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Caribbean

$90+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
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 2, 2025.

Round-trip from

$206
(eDestinos)

One-way from

$90
(Kiwi.com)

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. 7% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 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 2, 2025.

This eDestinos deal was found by Cheapflights users on 4/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/13:07 pmBNA - SJU
1 stop7h 45mSpirit Airlines
Thu 5/81:59 amSJU - BNA
1 stop6h 16mSpirit Airlines
Deal found 4/1$206
This Southwest deal was found by Cheapflights users on 4/1. 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 5/34:35 pmSDF - SJU
1 stop7h 00mSouthwest
Sat 5/107:05 amSJU - SDF
1 stop10h 10mSouthwest
Deal found 4/1$215
This Delta deal was found by Cheapflights users on 3/31. 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.
Wed 4/307:30 amCVG - SJU
1 stop8h 57mDelta
Wed 5/77:00 amSJU - CVG
1 stop10h 14mDelta
Deal found 3/31$215
This Mytrip deal was found by Cheapflights users on 3/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/33:07 pmBNA - SJU
1 stop7h 45mMultiple Airlines
Sat 5/1012:40 pmSJU - BNA
2 stops24h 08mMultiple Airlines
Deal found 3/31$215
This Delta deal was found by Cheapflights users on 4/1. 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 4/286:00 amSDF - SJU
1 stop10h 01mDelta
Wed 5/71:55 pmSJU - SDF
1 stop7h 31mDelta
Deal found 4/1$225
This United Airlines deal was found by Cheapflights users on 4/1. 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 4/296:02 amBNA - SJU
1 stop7h 42mUnited Airlines
Tue 5/61:05 amSJU - BNA
1 stop8h 00mUnited Airlines
Deal found 4/1$229
This Mytrip deal was found by Cheapflights users on 3/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/46:30 amCVG - STT
1 stop27h 30mMultiple Airlines
Sat 5/103:49 pmSTT - CVG
1 stop20h 52mMultiple Airlines
Deal found 3/31$234
This American Airlines deal was found by Cheapflights users on 4/1. 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 10/76:05 amCVG - SJU
2 stops10h 15mAmerican Airlines
Sat 10/114:05 pmSJU - CVG
1 stop6h 52mAmerican Airlines
Deal found 4/1$235
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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 4/265:45 amSDF - SJU
1 stop11h 48mSpirit Airlines
Sat 5/39:32 amSJU - SDF
1 stop12h 45mSpirit Airlines
Deal found 4/1$237
This United Airlines deal was found by Cheapflights users on 4/1. 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.
Thu 5/82:10 pmCVG - SJU
1 stop9h 44mUnited Airlines
Sat 5/101:05 amSJU - CVG
2 stops12h 09mUnited Airlines
Deal found 4/1$241
This American Airlines deal was found by Cheapflights users on 4/1. 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.
Sat 4/2611:03 amSDF - SJU
2 stops9h 25mAmerican Airlines
Sat 5/35:30 amSJU - SDF
1 stop15h 57mAmerican Airlines
Deal found 4/1$245
This United Airlines deal was found by Cheapflights users on 4/1. 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 5/76:00 amSDF - SJU
1 stop6h 34mUnited Airlines
Sat 5/101:05 amSJU - SDF
2 stops12h 20mUnited Airlines
Deal found 4/1$254

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 2, 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

Thu 5/1

3:07 pm-11:52 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Thu 5/8

1:59 am-7:15 am

1 stop6h 16m

$206

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sat 5/3

4:35 pm-11:35 pm

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Sat 5/10

7:05 am-5:15 pm

1 stop10h 10m

$215

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Wed 4/30

7:30 am-4:27 pm

1 stop8h 57m

San Juan Luis Munoz Marin Intl

Wed 5/7

7:00 am-5:14 pm

1 stop10h 14m

$215

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Sat 5/3

3:07 pm-11:52 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Sat 5/10

12:40 pm-11:48 am

2 stops24h 08m

$215

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 4/28

6:00 am-4:01 pm

1 stop10h 01m

San Juan Luis Munoz Marin Intl

Wed 5/7

1:55 pm-9:26 pm

1 stop7h 31m

$225

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Tue 4/29

6:02 am-2:44 pm

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Tue 5/6

1:05 am-8:05 am

1 stop8h 00m

$229

CincinnatiSaint Thomas Island

CVG - STT

CVGSTT

Cincinnati Cinci./N. Kentucky

Sun 5/4

6:30 am-10:00 am

1 stop27h 30m

Saint Thomas Island Cyril E King

Sat 5/10

3:49 pm-12:41 pm

1 stop20h 52m

$234

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sat 4/26

5:45 am-5:33 pm

1 stop11h 48m

San Juan Luis Munoz Marin Intl

Sat 5/3

9:32 am-10:17 pm

1 stop12h 45m

$237

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Thu 5/8

2:10 pm-11:54 pm

1 stop9h 44m

San Juan Luis Munoz Marin Intl

Sat 5/10

1:05 am-1:14 pm

2 stops12h 09m

$241

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sat 4/26

11:03 am-8:28 pm

2 stops9h 25m

San Juan Luis Munoz Marin Intl

Sat 5/3

5:30 am-9:27 pm

1 stop15h 57m

$245

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

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 2, 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 2, 2025.
Alaska Airlines
8.0
Very good
9,820 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,820 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,272 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,898 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Copa Airlines
7.6
Good
1,400 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,616 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $90. Delta flights start at $113 while deals on American Airlines start at $128 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 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$173Average$389FlexibilityNo cancel feeOn-time65%
DeltaCheapest$254Average$602FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$272Average$634FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$275Average$664FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$338Average$731FlexibilityNo cancel feeOn-time63%

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