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$91+ 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheap 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 January 28, 2026.

This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:30 am
BNA
-
STT
1 stop6h 04m
Spirit Airlines
Fri 2/275:40 pm
STT
-
BNA
1 stop15h 45m
Spirit Airlines
Deal found 1/27$188
This CheapOair deal was found by Cheapflights users on 1/25. 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.
Mon 4/206:15 am
BNA
-
STT
1 stop8h 19m
Spirit Airlines
Mon 4/274:40 pm
STT
-
BNA
1 stop26h 19m
Spirit Airlines
Deal found 1/25$194
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/127:24 am
BNA
-
STT
1 stop7h 04m
Spirit Airlines
Tue 3/174:35 pm
STT
-
BNA
1 stop7h 55m
Spirit Airlines
Deal found 1/28$197
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/268:30 am
BNA
-
STT
1 stop6h 04m
Spirit Airlines
Thu 3/55:40 pm
STT
-
BNA
1 stop15h 45m
Spirit Airlines
Deal found 1/27$201
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:52 pm
BNA
-
STT
2 stops15h 39m
Spirit Airlines
Sun 3/15:40 pm
STT
-
BNA
1 stop15h 45m
Spirit Airlines
Deal found 1/27$209
This Frontier deal was found by Cheapflights users on 1/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:14 pm
CVG
-
SJU
1 stop6h 39m
Frontier
Wed 2/253:53 am
SJU
-
CVG
1 stop8h 19m
Frontier
Deal found 1/27$212
This Frontier deal was found by Cheapflights users on 1/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:14 pm
CVG
-
SJU
1 stop6h 39m
Frontier
Tue 2/243:53 am
SJU
-
CVG
1 stop11h 17m
Frontier
Deal found 1/27$213
This Priceline deal was found by Cheapflights users on 1/27. 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.
Wed 2/251:19 pm
SDF
-
SJU
1 stop8h 50m
Spirit Airlines
Wed 3/46:00 am
SJU
-
SDF
1 stop7h 21m
Spirit Airlines
Deal found 1/27$215
This Priceline deal was found by Cheapflights users on 1/25. 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.
Tue 2/109:25 am
BNA
-
SJU
1 stop12h 08m
Multiple Airlines
Sat 2/147:54 pm
SJU
-
BNA
1 stop19h 46m
Multiple Airlines
Deal found 1/25$215
This Expedia deal was found by Cheapflights users on 1/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2610:55 am
BNA
-
SJU
1 stop14h 06m
Frontier
Wed 4/293:08 am
SJU
-
BNA
1 stop7h 20m
Frontier
Deal found 1/27$217
This Priceline deal was found by Cheapflights users on 1/26. 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 4/102:26 pm
CVG
-
SJU
1 stop9h 14m
Frontier
Fri 4/243:08 am
SJU
-
CVG
1 stop14h 42m
Frontier
Deal found 1/26$217
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/198:52 pm
BNA
-
STT
2 stops15h 39m
Spirit Airlines
Mon 2/235:40 pm
STT
-
BNA
1 stop15h 45m
Spirit Airlines
Deal found 1/27$218

Find flight deals from Kentucky to Caribbean

Keep the following information in mind while searching for Kentucky to Caribbean flight deals. Data was last updated January 28, 2026.

Round-trip from

$188
(CheapOair)

One-way from

$91
(Priceline)

Popular in

December

Cheapest in

September

Average price

$345
From Kentucky to Caribbean
Search Deals
One-way flight from Kentucky to Caribbean
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($16 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 January 2026
Search Deals

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 January 28, 2026.
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

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Tue 2/24

8:30 am-4:34 pm

1 stop6h 04m

Saint Thomas Island Cyril E King

Fri 2/27

5:40 pm-7:25 am

1 stop15h 45m

$188

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Wed 2/18

8:30 am-4:34 pm

1 stop6h 04m

Saint Thomas Island Cyril E King

Sun 2/22

5:40 pm-7:25 am

1 stop15h 45m

$188

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Tue 2/24

8:30 am-4:34 pm

1 stop6h 04m

Saint Thomas Island Cyril E King

Sun 3/1

5:40 pm-7:25 am

1 stop15h 45m

$188

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Mon 4/20

6:15 am-3:34 pm

1 stop8h 19m

Saint Thomas Island Cyril E King

Mon 4/27

4:40 pm-5:59 pm

1 stop26h 19m

$194

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Thu 2/19

8:30 am-4:34 pm

1 stop6h 04m

Saint Thomas Island Cyril E King

Mon 2/23

5:40 pm-7:25 am

1 stop15h 45m

$197

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Thu 3/12

7:24 am-3:28 pm

1 stop7h 04m

Saint Thomas Island Cyril E King

Tue 3/17

4:35 pm-11:30 pm

1 stop7h 55m

$197

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Thu 2/26

8:52 pm-2:31 pm

2 stops15h 39m

Saint Thomas Island Cyril E King

Thu 3/5

5:40 pm-7:25 am

1 stop15h 45m

$218

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Thu 5/14

9:52 am-8:34 pm

1 stop9h 42m

San Juan Luis Munoz Marin Intl

Sun 5/17

1:00 am-9:28 am

2 stops9h 28m

$236

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Thu 4/9

5:00 am-3:35 pm

1 stop9h 35m

San Juan Luis Munoz Marin Intl

Wed 4/15

11:25 am-5:55 pm

2 stops7h 30m

$236

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Sat 4/25

2:10 pm-7:05 pm

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Sat 5/2

6:25 am-5:25 pm

1 stop12h 00m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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, March is the cheapest month in which you can book a flight from Kentucky to Caribbean (average of $190). Flying from Kentucky to Caribbean 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.

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.

  • How long is the flight from Kentucky to Caribbean?

    Spirit Airlines, United Airlines, and Southwest can get you from Kentucky to Caribbean in just under 6h 04m. Your travel time can differ by up to 3h 38m. Kentucky and Caribbean are separated by a distance of 1804 mi. This flight may include one or multiple stops.

  • 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 $102. American Airlines flights start at $109 while deals on Delta start at $112 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, March is the cheapest month in which you can book a flight from Kentucky to Caribbean (average of $190). Flying from Kentucky to Caribbean 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$381FlexibilityNo cancel feeOn-time65%
DeltaCheapest$163Average$596FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$225Average$666FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$246Average$556FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$255Average$620FlexibilityNo cancel feeOn-time71%

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