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Caribbean

$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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Apr 27 — May 41
Sun 4/27
Sun 5/4
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 April 22, 2025.

Round-trip from

$215
(American Airlines)

One-way from

$104
(FlightHub)

Popular in

March

Cheapest in

August

Average price

$450
From Kentucky to Caribbean
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One-way flight from Kentucky to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 22, 2025.

This American Airlines deal was found by Cheapflights users on 4/21. 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 9/167:40 amSDF - SJU
2 stops12h 30mAmerican Airlines
Tue 9/231:55 pmSJU - SDF
2 stops9h 50mAmerican Airlines
Deal found 4/21$215
This American Airlines deal was found by Cheapflights users on 4/22. 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 5/15:35 amCVG - SJU
1 stop14h 53mAmerican Airlines
Sat 5/107:15 amSJU - CVG
2 stops10h 38mAmerican Airlines
Deal found 4/22$215
This Mytrip deal was found by Cheapflights users on 4/21. 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.
Sat 5/172:19 pmCVG - SJU
1 stop28h 48mMultiple Airlines
Thu 5/298:12 pmSJU - CVG
1 stop26h 56mMultiple Airlines
Deal found 4/21$220
This FlightHub deal was found by Cheapflights users on 4/21. 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.
Thu 5/88:10 amBNA - SJU
1 stop10h 52mSpirit Airlines
Sun 5/118:12 pmSJU - BNA
1 stop13h 08mSpirit Airlines
Deal found 4/21$226
This Southwest deal was found by Cheapflights users on 4/21. 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.
Mon 9/86:05 amBNA - SJU
1 stop7h 35mSouthwest
Tue 9/161:35 pmSJU - BNA
1 stop7h 25mSouthwest
Deal found 4/21$229
This Delta deal was found by Cheapflights users on 4/20. 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.
Sat 11/156:00 amSDF - SJU
1 stop5h 40mDelta
Thu 11/206:20 pmSJU - SDF
1 stop6h 36mDelta
Deal found 4/20$245
This United Airlines deal was found by Cheapflights users on 4/20. 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.
Tue 5/62:10 pmCVG - SJU
1 stop9h 44mUnited Airlines
Fri 5/91:05 amSJU - CVG
1 stop8h 49mUnited Airlines
Deal found 4/20$257
This CheapOair deal was found by Cheapflights users on 4/21. 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 5/510:01 amBNA - SJU
1 stop15h 50mMultiple Airlines
Fri 5/96:09 amSJU - BNA
1 stop13h 43mMultiple Airlines
Deal found 4/21$261
This American Airlines deal was found by Cheapflights users on 4/20. 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 9/156:29 pmBNA - SJU
1 stop15h 46mAmerican Airlines
Tue 9/231:55 pmSJU - BNA
2 stops10h 02mAmerican Airlines
Deal found 4/20$262
This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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.
Thu 5/1511:23 amSDF - SJU
1 stop13h 31mSpirit Airlines
Wed 5/211:33 amSJU - SDF
1 stop17h 51mSpirit Airlines
Deal found 4/22$267
This Delta deal was found by Cheapflights users on 4/21. 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.
Tue 10/147:55 amCVG - SJU
1 stop8h 30mDelta
Sat 10/185:30 pmSJU - CVG
1 stop6h 25mDelta
Deal found 4/21$269
This FlightHub deal was found by Cheapflights users on 4/22. 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.
Sat 5/171:00 pmBNA - MBJ
2 stops22h 02mSpirit Airlines
Sat 5/2412:07 pmMBJ - BNA
1 stop5h 33mSpirit Airlines
Deal found 4/22$271

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 April 22, 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

Tue 9/16

7:40 am-8:10 pm

2 stops12h 30m

San Juan Luis Munoz Marin Intl

Tue 9/23

1:55 pm-11:45 pm

2 stops9h 50m

$215

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Thu 5/1

5:35 am-8:28 pm

1 stop14h 53m

San Juan Luis Munoz Marin Intl

Sat 5/10

7:15 am-5:53 pm

2 stops10h 38m

$215

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sat 5/17

2:19 pm-7:07 pm

1 stop28h 48m

San Juan Luis Munoz Marin Intl

Thu 5/29

8:12 pm-11:08 pm

1 stop26h 56m

$220

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Tue 5/6

3:07 pm-11:52 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Fri 5/9

6:09 am-6:52 pm

1 stop13h 43m

$235

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Tue 5/6

2:10 pm-11:54 pm

1 stop9h 44m

San Juan Luis Munoz Marin Intl

Fri 5/9

1:05 am-9:54 am

1 stop8h 49m

$257

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Thu 5/15

11:23 am-12:54 am

1 stop13h 31m

San Juan Luis Munoz Marin Intl

Wed 5/21

1:33 am-7:24 pm

1 stop17h 51m

$267

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Fri 5/2

5:09 pm-11:15 pm

1 stop6h 06m

San Juan Luis Munoz Marin Intl

Tue 5/6

6:35 am-5:19 pm

1 stop10h 44m

$269

NashvilleMontego Bay

BNA - MBJ

BNAMBJ

Nashville Intl

Sat 5/17

1:00 pm-11:02 am

2 stops22h 02m

Montego Bay Sangster Intl

Sat 5/24

12:07 pm-5:40 pm

1 stop5h 33m

$271

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Tue 5/20

12:10 pm-10:45 am

2 stops21h 35m

San Juan Luis Munoz Marin Intl

Mon 5/26

1:59 am-4:49 pm

2 stops15h 50m

$273

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sun 5/4

12:31 pm-7:44 pm

1 stop7h 13m

San Juan Luis Munoz Marin Intl

Wed 5/7

3:56 am-11:36 am

1 stop7h 40m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

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 December is currently the most expensive (average of $336). 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 April 22, 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.

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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

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 April 22, 2025.
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,911 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
LATAM Airlines
7.5
Good
1,764 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Copa Airlines
7.5
Good
1,408 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 $104. Delta flights start at $108 while deals on American Airlines start at $111 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 December is currently the most expensive (average of $336). 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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$179Average$396FlexibilityNo cancel feeOn-time65%
DeltaCheapest$254Average$604FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$272Average$636FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$275Average$655FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$326Average$738FlexibilityNo cancel feeOn-time63%

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