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$92+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SDF
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
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Cheap flight deals from Stewart to Kentucky

Keep the following information in mind while searching for Stewart to Kentucky flight deals. Data was last updated September 14, 2025.

Round-trip from

$192
(Kiwi.com)

One-way from

$92
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$352
From New Windsor Stewart to Kentucky
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One-way flight from New Windsor Stewart to Kentucky
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Highest demand for flights based on searches. 8% potential increase in price ($31 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 September 2025
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Find 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 September 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/273:01 pmSWF - BNA
1 stop9h 58mMultiple Airlines
Thu 10/308:44 pmBNA - SWF
1 stop12h 57mMultiple Airlines
Deal found 9/13$192
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/1711:31 amSWF - BNA
1 stop13h 28mMultiple Airlines
Sun 10/196:30 amBNA - SWF
1 stop26h 41mMultiple Airlines
Deal found 9/12$208
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/318:06 pmSWF - SDF
1 stop13h 08mMultiple Airlines
Thu 11/610:55 amSDF - SWF
1 stop23h 46mMultiple Airlines
Deal found 9/12$209
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/2411:31 amSWF - CVG
1 stop12h 08mMultiple Airlines
Mon 10/276:00 amCVG - SWF
1 stop8h 11mMultiple Airlines
Deal found 9/12$215
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 11/1012:01 pmSWF - SDF
1 stop21h 58mMultiple Airlines
Sun 11/1610:55 amSDF - SWF
1 stop24h 16mMultiple Airlines
Deal found 9/12$217
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 11/1411:01 amSWF - SDF
1 stop22h 58mMultiple Airlines
Mon 11/179:33 pmSDF - SWF
1 stop12h 53mMultiple Airlines
Deal found 9/12$221
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/318:06 pmSWF - SDF
1 stop13h 08mAllegiant Air
Mon 11/32:38 pmSDF - SWF
1 stop19h 48mAllegiant Air
Deal found 9/12$225
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 9/2811:43 amSWF - BNA
1 stop7h 28mMultiple Airlines
Thu 10/28:35 pmBNA - SWF
1 stop13h 46mMultiple Airlines
Deal found 9/12$225
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 12/57:30 pmSWF - BNA
1 stop13h 53mMultiple Airlines
Sun 12/79:50 pmBNA - SWF
1 stop12h 47mMultiple Airlines
Deal found 9/12$226
This Mytrip deal was found by Cheapflights users on 9/12. 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 10/1711:31 amSWF - CVG
1 stop12h 08mAllegiant Air
Sun 10/195:32 pmCVG - SWF
1 stop16h 39mAllegiant Air
Deal found 9/12$236
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/38:21 pmSWF - SDF
1 stop16h 23mMultiple Airlines
Thu 10/96:58 pmSDF - SWF
1 stop15h 53mMultiple Airlines
Deal found 9/12$237
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/318:06 pmSWF - TYS
1 stop19h 16mAllegiant Air
Mon 11/38:31 pmTYS - SWF
1 stop13h 55mAllegiant Air
Deal found 9/12$239

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 September 14, 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 WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Mon 10/27

3:01 pm-11:59 pm

1 stop9h 58m

Nashville Intl

Thu 10/30

8:44 pm-10:41 am

1 stop12h 57m

$192

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Fri 10/31

8:06 pm-9:14 am

1 stop13h 08m

Louisville Intl

Thu 11/6

10:55 am-10:41 am

1 stop23h 46m

$209

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Fri 10/31

8:06 pm-9:14 am

1 stop13h 08m

Louisville Intl

Sun 11/2

6:58 pm-11:11 am

1 stop16h 13m

$209

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Fri 10/24

11:31 am-11:39 pm

1 stop12h 08m

Cincinnati Cinci./N. Kentucky

Mon 10/27

6:00 am-2:11 pm

1 stop8h 11m

$215

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Mon 11/10

12:01 pm-9:59 am

1 stop21h 58m

Louisville Intl

Sun 11/16

10:55 am-11:11 am

1 stop24h 16m

$217

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Fri 11/14

11:01 am-9:59 am

1 stop22h 58m

Louisville Intl

Mon 11/17

9:33 pm-10:26 am

1 stop12h 53m

$221

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Sun 9/28

11:43 am-6:11 pm

1 stop7h 28m

Nashville Intl

Thu 10/2

8:35 pm-11:21 am

1 stop13h 46m

$225

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Fri 10/3

8:21 pm-12:44 pm

1 stop16h 23m

Louisville Intl

Thu 10/9

6:58 pm-10:51 am

1 stop15h 53m

$237

New WindsorKnoxville

SWF - TYS

SWFTYS

New Windsor Stewart

Fri 10/31

8:06 pm-3:22 pm

1 stop19h 16m

Knoxville McGhee Tyson

Mon 11/3

8:31 pm-10:26 am

1 stop13h 55m

$239

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Fri 10/17

11:31 am-11:39 pm

1 stop12h 08m

Cincinnati Cinci./N. Kentucky

Sun 10/19

5:32 pm-10:11 am

1 stop16h 39m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

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, January is the cheapest month in which you can book a flight from New Windsor to Kentucky (average of $299). Flying from New Windsor 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.

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 19h 16m. 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 - Nashville Intl, New Windsor Stewart - Knoxville McGhee Tyson or New Windsor Stewart - Cincinnati Cinci./N. Kentucky 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, January is the cheapest month in which you can book a flight from New Windsor to Kentucky (average of $299). Flying from New Windsor 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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