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Kentucky

$87+ Cheap flights from Caribbean Islands 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SDF
Mar 4 — Mar 111
Wed 3/4
Wed 3/11
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Kentucky

Cheapest flights from Caribbean Islands to Kentucky
Explore the most affordable flight options available from Caribbean Islands to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.

This Frontier deal was found by Cheapflights users on 2/1. 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.
Thu 2/265:25 pm
SJU
-
CVG
1 stop8h 34m
Frontier
Mon 3/27:14 pm
CVG
-
SJU
1 stop6h 39m
Frontier
Deal found 2/1$192
This Frontier deal was found by Cheapflights users on 1/31. 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.
Mon 3/93:08 am
SJU
-
BNA
1 stop8h 33m
Frontier
Tue 3/1711:36 am
BNA
-
SJU
1 stop10h 09m
Frontier
Deal found 1/31$192
This OneTravel deal was found by Cheapflights users on 2/1. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/112:55 pm
SJU
-
BNA
1 stop11h 43m
Spirit Airlines
Wed 4/87:44 am
BNA
-
SJU
1 stop10h 11m
Spirit Airlines
Deal found 2/1$208
This Frontier deal was found by Cheapflights users on 2/2. 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 3/93:08 am
SJU
-
BNA
1 stop8h 33m
Frontier
Mon 3/169:33 pm
BNA
-
SJU
1 stop11h 12m
Frontier
Deal found 2/2$216
This Travelocity deal was found by Cheapflights users on 1/31. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:00 am
SJU
-
BNA
1 stop11h 03m
Spirit Airlines
Sat 3/76:15 am
BNA
-
SJU
1 stop14h 54m
Spirit Airlines
Deal found 1/31$226
This CheapOair deal was found by Cheapflights users on 2/1. 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.
Fri 2/2711:52 am
SJU
-
BNA
1 stop21h 33m
Spirit Airlines
Mon 3/29:25 am
BNA
-
SJU
1 stop22h 52m
Spirit Airlines
Deal found 2/1$227
This CheapOair deal was found by Cheapflights users on 1/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/184:31 pm
SJU
-
BNA
1 stop16h 54m
Spirit Airlines
Wed 3/49:25 am
BNA
-
SJU
1 stop11h 44m
Spirit Airlines
Deal found 1/31$228
This CheapOair deal was found by Cheapflights users on 2/2. 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 3/103:36 pm
SJU
-
BNA
1 stop16h 49m
Spirit Airlines
Wed 3/187:44 am
BNA
-
SJU
1 stop10h 11m
Spirit Airlines
Deal found 2/2$232
This Priceline deal was found by Cheapflights users on 2/2. 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 2/126:00 am
SJU
-
CVG
1 stop19h 59m
Frontier
Sat 2/2111:15 am
CVG
-
SJU
1 stop6h 44m
Frontier
Deal found 2/2$234
This CheapOair deal was found by Cheapflights users on 2/2. 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.
Wed 4/112:55 pm
SJU
-
BNA
1 stop11h 43m
Spirit Airlines
Mon 4/62:27 pm
BNA
-
SJU
1 stop20h 22m
Spirit Airlines
Deal found 2/2$235
This Southwest deal was found by Cheapflights users on 2/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:00 am
SJU
-
BNA
2 stops8h 55m
Southwest
Sun 3/112:25 pm
BNA
-
SJU
1 stop10h 40m
Southwest
Deal found 2/1$236
This Delta deal was found by Cheapflights users on 2/1. 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.
Wed 3/46:37 pm
SJU
-
SDF
1 stop6h 21m
Delta
Mon 3/95:35 pm
SDF
-
SJU
1 stop5h 40m
Delta
Deal found 2/1$246

Find flight deals from Caribbean Islands to Kentucky

Keep the following information in mind while searching for Caribbean Islands to Kentucky flight deals. Data was last updated February 2, 2026.

