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Cayman Islands

$142+ 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 3/28. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — GCM
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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 1/313:23 pm
CVG
-
GCM
1 stop22h 30m
Multiple Airlines
Thu 2/52:49 pm
GCM
-
CVG
1 stop23h 39m
Multiple Airlines
Deal found 1/28$353
This Booking.com deal was found by Cheapflights users on 1/27. 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.
Sun 5/318:15 am
BNA
-
GCM
2 stops27h 15m
Air Canada
Thu 6/412:25 pm
GCM
-
BNA
1 stop21h 14m
Air Canada
Deal found 1/27$379
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 1/313:23 pm
CVG
-
GCM
1 stop22h 30m
Multiple Airlines
Sun 2/82:49 pm
GCM
-
CVG
2 stops21h 06m
Multiple Airlines
Deal found 1/28$386
This Air Canada deal was found by Cheapflights users on 1/27. 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.
Sat 3/76:40 pm
CVG
-
GCM
1 stop16h 45m
Air Canada
Fri 3/1312:30 pm
GCM
-
CVG
1 stop28h 30m
Air Canada
Deal found 1/27$389
This Air Canada deal was found by Cheapflights users on 1/27. 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.
Sun 4/125:05 pm
CVG
-
GCM
1 stop19h 05m
Air Canada
Fri 4/1712:30 pm
GCM
-
CVG
1 stop26h 52m
Air Canada
Deal found 1/27$393
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 1/313:23 pm
CVG
-
GCM
1 stop22h 30m
Multiple Airlines
Wed 2/411:30 am
GCM
-
CVG
1 stop27h 42m
Multiple Airlines
Deal found 1/27$395
This Travelocity deal was found by Cheapflights users on 1/27. 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.
Sun 5/316:15 am
BNA
-
GCM
1 stop6h 28m
Multiple Airlines
Thu 6/412:25 pm
GCM
-
BNA
1 stop21h 14m
Multiple Airlines
Deal found 1/27$398
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Sun 2/18:00 am
CVG
-
GCM
1 stop27h 35m
Multiple Airlines
Thu 2/52:49 pm
GCM
-
CVG
1 stop23h 39m
Multiple Airlines
Deal found 1/28$399
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sun 3/81:06 pm
CVG
-
GCM
1 stop23h 29m
Multiple Airlines
Sat 3/141:15 pm
GCM
-
CVG
1 stop7h 17m
Multiple Airlines
Deal found 1/27$403
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:00 am
LEX
-
GCM
1 stop8h 25m
American Airlines
Thu 3/512:58 pm
GCM
-
LEX
1 stop10h 55m
American Airlines
Deal found 1/28$410
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sun 3/81:06 pm
CVG
-
GCM
1 stop23h 29m
Multiple Airlines
Sun 3/151:52 pm
GCM
-
CVG
2 stops16h 31m
Multiple Airlines
Deal found 1/27$411
This Air Canada deal was found by Cheapflights users on 1/27. 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 3/253:45 pm
BNA
-
GCM
1 stop19h 40m
Air Canada
Tue 3/3112:30 pm
GCM
-
BNA
1 stop24h 38m
Air Canada
Deal found 1/27$413

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$379
(Booking.com)

One-way from

$142
(Travelocity)

Popular in

October

Cheapest in

September

Average price

$476
Provider with most accurate pricing for Louisville Intl-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-George Town Owen Roberts Intl flights.
Search Deals
From Kentucky to Cayman Islands
Search Deals
One-way flight from Kentucky to Cayman Islands
Search Deals
High demand for flights, 3% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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

CincinnatiGeorge Town

CVG - GCM

CVGGCM

Cincinnati Cinci./N. Kentucky

Sun 3/8

6:40 pm-10:25 am

1 stop16h 45m

George Town Owen Roberts Intl

Fri 3/13

12:30 pm-6:00 pm

1 stop28h 30m

$389

CincinnatiGeorge Town

CVG - GCM

CVGGCM

Cincinnati Cinci./N. Kentucky

Sat 3/7

6:40 pm-11:25 am

1 stop16h 45m

George Town Owen Roberts Intl

Fri 3/13

12:30 pm-6:00 pm

1 stop28h 30m

$389

CincinnatiGeorge Town

CVG - GCM

CVGGCM

Cincinnati Cinci./N. Kentucky

Fri 5/22

4:30 pm-11:30 am

1 stop20h 00m

George Town Owen Roberts Intl

Mon 5/25

12:25 pm-9:23 pm

1 stop7h 58m

$389

CincinnatiGeorge Town

CVG - GCM

CVGGCM

Cincinnati Cinci./N. Kentucky

Sun 4/12

5:05 pm-11:10 am

1 stop19h 05m

George Town Owen Roberts Intl

Fri 4/17

12:30 pm-4:22 pm

1 stop26h 52m

$393

CincinnatiGeorge Town

CVG - GCM

CVGGCM

Cincinnati Cinci./N. Kentucky

Sun 3/8

1:06 pm-11:35 am

1 stop23h 29m

George Town Owen Roberts Intl

Sat 3/14

1:15 pm-9:32 pm

1 stop7h 17m

$403

LexingtonGeorge Town

LEX - GCM

LEXGCM

Lexington Blue Grass

Mon 3/2

7:00 am-3:25 pm

1 stop8h 25m

George Town Owen Roberts Intl

Thu 3/5

12:58 pm-11:53 pm

1 stop10h 55m

$410

CincinnatiGeorge Town

CVG - GCM

CVGGCM

Cincinnati Cinci./N. Kentucky

Sun 3/1

7:00 am-1:43 pm

1 stop6h 43m

George Town Owen Roberts Intl

Sat 3/14

1:15 pm-9:32 pm

1 stop7h 17m

$413

NashvilleGeorge Town

BNA - GCM

BNAGCM

Nashville Intl

Wed 3/25

3:45 pm-11:25 am

1 stop19h 40m

George Town Owen Roberts Intl

Tue 3/31

12:30 pm-1:08 pm

1 stop24h 38m

$413

CincinnatiGeorge Town

CVG - GCM

CVGGCM

Cincinnati Cinci./N. Kentucky

Sat 3/7

7:46 pm-12:43 pm

2 stops16h 57m

George Town Owen Roberts Intl

Sat 3/14

1:15 pm-9:32 pm

1 stop7h 17m

$419

LexingtonGeorge Town

LEX - GCM

LEXGCM

Lexington Blue Grass

Mon 2/23

6:00 am-12:29 pm

1 stop6h 29m

George Town Owen Roberts Intl

Sat 2/28

3:40 pm-11:48 pm

1 stop8h 08m

$424

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 36 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

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

Currently, April is the cheapest month in which you can book a flight from Kentucky to Cayman Islands (average of $289). Flying from Kentucky to Cayman Islands in December is currently the most expensive (average of $633). 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.

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.

  • How long is the flight from Kentucky to Cayman Islands?

    Departing from Kentucky to Cayman Islands will take you 6h 29m. The distance from Kentucky to Cayman Islands is about 1309 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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, April is the cheapest month in which you can book a flight from Kentucky to Cayman Islands (average of $289). Flying from Kentucky to Cayman Islands in December is currently the most expensive (average of $633). 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 Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$190Average$483FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$367Average$601FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$406Average$496FlexibilityNo cancel feeOn-time69%

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