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Caribbean Islands

$85+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
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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 October 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/223:40 pmBNA - SJU
1 stop9h 22mMultiple Airlines
Wed 10/295:51 pmSJU - BNA
1 stop19h 05mMultiple Airlines
Deal found 10/15$154
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/254:06 pmBNA - SJU
1 stop8h 56mMultiple Airlines
Wed 10/299:00 amSJU - BNA
1 stop27h 56mMultiple Airlines
Deal found 10/16$159
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/305:45 amBNA - SJU
1 stop18h 47mMultiple Airlines
Sat 11/19:00 amSJU - BNA
2 stops33h 33mMultiple Airlines
Deal found 10/16$195
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/254:06 pmBNA - SJU
1 stop8h 56mMultiple Airlines
Tue 10/289:00 amSJU - BNA
1 stop30h 35mMultiple Airlines
Deal found 10/16$199
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/248:51 pmBNA - SJU
1 stop27h 03mMultiple Airlines
Wed 10/299:00 amSJU - BNA
1 stop27h 56mMultiple Airlines
Deal found 10/16$200
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/254:06 pmBNA - SJU
1 stop8h 56mMultiple Airlines
Fri 10/319:00 amSJU - BNA
2 stops30h 47mMultiple Airlines
Deal found 10/16$201
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1212:52 pmCVG - SJU
2 stops13h 41mMultiple Airlines
Wed 11/199:00 amSJU - CVG
1 stop16h 59mMultiple Airlines
Deal found 10/16$205
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/254:06 pmBNA - SJU
1 stop8h 56mMultiple Airlines
Sat 11/15:51 pmSJU - BNA
2 stops24h 42mMultiple Airlines
Deal found 10/16$207
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/155:43 pmCVG - SJU
1 stop20h 36mFrontier
Wed 11/199:00 amSJU - CVG
1 stop16h 59mFrontier
Deal found 10/16$223
This American Airlines deal was found by Cheapflights users on 10/15. 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 11/158:10 amSDF - SJU
1 stop6h 44mAmerican Airlines
Tue 11/186:25 amSJU - SDF
1 stop16h 15mAmerican Airlines
Deal found 10/15$225
This United Airlines deal was found by Cheapflights users on 10/15. 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 11/122:56 pmCVG - SJU
1 stop6h 26mUnited Airlines
Tue 11/182:05 amSJU - CVG
2 stops12h 06mUnited Airlines
Deal found 10/15$225
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/254:06 pmBNA - SJU
1 stop8h 56mMultiple Airlines
Thu 10/306:54 pmSJU - BNA
1 stop13h 23mMultiple Airlines
Deal found 10/16$227

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 October 16, 2025.

Round-trip from

$195
(Kiwi.com)

One-way from

$85
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$344
From Kentucky to Caribbean Islands
Search Deals
One-way flight from Kentucky to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 16, 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

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Tue 2/24

8:25 am-5:05 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Sat 2/28

6:05 am-1:50 pm

1 stop9h 45m

$215

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Sun 2/22

5:45 am-4:30 pm

1 stop8h 45m

San Juan Luis Munoz Marin Intl

Sat 2/28

6:05 am-1:50 pm

1 stop9h 45m

$215

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 3/2

2:59 pm-11:49 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Wed 3/11

6:15 am-1:50 pm

1 stop7h 35m

$225

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Wed 10/29

11:45 am-8:26 pm

1 stop8h 41m

San Juan Luis Munoz Marin Intl

Wed 4/8

7:45 am-4:58 pm

1 stop9h 13m

$235

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Wed 11/26

1:25 pm-1:57 am

1 stop10h 32m

San Juan Luis Munoz Marin Intl

Wed 12/3

1:45 pm-9:07 pm

1 stop9h 22m

$242

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Wed 10/29

11:45 am-8:26 pm

1 stop8h 41m

San Juan Luis Munoz Marin Intl

Sat 11/1

3:52 pm-11:49 pm

1 stop7h 57m

$245

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Tue 3/3

9:00 am-9:26 pm

2 stops11h 26m

San Juan Luis Munoz Marin Intl

Tue 3/10

7:10 am-2:47 pm

1 stop7h 37m

$250

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Tue 2/24

8:10 am-5:12 pm

1 stop7h 02m

San Juan Luis Munoz Marin Intl

Thu 2/26

7:30 am-4:39 pm

1 stop11h 09m

$263

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sat 11/8

5:31 am-9:35 pm

1 stop15h 04m

San Juan Luis Munoz Marin Intl

Thu 11/13

6:25 am-3:40 pm

1 stop10h 15m

$275

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Sat 11/15

6:45 am-2:42 pm

1 stop5h 57m

San Juan Luis Munoz Marin Intl

Sat 11/22

7:20 am-1:48 pm

1 stop8h 28m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/15

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, January is the cheapest month in which you can book a flight from Kentucky to Caribbean Islands (average of $167). Flying from Kentucky to Caribbean Islands in June is currently the most expensive (average of $285). 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 October 16, 2025.

It’s optimal to fly from Kentucky to Caribbean Islands at noon. By choosing this option you can save up to 31% on the cost of your flight, compared to a flight in the evening.

What is the cheapest day to fly from Kentucky to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Kentucky to Caribbean Islands. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Kentucky to Caribbean Islands flight should consider departing on Thursday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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.

  • How long is the flight from Kentucky to Caribbean Islands?

    For as low as $215, Southwest can have you in Caribbean Islands from Kentucky in 6h 40m. The distance between Kentucky and Caribbean Islands is about 1753 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Kentucky to Caribbean Islands one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $108. Users have also found prices from $108 and $108 on United Airlines and Delta, 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, January is the cheapest month in which you can book a flight from Kentucky to Caribbean Islands (average of $167). Flying from Kentucky to Caribbean Islands in June is currently the most expensive (average of $285). 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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$393FlexibilityNo cancel feeOn-time65%
DeltaCheapest$225Average$596FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$225Average$700FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$261Average$602FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$275Average$600FlexibilityNo cancel feeOn-time69%

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