Round-trip from

$192
(Frontier)

One-way from

$87
(Priceline)
From Caribbean Islands to Kentucky
Search Deals
One-way flight from Caribbean Islands to Kentucky
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands 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 February 2, 2026.
Use the filters below to find and compare flights from Caribbean Islands to Kentucky that are best for you.

Fly from

Caribbean Islands

Fly to

Kentucky

Route

Depart

Return

Price

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Thu 2/26

5:25 pm-12:59 am

1 stop8h 34m

Cincinnati Cinci./N. Kentucky

Mon 3/2

7:14 pm-2:53 am

1 stop6h 39m

$192

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Mon 3/9

3:08 am-10:41 am

1 stop8h 33m

Nashville Intl

Tue 3/17

11:36 am-10:45 pm

1 stop10h 09m

$192

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Mon 3/9

3:08 am-10:41 am

1 stop8h 33m

Nashville Intl

Mon 3/16

9:33 pm-9:45 am

1 stop11h 12m

$216

San JuanCincinnati

SJU - CVG

SJUCVG

San Juan Luis Munoz Marin Intl

Fri 4/17

3:42 pm-10:37 am

1 stop18h 55m

Cincinnati Cinci./N. Kentucky

Mon 4/20

7:15 am-2:42 pm

1 stop7h 27m

$227

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Thu 2/26

7:00 am-1:55 pm

2 stops8h 55m

Nashville Intl

Sun 3/1

12:25 pm-1:05 am

1 stop10h 40m

$236

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Fri 2/27

8:05 am-1:47 pm

1 stop7h 42m

Nashville Intl

Mon 3/2

1:30 pm-10:22 pm

1 stop6h 52m

$236

San JuanNashville

SJU - BNA

SJUBNA

San Juan Luis Munoz Marin Intl

Sat 4/4

6:15 am-3:53 pm

1 stop10h 38m

Nashville Intl

Sat 4/11

3:45 pm-11:15 pm

1 stop6h 30m

$236

San JuanLouisville

SJU - SDF

SJUSDF

San Juan Luis Munoz Marin Intl

Wed 3/4

8:00 am-6:09 pm

2 stops11h 09m

Louisville Intl

Mon 3/9

12:07 pm-4:24 am

1 stop16h 17m

$246

San JuanLouisville

SJU - SDF

SJUSDF

San Juan Luis Munoz Marin Intl

Thu 2/26

6:00 am-6:05 pm

1 stop13h 05m

Louisville Intl

Wed 3/4

2:30 pm-11:10 pm

1 stop7h 40m

$246

San JuanLouisville

SJU - SDF

SJUSDF

San Juan Luis Munoz Marin Intl

Thu 5/14

4:30 pm-8:38 am

1 stop16h 08m

Louisville Intl

Mon 5/18

7:52 pm-12:03 pm

1 stop16h 11m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/31

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

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

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

Currently, January is the cheapest month in which you can book a flight from Caribbean Islands to Kentucky (average of $113). Flying from Caribbean Islands to Kentucky in June is currently the most expensive (average of $251). 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.

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 February 2, 2026.
Peruse reviews from past customers who have flown with American Airlines from Caribbean Islands to Kentucky to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,212 reviews

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Crew

8.0

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,212 reviews
American Airlines
7.2
Good
11,212 reviews

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Crew

8.0

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

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

    Frontier, Southwest, and United Airlines can get you from Caribbean Islands to Kentucky in just under 7h 42m. Your travel time can differ by up to 1h 13m. Caribbean Islands and Kentucky are separated by a distance of 1753 mi. This flight may include one or multiple stops.

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

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $110. Users have also found prices from $112 and $138 on American Airlines and Southwest, respectively.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Caribbean Islands to Kentucky (average of $113). Flying from Caribbean Islands to Kentucky in June is currently the most expensive (average of $251). 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 Caribbean Islands to Kentucky

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Top 4 airlines flying from Caribbean Islands to Kentucky

Discover the top 4 airlines that operate flights from Caribbean Islands 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 February 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$138Average$375FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$175Average$335FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$226Average$499FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$232Average$494FlexibilityNo cancel feeOn-time69%

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