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Caribbean Islands

$89+ Cheap flights from Kentucky to Caribbean Islands

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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
1 adult, Economy
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Cheap flight deals from Kentucky to Caribbean Islands

Cheapest flights from Kentucky to Caribbean Islands
Explore the most affordable flight options available from Kentucky to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 8, 2025.

This Priceline deal was found by Cheapflights users on 12/7. 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.
Sat 12/204:07 pmCVG - SJU
1 stop15h 32mFrontier
Wed 12/248:36 pmSJU - CVG
1 stop28h 32mFrontier
Deal found 12/7$229
This CheapOair deal was found by Cheapflights users on 12/7. 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.
Wed 12/319:57 amCVG - SJU
1 stop21h 42mFrontier
Thu 1/810:47 pmSJU - CVG
1 stop22h 44mFrontier
Deal found 12/7$230
This Frontier deal was found by Cheapflights users on 12/6. 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 12/115:05 amCVG - SJU
1 stop9h 54mFrontier
Sun 12/213:55 amSJU - CVG
1 stop7h 57mFrontier
Deal found 12/6$231
This Kiwi.com deal was found by Cheapflights users on 12/6. 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 12/145:05 amCVG - SJU
1 stop9h 54mFrontier
Tue 12/169:15 amSJU - CVG
1 stop16h 53mFrontier
Deal found 12/6$232
This eDestinos deal was found by Cheapflights users on 12/7. 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.
Tue 12/3011:57 amCVG - SJU
1 stop7h 30mFrontier
Thu 1/85:45 amSJU - CVG
1 stop15h 46mFrontier
Deal found 12/7$239
This Kiwi.com deal was found by Cheapflights users on 12/6. 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.
Mon 12/152:23 pmCVG - SJU
1 stop9h 22mMultiple Airlines
Fri 12/193:54 amSJU - CVG
1 stop12h 08mMultiple Airlines
Deal found 12/6$241
This eDestinos deal was found by Cheapflights users on 12/6. 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 12/135:45 amBNA - SJU
1 stop16h 31mSpirit Airlines
Mon 12/155:00 pmSJU - BNA
1 stop7h 08mSpirit Airlines
Deal found 12/6$243
This Kiwi.com deal was found by Cheapflights users on 12/6. 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 12/3111:14 amBNA - SJU
1 stop8h 51mMultiple Airlines
Thu 1/89:04 amSJU - BNA
1 stop12h 39mMultiple Airlines
Deal found 12/6$246
This Super.com deal was found by Cheapflights users on 12/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/118:59 pmBNA - SJU
1 stop13h 33mSpirit Airlines
Sat 12/135:00 pmSJU - BNA
1 stop7h 08mSpirit Airlines
Deal found 12/5$249
This Priceline deal was found by Cheapflights users on 12/7. 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.
Sat 12/1311:57 amCVG - SJU
1 stop13h 53mFrontier
Mon 12/1511:05 amSJU - CVG
1 stop9h 40mFrontier
Deal found 12/7$252
This Kiwi.com deal was found by Cheapflights users on 12/6. 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.
Sat 12/132:35 pmCVG - SJU
1 stop20h 57mMultiple Airlines
Fri 12/193:54 amSJU - CVG
1 stop12h 08mMultiple Airlines
Deal found 12/6$253
This Priceline deal was found by Cheapflights users on 12/6. 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.
Sun 12/145:15 amCVG - SJU
1 stop17h 35mFrontier
Fri 12/197:30 amSJU - CVG
1 stop11h 44mFrontier
Deal found 12/6$254

Find flight deals from Kentucky to Caribbean Islands

Keep the following information in mind while searching for Kentucky to Caribbean Islands flight deals. Data was last updated December 8, 2025.

Round-trip from

$225
(American Airlines)

One-way from

$89
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$565
From Kentucky to Caribbean Islands
Search Deals
One-way flight from Kentucky to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 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 Kentucky to Caribbean Islands 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 8, 2025.
Use the filters below to find and compare flights from Kentucky to Caribbean Islands that are best for you.

Fly from

Kentucky

Fly to

Caribbean Islands

Route

Depart

Return

Price

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 2/2

5:35 am-5:17 pm

1 stop10h 42m

San Juan Luis Munoz Marin Intl

Fri 2/6

6:27 pm-11:50 pm

1 stop6h 23m

$225

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Mon 2/2

11:15 am-12:36 am

2 stops12h 21m

San Juan Luis Munoz Marin Intl

Thu 2/5

8:35 am-3:30 pm

1 stop7h 55m

$225

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Tue 1/13

12:05 pm-9:39 pm

1 stop8h 34m

San Juan Luis Munoz Marin Intl

Fri 1/16

5:55 pm-11:28 pm

1 stop6h 33m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 2/2

5:35 am-2:31 pm

1 stop7h 56m

San Juan Luis Munoz Marin Intl

Thu 2/12

6:27 pm-11:58 pm

1 stop6h 31m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Tue 2/3

7:00 am-5:17 pm

1 stop9h 17m

San Juan Luis Munoz Marin Intl

Fri 2/6

6:27 pm-11:50 pm

1 stop6h 23m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 1/26

5:35 am-5:17 pm

1 stop10h 42m

San Juan Luis Munoz Marin Intl

Thu 1/29

2:15 pm-8:56 pm

1 stop7h 41m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Tue 2/3

5:35 am-5:17 pm

1 stop10h 42m

San Juan Luis Munoz Marin Intl

Thu 2/12

2:15 pm-11:58 pm

1 stop10h 43m

$225

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sun 1/25

12:20 pm-8:58 pm

1 stop7h 38m

San Juan Luis Munoz Marin Intl

Tue 2/3

7:00 am-5:09 pm

1 stop11h 09m

$225

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Fri 1/23

2:25 pm-11:45 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Tue 2/3

7:00 am-5:09 pm

1 stop11h 09m

$225

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Mon 1/26

6:42 am-4:50 pm

1 stop9h 08m

San Juan Luis Munoz Marin Intl

Tue 2/3

7:30 am-1:27 pm

1 stop6h 57m

$225

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

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

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

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

Currently, March is the cheapest month in which you can book a flight from Kentucky to Caribbean Islands (average of $190). Flying from Kentucky to Caribbean Islands in June is currently the most expensive (average of $285). 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 KY to EPX?

Find hourly flight availability from Kentucky to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 8, 2025.

It’s optimal to fly from Kentucky to Caribbean Islands at noon. By choosing this option you can save up to 28% on the cost of your flight, compared to a flight in the evening.

What is the cheapest day to fly from Kentucky to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Kentucky to Caribbean Islands. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Kentucky to Caribbean Islands flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Related info for your journey

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

    For as low as $225, Delta can have you in Caribbean Islands from Kentucky in 8h 34m. The distance between Kentucky and Caribbean Islands is about 1809 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $79. Users have also found prices from $109 and $137 on American Airlines and Delta, respectively.

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

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

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

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

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

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

    Currently, March is the cheapest month in which you can book a flight from Kentucky to Caribbean Islands (average of $190). Flying from Kentucky to Caribbean Islands in June is currently the most expensive (average of $285). 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 Kentucky to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Kentucky to Caribbean Islands

Discover the top 5 airlines that operate flights from Kentucky to Caribbean Islands. 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 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$389FlexibilityNo cancel feeOn-time65%
DeltaCheapest$224Average$614FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$225Average$691FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$255Average$621FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$259Average$615FlexibilityNo cancel feeOn-time69%

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