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Caribbean Islands

$101+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Round-trip from

$215
(United Airlines)

One-way from

$101
(Mytrip)

Popular in

March

Cheapest in

August

Average price

$451
From Kentucky to Caribbean Islands
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One-way flight from Kentucky to Caribbean Islands
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Highest demand for flights based on searches. 7% potential increase in price ($38 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 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 April 29, 2025.

This American Airlines deal was found by Cheapflights users on 4/28. 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.
Fri 5/911:08 amCVG - SJU
2 stops9h 25mAmerican Airlines
Wed 5/146:10 amSJU - CVG
2 stops9h 34mAmerican Airlines
Deal found 4/28$215
This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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 5/142:00 pmBNA - SJU
1 stop9h 54mSpirit Airlines
Sun 5/188:12 pmSJU - BNA
1 stop13h 08mSpirit Airlines
Deal found 4/28$230
This Delta deal was found by Cheapflights users on 4/28. 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 10/132:59 pmSDF - SJU
1 stop7h 22mDelta
Tue 10/285:30 pmSJU - SDF
1 stop6h 26mDelta
Deal found 4/28$255
This Delta deal was found by Cheapflights users on 4/28. 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 10/134:40 pmCVG - SJU
1 stop5h 41mDelta
Sat 10/185:30 pmSJU - CVG
1 stop6h 25mDelta
Deal found 4/28$258
This American Airlines deal was found by Cheapflights users on 4/27. 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 9/256:29 pmBNA - SJU
1 stop15h 46mAmerican Airlines
Tue 9/308:30 amSJU - BNA
1 stop7h 33mAmerican Airlines
Deal found 4/27$262
This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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.
Mon 5/127:47 pmBNA - PUJ
1 stop15h 00mSpirit Airlines
Fri 5/1612:42 pmPUJ - BNA
1 stop11h 00mSpirit Airlines
Deal found 4/28$263
This Delta deal was found by Cheapflights users on 4/28. 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 5/313:43 pmBNA - SJU
1 stop6h 04mDelta
Fri 6/67:30 amSJU - BNA
1 stop9h 08mDelta
Deal found 4/28$274
This American Airlines deal was found by Cheapflights users on 4/28. 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 5/107:24 amSDF - SJU
1 stop7h 36mAmerican Airlines
Tue 5/133:07 pmSJU - SDF
1 stop9h 18mAmerican Airlines
Deal found 4/28$275
This Priceline deal was found by Cheapflights users on 4/27. 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.
Fri 5/2310:01 amBNA - SJU
1 stop15h 31mMultiple Airlines
Sun 5/258:12 pmSJU - BNA
1 stop13h 08mMultiple Airlines
Deal found 4/27$288
This Cheapflightsfares deal was found by Cheapflights users on 4/27. 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.
Sun 5/256:15 amBNA - MBJ
1 stop4h 47mSpirit Airlines
Thu 5/2912:07 pmMBJ - BNA
1 stop9h 38mSpirit Airlines
Deal found 4/27$292
This Cheapflightsfares deal was found by Cheapflights users on 4/27. 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.
Sun 5/412:31 pmCVG - SJU
1 stop7h 13mFrontier
Wed 5/73:56 amSJU - CVG
1 stop7h 40mFrontier
Deal found 4/27$294
This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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 5/106:25 pmSDF - SJU
1 stop6h 29mSpirit Airlines
Mon 5/121:59 amSJU - SDF
1 stop10h 04mSpirit Airlines
Deal found 4/28$297

Cheapflights Fare Finder

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 April 29, 2025.
Use the filters below to find and compare flights from Kentucky to Caribbean Islands that are best for you.

Fly from

Kentucky

Fly to

Caribbean Islands

Route

Depart

Return

Price

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Fri 5/9

11:08 am-8:33 pm

2 stops9h 25m

San Juan Luis Munoz Marin Intl

Wed 5/14

6:10 am-3:44 pm

2 stops9h 34m

$215

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Wed 5/14

2:00 pm-12:54 am

1 stop9h 54m

San Juan Luis Munoz Marin Intl

Sun 5/18

8:12 pm-8:20 am

1 stop13h 08m

$230

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sat 5/17

1:49 pm-10:47 pm

1 stop8h 58m

San Juan Luis Munoz Marin Intl

Thu 5/29

7:00 am-5:14 pm

1 stop10h 14m

$258

NashvillePunta Cana

BNA - PUJ

BNAPUJ

Nashville Intl

Mon 5/12

7:47 pm-11:47 am

1 stop15h 00m

Punta Cana

Fri 5/16

12:42 pm-10:42 pm

1 stop11h 00m

$263

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Sat 5/31

3:43 pm-10:47 pm

1 stop6h 04m

San Juan Luis Munoz Marin Intl

Fri 6/6

7:30 am-3:38 pm

1 stop9h 08m

$274

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Fri 5/9

7:24 am-8:33 pm

1 stop13h 09m

San Juan Luis Munoz Marin Intl

Mon 5/12

3:50 pm-12:18 am

1 stop8h 28m

$275

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Fri 5/23

10:01 am-2:32 am

1 stop15h 31m

San Juan Luis Munoz Marin Intl

Sun 5/25

8:12 pm-8:20 am

1 stop13h 08m

$288

NashvilleMontego Bay

BNA - MBJ

BNAMBJ

Nashville Intl

Sun 5/25

6:15 am-11:02 am

1 stop4h 47m

Montego Bay Sangster Intl

Thu 5/29

12:07 pm-9:45 pm

1 stop9h 38m

$292

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

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Mon 5/5

10:01 am-10:01 pm

1 stop11h 00m

San Juan Luis Munoz Marin Intl

Thu 5/8

3:56 am-9:09 am

1 stop6h 13m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

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.

Cheapflights Insights

Everything you need to know about your flight from Kentucky to Caribbean Islands

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 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 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 April 29, 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 April 29, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest 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.
Alaska Airlines
8.0
Very good
9,949 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,949 reviews
Alaska Airlines
8.0
Very good
9,949 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,292 reviews
Alaska Airlines
8.0
Very good
9,949 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,929 reviews
Alaska Airlines
8.0
Very good
9,949 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
LATAM Airlines
7.5
Good
1,766 reviews
Alaska Airlines
8.0
Very good
9,949 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Copa Airlines
7.5
Good
1,410 reviews
Alaska Airlines
8.0
Very good
9,949 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 Spirit Airlines. According to our data, you can fly for as low as $101. Users have also found prices from $108 and $138 on American Airlines and United 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 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

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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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$179Average$397FlexibilityNo cancel feeOn-time65%
DeltaCheapest$254Average$605FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$271Average$636FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$275Average$655FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$326Average$737FlexibilityNo cancel feeOn-time63%

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