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Kentucky

$69+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SDF
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 November 3, 2025.

Round-trip from

$170
(CheapOair)

One-way from

$69
(Priceline)
From Caribbean Islands to Kentucky
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One-way flight from Caribbean Islands to Kentucky
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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 November 3, 2025.

This Orbitz deal was found by Cheapflights users on 11/2. 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.
Thu 12/41:59 amSJU - BNA
1 stop14h 02mMultiple Airlines
Mon 12/86:10 amBNA - SJU
1 stop16h 35mMultiple Airlines
Deal found 11/2$213
This United Airlines deal was found by Cheapflights users on 11/1. 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.
Thu 12/43:46 pmSJU - BNA
1 stop8h 29mUnited Airlines
Tue 12/91:30 pmBNA - SJU
1 stop6h 52mUnited Airlines
Deal found 11/1$215
This eDestinos deal was found by Cheapflights users on 11/1. 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.
Fri 11/145:36 pmSJU - BNA
1 stop7h 43mSpirit Airlines
Mon 11/176:45 amBNA - SJU
1 stop6h 28mSpirit Airlines
Deal found 11/1$216
This Delta deal was found by Cheapflights users on 11/3. 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 12/256:30 amSJU - SDF
1 stop10h 28mDelta
Thu 1/16:00 amSDF - SJU
1 stop5h 57mDelta
Deal found 11/3$225
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/41:59 amSJU - BNA
1 stop14h 02mMultiple Airlines
Sun 12/78:59 pmBNA - SJU
1 stop13h 33mMultiple Airlines
Deal found 11/2$228
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/127:00 amSJU - SDF
1 stop11h 38mAmerican Airlines
Tue 1/136:00 amSDF - SJU
1 stop11h 22mAmerican Airlines
Deal found 11/2$229
This Frontier deal was found by Cheapflights users on 11/2. 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 11/192:25 amSJU - BNA
1 stop9h 00mFrontier
Thu 11/2710:20 amBNA - SJU
1 stop8h 29mFrontier
Deal found 11/2$237
This Delta deal was found by Cheapflights users on 11/1. 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.
Wed 11/127:00 amSJU - CVG
1 stop8h 15mDelta
Mon 11/172:27 pmCVG - SJU
1 stop7h 46mDelta
Deal found 11/1$245
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Sun 12/217:35 amSJU - BNA
1 stop16h 39mMultiple Airlines
Tue 12/305:23 pmBNA - SJU
1 stop15h 10mMultiple Airlines
Deal found 11/3$247
This American Airlines deal was found by Cheapflights users on 11/1. 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 11/132:47 pmSJU - CVG
2 stops10h 11mAmerican Airlines
Sun 11/1610:31 amCVG - SJU
1 stop9h 27mAmerican Airlines
Deal found 11/1$250
This Southwest deal was found by Cheapflights users on 11/3. 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.
Thu 12/49:40 amSJU - BNA
1 stop8h 50mSouthwest
Mon 12/86:40 amBNA - SJU
1 stop6h 50mSouthwest
Deal found 11/3$255
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Sun 12/217:35 amSJU - BNA
1 stop16h 39mMultiple Airlines
Sat 1/35:23 pmBNA - SJU
1 stop6h 49mMultiple Airlines
Deal found 11/1$257

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 November 3, 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 JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Thu 2/5

3:55 am-10:52 am

1 stop7h 57m

Cincinnati Cinci./N. Kentucky

Tue 2/10

11:57 am-9:55 am

1 stop20h 58m

$170

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Thu 1/29

1:58 pm-10:27 pm

1 stop10h 29m

Nashville Intl

Mon 2/2

7:00 am-2:59 pm

1 stop5h 59m

$215

San JuanLouisville

SJU - SDF

SJUSDF

San Juan Luis Munoz Marin Intl

Thu 12/25

6:30 am-3:58 pm

1 stop10h 28m

Louisville Intl

Thu 1/1

6:00 am-12:57 pm

1 stop5h 57m

$225

San JuanLouisville

SJU - SDF

SJUSDF

San Juan Luis Munoz Marin Intl

Wed 2/18

5:47 pm-8:33 am

1 stop15h 46m

Louisville Intl

Sun 2/22

3:49 pm-11:48 pm

1 stop6h 59m

$225

San JuanLouisville

SJU - SDF

SJUSDF

San Juan Luis Munoz Marin Intl

Fri 12/12

7:00 am-5:38 pm

1 stop11h 38m

Louisville Intl

Tue 1/13

6:00 am-6:22 pm

1 stop11h 22m

$229

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Thu 12/4

3:46 pm-10:15 pm

1 stop8h 29m

Nashville Intl

Tue 12/9

1:30 pm-10:22 pm

1 stop6h 52m

$234

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Fri 11/14

6:36 pm-12:09 am

1 stop6h 33m

Cincinnati Cinci./N. Kentucky

Mon 11/17

12:14 pm-11:13 pm

1 stop9h 59m

$245

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Thu 11/13

1:57 pm-12:09 am

1 stop11h 12m

Cincinnati Cinci./N. Kentucky

Mon 11/17

2:27 pm-11:13 pm

1 stop7h 46m

$245

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Thu 3/5

2:55 am-10:49 am

1 stop8h 54m

Cincinnati Cinci./N. Kentucky

Tue 3/10

5:05 am-2:59 pm

1 stop9h 54m

$256

San JuanLouisville

SJU - SDF

SJUSDF

San Juan Luis Munoz Marin Intl

Thu 12/25

4:38 pm-8:50 am

2 stops17h 12m

Louisville Intl

Thu 1/1

5:00 am-11:39 am

1 stop5h 39m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

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, March is the cheapest month in which you can book a flight from Caribbean Islands to Kentucky (average of $138). Flying from Caribbean Islands to Kentucky in January is currently the most expensive (average of $374). 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 November 3, 2025.

When flying from Caribbean Islands to Kentucky, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 38% versus a flight at noon.

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 November 3, 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
7.9
Good
8,001 reviews

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.
Delta
7.9
Good
8,001 reviews
Delta
7.9
Good
8,001 reviews

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.
American Airlines
7.2
Good
11,034 reviews
Delta
7.9
Good
8,001 reviews

Overall

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.

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?

    Frontier, American Airlines, and Delta can get you from Caribbean Islands to Kentucky in just under 7h 57m. Your travel time can differ by up to 2h 32m. Caribbean Islands and Kentucky are separated by a distance of 1809 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 Frontier. According to our data, you can fly for as low as $91. Users have also found prices from $108 and $108 on Southwest and Delta, 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, March is the cheapest month in which you can book a flight from Caribbean Islands to Kentucky (average of $138). Flying from Caribbean Islands to Kentucky in January is currently the most expensive (average of $374). 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$138Average$520FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$175Average$335FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$225Average$497FlexibilityNo cancel feeOn-time71%

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