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Kentucky

$103+ Cheap flights from Caribbean Islands 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SDF
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Kentucky

Keep the following information in mind while searching for Caribbean Islands to Kentucky flight deals. Data was last updated September 16, 2025.

Round-trip from

$211
(Southwest)

One-way from

$103
(Southwest)
From Caribbean Islands to Kentucky
Search Deals
One-way flight from Caribbean Islands to Kentucky
Search Deals

Find flight deals from Caribbean Islands to Kentucky

Cheapest flights from Caribbean Islands to Kentucky
Explore the most affordable flight options available from Caribbean Islands to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/611:20 amSJU - BNA
Nonstop4h 35mSouthwest
Wed 12/106:55 amBNA - SJU
1 stop6h 35mSouthwest
Deal found 9/15$211
This Frontier deal was found by Cheapflights users on 9/16. 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 10/13:39 amSJU - CVG
1 stop7h 17mFrontier
Tue 10/77:27 pmCVG - SJU
2 stops19h 57mFrontier
Deal found 9/16$212
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:40 amSJU - BNA
2 stops8h 20mSouthwest
Mon 11/176:55 amBNA - SJU
1 stop6h 35mSouthwest
Deal found 9/15$215
This American Airlines deal was found by Cheapflights users on 9/14. 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 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 9/14$225
This American Airlines deal was found by Cheapflights users on 9/16. 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 12/42:05 pmSJU - CVG
1 stop10h 53mAmerican Airlines
Mon 12/86:05 pmCVG - SJU
1 stop16h 54mAmerican Airlines
Deal found 9/16$230
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 11/112:05 amSJU - BNA
1 stop9h 00mUnited Airlines
Mon 11/171:30 pmBNA - SJU
1 stop6h 52mUnited Airlines
Deal found 9/15$234
This Frontier deal was found by Cheapflights users on 9/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:22 amSJU - BNA
2 stops18h 37mFrontier
Mon 10/271:53 pmBNA - SJU
1 stop9h 36mFrontier
Deal found 9/13$244
This Frontier deal was found by Cheapflights users on 9/14. 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.
Tue 9/239:26 pmSJU - CVG
2 stops16h 57mFrontier
Wed 10/13:32 pmCVG - SJU
1 stop11h 02mFrontier
Deal found 9/14$252
This Frontier deal was found by Cheapflights users on 9/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/309:00 amSJU - CVG
2 stops14h 59mFrontier
Thu 11/611:00 amCVG - SJU
2 stops13h 32mFrontier
Deal found 9/13$253
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/112:05 amSJU - BNA
1 stop9h 00mUnited Airlines
Sun 11/166:07 amBNA - SJU
1 stop7h 33mUnited Airlines
Deal found 9/14$253
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2111:01 amSTT - BNA
1 stop12h 05mSpirit Airlines
Fri 10/248:05 pmBNA - STT
1 stop15h 54mSpirit Airlines
Deal found 9/15$254
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/179:00 amSJU - BNA
1 stop15h 59mMultiple Airlines
Mon 10/205:45 amBNA - SJU
1 stop8h 31mMultiple Airlines
Deal found 9/15$254

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands 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 16, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Kentucky that are best for you.

Fly from

Caribbean Islands

Fly to

Kentucky

Route

Depart

Return

Price

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Wed 11/19

9:40 am-4:30 pm

1 stop8h 50m

Nashville Intl

Wed 11/26

4:15 pm-1:40 am

1 stop7h 25m

$215

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Thu 11/13

1:57 pm-11:04 pm

1 stop11h 07m

Nashville Intl

Mon 11/17

6:20 am-5:26 pm

1 stop9h 06m

$215

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Thu 11/6

4:56 pm-11:59 pm

1 stop9h 03m

Nashville Intl

Mon 11/10

7:05 am-5:05 pm

1 stop8h 00m

$215

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Wed 11/12

6:40 am-1:00 pm

2 stops8h 20m

Nashville Intl

Sun 11/16

5:25 am-2:35 pm

1 stop7h 10m

$215

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Fri 11/14

8:20 am-10:41 pm

1 stop16h 21m

Nashville Intl

Mon 11/17

10:15 am-8:48 pm

1 stop8h 33m

$215

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Sat 12/6

10:50 am-6:05 pm

1 stop9h 15m

Nashville Intl

Wed 12/10

6:55 am-3:30 pm

1 stop6h 35m

$215

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Thu 12/4

2:05 pm-11:58 pm

1 stop10h 53m

Cincinnati Cinci./N. Kentucky

Mon 12/8

6:05 pm-11:59 am

1 stop16h 54m

$230

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Sat 10/4

5:00 am-10:55 am

1 stop5h 55m

Cincinnati Cinci./N. Kentucky

Tue 10/7

3:45 pm-10:45 pm

1 stop7h 00m

$235

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Thu 10/30

9:00 am-11:59 pm

2 stops14h 59m

Cincinnati Cinci./N. Kentucky

Thu 11/6

11:00 am-1:32 am

2 stops13h 32m

$253

Saint Thomas IslandNashville

STT - BNA

STTBNA

Saint Thomas Island Cyril E King

Tue 10/21

11:01 am-10:06 pm

1 stop12h 05m

Nashville Intl

Fri 10/24

8:05 pm-12:59 pm

1 stop15h 54m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 60 results
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Best time to book a flight from Caribbean Islands to Kentucky

Have a flexible travel schedule? Discover the best time to fly to Kentucky from Caribbean Islands 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 Islands to Kentucky

What is the cheapest month to book a flight from Caribbean Islands to Kentucky?

Currently, January is the cheapest month in which you can book a flight from Caribbean Islands to Kentucky (average of $299). Flying from Caribbean Islands 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 EPX to KY?

Find hourly flight availability from Caribbean Islands 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 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean Islands to Kentucky as you normally would.

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 16, 2025.
Peruse reviews from past customers who have flown with Delta and American Airlines from Caribbean Islands to Kentucky to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,957 reviews

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,957 reviews
Delta
8.0
Very good
7,957 reviews

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,957 reviews

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands 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 Islands to Kentucky?

    Southwest, Delta, and American Airlines can get you from Caribbean Islands to Kentucky in just under 8h 50m. Your travel time can differ by up to 2h 17m. Caribbean Islands and Kentucky are separated by a distance of 1753 mi. This flight may include one or multiple stops.

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

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $103. Users have also found prices from $108 and $113 on Delta and United Airlines, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean Islands 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 Islands to Kentucky?

    Currently, January is the cheapest month in which you can book a flight from Caribbean Islands to Kentucky (average of $299). Flying from Caribbean Islands 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

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Alternative routes for Caribbean Islands 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 Islands to Kentucky

Discover the top 3 airlines that operate flights from Caribbean Islands 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 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$138Average$526FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$175Average$320FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$255Average$465FlexibilityNo cancel feeOn-time71%

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