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$84+ Cheap flights from Kentucky to Caribbean

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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
ene. 14 — ene. 211
mié. 1/14
mié. 1/21
1 adult, Economy
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Cheap flight deals from Kentucky to Caribbean

Cheapest flights from Kentucky to Caribbean
Explore the most affordable flight options available from Kentucky to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 15, 2025.

This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/317:16 pmCVG - SJU
1 stop6h 34mFrontier
jue. 1/87:35 amSJU - CVG
1 stop11h 52mFrontier
Deal found 12/15$232
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.
lun. 12/229:57 amCVG - SJU
1 stop21h 42mFrontier
jue. 12/253:21 pmSJU - CVG
1 stop26h 16mFrontier
Deal found 12/13$243
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/305:05 amCVG - SJU
1 stop20h 45mFrontier
jue. 1/87:35 amSJU - CVG
1 stop11h 52mFrontier
Deal found 12/13$248
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/217:48 amBNA - SJU
1 stop15h 36mMultiple Airlines
sáb. 1/176:00 amSJU - BNA
1 stop12h 55mMultiple Airlines
Deal found 12/13$254
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/187:30 amCVG - SJU
1 stop7h 01mFrontier
lun. 12/223:55 amSJU - CVG
1 stop7h 57mFrontier
Deal found 12/15$264
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/196:01 pmCVG - SJU
1 stop7h 49mFrontier
dom. 12/213:55 amSJU - CVG
1 stop7h 57mFrontier
Deal found 12/13$276
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/229:57 amCVG - SJU
1 stop21h 42mFrontier
lun. 12/296:00 amSJU - CVG
1 stop12h 44mFrontier
Deal found 12/15$283
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/3111:14 amBNA - SJU
1 stop8h 51mSpirit Airlines
vie. 5/13:43 pmSJU - BNA
1 stop6h 54mSpirit Airlines
Deal found 12/13$296
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/206:00 amCVG - SJU
1 stop17h 54mFrontier
jue. 1/87:35 amSJU - CVG
1 stop11h 52mFrontier
Deal found 12/15$297
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/255:05 amCVG - SJU
1 stop9h 54mFrontier
mar. 12/307:00 amSJU - CVG
1 stop13h 18mFrontier
Deal found 12/15$305
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/196:01 pmCVG - SJU
1 stop7h 49mFrontier
jue. 1/87:35 amSJU - CVG
1 stop11h 52mFrontier
Deal found 12/15$317
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/217:48 amBNA - SJU
1 stop15h 36mMultiple Airlines
vie. 12/264:10 amSJU - BNA
1 stop7h 59mMultiple Airlines
Deal found 12/13$325

Find flight deals from Kentucky to Caribbean

Keep the following information in mind while searching for Kentucky to Caribbean flight deals. Data was last updated diciembre 15, 2025.

Round-trip from

$220
(American Airlines)

One-way from

$84
(Super.com)

Popular in

December

Cheapest in

September

Average price

$565
From Kentucky to Caribbean
Search Deals
One-way flight from Kentucky to Caribbean
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($18 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 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 diciembre 15, 2025.
Use the filters below to find and compare flights from Kentucky to Caribbean that are best for you.

Fly from

Kentucky

Fly to

Caribbean

Route

Depart

Return

Price

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

sáb. 1/24

5:35 am-1:05 pm

1 stop6h 30m

San Juan Luis Munoz Marin Intl

vie. 2/6

6:27 pm-11:50 pm

1 stop6h 23m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

lun. 1/19

6:00 am-5:03 pm

2 stops10h 03m

San Juan Luis Munoz Marin Intl

vie. 1/23

8:20 am-6:39 pm

2 stops11h 19m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

mié. 1/28

9:15 am-9:26 pm

1 stop11h 11m

San Juan Luis Munoz Marin Intl

vie. 2/6

2:15 pm-11:23 pm

1 stop10h 08m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

mar. 1/27

5:35 am-1:06 pm

1 stop6h 31m

San Juan Luis Munoz Marin Intl

mar. 2/3

6:27 pm-11:50 pm

1 stop6h 23m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

lun. 3/2

5:35 am-3:40 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

mié. 3/4

2:05 am-1:17 pm

2 stops12h 12m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

mié. 1/28

5:35 am-1:06 pm

1 stop6h 31m

San Juan Luis Munoz Marin Intl

vie. 2/6

6:27 pm-11:50 pm

1 stop6h 23m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

mié. 1/28

5:35 am-1:06 pm

1 stop6h 31m

San Juan Luis Munoz Marin Intl

jue. 2/5

6:27 pm-11:50 pm

1 stop6h 23m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

mié. 1/28

5:35 am-1:06 pm

1 stop6h 31m

San Juan Luis Munoz Marin Intl

mié. 2/4

6:27 pm-11:50 pm

1 stop6h 23m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

dom. 1/25

5:35 am-5:17 pm

1 stop10h 42m

San Juan Luis Munoz Marin Intl

vie. 2/6

6:27 pm-11:50 pm

1 stop6h 23m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

lun. 1/26

5:35 am-2:31 pm

1 stop7h 56m

San Juan Luis Munoz Marin Intl

mié. 2/4

6:27 pm-11:50 pm

1 stop6h 23m

$225

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 Kentucky to Caribbean

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

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

Currently, March is the cheapest month in which you can book a flight from Kentucky to Caribbean (average of $190). Flying from Kentucky to Caribbean 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 CB?

Find hourly flight availability from Kentucky to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated diciembre 15, 2025.

When flying from Kentucky to Caribbean, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 28% versus a flight in the evening.

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

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

Travelers seeking maximum savings on their Kentucky to Caribbean 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. 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?

    Delta, American Airlines, and United Airlines can get you from Kentucky to Caribbean in just under 6h 30m. Your travel time can differ by up to 4h 41m. Kentucky and Caribbean are separated by a distance of 1807 mi. This flight may include one or multiple stops.

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

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $86. American Airlines flights start at $109 while deals on United Airlines start at $138 one-way.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Kentucky to Caribbean 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?

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

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 Kentucky to Caribbean

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

Discover the top 5 airlines that operate flights from Kentucky to Caribbean. 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 diciembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$387FlexibilityNo cancel feeOn-time65%
DeltaCheapest$218Average$617FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$225Average$685FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$259Average$589FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$262Average$620FlexibilityNo cancel feeOn-time71%

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