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Westchester County

$94+ Cheap flights from Kentucky to Westchester County

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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — HPN
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Kentucky to Westchester County

Keep the following information in mind while searching for Kentucky to Westchester County flight deals. Data was last updated September 16, 2025.

Round-trip from

$159
(American Airlines)

One-way from

$94
(American Airlines)

Popular in

December

Cheapest in

February

Average price

$329
From Kentucky to Westchester County
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One-way flight from Kentucky to Westchester County
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Highest demand for flights based on searches. 7% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Kentucky to Westchester County

Cheapest flights from Kentucky to Westchester County
Explore the most affordable flight options available from Kentucky to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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 9/303:47 pmBNA - HPN
1 stop6h 39mAmerican Airlines
Sat 10/41:41 pmHPN - BNA
1 stop5h 01mAmerican Airlines
Deal found 9/15$159
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/76:00 amCVG - HPN
1 stop4h 34mAmerican Airlines
Tue 10/146:00 amHPN - CVG
1 stop5h 35mAmerican Airlines
Deal found 9/14$215
This Delta deal was found by Cheapflights users on 9/15. 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 10/257:10 amCVG - HPN
1 stop4h 50mDelta
Tue 10/286:00 amHPN - CVG
1 stop5h 18mDelta
Deal found 9/15$217
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/306:05 amCVG - HPN
1 stop4h 40mAmerican Airlines
Sat 10/1112:00 pmHPN - CVG
1 stop6h 21mAmerican Airlines
Deal found 9/15$234
This American Airlines deal was found by Cheapflights users on 9/14. 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 9/233:23 pmCVG - HPN
1 stop7h 36mAmerican Airlines
Sat 9/277:01 amHPN - CVG
1 stop6h 51mAmerican Airlines
Deal found 9/14$239
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/272:52 pmCVG - HPN
1 stop5h 08mAmerican Airlines
Thu 10/26:00 amHPN - CVG
1 stop7h 21mAmerican Airlines
Deal found 9/15$244
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/226:00 amCVG - HPN
1 stop5h 29mAmerican Airlines
Sun 10/265:57 pmHPN - CVG
1 stop5h 09mAmerican Airlines
Deal found 9/15$250
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 11/612:21 pmCVG - HPN
1 stop5h 08mAmerican Airlines
Sun 11/97:10 amHPN - CVG
1 stop5h 16mAmerican Airlines
Deal found 9/14$264
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/146:03 amTYS - HPN
1 stop4h 31mAmerican Airlines
Tue 10/215:29 pmHPN - TYS
1 stop4h 40mAmerican Airlines
Deal found 9/14$267
This Delta deal was found by Cheapflights users on 9/15. 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 9/2010:13 amBNA - HPN
1 stop4h 36mDelta
Mon 9/223:25 pmHPN - BNA
1 stop7h 50mDelta
Deal found 9/15$278
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/812:02 pmCVG - HPN
1 stop5h 25mAmerican Airlines
Sun 10/126:00 amHPN - CVG
1 stop5h 35mAmerican Airlines
Deal found 9/14$287
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:00 amSDF - HPN
1 stop5h 59mDelta
Mon 11/176:41 pmHPN - SDF
1 stop5h 25mDelta
Deal found 9/16$295

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kentucky to Westchester County 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 September 16, 2025.
Use the filters below to find and compare flights from Kentucky to Westchester County that are best for you.

