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$69+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Kentucky to Caribbean

Keep the following information in mind while searching for Kentucky to Caribbean flight deals. Data was last updated October 30, 2025.

Round-trip from

$168
(Frontier)

One-way from

$69
(Frontier)

Popular in

December

Cheapest in

September

Average price

$344
From Kentucky to Caribbean
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One-way flight from Kentucky to Caribbean
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Highest demand for flights based on searches. 5% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 30, 2025.

This Frontier deal was found by Cheapflights users on 10/30. 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.
Mon 12/812:56 pmBNA - SJU
1 stop9h 53mFrontier
Thu 12/111:59 amSJU - BNA
1 stop14h 02mFrontier
Deal found 10/30$168
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Tue 11/186:45 amBNA - SJU
1 stop5h 57mMultiple Airlines
Sun 11/235:28 pmSJU - BNA
1 stop16h 34mMultiple Airlines
Deal found 10/29$209
This Delta deal was found by Cheapflights users on 10/30. 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.
Mon 12/82:50 pmBNA - SJU
1 stop6h 30mDelta
Thu 12/116:38 pmSJU - BNA
1 stop6h 31mDelta
Deal found 10/30$215
This Delta deal was found by Cheapflights users on 10/30. 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.
Mon 12/82:20 pmCVG - SJU
1 stop8h 00mDelta
Sat 12/137:19 amSJU - CVG
1 stop10h 50mDelta
Deal found 10/30$225
This Frontier deal was found by Cheapflights users on 10/29. 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 11/132:22 pmBNA - SJU
1 stop8h 19mFrontier
Sat 11/152:11 amSJU - BNA
1 stop13h 28mFrontier
Deal found 10/29$231
This Mytrip deal was found by Cheapflights users on 10/30. 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.
Tue 12/28:05 pmCVG - SJU
1 stop21h 18mFrontier
Sat 12/68:00 amSJU - CVG
1 stop15h 48mFrontier
Deal found 10/30$232
This Frontier deal was found by Cheapflights users on 10/30. 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 11/1412:01 pmCVG - SJU
1 stop8h 23mFrontier
Sat 11/2211:28 amSJU - CVG
1 stop10h 34mFrontier
Deal found 10/30$235
This Trip.com deal was found by Cheapflights users on 10/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:30 pmCVG - SJU
1 stop7h 24mFrontier
Fri 11/216:10 amSJU - CVG
1 stop8h 24mFrontier
Deal found 10/30$236
This Frontier deal was found by Cheapflights users on 10/29. 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.
Sat 11/81:00 pmCVG - SJU
1 stop12h 54mFrontier
Thu 11/1312:29 pmSJU - CVG
1 stop12h 42mFrontier
Deal found 10/29$237
This United Airlines deal was found by Cheapflights users on 10/30. 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.
Sat 11/811:15 amCVG - SJU
1 stop8h 45mUnited Airlines
Wed 11/122:20 pmSJU - CVG
1 stop7h 48mUnited Airlines
Deal found 10/30$245
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/218:49 amBNA - SJU
2 stops40h 05mMultiple Airlines
Mon 11/245:19 pmSJU - BNA
1 stop8h 23mMultiple Airlines
Deal found 10/28$249
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/138:00 amCVG - SJU
1 stop14h 52mAmerican Airlines
Sat 11/156:25 amSJU - CVG
1 stop10h 10mAmerican Airlines
Deal found 10/30$250

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 October 30, 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

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Mon 12/8

2:50 pm-11:20 pm

1 stop6h 30m

San Juan Luis Munoz Marin Intl

Thu 12/11

6:38 pm-11:09 pm

1 stop6h 31m

$215

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Thu 11/13

8:00 am-11:52 pm

1 stop14h 52m

San Juan Luis Munoz Marin Intl

Sat 11/15

6:25 am-3:35 pm

1 stop10h 10m

$250

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sun 2/1

6:25 am-4:36 pm

1 stop9h 11m

San Juan Luis Munoz Marin Intl

Mon 2/9

2:05 am-10:45 am

1 stop9h 40m

$252

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Sun 1/25

12:55 pm-9:50 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Sat 1/31

5:30 am-11:15 am

2 stops7h 45m

$255

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Mon 11/10

12:01 pm-9:24 pm

1 stop8h 23m

San Juan Luis Munoz Marin Intl

Fri 11/14

1:04 pm-11:59 pm

1 stop11h 55m

$256

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Mon 12/8

2:35 pm-12:36 am

1 stop8h 01m

San Juan Luis Munoz Marin Intl

Wed 12/10

2:05 am-9:06 am

1 stop9h 01m

$257

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sun 2/1

4:15 pm-12:05 am

1 stop6h 50m

San Juan Luis Munoz Marin Intl

Sat 2/28

6:05 am-12:40 pm

1 stop7h 35m

$265

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Mon 11/17

6:30 pm-2:54 am

1 stop7h 24m

San Juan Luis Munoz Marin Intl

Thu 11/20

3:59 am-11:15 am

1 stop8h 16m

$265

CincinnatiSaint Thomas Island

CVG - STT

CVGSTT

Cincinnati Cinci./N. Kentucky

Sat 1/3

5:05 am-2:28 pm

1 stop8h 23m

Saint Thomas Island Cyril E King

Thu 1/8

4:06 pm-1:01 am

1 stop9h 55m

$270

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Sat 11/15

6:45 am-3:24 pm

1 stop6h 39m

Saint Thomas Island Cyril E King

Sat 11/22

2:00 pm-11:42 pm

1 stop11h 42m

$280

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

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, January is the cheapest month in which you can book a flight from Kentucky to Caribbean (average of $167). 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 October 30, 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. Saturday 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 8h 22m. Kentucky and Caribbean are separated by a distance of 1753 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 Frontier, which is currently one of the cheapest options available, starting at $84. American Airlines flights start at $108 while deals on Delta start at $108 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, January is the cheapest month in which you can book a flight from Kentucky to Caribbean (average of $167). 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

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$393FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$225Average$692FlexibilityNo cancel feeOn-time63%
DeltaCheapest$225Average$603FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$257Average$617FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$275Average$615FlexibilityNo cancel feeOn-time69%

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