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$108+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SDF
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$159
(American Airlines)

One-way from

$108
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$313
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 ($27 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 July 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 julio 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/45:29 pmHPN - BNA
1 stop4h 40mAmerican Airlines
lun. 9/83:47 pmBNA - HPN
1 stop6h 39mAmerican Airlines
Deal found 7/30$159
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/46:50 pmHPN - CVG
1 stop4h 14mAmerican Airlines
lun. 10/65:25 pmCVG - HPN
1 stop4h 34mAmerican Airlines
Deal found 7/30$215
This Delta deal was found by Cheapflights users on 7/31. 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.
sáb. 10/185:20 pmHPN - BNA
1 stop4h 30mDelta
mié. 10/226:00 amBNA - HPN
1 stop5h 04mDelta
Deal found 7/31$217
This Delta deal was found by Cheapflights users on 7/29. 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.
sáb. 11/86:40 pmHPN - CVG
1 stop5h 19mDelta
mar. 11/116:15 amCVG - HPN
1 stop5h 31mDelta
Deal found 7/29$228
This Delta deal was found by Cheapflights users on 7/31. 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.
sáb. 9/66:00 amHPN - TYS
1 stop7h 12mDelta
mié. 9/105:45 amTYS - HPN
1 stop4h 01mDelta
Deal found 7/31$267
This American Airlines deal was found by Cheapflights users on 7/31. 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.
sáb. 9/611:15 amHPN - TYS
2 stops7h 50mAmerican Airlines
mié. 9/1011:18 amTYS - HPN
1 stop5h 41mAmerican Airlines
Deal found 7/31$272
This Delta deal was found by Cheapflights users on 7/30. 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.
dom. 8/315:15 pmHPN - SDF
1 stop5h 27mDelta
mié. 9/37:10 amSDF - HPN
1 stop4h 50mDelta
Deal found 7/30$295
This American Airlines deal was found by Cheapflights users on 7/31. 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.
jue. 8/213:09 pmHPN - SDF
1 stop6h 51mAmerican Airlines
jue. 8/286:08 amSDF - HPN
1 stop4h 22mAmerican Airlines
Deal found 7/31$309
This American Airlines deal was found by Cheapflights users on 7/31. 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.
jue. 11/612:00 pmHPN - LEX
1 stop6h 21mAmerican Airlines
dom. 11/96:00 amLEX - HPN
1 stop5h 28mAmerican Airlines
Deal found 7/31$309
This Delta deal was found by Cheapflights users on 7/31. 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.
sáb. 8/305:15 pmHPN - LEX
1 stop5h 21mDelta
dom. 8/317:45 amLEX - HPN
1 stop4h 12mDelta
Deal found 7/31$334
This Delta deal was found by Cheapflights users on 7/30. 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.
sáb. 9/66:00 amHPN - TRI
1 stop6h 41mDelta
lun. 9/156:11 amTRI - HPN
1 stop5h 48mDelta
Deal found 7/30$347
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/2711:15 amHPN - TRI
2 stops9h 40mAmerican Airlines
lun. 9/296:22 amTRI - HPN
1 stop4h 23mAmerican Airlines
Deal found 7/30$352

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 julio 31, 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

jue. 9/4

5:29 pm-9:09 pm

1 stop4h 40m

Nashville Intl

lun. 9/8

3:47 pm-11:26 pm

1 stop6h 39m

$159

White PlainsCincinnati

HPN - CVG

HPNCVG

White Plains Westchester County

sáb. 10/4

6:50 pm-11:04 pm

1 stop4h 14m

Cincinnati Cinci./N. Kentucky

lun. 10/6

5:25 pm-9:59 pm

1 stop4h 34m

$215

White PlainsNashville

HPN - BNA

HPNBNA

White Plains Westchester County

sáb. 10/18

5:20 pm-8:50 pm

1 stop4h 30m

Nashville Intl

mié. 10/22

6:00 am-12:04 pm

1 stop5h 04m

$217

White PlainsCincinnati

HPN - CVG

HPNCVG

White Plains Westchester County

jue. 8/7

6:00 am-11:09 am

1 stop5h 09m

Cincinnati Cinci./N. Kentucky

sáb. 9/6

12:20 pm-3:49 pm

1 stop3h 29m

$258

White PlainsLouisville

HPN - SDF

HPNSDF

White Plains Westchester County

dom. 8/31

5:15 pm-10:42 pm

1 stop5h 27m

Louisville Intl

mié. 9/3

7:10 am-12:00 pm

1 stop4h 50m

$295

White PlainsLouisville

HPN - SDF

HPNSDF

White Plains Westchester County

jue. 8/21

3:09 pm-10:00 pm

1 stop6h 51m

Louisville Intl

jue. 8/28

6:08 am-10:30 am

1 stop4h 22m

$309

White PlainsLexington

HPN - LEX

HPNLEX

White Plains Westchester County

jue. 11/6

12:00 pm-6:21 pm

1 stop6h 21m

Lexington Blue Grass

dom. 11/9

6:00 am-11:28 am

1 stop5h 28m

$309

White PlainsKnoxville

HPN - TYS

HPNTYS

White Plains Westchester County

mié. 9/3

6:50 pm-11:48 pm

1 stop4h 58m

Knoxville McGhee Tyson

dom. 9/7

6:14 pm-10:23 pm

1 stop4h 09m

$313

White PlainsKnoxville

HPN - TYS

HPNTYS

White Plains Westchester County

lun. 8/25

5:29 pm-10:01 pm

1 stop4h 32m

Knoxville McGhee Tyson

sáb. 8/30

6:13 am-10:30 am

1 stop4h 17m

$317

White PlainsLexington

HPN - LEX

HPNLEX

White Plains Westchester County

sáb. 8/30

5:15 pm-10:36 pm

1 stop5h 21m

Lexington Blue Grass

dom. 8/31

7:45 am-11:57 am

1 stop4h 12m

$334

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 39 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 julio 31, 2025.
Read through reviews of airlines operating flights from Westchester County to Kentucky, such as Alaska Airlines, Delta, and Breeze Airways. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Breeze Airways
8.0
Very good
191 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
JetBlue
7.3
Good
2,914 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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.

  • 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 ($108), Delta ($115), and Breeze Airways ($395).

  • 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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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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$228Average$411FlexibilityNo cancel feeOn-time71%
DeltaCheapest$238Average$320FlexibilityNo cancel feeOn-timeN/A

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