Fly from

Kentucky

Fly to

Westchester County

Route

Depart

Return

Price

NashvilleWhite Plains

BNA - HPN

BNAHPN

Nashville Intl

Tue 9/30

3:47 pm-11:26 pm

1 stop6h 39m

White Plains Westchester County

Sat 10/4

1:41 pm-5:42 pm

1 stop5h 01m

$159

CincinnatiWhite Plains

CVG - HPN

CVGHPN

Cincinnati Cinci./N. Kentucky

Tue 10/7

6:00 am-10:34 am

1 stop4h 34m

White Plains Westchester County

Tue 10/14

6:00 am-11:35 am

1 stop5h 35m

$215

CincinnatiWhite Plains

CVG - HPN

CVGHPN

Cincinnati Cinci./N. Kentucky

Thu 10/16

12:05 pm-5:27 pm

1 stop5h 22m

White Plains Westchester County

Sat 10/18

1:35 pm-6:51 pm

1 stop5h 16m

$215

CincinnatiWhite Plains

CVG - HPN

CVGHPN

Cincinnati Cinci./N. Kentucky

Sat 10/25

7:10 am-12:00 pm

1 stop4h 50m

White Plains Westchester County

Tue 10/28

6:00 am-11:18 am

1 stop5h 18m

$217

CincinnatiWhite Plains

CVG - HPN

CVGHPN

Cincinnati Cinci./N. Kentucky

Tue 9/30

6:05 am-10:45 am

1 stop4h 40m

White Plains Westchester County

Sat 10/11

12:00 pm-6:21 pm

1 stop6h 21m

$234

CincinnatiWhite Plains

CVG - HPN

CVGHPN

Cincinnati Cinci./N. Kentucky

Sat 10/4

8:00 am-11:59 am

1 stop3h 59m

White Plains Westchester County

Wed 10/8

6:00 am-11:18 am

1 stop5h 18m

$239

CincinnatiWhite Plains

CVG - HPN

CVGHPN

Cincinnati Cinci./N. Kentucky

Tue 9/30

12:24 pm-6:20 pm

1 stop5h 56m

White Plains Westchester County

Sat 10/4

12:00 pm-5:45 pm

1 stop5h 45m

$239

CincinnatiWhite Plains

CVG - HPN

CVGHPN

Cincinnati Cinci./N. Kentucky

Sat 9/27

2:52 pm-8:00 pm

1 stop5h 08m

White Plains Westchester County

Thu 10/2

6:00 am-1:21 pm

1 stop7h 21m

$244

CincinnatiWhite Plains

CVG - HPN

CVGHPN

Cincinnati Cinci./N. Kentucky

Fri 11/7

7:15 am-10:57 am

1 stop3h 42m

White Plains Westchester County

Sun 11/9

7:10 am-12:26 pm

1 stop5h 16m

$264

CincinnatiWhite Plains

CVG - HPN

CVGHPN

Cincinnati Cinci./N. Kentucky

Thu 11/6

12:21 pm-5:29 pm

1 stop5h 08m

White Plains Westchester County

Sun 11/9

7:10 am-12:26 pm

1 stop5h 16m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 60 results
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Best time to book a flight from Kentucky to Westchester County

Have a flexible travel schedule? Discover the best time to fly to Westchester County 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 Westchester County

What is the cheapest time of day to fly from KY to REU?

Find hourly flight availability from Kentucky to Westchester County. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Kentucky to Westchester County as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Kentucky to Westchester County. 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 Westchester County?

    There are many flights that can get you from Kentucky to Westchester County in 4h 50m. Fly via American Airlines or Delta to get the fastest option. The distance between Kentucky and Westchester County is about 595 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Kentucky to Westchester County that include hotel bookings?

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

  • How can I find direct flights from Kentucky to Westchester County?

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

  • Can I find deals for business class flights from Kentucky to Westchester County?

    Yes. Cheapflights offers flight deals from Kentucky to Westchester County 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 Westchester County?

    Currently, January is the cheapest month in which you can book a flight from Kentucky to Westchester County (average of $276). Flying from Kentucky to Westchester County in March is currently the most expensive (average of $338). 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 2 airlines flying from Kentucky to Westchester County

Discover the top 2 airlines that operate flights from Kentucky to Westchester County. 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$222Average$375FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$228Average$359FlexibilityNo cancel feeOn-time71%

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