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$65+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Round-trip from

$147
(CheapOair)

One-way from

$65
(Frontier)

Popular in

December

Cheapest in

August

Average price

$394
From Kentucky to Caribbean
Search Deals
One-way flight from Kentucky to Caribbean
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 20, 2025.

This CheapOair deal was found by Cheapflights users on 2/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/115:15 amCVG - SJU
1 stop18h 23mFrontier
Tue 3/189:35 pmSJU - CVG
1 stop16h 16mFrontier
Deal found 2/20$147
This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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.
Wed 3/126:00 amBNA - STT
1 stop5h 45mSpirit Airlines
Wed 3/1911:11 amSTT - BNA
1 stop9h 52mSpirit Airlines
Deal found 2/19$162
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/286:00 amCVG - SJU
1 stop10h 37mMultiple Airlines
Wed 5/71:10 amSJU - CVG
2 stops35h 01mMultiple Airlines
Deal found 2/20$188
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Thu 4/36:00 amBNA - STT
2 stops30h 00mMultiple Airlines
Tue 4/1510:45 amSTT - BNA
1 stop10h 11mMultiple Airlines
Deal found 2/19$192
This FlightHub deal was found by Cheapflights users on 2/18. 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 3/152:59 pmBNA - SJU
1 stop8h 24mSpirit Airlines
Sat 3/225:52 amSJU - BNA
1 stop14h 49mSpirit Airlines
Deal found 2/18$232
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/135:45 amBNA - SJU
1 stop7h 59mMultiple Airlines
Tue 3/189:35 pmSJU - BNA
1 stop11h 52mMultiple Airlines
Deal found 2/20$234
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Sun 4/275:52 amCVG - SJU
2 stops8h 43mAmerican Airlines
Thu 5/111:45 amSJU - CVG
1 stop12h 26mAmerican Airlines
Deal found 2/20$235
This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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.
Tue 3/115:30 amBNA - MBJ
1 stop5h 32mSpirit Airlines
Tue 3/1812:07 pmMBJ - BNA
1 stop7h 51mSpirit Airlines
Deal found 2/19$238
This Delta deal was found by Cheapflights users on 2/20. 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.
Fri 5/1610:45 amCVG - SJU
1 stop8h 49mDelta
Sat 5/247:30 amSJU - CVG
1 stop6h 51mDelta
Deal found 2/20$250
This Frontier deal was found by Cheapflights users on 2/18. 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.
Mon 3/179:17 amBNA - SJU
1 stop11h 19mFrontier
Thu 3/206:25 amSJU - BNA
1 stop8h 10mFrontier
Deal found 2/18$281
This Delta deal was found by Cheapflights users on 2/19. 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 5/209:25 amBNA - SJU
1 stop9h 09mDelta
Sun 5/255:35 pmSJU - BNA
1 stop6h 03mDelta
Deal found 2/19$295
This United deal was found by Cheapflights users on 2/20. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/112:59 pmCVG - SJU
1 stop6h 23mUnited Airlines
Wed 3/121:05 amSJU - CVG
1 stop10h 03mUnited Airlines
Deal found 2/20$305

Find flights from Kentucky to Caribbean within your budget

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 February 20, 2025.

Fly from

Kentucky

Fly to

Caribbean

Route

Depart

Return

Price

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Tue 3/11

5:15 am-11:38 pm

1 stop18h 23m

San Juan Luis Munoz Marin Intl

Tue 3/18

9:35 pm-1:51 pm

1 stop16h 16m

$147

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Wed 3/12

6:00 am-12:45 pm

1 stop5h 45m

Saint Thomas Island Cyril E King

Wed 3/19

11:11 am-8:03 pm

1 stop9h 52m

$162

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Mon 4/28

6:00 am-4:37 pm

1 stop10h 37m

San Juan Luis Munoz Marin Intl

Wed 5/7

1:10 am-12:11 pm

2 stops35h 01m

$188

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Thu 4/3

6:00 am-1:00 pm

2 stops30h 00m

Saint Thomas Island Cyril E King

Tue 4/15

10:45 am-7:56 pm

1 stop10h 11m

$192

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Sat 3/15

2:59 pm-12:23 am

1 stop8h 24m

San Juan Luis Munoz Marin Intl

Sat 3/22

5:52 am-7:41 pm

1 stop14h 49m

$232

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Thu 3/13

5:45 am-2:44 pm

1 stop7h 59m

San Juan Luis Munoz Marin Intl

Tue 3/18

9:35 pm-8:27 am

1 stop11h 52m

$234

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sun 4/27

5:52 am-2:35 pm

2 stops8h 43m

San Juan Luis Munoz Marin Intl

Thu 5/1

11:45 am-12:11 am

1 stop12h 26m

$235

NashvilleMontego Bay

BNA - MBJ

BNAMBJ

Nashville Intl

Tue 3/11

5:30 am-11:02 am

1 stop5h 32m

Montego Bay Sangster Intl

Tue 3/18

12:07 pm-7:58 pm

1 stop7h 51m

$238

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Fri 5/16

10:45 am-7:34 pm

1 stop8h 49m

San Juan Luis Munoz Marin Intl

Sat 5/24

7:30 am-2:21 pm

1 stop6h 51m

$250

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Mon 3/17

9:17 am-9:36 pm

1 stop11h 19m

San Juan Luis Munoz Marin Intl

Thu 3/20

6:25 am-1:35 pm

1 stop8h 10m

$281

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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.

Travel insights for flights from Kentucky to Caribbean

Get recent, data-driven insights about flights from Kentucky to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $363). 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 February 20, 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 February 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Copa Airlines
7.6
Good
1,510 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

LATAM Airlines
7.5
Good
1,795 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Frontier, which is currently one of the cheapest options available, starting at $65. Spirit Airlines flights start at $69 while deals on Delta start at $108 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 March is currently the most expensive (average of $363). 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$166Average$395FlexibilityNo cancel feeOn-time65%
DeltaCheapest$254Average$598FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$267Average$628FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$275Average$656FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$378Average$724FlexibilityNo cancel feeOn-time63%
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