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Kentucky

$94+ Cheap flights from Westchester County to Kentucky

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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SDF
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Westchester County to Kentucky

Keep the following information in mind while searching for Westchester County to Kentucky 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

January

Average price

$352
From Westchester County to Kentucky
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One-way flight from Westchester County to Kentucky
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Highest demand for flights based on searches. 8% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 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 Westchester County to Kentucky

Cheapest flights from Westchester County to Kentucky
Explore the most affordable flight options available from Westchester County to Kentucky. 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 9/14. 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.
Fri 10/36:50 pmHPN - BNA
1 stop4h 49mAmerican Airlines
Mon 10/65:35 amBNA - HPN
1 stop4h 54mAmerican Airlines
Deal found 9/14$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.
Sat 11/85:59 pmHPN - BNA
1 stop5h 11mAmerican Airlines
Tue 11/1111:59 amBNA - HPN
2 stops7h 11mAmerican Airlines
Deal found 9/14$164
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.
Thu 10/26:00 amHPN - BNA
1 stop5h 11mAmerican Airlines
Fri 10/36:02 pmBNA - HPN
1 stop4h 24mAmerican Airlines
Deal found 9/15$187
This American Airlines deal was found by Cheapflights users on 9/13. 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 11/74:30 pmHPN - BNA
1 stop6h 38mAmerican Airlines
Tue 11/117:08 amBNA - HPN
1 stop7h 51mAmerican Airlines
Deal found 9/13$193
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 9/305:29 pmHPN - BNA
2 stops6h 10mAmerican Airlines
Tue 10/79:22 amBNA - HPN
1 stop7h 05mAmerican Airlines
Deal found 9/14$198
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 11/11:35 pmHPN - CVG
1 stop5h 15mAmerican Airlines
Tue 11/46:00 amCVG - HPN
1 stop7h 00mAmerican Airlines
Deal found 9/15$201
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 10/145:29 pmHPN - BNA
1 stop5h 28mAmerican Airlines
Thu 10/169:22 amBNA - HPN
1 stop5h 37mAmerican Airlines
Deal found 9/14$207
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.
Fri 10/316:50 pmHPN - BNA
1 stop4h 49mDelta
Tue 11/410:11 amBNA - HPN
1 stop4h 38mDelta
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 10/145:29 pmHPN - BNA
1 stop5h 28mAmerican Airlines
Fri 10/179:22 amBNA - HPN
1 stop7h 05mAmerican Airlines
Deal found 9/15$227
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 10/225:57 pmHPN - BNA
1 stop6h 55mAmerican Airlines
Sun 10/265:35 amBNA - HPN
1 stop4h 54mAmerican Airlines
Deal found 9/15$229
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.
Fri 11/74:30 pmHPN - CVG
1 stop5h 24mAmerican Airlines
Mon 11/103:20 pmCVG - HPN
1 stop6h 39mAmerican Airlines
Deal found 9/14$229
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 10/155:57 pmHPN - BNA
1 stop6h 55mAmerican Airlines
Sat 10/189:22 amBNA - HPN
2 stops7h 58mAmerican Airlines
Deal found 9/15$234

Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County to Kentucky 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 Westchester County to Kentucky that are best for you.

Fly from

Westchester County

Fly to

Kentucky

Route

Depart

Return

Price

White PlainsNashville

HPN - BNA

HPNBNA

White Plains Westchester County

Fri 10/24

5:57 pm-11:52 pm

1 stop6h 55m

Nashville Intl

Mon 10/27

5:35 am-11:29 am

1 stop4h 54m

$159

White PlainsNashville

HPN - BNA

HPNBNA

White Plains Westchester County

Fri 10/3

4:30 pm-10:05 pm

1 stop6h 35m

Nashville Intl

Mon 10/6

5:35 am-11:29 am

1 stop4h 54m

$159

White PlainsNashville

HPN - BNA

HPNBNA

White Plains Westchester County

Fri 10/24

5:57 pm-11:52 pm

1 stop6h 55m

Nashville Intl

Tue 10/28

7:20 am-3:59 pm

1 stop7h 39m

$159

White PlainsNashville

HPN - BNA

HPNBNA

White Plains Westchester County

Sat 11/8

6:49 pm-11:40 pm

1 stop5h 51m

Nashville Intl

Tue 11/11

2:14 pm-11:29 pm

1 stop8h 15m

$159

White PlainsNashville

HPN - BNA

HPNBNA

White Plains Westchester County

Sat 11/1

6:30 am-2:57 pm

2 stops9h 27m

Nashville Intl

Tue 11/4

9:05 am-2:39 pm

1 stop4h 34m

$164

White PlainsNashville

HPN - BNA

HPNBNA

White Plains Westchester County

Fri 11/7

4:30 pm-10:08 pm

1 stop6h 38m

Nashville Intl

Tue 11/11

7:08 am-3:59 pm

1 stop7h 51m

$193

White PlainsCincinnati

HPN - CVG

HPNCVG

White Plains Westchester County

Sat 11/1

1:35 pm-6:50 pm

1 stop5h 15m

Cincinnati Cinci./N. Kentucky

Tue 11/4

6:00 am-1:00 pm

1 stop7h 00m

$201

White PlainsNashville

HPN - BNA

HPNBNA

White Plains Westchester County

Fri 10/31

6:50 pm-10:39 pm

1 stop4h 49m

Nashville Intl

Tue 11/4

10:11 am-3:49 pm

1 stop4h 38m

$217

White PlainsCincinnati

HPN - CVG

HPNCVG

White Plains Westchester County

Sat 2/21

6:40 pm-11:55 pm

1 stop5h 15m

Cincinnati Cinci./N. Kentucky

Wed 2/25

11:45 am-4:35 pm

1 stop4h 50m

$217

White PlainsNashville

HPN - BNA

HPNBNA

White Plains Westchester County

Fri 10/24

5:57 pm-11:52 pm

1 stop6h 55m

Nashville Intl

Sun 10/26

5:35 am-11:29 am

1 stop4h 54m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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

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

What is the cheapest month to book a flight from Westchester County to Kentucky?

Currently, January is the cheapest month in which you can book a flight from Westchester County to Kentucky (average of $299). Flying from Westchester County to Kentucky in April is currently the most expensive (average of $369). 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.

Reviews of airlines servicing Kentucky

Get insights into the airlines that provide service to Kentucky. 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 Kentucky. Reviews last updated September 16, 2025.
Read through reviews of airlines operating flights from Westchester County to Kentucky, such as Delta and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

Related info for your journey

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

    Departing from Westchester County to Kentucky will take you 5h 15m. Airlines will cover a distance of 595 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Westchester County to Kentucky one-way?

    The cheapest airlines for a one-way flight from Westchester County to Kentucky are American Airlines ($94), Delta ($109), and Breeze Airways ($151).

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Westchester County to Kentucky (average of $299). Flying from Westchester County to Kentucky in April is currently the most expensive (average of $369). 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 Westchester County to Kentucky

Discover the top 2 airlines that operate flights from Westchester County to Kentucky. 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
American AirlinesCheapest$228Average$411FlexibilityNo cancel feeOn-time71%
DeltaCheapest$238Average$323FlexibilityNo cancel feeOn-timeN/A

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