HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$57+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Kentucky to Caribbean with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Kentucky to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Kentucky (USKY) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 20, 2024.

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 November 20, 2024.

This Trip.com deal was found by Cheapflights users on 11/19. 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.
Tue 12/1011:25 amCVG - SJU
1 stop7h 06mFrontier
Sat 12/147:14 pmSJU - CVG
1 stop19h 25mFrontier
Deal found 11/19$165
This eDestinos deal was found by Cheapflights users on 11/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/93:26 pmCVG - SJU
2 stops29h 08mMultiple Airlines
Wed 12/116:20 amSJU - CVG
2 stops28h 34mMultiple Airlines
Deal found 11/18$203
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Mon 12/93:47 pmCVG - SJU
1 stop7h 49mUnited Airlines
Wed 12/112:05 amSJU - CVG
1 stop10h 13mUnited Airlines
Deal found 11/19$204
This Booking.com deal was found by Cheapflights users on 11/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/67:13 pmBNA - PUJ
1 stop14h 18mFrontier
Thu 12/126:45 pmPUJ - BNA
1 stop24h 01mFrontier
Deal found 11/19$242
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Sat 12/71:35 pmBNA - SJU
1 stop6h 55mSpirit Airlines
Fri 12/133:05 amSJU - BNA
2 stops17h 30mSpirit Airlines
Deal found 11/19$283
This Delta deal was found by Cheapflights users on 11/19. 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.
Sat 12/1412:14 pmBNA - SJU
1 stop9h 09mDelta
Mon 12/167:30 amSJU - BNA
1 stop10h 06mDelta
Deal found 11/19$284
This FlightHub deal was found by Cheapflights users on 11/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/159:53 pmSDF - SJU
1 stop21h 29mSpirit Airlines
Sat 12/219:13 pmSJU - SDF
1 stop22h 46mSpirit Airlines
Deal found 11/19$297
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Thu 12/1210:00 amBNA - SJU
2 stops14h 52mMultiple Airlines
Thu 12/199:13 pmSJU - BNA
2 stops23h 11mMultiple Airlines
Deal found 11/19$298
This Delta deal was found by Cheapflights users on 11/19. 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.
Sat 12/73:32 pmSDF - SJU
1 stop6h 51mDelta
Wed 12/113:30 pmSJU - SDF
1 stop8h 06mDelta
Deal found 11/19$308
This Delta deal was found by Cheapflights users on 11/20. 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.
Sun 12/222:25 pmCVG - SJU
1 stop10h 53mDelta
Thu 12/2612:45 pmSJU - CVG
1 stop9h 38mDelta
Deal found 11/20$319
This CheapOair deal was found by Cheapflights users on 11/18. 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 12/106:16 amBNA - MBJ
1 stop6h 17mSpirit Airlines
Fri 12/132:38 pmMBJ - BNA
2 stops22h 21mSpirit Airlines
Deal found 11/18$335
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Sun 12/87:00 amCVG - STT
2 stops29h 23mMultiple Airlines
Thu 12/1211:56 amSTT - CVG
2 stops26h 04mMultiple Airlines
Deal found 11/19$345

