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Cayman Islands

$155+ Cheap flights from Kentucky to the Cayman Islands

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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — GCM
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap flight deals from Kentucky to Cayman Islands

Keep the following information in mind while searching for Kentucky to Cayman Islands flight deals. Data was last updated June 12, 2025.

Round-trip from

$392
(Delta)

One-way from

$172
(United Airlines)

Popular in

August

Cheapest in

September

Average price

$605
From Kentucky to Cayman Islands
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One-way flight from Kentucky to Cayman Islands
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Highest demand for flights based on searches. 10% potential increase in price ($70 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Kentucky to Cayman Islands

Cheapest flights from Kentucky to Cayman Islands
Explore the most affordable flight options available from Kentucky to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This Delta deal was found by Cheapflights users on 6/11. 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 11/127:00 amSDF - GCM
1 stop5h 37mDelta
Tue 11/182:02 pmGCM - SDF
1 stop7h 28mDelta
Deal found 6/11$392
This Delta deal was found by Cheapflights users on 6/11. 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 11/126:30 amBNA - GCM
1 stop5h 07mDelta
Thu 11/202:02 pmGCM - BNA
1 stop5h 32mDelta
Deal found 6/11$400
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Sat 11/17:26 pmBNA - GCM
1 stop16h 34mAmerican Airlines
Wed 11/52:20 pmGCM - BNA
1 stop7h 40mAmerican Airlines
Deal found 6/11$407
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Sun 9/146:00 amSDF - GCM
1 stop6h 22mAmerican Airlines
Sat 9/2012:10 pmGCM - SDF
2 stops21h 31mAmerican Airlines
Deal found 6/12$441
This United Airlines deal was found by Cheapflights users on 6/11. 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 7/76:15 amBNA - GCM
1 stop6h 15mUnited Airlines
Thu 7/101:35 pmGCM - BNA
1 stop6h 54mUnited Airlines
Deal found 6/11$448
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 11/14:50 pmBNA - GCM
2 stops19h 45mSouthwest
Wed 11/51:30 pmGCM - BNA
2 stops8h 35mSouthwest
Deal found 6/11$487
This Air Canada deal was found by Cheapflights users on 6/11. 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.
Wed 10/14:30 pmCVG - GCM
1 stop20h 25mAir Canada
Thu 10/912:50 pmGCM - CVG
1 stop25h 57mAir Canada
Deal found 6/11$500
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Mon 7/2811:49 amCVG - GCM
1 stop10h 31mMultiple Airlines
Fri 8/87:00 amGCM - CVG
1 stop10h 30mMultiple Airlines
Deal found 6/11$509
This American Airlines deal was found by Cheapflights users on 6/12. 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 7/146:44 amCVG - GCM
1 stop5h 26mAmerican Airlines
Tue 7/2212:10 pmGCM - CVG
1 stop9h 33mAmerican Airlines
Deal found 6/12$524
This United Airlines deal was found by Cheapflights users on 6/11. 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 10/289:32 amSDF - GCM
1 stop6h 53mUnited Airlines
Mon 11/35:35 pmGCM - SDF
2 stops16h 09mUnited Airlines
Deal found 6/11$526
This Delta deal was found by Cheapflights users on 6/11. 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 10/266:00 amCVG - GCM
1 stop6h 42mDelta
Sat 11/11:02 pmGCM - CVG
1 stop7h 01mDelta
Deal found 6/11$536
This American Airlines deal was found by Cheapflights users on 6/10. 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 7/256:40 amLEX - GCM
1 stop5h 42mAmerican Airlines
Fri 8/112:25 pmGCM - LEX
1 stop10h 34mAmerican Airlines
Deal found 6/10$548

Cheapflights Fare Finder

Customize your flight search to find flights from Kentucky to Cayman Islands 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 June 12, 2025.
Use the filters below to find and compare flights from Kentucky to the Cayman Islands that are best for you.

