Caribbean

$64+ 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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Dec 23 — Dec 301
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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 December 18, 2024.

Round-trip from

$150
(CheapOair)

One-way from

$64
(Frontier)
From Kentucky to Caribbean
One-way flight from Kentucky to Caribbean

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 December 18, 2024.

This Frontier deal was found by Cheapflights users on 12/16. 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 12/197:30 amCVG - SJU
1 stop7h 55mFrontier
Mon 12/233:54 amSJU - CVG
1 stop7h 47mFrontier
Deal found 12/16$318
This Booking.com deal was found by Cheapflights users on 12/17. 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 12/274:50 pmCVG - PUJ
1 stop18h 59mFrontier
Mon 12/301:59 pmPUJ - CVG
1 stop10h 51mFrontier
Deal found 12/17$348
This CheapOair deal was found by Cheapflights users on 12/17. 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 12/314:14 pmBNA - STT
2 stops40h 25mSpirit Airlines
Mon 2/1011:51 amSTT - BNA
1 stop13h 01mSpirit Airlines
Deal found 12/17$371
This Priceline deal was found by Cheapflights users on 12/17. 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 12/2710:00 amBNA - PUJ
1 stop23h 45mMultiple Airlines
Tue 12/316:45 pmPUJ - BNA
1 stop23h 37mMultiple Airlines
Deal found 12/17$396
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/245:00 amCVG - SJU
1 stop17h 10mAmerican Airlines
Mon 12/309:00 amSJU - CVG
1 stop15h 50mAmerican Airlines
Deal found 12/17$424
This Air Canada deal was found by Cheapflights users on 12/16. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/304:00 pmCVG - PUJ
2 stops20h 45mAir Canada
Thu 3/272:20 pmPUJ - CVG
2 stops25h 06mAir Canada
Deal found 12/16$454
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Mon 12/307:30 amSDF - SJU
1 stop15h 25mAmerican Airlines
Fri 1/106:00 amSJU - SDF
2 stops10h 00mAmerican Airlines
Deal found 12/17$457
This Delta deal was found by Cheapflights users on 12/17. 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 12/295:15 amBNA - PUJ
1 stop5h 25mDelta
Wed 1/12:40 pmPUJ - BNA
1 stop10h 47mDelta
Deal found 12/17$475
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/315:00 amBNA - SJU
1 stop8h 35mAmerican Airlines
Sun 3/21:05 pmSJU - BNA
1 stop13h 15mAmerican Airlines
Deal found 12/17$488
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/3110:45 amBNA - SJU
1 stop8h 41mUnited Airlines
Sat 3/12:05 amSJU - BNA
1 stop9h 00mUnited Airlines
Deal found 12/17$490
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/185:19 pmBNA - PUJ
1 stop16h 37mAmerican Airlines
Wed 12/255:45 pmPUJ - BNA
1 stop7h 48mAmerican Airlines
Deal found 12/17$493
This Air Canada deal was found by Cheapflights users on 12/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2710:00 amBNA - PUJ
1 stop23h 45mAir Canada
Tue 12/313:20 pmPUJ - BNA
2 stops19h 54mAir Canada
Deal found 12/17$504

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 2,558,603 searches. Data last updated December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Thu 2/27

9:29 pm-2:54 am

1 stop28h 25m

San Juan Luis Munoz Marin Intl

Mon 3/3

6:35 am-1:18 am

1 stop19h 43m

$150

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Thu 1/9

4:32 pm-10:46 am

1 stop16h 14m

Saint Thomas Island Cyril E King

Mon 1/13

11:51 am-10:52 pm

1 stop13h 01m

$191

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Wed 2/26

8:06 am-11:54 pm

1 stop14h 48m

San Juan Luis Munoz Marin Intl

Wed 3/5

6:29 pm-12:34 am

1 stop7h 05m

$194

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sun 1/5

6:00 am-3:50 pm

1 stop8h 50m

San Juan Luis Munoz Marin Intl

Fri 1/17

6:15 am-11:59 am

1 stop6h 44m

$224

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Thu 1/23

11:25 am-10:22 pm

2 stops9h 57m

San Juan Luis Munoz Marin Intl

Wed 2/5

2:05 am-4:53 pm

2 stops15h 48m

$240

NashvillePunta Cana

BNA - PUJ

BNAPUJ

Nashville Intl

Fri 1/24

7:29 pm-1:02 pm

1 stop15h 33m

Punta Cana

Sat 2/1

2:17 pm-6:04 pm

1 stop29h 47m

$240

CincinnatiPunta Cana

CVG - PUJ

CVGPUJ

Cincinnati Cinci./N. Kentucky

Fri 1/17

7:25 am-11:10 am

1 stop26h 45m

Punta Cana

Sat 1/25

12:20 pm-4:48 pm

1 stop29h 28m

$240

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Mon 1/13

8:15 am-9:50 pm

3 stops35h 35m

San Juan Luis Munoz Marin Intl

Sat 1/18

10:09 pm-7:13 pm

2 stops23h 04m

$264

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Wed 1/15

7:29 am-12:48 am

1 stop15h 19m

San Juan Luis Munoz Marin Intl

Wed 1/22

8:40 pm-1:07 pm

2 stops18h 27m

$265

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Fri 1/24

9:00 am-9:21 am

1 stop23h 21m

San Juan Luis Munoz Marin Intl

Mon 1/27

9:42 pm-1:51 pm

2 stops17h 09m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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.

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 $334). 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 December 18, 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 December 18, 2024.
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,848 reviews
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
9,552 reviews
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,604 reviews
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.7
Good
1,723 reviews
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
3,279 reviews
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $64. Spirit Airlines flights start at $88 while deals on Southwest start at $97 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 $334). 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 Kentucky to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.

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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$170Average$369FlexibilityNo cancel feeOn-time65%
DeltaCheapest$254Average$591FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$268Average$620FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$277Average$683FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$338Average$583FlexibilityNo cancel feeOn-time63%
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