Find flights from Kentucky to Caribbean within your budget

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Tue 12/10

11:25 am-7:31 pm

1 stop7h 06m

San Juan Luis Munoz Marin Intl

Sat 12/14

7:14 pm-1:39 pm

1 stop19h 25m

$165

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Mon 12/9

3:26 pm-9:34 pm

2 stops29h 08m

San Juan Luis Munoz Marin Intl

Wed 12/11

6:20 am-9:54 am

2 stops28h 34m

$203

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Mon 12/9

3:47 pm-12:36 am

1 stop7h 49m

San Juan Luis Munoz Marin Intl

Wed 12/11

2:05 am-11:18 am

1 stop10h 13m

$204

NashvillePunta Cana

BNA - PUJ

BNAPUJ

Nashville Intl

Fri 12/6

7:13 pm-11:31 am

1 stop14h 18m

Punta Cana

Thu 12/12

6:45 pm-4:46 pm

1 stop24h 01m

$242

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Wed 1/29

6:11 am-2:13 pm

1 stop7h 02m

San Juan Luis Munoz Marin Intl

Fri 1/31

7:00 am-4:31 pm

1 stop10h 31m

$244

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sun 1/19

7:35 pm-9:35 am

1 stop13h 00m

San Juan Luis Munoz Marin Intl

Thu 1/23

10:09 pm-6:40 pm

1 stop21h 31m

$247

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sun 1/19

6:12 am-5:30 pm

2 stops10h 18m

San Juan Luis Munoz Marin Intl

Thu 1/23

8:05 am-5:30 pm

1 stop10h 25m

$274

NashvillePunta Cana

BNA - PUJ

BNAPUJ

Nashville Intl

Sat 1/18

8:00 am-3:49 pm

1 stop5h 49m

Punta Cana

Sat 1/25

6:10 pm-4:48 pm

1 stop24h 38m

$276

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Sat 12/7

1:35 pm-10:30 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Fri 12/13

3:05 am-6:35 pm

2 stops17h 30m

$283

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Sat 12/14

11:01 am-11:23 pm

1 stop10h 22m

San Juan Luis Munoz Marin Intl

Wed 12/18

1:49 pm-10:09 pm

1 stop10h 20m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 60 results
1
2
3
...
6

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.

Travel insights for flights from Kentucky to Caribbean

Get recent, data-driven insights about flights from Kentucky to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $335). 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 November 20, 2024.

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 November 20, 2024.
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,461 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Copa Airlines
7.8
Good
1,785 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 Frontier, which is currently one of the cheapest options available, starting at $83. Spirit Airlines flights start at $106 while deals on United Airlines start at $118 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 March is currently the most expensive (average of $335). 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.
LaGuardia to Fort Lauderdale flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to Cancún flights
Newark to Cancún flights
LaGuardia to Miami flights
John F Kennedy Intl to Miami flights
Dallas/Fort Worth to LaGuardia flights
Newark to Miami flights
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Orlando flights
Los Angeles to John F Kennedy Intl flights
Newark to Los Angeles flights
O'Hare Intl to Cancún flights
LaGuardia to Dallas/Fort Worth flights
John F Kennedy Intl to Heathrow flights
Los Angeles to Newark flights
Dallas/Fort Worth to John F Kennedy Intl flights
Newark to Orlando flights
Newark to Heathrow flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to Dallas/Fort Worth flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
Dallas/Fort Worth to Newark flights
John F Kennedy Intl to Fort Lauderdale flights
San Francisco to John F Kennedy Intl flights
Fort Lauderdale to LaGuardia flights
John F Kennedy Intl to Gatwick flights
Newark to Dallas/Fort Worth flights
Fort Lauderdale to Newark flights
LaGuardia to Orlando flights
Atlanta to John F Kennedy Intl flights
Los Angeles to Dallas/Fort Worth flights
Boston to Orlando flights
John F Kennedy Intl to Charles de Gaulle flights
Dallas/Fort Worth to Cancún flights
John F Kennedy Intl to San Francisco flights
Newark to Luis Munoz Marin Intl flights
Dulles Intl to Cancún flights
Los Angeles to Haneda flights
Los Angeles to Honolulu flights
LaGuardia to Cancún flights
Miami to LaGuardia flights
Seattle to Los Angeles flights
Dallas/Fort Worth to Los Angeles flights
Miami to John F Kennedy Intl flights
John F Kennedy Intl to Atlanta flights
O'Hare Intl to Orlando flights
Los Angeles to Seattle flights
Dallas/Fort Worth to Las Vegas flights
Miami to Newark flights

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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$179Average$372FlexibilityNo cancel feeOn-time65%
DeltaCheapest$254Average$591FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$264Average$619FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$301Average$709FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$338Average$439FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines