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Kentucky

$98+ Cheap flights from New Windsor (SWF) 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SDF
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Stewart to Kentucky

Cheapest flights from Stewart to Kentucky
Explore the most affordable flight options available from Stewart to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Mytrip deal was found by Cheapflights users on 12/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2912:52 pmSWF - CVG
1 stop8h 57mAllegiant Air
Fri 1/239:00 amCVG - SWF
1 stop9h 43mAllegiant Air
Deal found 12/16$426
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:50 pmSWF - CVG
1 stop15h 41mMultiple Airlines
Mon 12/229:26 pmCVG - SWF
1 stop13h 37mMultiple Airlines
Deal found 12/16$437
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/207:50 pmSWF - SDF
1 stop24h 46mAllegiant Air
Tue 12/239:22 pmSDF - SWF
1 stop12h 28mAllegiant Air
Deal found 12/17$447
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:50 pmSWF - CVG
1 stop15h 41mMultiple Airlines
Sun 12/219:03 pmCVG - SWF
1 stop14h 41mMultiple Airlines
Deal found 12/16$461
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:50 pmSWF - TYS
1 stop21h 02mAllegiant Air
Mon 12/296:30 amTYS - SWF
1 stop5h 32mAllegiant Air
Deal found 12/16$471
This Mytrip deal was found by Cheapflights users on 12/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2912:52 pmSWF - CVG
1 stop8h 57mAllegiant Air
Sat 2/148:00 amCVG - SWF
1 stop9h 09mAllegiant Air
Deal found 12/16$475
This Mytrip deal was found by Cheapflights users on 12/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2912:52 pmSWF - CVG
1 stop8h 57mMultiple Airlines
Sat 2/143:30 pmCVG - SWF
2 stops19h 22mMultiple Airlines
Deal found 12/16$481
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:50 pmSWF - TYS
1 stop21h 02mAllegiant Air
Thu 12/257:49 pmTYS - SWF
1 stop15h 18mAllegiant Air
Deal found 12/16$490
This Kiwi.com deal was found by Cheapflights users on 12/18. 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 12/207:50 pmSWF - CVG
1 stop15h 41mMultiple Airlines
Wed 12/317:16 pmCVG - SWF
1 stop15h 47mMultiple Airlines
Deal found 12/18$493
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/198:11 pmSWF - BNA
1 stop24h 35mMultiple Airlines
Sun 12/288:38 pmBNA - SWF
1 stop13h 09mMultiple Airlines
Deal found 12/15$494
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/209:45 amSWF - BNA
1 stop11h 01mMultiple Airlines
Sun 12/288:38 pmBNA - SWF
1 stop13h 09mMultiple Airlines
Deal found 12/16$499
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/228:25 pmSWF - BNA
1 stop27h 42mMultiple Airlines
Wed 12/245:45 amBNA - SWF
1 stop9h 59mMultiple Airlines
Deal found 12/15$504

Find flight deals from Stewart to Kentucky

Keep the following information in mind while searching for Stewart to Kentucky flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$226
(Mytrip)

One-way from

$98
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$507
Provider with most accurate pricing for New York (NYC)-Louisville Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Louisville Intl flights.
Search Deals
From New Windsor Stewart to Kentucky
Search Deals
One-way flight from New Windsor Stewart to Kentucky
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart 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 December 18, 2025.
Use the filters below to find and compare flights from New Windsor to Kentucky that are best for you.

Fly from

Stewart

Fly to

Kentucky

Route

Depart

Return

Price

New WindsorKnoxville

SWF - TYS

SWFTYS

New Windsor Stewart

Fri 1/23

7:33 pm-11:40 am

1 stop16h 07m

Knoxville McGhee Tyson

Mon 1/26

6:00 am-6:43 pm

1 stop12h 43m

$226

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Thu 1/22

10:48 am-6:50 pm

1 stop8h 02m

Cincinnati Cinci./N. Kentucky

Mon 1/26

9:00 am-6:43 pm

1 stop9h 43m

$262

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Thu 1/8

10:48 am-10:07 am

1 stop23h 19m

Louisville Intl

Sun 1/11

8:27 pm-5:12 pm

1 stop20h 45m

$285

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Sun 2/1

10:48 am-6:50 pm

1 stop8h 02m

Cincinnati Cinci./N. Kentucky

Sun 2/8

5:07 pm-10:19 am

1 stop17h 12m

$287

New WindsorKnoxville

SWF - TYS

SWFTYS

New Windsor Stewart

Mon 1/12

7:33 pm-12:10 pm

1 stop16h 37m

Knoxville McGhee Tyson

Sun 1/25

2:26 pm-6:43 pm

1 stop28h 17m

$301

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Fri 4/17

11:40 am-10:47 pm

1 stop12h 07m

Nashville Intl

Sun 4/19

5:58 pm-10:50 am

1 stop15h 52m

$311

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Thu 2/12

11:42 am-7:48 pm

1 stop9h 06m

Nashville Intl

Sat 2/14

8:47 pm-10:52 am

1 stop13h 05m

$325

New WindsorKnoxville

SWF - TYS

SWFTYS

New Windsor Stewart

Thu 1/29

10:48 am-3:19 pm

1 stop28h 31m

Knoxville McGhee Tyson

Thu 2/5

2:00 pm-5:12 pm

1 stop27h 12m

$325

New WindsorKnoxville

SWF - TYS

SWFTYS

New Windsor Stewart

Fri 1/16

7:33 pm-11:40 am

1 stop16h 07m

Knoxville McGhee Tyson

Fri 1/23

6:00 am-6:43 pm

1 stop12h 43m

$325

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Thu 5/28

10:28 am-5:59 pm

1 stop8h 31m

Nashville Intl

Sat 5/30

3:38 pm-8:58 am

1 stop16h 20m

$331

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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

Have a flexible travel schedule? Discover the best time to fly to Kentucky from Stewart 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 New Windsor to Kentucky

What is the cheapest month to book a flight from New Windsor to Kentucky?

Currently, June is the cheapest month in which you can book a flight from New Windsor to Kentucky (average of $60). Flying from New Windsor to Kentucky in December is currently the most expensive (average of $229). 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 Stewart to Kentucky. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from New Windsor to Kentucky?

    Most people fly from New Windsor Stewart (SWF) if they book a flight from New Windsor to Kentucky. New Windsor Stewart is conveniently located just 4.3 mi from New Windsor’s city center.

  • How long is the flight from New Windsor to Kentucky?

    Allegiant Air can get you from New Windsor to Kentucky in just under 16h 07m. Your travel time can differ by up to . There are 662 mi between New Windsor and Kentucky.

  • What are the most popular routes from New Windsor to Kentucky?

    When deciding which route to take from New Windsor to Kentucky consider New Windsor Stewart - Cincinnati Cinci./N. Kentucky, New Windsor Stewart - Nashville Intl or New Windsor Stewart - Knoxville McGhee Tyson as they are the most popular.

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

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

  • How can I find direct flights from Stewart to Kentucky?

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

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

    Yes. Cheapflights offers flight deals from Stewart 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 New Windsor to Kentucky?

    Currently, June is the cheapest month in which you can book a flight from New Windsor to Kentucky (average of $60). Flying from New Windsor to Kentucky in December is currently the most expensive (average of $229). 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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