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Caribbean Islands

$65+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
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 February 23, 2025.

Round-trip from

$150
(Frontier)

One-way from

$65
(Frontier)

Popular in

December

Cheapest in

August

Average price

$394
From Kentucky to Caribbean Islands
Search Deals
One-way flight from Kentucky to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
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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 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 February 23, 2025.

This Frontier deal was found by Cheapflights users on 2/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/287:29 pmCVG - SJU
1 stop7h 20mFrontier
Sun 5/411:20 amSJU - CVG
1 stop13h 20mFrontier
Deal found 2/22$150
This CheapOair deal was found by Cheapflights users on 2/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/122:54 pmBNA - STT
1 stop18h 07mSpirit Airlines
Tue 3/1811:11 amSTT - BNA
1 stop9h 47mSpirit Airlines
Deal found 2/22$174
This Mytrip deal was found by Cheapflights users on 2/21. 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.
Mon 4/286:00 amCVG - SJU
2 stops27h 40mMultiple Airlines
Wed 5/71:10 amSJU - CVG
2 stops35h 01mMultiple Airlines
Deal found 2/21$208
This Delta deal was found by Cheapflights users on 2/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/305:09 pmCVG - SJU
1 stop6h 06mDelta
Mon 5/56:35 amSJU - CVG
1 stop10h 44mDelta
Deal found 2/22$215
This CheapOair deal was found by Cheapflights users on 2/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/112:59 pmBNA - SJU
1 stop8h 24mSpirit Airlines
Mon 3/173:38 amSJU - BNA
2 stops17h 42mSpirit Airlines
Deal found 2/22$232
This American Airlines deal was found by Cheapflights users on 2/22. 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.
Tue 10/76:05 amCVG - SJU
2 stops10h 15mAmerican Airlines
Sat 10/114:05 pmSJU - CVG
1 stop6h 52mAmerican Airlines
Deal found 2/22$235
This FlightHub deal was found by Cheapflights users on 2/22. 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.
Thu 3/1312:17 pmBNA - SJU
1 stop11h 25mMultiple Airlines
Tue 3/189:35 pmSJU - BNA
1 stop11h 52mMultiple Airlines
Deal found 2/22$249
This Cheapflightsfares deal was found by Cheapflights users on 2/22. 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.
Tue 3/115:30 amBNA - MBJ
1 stop5h 32mSpirit Airlines
Tue 3/1812:07 pmMBJ - BNA
1 stop7h 51mSpirit Airlines
Deal found 2/22$251
This Mytrip deal was found by Cheapflights users on 2/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/58:06 pmCVG - STT
1 stop14h 00mMultiple Airlines
Tue 4/1510:45 amSTT - CVG
2 stops29h 49mMultiple Airlines
Deal found 2/22$272
This American Airlines deal was found by Cheapflights users on 2/22. 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.
Sat 5/35:00 amBNA - SJU
2 stops8h 35mAmerican Airlines
Sat 5/103:35 pmSJU - BNA
2 stops8h 58mAmerican Airlines
Deal found 2/22$295
This United Airlines deal was found by Cheapflights users on 2/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/84:00 pmCVG - SJU
1 stop7h 36mUnited Airlines
Fri 11/142:05 amSJU - CVG
2 stops13h 56mUnited Airlines
Deal found 2/22$298
This JetBlue Airways deal was found by Cheapflights users on 2/22. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/307:00 amBNA - SJU
1 stop11h 00mJetBlue
Fri 6/68:50 amSJU - BNA
1 stop11h 26mJetBlue
Deal found 2/22$340

Find flights from Kentucky to Caribbean Islands within your budget

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 February 23, 2025.

Fly from

Kentucky

Fly to

Caribbean Islands

Route

Depart

Return

Price

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Mon 4/28

7:29 pm-2:49 am

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Sun 5/4

11:20 am-12:40 am

1 stop13h 20m

$150

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Wed 3/12

2:54 pm-10:01 am

1 stop18h 07m

Saint Thomas Island Cyril E King

Tue 3/18

11:11 am-7:58 pm

1 stop9h 47m

$174

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Mon 4/28

6:00 am-9:40 am

2 stops27h 40m

San Juan Luis Munoz Marin Intl

Wed 5/7

1:10 am-12:11 pm

2 stops35h 01m

$208

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Wed 4/30

5:09 pm-11:15 pm

1 stop6h 06m

San Juan Luis Munoz Marin Intl

Mon 5/5

6:35 am-5:19 pm

1 stop10h 44m

$215

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Tue 3/11

2:59 pm-12:23 am

1 stop8h 24m

San Juan Luis Munoz Marin Intl

Tue 3/18

6:18 am-8:20 pm

2 stops15h 02m

$232

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Thu 3/13

12:17 pm-12:42 am

1 stop11h 25m

San Juan Luis Munoz Marin Intl

Tue 3/18

9:35 pm-8:27 am

1 stop11h 52m

$249

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

$251

CincinnatiSaint Thomas Island

CVG - STT

CVGSTT

Cincinnati Cinci./N. Kentucky

Sat 4/5

8:06 pm-10:06 am

1 stop14h 00m

Saint Thomas Island Cyril E King

Tue 4/15

10:45 am-4:34 pm

2 stops29h 49m

$272

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Wed 4/2

4:58 pm-5:00 am

1 stop12h 02m

San Juan Luis Munoz Marin Intl

Tue 4/8

6:21 am-2:45 pm

2 stops8h 24m

$276

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Sat 5/3

5:00 am-2:35 pm

2 stops8h 35m

San Juan Luis Munoz Marin Intl

Sat 5/10

3:35 pm-11:33 pm

2 stops8h 58m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

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.

Travel insights for flights from Kentucky to Caribbean Islands

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

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 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 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 February 23, 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 February 23, 2025.
Get a feel of what it's like to fly with Southwest, Alaska Airlines and Delta 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
8.1
Very good
4,385 reviews

Entertainment

7.6

Crew

8.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Food

7.1

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
4,385 reviews
Southwest
8.1
Very good
4,385 reviews

Entertainment

7.6

Crew

8.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Food

7.1

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
9,706 reviews
Southwest
8.1
Very good
4,385 reviews

Entertainment

7.6

Crew

8.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Food

7.1

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
8,203 reviews
Southwest
8.1
Very good
4,385 reviews

Entertainment

7.6

Crew

8.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Food

7.1

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
1,500 reviews
Southwest
8.1
Very good
4,385 reviews

Entertainment

7.6

Crew

8.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Food

7.1

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.

JetBlue
7.4
Good
3,065 reviews
Southwest
8.1
Very good
4,385 reviews

Entertainment

7.6

Crew

8.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Food

7.1

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 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 Frontier. According to our data, you can fly for as low as $65. Users have also found prices from $77 and $108 on Spirit Airlines and American Airlines, 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 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

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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 February 23, 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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