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Stewart

$90+ Cheap flights from Kentucky to New Windsor (SWF)

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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SWF
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Kentucky to Stewart

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

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.
Sun 12/285:05 amSDF - SWF
1 stop29h 42mMultiple Airlines
Thu 1/2910:48 amSWF - SDF
1 stop23h 19mMultiple Airlines
Deal found 12/16$400
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.
Mon 12/296:00 amTYS - SWF
1 stop29h 03mMultiple Airlines
Sat 1/38:45 pmSWF - TYS
1 stop26h 24mMultiple Airlines
Deal found 12/17$405
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.
Thu 12/189:21 pmSDF - SWF
1 stop19h 17mAllegiant Air
Thu 1/2910:48 amSWF - SDF
1 stop23h 19mAllegiant Air
Deal found 12/16$432
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.
Fri 12/196:01 pmCVG - SWF
1 stop14h 54mMultiple Airlines
Sun 1/1110:48 amSWF - CVG
1 stop13h 54mMultiple Airlines
Deal found 12/16$439
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 12/196:30 amTYS - SWF
1 stop26h 25mAllegiant Air
Sat 12/207:50 pmSWF - TYS
1 stop21h 02mAllegiant Air
Deal found 12/15$449
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.
Thu 12/189:03 pmCVG - SWF
1 stop14h 41mMultiple Airlines
Sat 12/207:50 pmSWF - CVG
1 stop15h 41mMultiple Airlines
Deal found 12/15$469
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.
Mon 12/226:00 amTYS - SWF
1 stop10h 38mAllegiant Air
Mon 12/2912:52 pmSWF - TYS
1 stop7h 01mAllegiant Air
Deal found 12/17$494
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/198:36 pmBNA - SWF
1 stop21h 24mAllegiant Air
Mon 12/228:25 pmSWF - BNA
1 stop27h 42mAllegiant Air
Deal found 12/14$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.
Sun 12/219:29 pmLEX - SWF
1 stop20h 51mAllegiant Air
Sun 1/1810:48 amSWF - LEX
1 stop6h 31mAllegiant Air
Deal found 12/16$502
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.
Sun 12/219:29 pmLEX - SWF
2 stops14h 15mMultiple Airlines
Sun 1/1810:48 amSWF - LEX
1 stop6h 31mMultiple Airlines
Deal found 12/16$505
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.
Thu 12/189:03 pmCVG - SWF
1 stop14h 41mMultiple Airlines
Fri 12/198:11 pmSWF - CVG
1 stop14h 41mMultiple Airlines
Deal found 12/16$517
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.
Wed 12/249:22 pmLEX - SWF
1 stop13h 41mMultiple Airlines
Mon 12/2912:52 pmSWF - LEX
1 stop7h 25mMultiple Airlines
Deal found 12/15$519

Find flight deals from Kentucky to Stewart

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

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$208
(Mytrip)

One-way from

$90
(Mytrip)

Popular in

December

Cheapest in

July

Average price

$383
Provider with most accurate pricing for Louisville Intl-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Louisville Intl-New York (NYC) flights.
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From Kentucky to New Windsor Stewart
Search Deals
One-way flight from Kentucky to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 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 Kentucky to Stewart 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 Kentucky to New Windsor that are best for you.

Fly from

Kentucky

Fly to

Stewart

Route

Depart

Return

Price

KnoxvilleNew Windsor

TYS - SWF

TYSSWF

Knoxville McGhee Tyson

Fri 1/9

6:00 am-6:43 pm

1 stop12h 43m

New Windsor Stewart

Mon 1/12

7:33 pm-12:10 pm

1 stop16h 37m

$208

KnoxvilleNew Windsor

TYS - SWF

TYSSWF

Knoxville McGhee Tyson

Fri 1/23

6:00 am-6:43 pm

1 stop12h 43m

New Windsor Stewart

Mon 1/26

7:33 pm-12:10 pm

1 stop16h 37m

$230

NashvilleNew Windsor

BNA - SWF

BNASWF

Nashville Intl

Thu 1/15

8:12 pm-10:19 am

1 stop13h 07m

New Windsor Stewart

Sun 1/18

12:13 pm-7:17 pm

1 stop8h 04m

$232

KnoxvilleNew Windsor

TYS - SWF

TYSSWF

Knoxville McGhee Tyson

Fri 1/9

6:00 am-6:43 pm

1 stop12h 43m

New Windsor Stewart

Sun 1/11

10:48 am-3:19 pm

1 stop28h 31m

$263

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Mon 2/2

9:00 am-6:43 pm

1 stop9h 43m

New Windsor Stewart

Thu 2/5

10:48 am-6:50 pm

1 stop8h 02m

$270

KnoxvilleNew Windsor

TYS - SWF

TYSSWF

Knoxville McGhee Tyson

Fri 2/13

5:49 pm-6:39 pm

1 stop24h 50m

New Windsor Stewart

Wed 2/18

5:46 pm-5:06 pm

1 stop23h 20m

$271

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Thu 1/8

8:27 pm-5:12 pm

1 stop20h 45m

New Windsor Stewart

Sun 1/11

10:48 am-10:07 am

1 stop23h 19m

$281

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Sun 2/1

9:00 am-10:19 am

2 stops25h 19m

New Windsor Stewart

Thu 2/5

10:48 am-6:50 pm

1 stop8h 02m

$293

KnoxvilleNew Windsor

TYS - SWF

TYSSWF

Knoxville McGhee Tyson

Thu 2/12

12:54 pm-6:38 pm

1 stop5h 44m

New Windsor Stewart

Wed 2/18

5:46 pm-5:06 pm

1 stop23h 20m

$296

NashvilleNew Windsor

BNA - SWF

BNASWF

Nashville Intl

Thu 1/29

8:12 pm-10:19 am

1 stop13h 07m

New Windsor Stewart

Sun 2/1

12:13 pm-7:17 pm

1 stop8h 04m

$299

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 Kentucky to Stewart

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

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

Currently, May is the cheapest month in which you can book a flight from Kentucky to New Windsor (average of $71). Flying from Kentucky to New Windsor in March is currently the most expensive (average of $197). 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 Kentucky to Stewart. 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 into for flights to New Windsor from Kentucky?

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

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

    For as low as $208, Allegiant Air can have you in New Windsor from Kentucky in 12h 43m. The distance from Kentucky to New Windsor is about 662 mi.

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

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

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from Kentucky to New Windsor (average of $71). Flying from Kentucky to New Windsor in March is currently the most expensive (average of $197). 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

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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