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Caribbean

$89+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$189
(Mytrip)

One-way from

$89
(Booking.com)

Popular in

March

Cheapest in

October

Average price

$452
From Kentucky to Caribbean
Search Deals
One-way flight from Kentucky to Caribbean
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($27 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 July 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 July 31, 2025.

This Mytrip deal was found by Cheapflights users on 7/30. 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.
Wed 8/275:05 amBNA - STT
1 stop7h 43mSpirit Airlines
Wed 9/32:43 pmSTT - BNA
1 stop9h 37mSpirit Airlines
Deal found 7/30$189
This American Airlines deal was found by Cheapflights users on 7/31. 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 10/133:35 pmSDF - SJU
1 stop8h 24mAmerican Airlines
Tue 10/287:05 amSJU - SDF
2 stops10h 49mAmerican Airlines
Deal found 7/31$205
This Delta deal was found by Cheapflights users on 7/31. 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.
Sun 9/76:00 amSDF - SJU
1 stop10h 36mDelta
Thu 9/115:41 pmSJU - SDF
1 stop6h 11mDelta
Deal found 7/31$215
This Frontier deal was found by Cheapflights users on 7/29. 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 8/168:00 amCVG - SJU
1 stop7h 54mFrontier
Sat 8/169:30 pmSJU - CVG
1 stop13h 17mFrontier
Deal found 7/29$233
This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/101:05 pmCVG - SJU
1 stop10h 54mAmerican Airlines
Sat 10/185:30 amSJU - CVG
1 stop7h 05mAmerican Airlines
Deal found 7/29$235
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/15:05 amBNA - SJU
1 stop9h 05mSpirit Airlines
Thu 9/43:19 pmSJU - BNA
1 stop9h 04mSpirit Airlines
Deal found 7/29$235
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/245:05 amBNA - SJU
1 stop8h 06mMultiple Airlines
Sat 9/273:39 amSJU - BNA
1 stop15h 32mMultiple Airlines
Deal found 7/29$237
This Southwest deal was found by Cheapflights users on 7/31. 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 11/83:35 pmCVG - SJU
1 stop6h 25mSouthwest
Sat 11/156:15 amSJU - CVG
1 stop7h 05mSouthwest
Deal found 7/31$242
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/194:20 pmSDF - SJU
1 stop7h 10mSouthwest
Sun 9/215:45 amSJU - SDF
1 stop6h 40mSouthwest
Deal found 7/30$245
This Delta deal was found by Cheapflights users on 7/30. 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.
Wed 10/292:54 pmBNA - SJU
1 stop6h 05mDelta
Tue 11/43:29 pmSJU - BNA
1 stop9h 10mDelta
Deal found 7/30$245
This Delta deal was found by Cheapflights users on 7/30. 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 12/87:00 amCVG - SJU
1 stop9h 10mDelta
Sat 12/137:30 amSJU - CVG
1 stop10h 51mDelta
Deal found 7/30$252
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/148:30 amSDF - SJU
1 stop26h 34mSpirit Airlines
Wed 9/171:59 amSJU - SDF
2 stops20h 29mSpirit Airlines
Deal found 7/30$253

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 July 31, 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

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Wed 8/27

5:05 am-1:48 pm

1 stop7h 43m

Saint Thomas Island Cyril E King

Wed 9/3

2:43 pm-11:20 pm

1 stop9h 37m

$189

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 10/13

3:35 pm-11:59 pm

1 stop8h 24m

San Juan Luis Munoz Marin Intl

Tue 10/28

7:05 am-5:54 pm

2 stops10h 49m

$205

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sun 9/7

6:00 am-4:36 pm

1 stop10h 36m

San Juan Luis Munoz Marin Intl

Thu 9/11

5:41 pm-11:52 pm

1 stop6h 11m

$215

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sat 8/16

8:00 am-3:54 pm

1 stop7h 54m

San Juan Luis Munoz Marin Intl

Sat 8/16

9:30 pm-10:47 am

1 stop13h 17m

$233

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Fri 10/10

1:05 pm-11:59 pm

1 stop10h 54m

San Juan Luis Munoz Marin Intl

Sat 10/18

5:30 am-12:35 pm

1 stop7h 05m

$235

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Mon 9/1

5:05 am-3:10 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Thu 9/4

3:19 pm-11:23 pm

1 stop9h 04m

$235

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Wed 9/24

5:05 am-2:11 pm

1 stop8h 06m

San Juan Luis Munoz Marin Intl

Sat 9/27

3:39 am-6:11 pm

1 stop15h 32m

$237

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sat 11/8

3:35 pm-11:00 pm

1 stop6h 25m

San Juan Luis Munoz Marin Intl

Sat 11/15

6:15 am-12:20 pm

1 stop7h 05m

$242

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Fri 9/19

4:20 pm-11:30 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Sun 9/21

5:45 am-12:25 pm

1 stop6h 40m

$245

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Wed 10/29

2:54 pm-9:59 pm

1 stop6h 05m

San Juan Luis Munoz Marin Intl

Tue 11/4

3:29 pm-10:39 pm

1 stop9h 10m

$245

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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, 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 July 31, 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.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated July 31, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Kentucky to Caribbean have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Air Canada
7.1
Good
9,851 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 $89. American Airlines flights start at $98 while deals on Delta start at $103 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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Dallas/Fort Worth to LaGuardia flights
John F Kennedy Intl to Heathrow flights
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John F Kennedy Intl to San Francisco flights
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O'Hare Intl to Newark flights
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Newark to San Francisco flights
Los Angeles to Dallas/Fort Worth flights
John F Kennedy Intl to Leonardo da Vinci/Fiumicino flights
Dallas/Fort Worth to Newark flights
John F Kennedy Intl to Fort Lauderdale flights

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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$390FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$225Average$647FlexibilityNo cancel feeOn-time63%
DeltaCheapest$225Average$617FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$275Average$652FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$276Average$639FlexibilityNo cancel feeOn-time71%

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