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Stewart

$95+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SWF
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
1 adult, Economy
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Cheap flight deals from Kentucky to Stewart

Keep the following information in mind while searching for Kentucky to Stewart flight deals. Data was last updated septiembre 17, 2025.

Round-trip from

$185
(Kiwi.com)

One-way from

$95
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$329
From Kentucky to New Windsor Stewart
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One-way flight from Kentucky to New Windsor Stewart
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Highest demand for flights based on searches. 7% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 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 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 septiembre 17, 2025.

This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/49:47 pmBNA - SWF
1 stop19h 53mMultiple Airlines
lun. 12/87:30 pmSWF - BNA
1 stop13h 53mMultiple Airlines
Deal found 9/15$185
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/125:30 amCVG - SWF
1 stop13h 10mMultiple Airlines
lun. 12/1512:27 pmSWF - CVG
1 stop8h 59mMultiple Airlines
Deal found 9/15$230
This Mytrip deal was found by Cheapflights users on 9/16. 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.
vie. 10/36:30 amCVG - SWF
1 stop13h 01mAllegiant Air
lun. 10/611:01 amSWF - CVG
1 stop10h 36mAllegiant Air
Deal found 9/16$236
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
jue. 12/119:26 pmSDF - SWF
1 stop21h 14mAllegiant Air
lun. 12/155:20 pmSWF - SDF
1 stop23h 35mAllegiant Air
Deal found 9/17$242
This Mytrip deal was found by Cheapflights users on 9/16. 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.
vie. 10/316:45 amTYS - SWF
1 stop12h 31mAllegiant Air
vie. 11/77:05 pmSWF - TYS
1 stop14h 12mAllegiant Air
Deal found 9/16$251
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/126:00 amSDF - SWF
1 stop12h 40mMultiple Airlines
dom. 12/1411:43 amSWF - SDF
1 stop12h 02mMultiple Airlines
Deal found 9/15$253
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/306:58 pmSDF - SWF
1 stop15h 43mMultiple Airlines
dom. 11/26:16 pmSWF - SDF
2 stops16h 36mMultiple Airlines
Deal found 9/17$259
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
jue. 9/2511:00 amTYS - SWF
1 stop24h 03mMultiple Airlines
dom. 9/2811:43 amSWF - TYS
1 stop29h 51mMultiple Airlines
Deal found 9/16$259
This Mytrip deal was found by Cheapflights users on 9/16. 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.
vie. 10/318:53 amBNA - SWF
1 stop9h 23mMultiple Airlines
vie. 11/711:31 amSWF - BNA
1 stop12h 23mMultiple Airlines
Deal found 9/16$270
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
vie. 10/36:30 amCVG - SWF
1 stop13h 01mMultiple Airlines
lun. 10/611:01 amSWF - CVG
2 stops31h 04mMultiple Airlines
Deal found 9/17$275
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
jue. 10/21:21 pmCVG - SWF
2 stops22h 00mMultiple Airlines
lun. 10/611:01 amSWF - CVG
1 stop10h 36mMultiple Airlines
Deal found 9/17$277
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/176:30 amCVG - SWF
1 stop13h 01mAllegiant Air
lun. 10/2011:01 amSWF - CVG
1 stop10h 36mAllegiant Air
Deal found 9/15$279

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 septiembre 17, 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

NashvilleNew Windsor

BNA - SWF

BNASWF

Nashville Intl

jue. 12/4

9:47 pm-6:40 pm

1 stop19h 53m

New Windsor Stewart

lun. 12/8

7:30 pm-8:23 am

1 stop13h 53m

$185

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

vie. 10/3

6:30 am-7:31 pm

1 stop13h 01m

New Windsor Stewart

lun. 10/6

11:01 am-9:37 pm

1 stop10h 36m

$236

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

jue. 12/11

9:26 pm-6:40 pm

1 stop21h 14m

New Windsor Stewart

lun. 12/15

5:20 pm-4:55 pm

1 stop23h 35m

$242

KnoxvilleNew Windsor

TYS - SWF

TYSSWF

Knoxville McGhee Tyson

vie. 10/31

6:45 am-7:16 pm

1 stop12h 31m

New Windsor Stewart

vie. 11/7

7:05 pm-9:17 am

1 stop14h 12m

$251

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

vie. 12/12

6:00 am-6:40 pm

1 stop12h 40m

New Windsor Stewart

dom. 12/14

11:43 am-11:45 pm

1 stop12h 02m

$253

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

jue. 10/30

6:58 pm-10:41 am

1 stop15h 43m

New Windsor Stewart

dom. 11/2

6:16 pm-10:52 am

2 stops16h 36m

$259

KnoxvilleNew Windsor

TYS - SWF

TYSSWF

Knoxville McGhee Tyson

jue. 9/25

11:00 am-11:03 am

1 stop24h 03m

New Windsor Stewart

dom. 9/28

11:43 am-5:34 pm

1 stop29h 51m

$259

NashvilleNew Windsor

BNA - SWF

BNASWF

Nashville Intl

vie. 10/31

8:53 am-7:16 pm

1 stop9h 23m

New Windsor Stewart

vie. 11/7

11:31 am-10:54 pm

1 stop12h 23m

$270

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

jue. 10/2

1:21 pm-11:21 am

2 stops22h 00m

New Windsor Stewart

lun. 10/6

11:01 am-9:37 pm

1 stop10h 36m

$277

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

vie. 10/17

6:30 am-7:31 pm

1 stop13h 01m

New Windsor Stewart

lun. 10/20

11:01 am-9:37 pm

1 stop10h 36m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

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, October is the cheapest month in which you can book a flight from Kentucky to New Windsor (average of $109). Flying from Kentucky to New Windsor in December is currently the most expensive (average of $202). 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 $236, Allegiant Air can have you in New Windsor from Kentucky in 13h 01m. The distance from Kentucky to New Windsor is about 581 mi.

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

    When deciding which route to take from Kentucky to New Windsor consider Cincinnati Cinci./N. Kentucky - New Windsor Stewart, Nashville Intl - New Windsor Stewart or Knoxville McGhee Tyson - 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, October is the cheapest month in which you can book a flight from Kentucky to New Windsor (average of $109). Flying from Kentucky to New Windsor in December is currently the most expensive (average of $202). 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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Alternative routes for Kentucky to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
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