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Caribbean Islands

$92+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
1 adult, Economy
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Cheap 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 June 16, 2025.

Round-trip from

$225
(Delta)

One-way from

$92
(SmartFares)

Popular in

March

Cheapest in

January

Average price

$526
From Kentucky to Caribbean Islands
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One-way flight from Kentucky to Caribbean Islands
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Highest demand for flights based on searches. 5% potential increase in price ($24 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 June 2025
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Find 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 June 16, 2025.

This Delta deal was found by Cheapflights users on 6/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/37:00 amSDF - SJU
1 stop9h 08mDelta
Thu 10/95:30 pmSJU - SDF
1 stop6h 26mDelta
Deal found 6/13$225
This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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.
Mon 6/305:03 amSDF - SJU
1 stop14h 16mSpirit Airlines
Thu 7/32:36 amSJU - SDF
1 stop8h 44mSpirit Airlines
Deal found 6/16$239
This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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.
Fri 9/197:43 pmBNA - STT
1 stop12h 02mSpirit Airlines
Mon 9/221:47 pmSTT - BNA
1 stop11h 12mSpirit Airlines
Deal found 6/16$250
This Priceline deal was found by Cheapflights users on 6/16. 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.
Thu 6/197:27 pmCVG - SJU
1 stop7h 08mFrontier
Sat 6/213:40 amSJU - CVG
1 stop21h 38mFrontier
Deal found 6/16$257
This United Airlines deal was found by Cheapflights users on 6/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/177:00 amSDF - SJU
1 stop7h 44mUnited Airlines
Tue 9/231:05 amSJU - SDF
2 stops12h 12mUnited Airlines
Deal found 6/14$259
This American Airlines deal was found by Cheapflights users on 6/14. 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 12/86:09 pmCVG - SJU
1 stop16h 31mAmerican Airlines
Sat 12/136:40 amSJU - CVG
1 stop9h 55mAmerican Airlines
Deal found 6/14$260
This Cheapflightsfares deal was found by Cheapflights users on 6/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/129:16 amBNA - PUJ
1 stop5h 39mSpirit Airlines
Sat 7/195:00 pmPUJ - BNA
1 stop7h 41mSpirit Airlines
Deal found 6/15$265
This FlightHub deal was found by Cheapflights users on 6/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/76:00 amBNA - SJU
2 stops18h 31mSpirit Airlines
Thu 7/1010:14 pmSJU - BNA
1 stop10h 57mSpirit Airlines
Deal found 6/15$273
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Wed 9/176:44 amBNA - SJU
2 stops10h 30mAmerican Airlines
Wed 9/244:42 pmSJU - BNA
1 stop6h 57mAmerican Airlines
Deal found 6/14$277
This Frontier deal was found by Cheapflights users on 6/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/308:55 pmBNA - SJU
1 stop13h 12mFrontier
Mon 11/1010:07 amSJU - BNA
1 stop6h 22mFrontier
Deal found 6/14$278
This Priceline deal was found by Cheapflights users on 6/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/268:50 pmBNA - SJU
1 stop26h 38mMultiple Airlines
Mon 6/3011:44 amSJU - BNA
1 stop8h 54mMultiple Airlines
Deal found 6/14$281
This Southwest deal was found by Cheapflights users on 6/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/214:35 pmSDF - SJU
1 stop7h 35mSouthwest
Fri 6/2710:05 amSJU - SDF
1 stop13h 00mSouthwest
Deal found 6/14$285

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 June 16, 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

Tue 9/9

6:00 am-4:36 pm

1 stop10h 36m

San Juan Luis Munoz Marin Intl

Fri 9/19

5:19 pm-11:56 pm

1 stop6h 37m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 6/30

5:03 am-7:19 pm

1 stop14h 16m

San Juan Luis Munoz Marin Intl

Thu 7/3

2:36 am-11:20 am

1 stop8h 44m

$239

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Sat 7/12

6:14 pm-9:48 am

1 stop14h 34m

Saint Thomas Island Cyril E King

Sat 7/19

10:43 am-11:41 pm

1 stop13h 58m

$252

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Thu 6/19

7:27 pm-2:35 am

1 stop7h 08m

San Juan Luis Munoz Marin Intl

Sat 6/21

3:40 am-1:18 am

1 stop21h 38m

$257

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Fri 7/18

5:50 pm-12:30 am

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Sat 7/26

3:25 pm-11:30 pm

1 stop8h 05m

$260

NashvillePunta Cana

BNA - PUJ

BNAPUJ

Nashville Intl

Sat 7/12

9:16 am-3:55 pm

1 stop5h 39m

Punta Cana

Sat 7/19

5:00 pm-11:41 pm

1 stop7h 41m

$265

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Thu 6/26

6:15 am-7:19 pm

1 stop13h 04m

San Juan Luis Munoz Marin Intl

Tue 7/1

8:24 pm-1:23 pm

1 stop16h 59m

$268

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Mon 7/7

6:00 am-1:31 am

2 stops18h 31m

San Juan Luis Munoz Marin Intl

Thu 7/10

10:14 pm-8:11 am

1 stop10h 57m

$273

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Wed 7/9

8:05 am-5:25 pm

1 stop9h 20m

San Juan Luis Munoz Marin Intl

Sat 7/12

5:30 am-6:20 pm

1 stop12h 50m

$275

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Thu 6/26

8:50 pm-12:28 am

1 stop26h 38m

San Juan Luis Munoz Marin Intl

Mon 6/30

11:44 am-7:38 pm

1 stop8h 54m

$281

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

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, September is the cheapest month in which you can book a flight from Kentucky to Caribbean Islands (average of $254). Flying from Kentucky to Caribbean Islands 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 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 June 16, 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 Islands as you normally would.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated June 16, 2025.
Get a feel of what it's like to fly with Southwest, Delta and LATAM Airlines from Kentucky to Caribbean Islands by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,963 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
LATAM Airlines
7.5
Good
1,785 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Copa Airlines
7.5
Good
1,453 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,801 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • 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 $92. Users have also found prices from $95 and $113 on Frontier 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, September is the cheapest month in which you can book a flight from Kentucky to Caribbean Islands (average of $254). Flying from Kentucky to Caribbean Islands 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

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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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$383FlexibilityNo cancel feeOn-time65%
DeltaCheapest$254Average$620FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$267Average$630FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$275Average$629FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$310Average$700FlexibilityNo cancel feeOn-time63%

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