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$92+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$220
(Southwest)

One-way from

$92
(SmartFares)

Popular in

March

Cheapest in

January

Average price

$530
From Kentucky to Caribbean
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One-way flight from Kentucky to Caribbean
Search Deals
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

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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/11. 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 11/83:30 pmSDF - SJU
1 stop6h 30mSouthwest
Sun 11/96:10 amSJU - SDF
1 stop7h 10mSouthwest
Deal found 6/11$220
This Delta deal was found by Cheapflights users on 6/10. 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 9/177:00 amSDF - SJU
1 stop6h 23mDelta
Wed 9/242:28 pmSJU - SDF
1 stop9h 28mDelta
Deal found 6/10$225
This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/207:43 pmBNA - STT
1 stop12h 02mSpirit Airlines
Sat 9/279:40 amSTT - BNA
1 stop13h 15mSpirit Airlines
Deal found 6/12$252
This Frontier deal was found by Cheapflights users on 6/9. 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.
Sun 6/158:45 amCVG - SJU
1 stop7h 05mFrontier
Thu 6/192:05 pmSJU - CVG
1 stop9h 44mFrontier
Deal found 6/9$262
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Mon 7/2112:16 pmSDF - SJU
1 stop8h 53mMultiple Airlines
Thu 7/241:37 amSJU - SDF
1 stop12h 18mMultiple Airlines
Deal found 6/11$264
This American Airlines deal was found by Cheapflights users on 6/11. 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 9/235:32 amCVG - SJU
2 stops9h 21mAmerican Airlines
Tue 9/306:10 amSJU - CVG
2 stops16h 54mAmerican Airlines
Deal found 6/11$265
This FlightHub deal was found by Cheapflights users on 6/9. 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.
Tue 7/16:00 amBNA - SJU
1 stop12h 19mSpirit Airlines
Sat 7/58:24 pmSJU - BNA
1 stop13h 02mSpirit Airlines
Deal found 6/9$271
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 6/11$273
This United Airlines deal was found by Cheapflights users on 6/10. 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 10/116:15 amSDF - SJU
1 stop7h 30mUnited Airlines
Sat 10/181:30 pmSJU - SDF
1 stop10h 00mUnited Airlines
Deal found 6/10$273
This Southwest deal was found by Cheapflights users on 6/10. 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 7/42:00 pmCVG - SJU
1 stop7h 40mSouthwest
Tue 7/811:35 amSJU - CVG
1 stop11h 45mSouthwest
Deal found 6/10$274
This Frontier deal was found by Cheapflights users on 6/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1110:12 amBNA - SJU
1 stop7h 28mFrontier
Sun 10/193:40 amSJU - BNA
1 stop11h 49mFrontier
Deal found 6/12$275
This Priceline deal was found by Cheapflights users on 6/11. 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 7/101:45 pmBNA - SJU
1 stop9h 14mMultiple Airlines
Thu 8/71:21 amSJU - BNA
1 stop10h 12mMultiple Airlines
Deal found 6/11$276

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 June 12, 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

Sat 11/8

3:30 pm-11:00 pm

1 stop6h 30m

San Juan Luis Munoz Marin Intl

Sun 11/9

6:10 am-12:20 pm

1 stop7h 10m

$220

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Wed 9/17

7:00 am-1:23 pm

1 stop6h 23m

San Juan Luis Munoz Marin Intl

Wed 9/24

2:28 pm-11:56 pm

1 stop9h 28m

$225

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Sat 9/20

7:43 pm-8:45 am

1 stop12h 02m

Saint Thomas Island Cyril E King

Sat 9/27

9:40 am-9:55 pm

1 stop13h 15m

$252

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sun 6/15

8:45 am-3:50 pm

1 stop7h 05m

San Juan Luis Munoz Marin Intl

Thu 6/19

2:05 pm-11:49 pm

1 stop9h 44m

$262

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 7/21

12:16 pm-9:09 pm

1 stop8h 53m

San Juan Luis Munoz Marin Intl

Thu 7/24

1:37 am-1:55 pm

1 stop12h 18m

$264

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Tue 8/26

6:00 am-6:15 pm

2 stops12h 15m

San Juan Luis Munoz Marin Intl

Wed 9/3

6:10 am-6:40 pm

1 stop12h 30m

$265

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Tue 7/1

6:00 am-7:19 pm

1 stop12h 19m

San Juan Luis Munoz Marin Intl

Sat 7/5

8:24 pm-8:26 am

1 stop13h 02m

$271

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sat 10/11

6:15 am-1:45 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Sat 10/18

1:30 pm-11:30 pm

1 stop10h 00m

$273

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

$273

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Fri 7/4

2:00 pm-9:40 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Tue 7/8

11:35 am-11:20 pm

1 stop11h 45m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 June 12, 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 June 12, 2025.
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

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
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

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.
JetBlue
7.3
Good
2,925 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

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.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

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. 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 $92. Frontier flights start at $95 while deals on Delta 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

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$175Average$390FlexibilityNo cancel feeOn-time65%
DeltaCheapest$254Average$617FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$267Average$630FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$275Average$633FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$338Average$701FlexibilityNo cancel feeOn-time63%

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