Fly from

Kentucky

Fly to

Cayman Islands

Route

Depart

Return

Price

LouisvilleGeorge Town

SDF - GCM

SDFGCM

Louisville Intl

Wed 11/12

7:00 am-12:37 pm

1 stop5h 37m

George Town Owen Roberts Intl

Tue 11/18

2:02 pm-9:30 pm

1 stop7h 28m

$392

NashvilleGeorge Town

BNA - GCM

BNAGCM

Nashville Intl

Wed 11/12

6:30 am-12:37 pm

1 stop5h 07m

George Town Owen Roberts Intl

Thu 11/20

2:02 pm-6:34 pm

1 stop5h 32m

$400

NashvilleGeorge Town

BNA - GCM

BNAGCM

Nashville Intl

Sat 11/1

7:26 pm-12:00 pm

1 stop16h 34m

George Town Owen Roberts Intl

Wed 11/5

2:20 pm-9:00 pm

1 stop7h 40m

$407

LouisvilleGeorge Town

SDF - GCM

SDFGCM

Louisville Intl

Sun 9/14

6:00 am-11:22 am

1 stop6h 22m

George Town Owen Roberts Intl

Sat 9/20

12:10 pm-10:41 am

2 stops21h 31m

$441

NashvilleGeorge Town

BNA - GCM

BNAGCM

Nashville Intl

Mon 7/7

6:15 am-12:30 pm

1 stop6h 15m

George Town Owen Roberts Intl

Thu 7/10

1:35 pm-8:29 pm

1 stop6h 54m

$448

NashvilleGeorge Town

BNA - GCM

BNAGCM

Nashville Intl

Sat 11/1

4:50 pm-12:35 pm

2 stops19h 45m

George Town Owen Roberts Intl

Wed 11/5

1:30 pm-9:05 pm

2 stops8h 35m

$487

CincinnatiGeorge Town

CVG - GCM

CVGGCM

Cincinnati Cinci./N. Kentucky

Mon 7/28

11:49 am-9:20 pm

1 stop10h 31m

George Town Owen Roberts Intl

Fri 8/8

7:00 am-6:30 pm

1 stop10h 30m

$509

CincinnatiGeorge Town

CVG - GCM

CVGGCM

Cincinnati Cinci./N. Kentucky

Mon 7/14

6:44 am-11:10 am

1 stop5h 26m

George Town Owen Roberts Intl

Tue 7/22

12:10 pm-10:43 pm

1 stop9h 33m

$524

LouisvilleGeorge Town

SDF - GCM

SDFGCM

Louisville Intl

Tue 10/28

9:32 am-3:25 pm

1 stop6h 53m

George Town Owen Roberts Intl

Mon 11/3

5:35 pm-9:44 am

2 stops16h 09m

$526

LexingtonGeorge Town

LEX - GCM

LEXGCM

Lexington Blue Grass

Fri 7/25

6:40 am-11:22 am

1 stop5h 42m

George Town Owen Roberts Intl

Fri 8/1

12:25 pm-11:59 pm

1 stop10h 34m

$548

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 21 results
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Best time to book a flight from Kentucky to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands 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 the Cayman Islands
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. 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 Cayman Islands. Reviews last updated June 12, 2025.
To help decide which airline to fly from Kentucky to Cayman Islands, see what other customers have to say about Southwest, Delta and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

Find useful and relevant information for your journey from Kentucky to Cayman Islands. 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 Cayman Islands one-way?

    $172 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $206 and $300, respectively.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Kentucky to Cayman Islands (average of $467). Flying from Kentucky to Cayman Islands in March is currently the most expensive (average of $594). 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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Top 3 airlines flying from Kentucky to Cayman Islands

Discover the top 3 airlines that operate flights from Kentucky to Cayman Islands. 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$418Average$493FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$439Average$568FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$472Average$612FlexibilityNo cancel feeOn-time71%

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