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Kentucky

$69+ Cheap flights from Caribbean to Kentucky

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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SDF
Nov 30 — Dec 71
Sun 11/30
Sun 12/7
1 adult, Economy
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Cheap flight deals from Caribbean to Kentucky

Keep the following information in mind while searching for Caribbean to Kentucky flight deals. Data was last updated October 31, 2025.

Round-trip from

$208
(Kiwi.com)

One-way from

$69
(Priceline)

Popular in

June

Cheapest in

August

Average price

$342
From Caribbean to Kentucky
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One-way flight from Caribbean to Kentucky
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Highest demand for flights based on searches. 8% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Caribbean to Kentucky

Cheapest flights from Caribbean to Kentucky
Explore the most affordable flight options available from Caribbean to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/215:19 pmSJU - BNA
1 stop16h 43mMultiple Airlines
Mon 11/248:55 pmBNA - SJU
1 stop24h 49mMultiple Airlines
Deal found 10/29$208
This Orbitz deal was found by Cheapflights users on 10/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/192:25 amSJU - BNA
1 stop9h 00mMultiple Airlines
Thu 11/276:00 amBNA - SJU
1 stop12h 27mMultiple Airlines
Deal found 10/30$213
This United Airlines deal was found by Cheapflights users on 10/31. 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.
Thu 12/188:10 amSJU - BNA
1 stop9h 40mUnited Airlines
Sun 1/116:20 pmBNA - SJU
1 stop9h 51mUnited Airlines
Deal found 10/31$215
This Priceline deal was found by Cheapflights users on 10/30. 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.
Thu 11/133:59 amSJU - BNA
1 stop10h 20mMultiple Airlines
Tue 11/186:45 amBNA - SJU
1 stop5h 57mMultiple Airlines
Deal found 10/30$223
This American Airlines deal was found by Cheapflights users on 10/31. 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 12/268:35 pmSJU - CVG
1 stop14h 54mAmerican Airlines
Sat 1/312:44 pmCVG - SJU
1 stop15h 16mAmerican Airlines
Deal found 10/31$225
This Delta deal was found by Cheapflights users on 10/31. 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.
Thu 12/256:30 amSJU - SDF
1 stop7h 21mDelta
Thu 1/16:00 amSDF - SJU
1 stop5h 57mDelta
Deal found 10/31$225
This Orbitz deal was found by Cheapflights users on 10/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/45:00 pmSJU - BNA
1 stop7h 08mMultiple Airlines
Mon 12/812:56 pmBNA - SJU
1 stop9h 53mMultiple Airlines
Deal found 10/29$228
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Fri 12/124:41 pmSJU - SDF
1 stop8h 13mAmerican Airlines
Tue 1/137:20 pmSDF - SJU
2 stops16h 10mAmerican Airlines
Deal found 10/29$229
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/43:46 pmSJU - BNA
1 stop8h 29mUnited Airlines
Tue 12/98:00 amBNA - SJU
2 stops12h 22mUnited Airlines
Deal found 10/29$234
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/225:00 pmSJU - BNA
1 stop8h 42mMultiple Airlines
Fri 11/282:47 pmBNA - SJU
1 stop8h 08mMultiple Airlines
Deal found 10/28$236
This Frontier deal was found by Cheapflights users on 10/31. 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.
Wed 11/192:25 amSJU - BNA
1 stop9h 00mFrontier
Thu 11/2710:20 amBNA - SJU
1 stop12h 35mFrontier
Deal found 10/31$237
This American Airlines deal was found by Cheapflights users on 10/31. 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 11/204:44 pmSJU - CVG
1 stop8h 14mAmerican Airlines
Mon 11/246:00 amCVG - SJU
1 stop9h 19mAmerican Airlines
Deal found 10/31$240

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean to Kentucky 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 31, 2025.
Use the filters below to find and compare flights from Caribbean to Kentucky that are best for you.

