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$108+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
may. 5 — may. 121
lun. 5/5
lun. 5/12
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 abril 30, 2025.

Round-trip from

$225
(Delta)

One-way from

$108
(Delta)

Popular in

March

Cheapest in

August

Average price

$451
From Kentucky to Caribbean
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One-way flight from Kentucky to Caribbean
Search Deals
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

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 abril 30, 2025.

This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/92:10 pmCVG - SJU
1 stop9h 44mUnited Airlines
mié. 5/143:56 pmSJU - CVG
1 stop7h 44mUnited Airlines
Deal found 4/28$215
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.
vie. 5/911:08 amCVG - SJU
2 stops9h 25mAmerican Airlines
mar. 5/136:10 amSJU - CVG
2 stops10h 13mAmerican Airlines
Deal found 4/28$217
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/172:19 pmCVG - SJU
1 stop28h 48mMultiple Airlines
jue. 5/298:12 pmSJU - CVG
1 stop26h 56mMultiple Airlines
Deal found 4/28$224
This Delta deal was found by Cheapflights users on 4/29. 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.
mar. 9/1612:40 pmSDF - SJU
1 stop9h 28mDelta
mar. 9/235:19 pmSJU - SDF
1 stop6h 37mDelta
Deal found 4/29$225
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/246:15 amBNA - SJU
2 stops26h 28mMultiple Airlines
lun. 6/28:12 pmSJU - BNA
1 stop21h 37mMultiple Airlines
Deal found 4/28$238
This American Airlines deal was found by Cheapflights users on 4/29. 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.
mar. 8/1911:19 amBNA - SJU
1 stop11h 46mAmerican Airlines
vie. 8/223:50 pmSJU - BNA
1 stop8h 47mAmerican Airlines
Deal found 4/29$239
This Trip.com deal was found by Cheapflights users on 4/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/88:10 amBNA - SJU
1 stop10h 52mSpirit Airlines
sáb. 5/108:12 pmSJU - BNA
1 stop13h 08mSpirit Airlines
Deal found 4/29$244
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
lun. 5/127:47 pmBNA - PUJ
1 stop15h 00mSpirit Airlines
vie. 5/1612:42 pmPUJ - BNA
1 stop11h 00mSpirit Airlines
Deal found 4/29$257
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.
lun. 10/134:40 pmCVG - SJU
1 stop5h 41mDelta
sáb. 10/185:30 pmSJU - CVG
1 stop6h 25mDelta
Deal found 4/28$258
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.
sáb. 5/107:24 amSDF - SJU
1 stop7h 36mAmerican Airlines
mar. 5/133:07 pmSJU - SDF
1 stop9h 18mAmerican Airlines
Deal found 4/28$275
This Mytrip deal was found by Cheapflights users on 4/29. 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.
vie. 5/3012:07 pmSDF - SJU
1 stop23h 24mSpirit Airlines
mié. 6/410:38 amSJU - SDF
2 stops23h 40mSpirit Airlines
Deal found 4/29$279
This Mytrip deal was found by Cheapflights users on 4/29. 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.
lun. 6/25:13 pmCVG - STT
1 stop16h 44mMultiple Airlines
mar. 6/32:41 pmSTT - CVG
1 stop22h 48mMultiple Airlines
Deal found 4/29$296

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 abril 30, 2025.
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

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

vie. 5/9

2:10 pm-11:54 pm

1 stop9h 44m

San Juan Luis Munoz Marin Intl

mié. 5/14

3:56 pm-11:40 pm

1 stop7h 44m

$215

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

vie. 5/9

11:08 am-8:33 pm

2 stops9h 25m

San Juan Luis Munoz Marin Intl

mar. 5/13

6:10 am-4:23 pm

2 stops10h 13m

$217

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

sáb. 5/17

2:19 pm-7:07 pm

1 stop28h 48m

San Juan Luis Munoz Marin Intl

jue. 5/29

8:12 pm-11:08 pm

1 stop26h 56m

$224

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

mar. 9/16

12:40 pm-10:08 pm

1 stop9h 28m

San Juan Luis Munoz Marin Intl

mar. 9/23

5:19 pm-11:56 pm

1 stop6h 37m

$225

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

sáb. 5/24

6:15 am-9:43 am

2 stops26h 28m

San Juan Luis Munoz Marin Intl

lun. 6/2

8:12 pm-4:49 pm

1 stop21h 37m

$238

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

jue. 5/8

8:10 am-8:02 pm

1 stop10h 52m

San Juan Luis Munoz Marin Intl

sáb. 5/10

8:12 pm-8:20 am

1 stop13h 08m

$244

NashvillePunta Cana

BNA - PUJ

BNAPUJ

Nashville Intl

lun. 5/12

7:47 pm-11:47 am

1 stop15h 00m

Punta Cana

vie. 5/16

12:42 pm-10:42 pm

1 stop11h 00m

$257

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

lun. 10/13

4:40 pm-10:21 pm

1 stop5h 41m

San Juan Luis Munoz Marin Intl

sáb. 10/18

5:30 pm-11:55 pm

1 stop6h 25m

$258

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

sáb. 5/10

7:24 am-3:00 pm

1 stop7h 36m

San Juan Luis Munoz Marin Intl

mar. 5/13

3:07 pm-12:25 am

1 stop9h 18m

$275

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

vie. 5/30

12:07 pm-11:31 am

1 stop23h 24m

San Juan Luis Munoz Marin Intl

mié. 6/4

10:38 am-10:18 am

2 stops23h 40m

$279

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

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, 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 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 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 abril 30, 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 abril 30, 2025.
Delta
8.0
Very good
7,929 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,929 reviews
Delta
8.0
Very good
7,929 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Alaska Airlines
8.0
Very good
9,961 reviews
Delta
8.0
Very good
7,929 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Southwest
8.0
Very good
4,295 reviews
Delta
8.0
Very good
7,929 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Copa Airlines
7.5
Good
1,411 reviews
Delta
8.0
Very good
7,929 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
LATAM Airlines
7.5
Good
1,767 reviews
Delta
8.0
Very good
7,929 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 Delta, which is currently one of the cheapest options available, starting at $108. Spirit Airlines flights start at $109 while deals on American Airlines start at $116 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 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

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 abril 30, 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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