30m. 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 Southwest ($108), Delta ($108), and United Airlines ($113).

  • 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 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$138Average$526FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$175Average$335FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$232Average$390FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$255Average$465FlexibilityNo cancel feeOn-time71%

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