Fly from

Caribbean

Fly to

Kentucky

Route

Depart

Return

Price

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Thu 12/18

8:10 am-3:50 pm

1 stop9h 40m

Nashville Intl

Sun 1/11

6:20 pm-6:11 am

1 stop9h 51m

$215

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Thu 1/22

3:55 pm-8:15 pm

1 stop6h 20m

Nashville Intl

Tue 1/27

5:25 am-1:05 pm

1 stop5h 40m

$215

San JuanLouisville

SJU - SDF

SJUSDF

San Juan Luis Munoz Marin Intl

Thu 12/25

6:30 am-3:58 pm

1 stop10h 28m

Louisville Intl

Thu 1/1

6:00 am-12:57 pm

1 stop5h 57m

$225

San JuanLouisville

SJU - SDF

SJUSDF

San Juan Luis Munoz Marin Intl

Wed 3/4

8:10 am-2:47 pm

1 stop7h 37m

Louisville Intl

Mon 3/9

9:00 am-9:22 pm

2 stops12h 22m

$225

San JuanLouisville

SJU - SDF

SJUSDF

San Juan Luis Munoz Marin Intl

Fri 12/12

7:00 am-2:11 pm

1 stop8h 11m

Louisville Intl

Tue 1/13

6:00 am-1:04 pm

1 stop6h 04m

$225

San JuanLouisville

SJU - SDF

SJUSDF

San Juan Luis Munoz Marin Intl

Fri 12/12

2:36 pm-11:54 pm

2 stops10h 18m

Louisville Intl

Tue 1/13

7:20 pm-12:30 pm

2 stops16h 10m

$229

San JuanLouisville

SJU - SDF

SJUSDF

San Juan Luis Munoz Marin Intl

Thu 12/25

4:38 pm-8:50 am

2 stops17h 12m

Louisville Intl

Thu 1/1

5:00 am-11:39 am

1 stop5h 39m

$230

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Thu 12/4

3:46 pm-10:15 pm

1 stop8h 29m

Nashville Intl

Tue 12/9

8:00 am-10:22 pm

2 stops12h 22m

$234

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Thu 11/6

2:47 pm-11:09 pm

2 stops9h 22m

Cincinnati Cinci./N. Kentucky

Thu 11/13

10:31 am-8:58 pm

1 stop9h 27m

$245

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Wed 11/5

8:20 am-6:00 pm

2 stops10h 40m

Cincinnati Cinci./N. Kentucky

Thu 11/13

5:00 am-8:58 pm

1 stop14h 58m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

Showing 1-10 of 60 results
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Best time to book a flight from Caribbean to Kentucky

Have a flexible travel schedule? Discover the best time to fly to Kentucky from Caribbean 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 Caribbean to Kentucky

What is the cheapest month to book a flight from Caribbean to Kentucky?

Currently, March is the cheapest month in which you can book a flight from Caribbean to Kentucky (average of $138). Flying from Caribbean to Kentucky in January is currently the most expensive (average of $374). 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 CB to KY?

Find hourly flight availability from Caribbean to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 31, 2025.

It’s typically best to fly out from Caribbean to Kentucky in the evening. Doing so could potentially save you 38% on the flight price compared to flying at noon, which is usually more expensive.

Reviews of airlines servicing Kentucky

Get insights into the airlines that provide service to Kentucky. 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 Kentucky. Reviews last updated October 31, 2025.
See what other customers who have flown with Southwest, Delta, and American Airlines from Caribbean to Kentucky have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,034 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Caribbean to Kentucky. 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 Caribbean to Kentucky?

    Airlines like United Airlines, Delta, and American Airlines fly from Caribbean to Kentucky in about 6h 20m. The time it takes to get you to your destination can typically vary by up to 3h 58m. Caribbean and Kentucky are separated by a distance of 1753 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The cheapest airlines for a one-way flight from Caribbean to Kentucky are Frontier ($75), Delta ($108), and Southwest ($108).

  • Can I find deals for flights from Caribbean to Kentucky that include hotel bookings?

    Yes. In addition to deals on Caribbean to Kentucky flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean to Kentucky?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean to Kentucky.

  • Can I find deals for business class flights from Caribbean to Kentucky?

    Yes. Cheapflights offers flight deals from Caribbean to Kentucky 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 Caribbean to Kentucky?

    Currently, March is the cheapest month in which you can book a flight from Caribbean to Kentucky (average of $138). Flying from Caribbean to Kentucky in January is currently the most expensive (average of $374). 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

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Alternative routes for Caribbean to Kentucky

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Caribbean to Kentucky

Discover the top 3 airlines that operate flights from Caribbean to Kentucky. 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 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$138Average$526FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$175Average$335FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$255Average$469FlexibilityNo cancel feeOn-time71%

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