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$103+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$206
(Southwest)

One-way from

$103
(Southwest)

Popular in

December

Cheapest in

October

Average price

$368
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. 1% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/12. 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 11/155:20 pmBNA - SJU
Nonstop3h 55mSouthwest
Sat 12/611:20 amSJU - BNA
Nonstop4h 35mSouthwest
Deal found 9/12$206
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 11/155:20 pmBNA - SJU
Nonstop3h 55mSouthwest
Tue 11/189:40 amSJU - BNA
1 stop8h 50mSouthwest
Deal found 9/15$211
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/137:59 pmCVG - SJU
1 stop19h 25mFrontier
Wed 10/299:00 amSJU - CVG
1 stop15h 59mFrontier
Deal found 9/13$216
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.
Mon 12/86:50 amSDF - SJU
1 stop16h 02mAmerican Airlines
Thu 12/112:50 pmSJU - SDF
2 stops7h 58mAmerican Airlines
Deal found 9/14$225
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.
Tue 10/141:05 pmCVG - SJU
1 stop10h 54mAmerican Airlines
Sat 10/255:25 amSJU - CVG
1 stop10h 04mAmerican Airlines
Deal found 9/14$225
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/308:18 amSDF - SJU
1 stop13h 52mAmerican Airlines
Thu 11/64:56 pmSJU - SDF
1 stop7h 47mAmerican Airlines
Deal found 9/15$226
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/175:25 pmBNA - SJU
1 stop8h 05mMultiple Airlines
Sat 10/189:48 amSJU - BNA
1 stop29h 29mMultiple Airlines
Deal found 9/13$234
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:49 pmCVG - SJU
2 stops16h 22mAmerican Airlines
Tue 10/75:30 amSJU - CVG
1 stop12h 10mAmerican Airlines
Deal found 9/13$235
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/114:06 pmBNA - SJU
1 stop8h 56mMultiple Airlines
Sat 10/189:48 amSJU - BNA
1 stop29h 29mMultiple Airlines
Deal found 9/13$236
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/248:23 amBNA - SJU
1 stop10h 33mMultiple Airlines
Sun 10/265:30 amSJU - BNA
1 stop15h 09mMultiple Airlines
Deal found 9/13$240
This United Airlines deal was found by Cheapflights users on 9/12. 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 11/152:25 pmBNA - SJU
1 stop8h 11mUnited Airlines
Fri 12/52:05 amSJU - BNA
1 stop8h 57mUnited Airlines
Deal found 9/12$243
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.
Mon 10/2012:01 pmCVG - SJU
1 stop7h 55mFrontier
Wed 10/295:51 pmSJU - CVG
2 stops23h 19mFrontier
Deal found 9/13$243

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 September 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

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Sat 11/15

5:20 pm-11:15 pm

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Sat 12/6

11:20 am-1:55 pm

Nonstop4h 35m

$206

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Sat 11/15

5:20 pm-11:15 pm

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Tue 11/18

9:40 am-4:30 pm

1 stop8h 50m

$211

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Mon 11/10

2:52 pm-11:13 pm

1 stop6h 21m

San Juan Luis Munoz Marin Intl

Thu 11/13

1:57 pm-11:04 pm

1 stop11h 07m

$215

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Tue 11/4

11:19 am-9:00 pm

1 stop7h 41m

San Juan Luis Munoz Marin Intl

Thu 11/20

8:10 am-2:28 pm

1 stop8h 18m

$215

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Sun 2/15

7:25 pm-9:55 am

1 stop12h 30m

San Juan Luis Munoz Marin Intl

Thu 2/19

2:20 pm-8:05 pm

1 stop7h 45m

$215

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Sat 10/25

3:30 pm-11:45 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

Tue 10/28

6:10 am-2:20 pm

2 stops9h 10m

$215

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sun 11/9

5:00 am-8:58 pm

1 stop14h 58m

San Juan Luis Munoz Marin Intl

Wed 11/12

4:43 pm-11:09 pm

1 stop7h 26m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Thu 10/30

8:18 am-10:10 pm

1 stop13h 52m

San Juan Luis Munoz Marin Intl

Thu 11/6

4:56 pm-11:43 pm

1 stop7h 47m

$226

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Sat 11/15

2:25 pm-12:36 am

1 stop8h 11m

San Juan Luis Munoz Marin Intl

Fri 12/5

2:05 am-9:02 am

1 stop8h 57m

$243

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sun 9/28

7:00 am-2:44 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

Thu 10/2

3:56 pm-11:52 pm

1 stop7h 56m

$245

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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, September is the cheapest month in which you can book a flight from Kentucky to Caribbean (average of $254). Flying from Kentucky to Caribbean in June is currently the most expensive (average of $339). 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 September 15, 2025.

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

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?

    Southwest, Delta, and American Airlines can get you from Kentucky to Caribbean in just under 3h 55m. Your travel time can differ by up to 11h 03m. 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 Southwest, which is currently one of the cheapest options available, starting at $103. Delta flights start at $108 while deals on American Airlines start at $113 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, September is the cheapest month in which you can book a flight from Kentucky to Caribbean (average of $254). Flying from Kentucky to Caribbean in June is currently the most expensive (average of $339). 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$389FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$225Average$693FlexibilityNo cancel feeOn-time63%
DeltaCheapest$225Average$608FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$263Average$624FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$275Average$596FlexibilityNo cancel feeOn-time69%

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