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Stewart

$94+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SWF
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$189
(Mytrip)

One-way from

$94
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$311
Provider with most accurate pricing for Louisville Intl-New York (NYC) flight deals.
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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. 8% potential increase in price ($27 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 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 October 30, 2025.

This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/138:16 pmBNA - SWF
1 stop12h 55mMultiple Airlines
Mon 11/1712:01 pmSWF - BNA
1 stop8h 10mMultiple Airlines
Deal found 10/29$189
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:45 amBNA - SWF
1 stop11h 55mMultiple Airlines
Mon 12/812:27 pmSWF - BNA
1 stop11h 00mMultiple Airlines
Deal found 10/28$210
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/68:16 pmBNA - SWF
1 stop13h 25mMultiple Airlines
Mon 11/1012:01 pmSWF - BNA
1 stop8h 10mMultiple Airlines
Deal found 10/28$211
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/118:59 pmBNA - SWF
1 stop13h 38mMultiple Airlines
Sun 12/1411:09 amSWF - BNA
1 stop12h 05mMultiple Airlines
Deal found 10/29$220
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/49:03 pmCVG - SWF
1 stop14h 41mMultiple Airlines
Mon 12/87:30 pmSWF - CVG
1 stop15h 09mMultiple Airlines
Deal found 10/29$227
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/49:03 pmCVG - SWF
1 stop14h 41mMultiple Airlines
Sun 12/711:09 amSWF - CVG
1 stop13h 48mMultiple Airlines
Deal found 10/28$234
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/49:03 pmCVG - SWF
1 stop14h 41mBreeze Airways
Mon 12/812:24 pmSWF - CVG
1 stop20h 35mBreeze Airways
Deal found 10/30$236
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/49:26 pmSDF - SWF
2 stops14h 18mMultiple Airlines
Mon 12/85:44 pmSWF - SDF
1 stop23h 11mMultiple Airlines
Deal found 10/29$241
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1112:50 pmCVG - SWF
2 stops22h 47mMultiple Airlines
Mon 12/157:30 pmSWF - CVG
1 stop15h 09mMultiple Airlines
Deal found 10/30$248
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/79:03 pmCVG - SWF
1 stop14h 41mMultiple Airlines
Mon 12/87:30 pmSWF - CVG
1 stop15h 09mMultiple Airlines
Deal found 10/29$254
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:38 pmTYS - SWF
1 stop16h 33mAllegiant Air
Sun 11/166:14 pmSWF - TYS
1 stop26h 15mAllegiant Air
Deal found 10/30$255
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:11 pmSDF - SWF
1 stop15h 00mMultiple Airlines
Fri 11/147:05 pmSWF - SDF
1 stop14h 49mMultiple Airlines
Deal found 10/29$268

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 October 30, 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

Thu 11/13

8:16 pm-10:11 am

1 stop12h 55m

New Windsor Stewart

Mon 11/17

12:01 pm-7:11 pm

1 stop8h 10m

$189

NashvilleNew Windsor

BNA - SWF

BNASWF

Nashville Intl

Thu 12/11

8:59 pm-11:37 am

1 stop13h 38m

New Windsor Stewart

Sun 12/14

11:09 am-10:14 pm

1 stop12h 05m

$220

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Thu 12/4

9:03 pm-11:44 am

1 stop14h 41m

New Windsor Stewart

Mon 12/8

7:30 pm-10:39 am

1 stop15h 09m

$227

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Thu 12/4

9:03 pm-11:44 am

1 stop14h 41m

New Windsor Stewart

Mon 12/8

12:24 pm-8:59 am

1 stop20h 35m

$236

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Thu 12/4

9:26 pm-11:44 am

2 stops14h 18m

New Windsor Stewart

Mon 12/8

5:44 pm-4:55 pm

1 stop23h 11m

$241

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Thu 12/4

9:03 pm-11:44 am

1 stop14h 41m

New Windsor Stewart

Sun 12/7

11:09 am-12:57 am

1 stop13h 48m

$241

KnoxvilleNew Windsor

TYS - SWF

TYSSWF

Knoxville McGhee Tyson

Thu 11/13

5:38 pm-10:11 am

1 stop16h 33m

New Windsor Stewart

Sun 11/16

6:14 pm-8:29 pm

1 stop26h 15m

$255

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Thu 12/11

9:03 pm-11:44 am

1 stop14h 41m

New Windsor Stewart

Mon 12/15

12:27 pm-8:34 pm

1 stop8h 07m

$255

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Thu 11/13

7:11 pm-10:11 am

1 stop15h 00m

New Windsor Stewart

Fri 11/14

7:05 pm-9:54 am

1 stop14h 49m

$261

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Mon 11/10

9:33 pm-10:26 am

1 stop12h 53m

New Windsor Stewart

Fri 11/14

11:01 am-6:16 pm

1 stop7h 15m

$266

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

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 $70). Flying from Kentucky to New Windsor in October is currently the most expensive (average of $201). 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, Breeze Airways can have you in New Windsor from Kentucky in 14h 41m. The distance from Kentucky to New Windsor is about 581 mi. This flight may include one or multiple stops.

  • 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, May is the cheapest month in which you can book a flight from Kentucky to New Windsor (average of $70). Flying from Kentucky to New Windsor in October is currently the most expensive (average of $201). 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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