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Kentucky

$99+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SDF
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$177
(American Airlines)

One-way from

$99
(Delta)

Popular in

December

Cheapest in

January

Average price

$379
Provider with most accurate pricing for New York (NYC)-Louisville Intl flight deals.
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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. 7% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 11/1212:00 pmHPN - BNA
1 stop5h 49mAmerican Airlines
Sat 11/1510:14 amBNA - HPN
1 stop6h 15mAmerican Airlines
Deal found 10/28$159
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 12/63:00 pmHPN - BNA
2 stops7h 34mAmerican Airlines
Wed 12/1011:59 amBNA - HPN
2 stops7h 07mAmerican Airlines
Deal found 10/28$169
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:50 pmHPN - BNA
1 stop5h 19mDelta
Mon 12/86:25 amBNA - HPN
1 stop4h 35mDelta
Deal found 10/28$197
This Delta deal was found by Cheapflights users on 10/30. 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 12/66:50 pmHPN - CVG
1 stop5h 14mDelta
Mon 12/812:05 pmCVG - HPN
1 stop3h 44mDelta
Deal found 10/30$215
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/85:20 pmHPN - BNA
1 stop5h 02mDelta
Tue 11/116:16 amBNA - HPN
1 stop4h 44mDelta
Deal found 10/28$217
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/45:17 pmHPN - BNA
1 stop4h 48mDelta
Sun 12/76:00 amBNA - HPN
1 stop4h 59mDelta
Deal found 10/28$228
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:16 pmHPN - BNA
1 stop6h 16mAmerican Airlines
Thu 1/15:30 amBNA - HPN
1 stop4h 59mAmerican Airlines
Deal found 10/27$229
This Delta deal was found by Cheapflights users on 10/29. 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.
Thu 12/46:10 amHPN - CVG
1 stop4h 57mDelta
Sun 12/78:05 amCVG - HPN
1 stop3h 54mDelta
Deal found 10/29$229
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 12/55:19 pmHPN - BNA
1 stop5h 20mAmerican Airlines
Sun 12/75:20 amBNA - HPN
2 stops8h 22mAmerican Airlines
Deal found 10/28$234
This Delta deal was found by Cheapflights users on 10/29. 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.
Mon 11/174:29 pmHPN - BNA
1 stop6h 16mDelta
Wed 11/195:15 amBNA - HPN
1 stop5h 45mDelta
Deal found 10/29$237
This Delta deal was found by Cheapflights users on 10/30. 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.
Thu 11/1312:45 pmHPN - CVG
1 stop5h 06mDelta
Tue 12/910:00 amCVG - HPN
1 stop4h 28mDelta
Deal found 10/30$265
This Delta deal was found by Cheapflights users on 10/29. 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.
Thu 12/116:10 amHPN - CVG
1 stop4h 57mDelta
Sun 12/148:05 amCVG - HPN
1 stop3h 54mDelta
Deal found 10/29$266

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 October 30, 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 12/5

5:59 pm-11:56 pm

1 stop6h 57m

Nashville Intl

Tue 12/9

3:29 pm-10:30 pm

1 stop6h 01m

$159

White PlainsNashville

HPN - BNA

HPNBNA

White Plains Westchester County

Thu 12/4

5:19 pm-9:39 pm

1 stop5h 20m

Nashville Intl

Wed 12/10

9:09 am-2:42 pm

1 stop4h 33m

$159

White PlainsNashville

HPN - BNA

HPNBNA

White Plains Westchester County

Wed 11/12

5:16 pm-10:41 pm

2 stops6h 25m

Nashville Intl

Sat 11/15

5:20 am-1:00 pm

1 stop6h 40m

$184

White PlainsNashville

HPN - BNA

HPNBNA

White Plains Westchester County

Fri 12/5

6:50 pm-11:09 pm

1 stop5h 19m

Nashville Intl

Mon 12/8

6:25 am-12:00 pm

1 stop4h 35m

$197

White PlainsNashville

HPN - BNA

HPNBNA

White Plains Westchester County

Fri 12/5

6:50 pm-11:09 pm

1 stop5h 19m

Nashville Intl

Sun 12/7

6:00 am-11:59 am

1 stop4h 59m

$197

White PlainsCincinnati

HPN - CVG

HPNCVG

White Plains Westchester County

Sat 12/6

6:50 pm-12:04 am

1 stop5h 14m

Cincinnati Cinci./N. Kentucky

Mon 12/8

12:05 pm-3:49 pm

1 stop3h 44m

$215

White PlainsCincinnati

HPN - CVG

HPNCVG

White Plains Westchester County

Thu 1/8

12:03 pm-1:01 am

2 stops12h 58m

Cincinnati Cinci./N. Kentucky

Sun 1/11

7:31 pm-12:30 pm

1 stop16h 59m

$216

White PlainsNashville

HPN - BNA

HPNBNA

White Plains Westchester County

Sat 11/8

5:20 pm-9:22 pm

1 stop5h 02m

Nashville Intl

Tue 11/11

6:16 am-12:00 pm

1 stop4h 44m

$217

White PlainsNashville

HPN - BNA

HPNBNA

White Plains Westchester County

Thu 12/4

5:17 pm-9:05 pm

1 stop4h 48m

Nashville Intl

Sun 12/7

6:00 am-11:59 am

1 stop4h 59m

$228

White PlainsNashville

HPN - BNA

HPNBNA

White Plains Westchester County

Tue 12/30

5:16 pm-10:32 pm

1 stop6h 16m

Nashville Intl

Fri 1/2

1:11 pm-8:27 pm

1 stop6h 16m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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, May is the cheapest month in which you can book a flight from Westchester County to Kentucky (average of $217). Flying from Westchester County to Kentucky in January is currently the most expensive (average of $536). 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 October 30, 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
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

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
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

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
11,035 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

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 19m. Airlines will cover a distance of 778 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 Delta ($99), Breeze Airways ($151), and American Airlines ($249).

  • 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, May is the cheapest month in which you can book a flight from Westchester County to Kentucky (average of $217). Flying from Westchester County to Kentucky in January is currently the most expensive (average of $536). 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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Alternative routes for Westchester County to Kentucky

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$207Average$391FlexibilityNo cancel feeOn-time71%
DeltaCheapest$238Average$323FlexibilityNo cancel feeOn-timeN/A

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