HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kentucky

$94+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SDF
Nov 30 — Dec 71
Sun 11/30
Sun 12/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Kentucky with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 31, 2025.

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.
Fri 12/512:27 pmSWF - BNA
1 stop20h 30mMultiple Airlines
Sun 12/711:19 amBNA - SWF
1 stop23h 18mMultiple Airlines
Deal found 10/29$181
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.
Fri 12/1212:27 pmSWF - BNA
1 stop11h 00mMultiple Airlines
Sun 12/148:59 pmBNA - SWF
1 stop13h 38mMultiple Airlines
Deal found 10/30$185
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.
Fri 11/1411:01 amSWF - BNA
1 stop9h 10mMultiple Airlines
Sun 11/169:03 pmBNA - SWF
1 stop13h 08mMultiple Airlines
Deal found 10/29$229
This Mytrip deal was found by Cheapflights users on 10/31. 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 12/512:27 pmSWF - CVG
1 stop8h 59mMultiple Airlines
Sun 12/712:50 pmCVG - SWF
2 stops22h 47mMultiple Airlines
Deal found 10/31$238
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.
Fri 11/1411:01 amSWF - SDF
1 stop7h 15mMultiple Airlines
Mon 11/179:33 pmSDF - SWF
1 stop12h 53mMultiple Airlines
Deal found 10/30$238
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/157:30 pmSWF - TYS
1 stop20h 32mAllegiant Air
Mon 12/226:00 amTYS - SWF
1 stop10h 38mAllegiant Air
Deal found 10/31$243
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 12/711:09 amSWF - CVG
1 stop13h 48mMultiple Airlines
Thu 12/119:03 pmCVG - SWF
1 stop14h 41mMultiple Airlines
Deal found 10/29$244
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/812:24 pmSWF - BNA
2 stops10h 44mMultiple Airlines
Thu 12/118:59 pmBNA - SWF
1 stop13h 38mMultiple Airlines
Deal found 10/31$248
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.
Fri 12/1212:27 pmSWF - CVG
1 stop8h 59mMultiple Airlines
Sun 12/1412:50 pmCVG - SWF
2 stops22h 47mMultiple Airlines
Deal found 10/30$256
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 11/1311:43 amSWF - BNA
1 stop25h 36mMultiple Airlines
Sun 11/169:03 pmBNA - SWF
1 stop13h 08mMultiple Airlines
Deal found 10/28$263
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 - CVG
1 stop13h 41mMultiple Airlines
Mon 1/195:05 amCVG - SWF
1 stop13h 38mMultiple Airlines
Deal found 10/31$265
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 11/2011:06 amSWF - BNA
1 stop11h 53mMultiple Airlines
Thu 12/48:59 pmBNA - SWF
1 stop13h 38mMultiple Airlines
Deal found 10/30$265

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 October 31, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$181
(Kiwi.com)

One-way from

$94
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$379
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. 7% potential increase in price ($25 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 October 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 October 31, 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

Fri 12/5

12:27 pm-7:57 am

1 stop20h 30m

Nashville Intl

Sun 12/7

11:19 am-11:37 am

1 stop23h 18m

$181

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Fri 11/14

11:01 am-7:11 pm

1 stop9h 10m

Nashville Intl

Sun 11/16

9:03 pm-11:11 am

1 stop13h 08m

$229

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Fri 12/5

12:27 pm-9:26 pm

1 stop8h 59m

Cincinnati Cinci./N. Kentucky

Sun 12/7

12:50 pm-11:37 am

2 stops22h 47m

$238

New WindsorKnoxville

SWF - TYS

SWFTYS

New Windsor Stewart

Mon 12/15

7:30 pm-4:02 pm

1 stop20h 32m

Knoxville McGhee Tyson

Mon 12/22

6:00 am-4:38 pm

1 stop10h 38m

$243

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Mon 12/8

12:24 pm-10:08 pm

2 stops10h 44m

Nashville Intl

Thu 12/11

8:59 pm-11:37 am

1 stop13h 38m

$248

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Fri 12/12

12:27 pm-9:26 pm

1 stop8h 59m

Cincinnati Cinci./N. Kentucky

Sun 12/14

12:50 pm-11:37 am

2 stops22h 47m

$256

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Thu 11/13

11:43 am-12:19 pm

1 stop25h 36m

Nashville Intl

Sun 11/16

9:03 pm-11:11 am

1 stop13h 08m

$263

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Sat 12/20

9:45 am-11:26 pm

1 stop13h 41m

Cincinnati Cinci./N. Kentucky

Mon 1/19

5:05 am-6:43 pm

1 stop13h 38m

$265

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Fri 12/19

6:56 pm-10:09 am

1 stop16h 13m

Nashville Intl

Mon 12/22

11:14 am-7:35 pm

1 stop7h 21m

$276

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Fri 11/14

7:05 pm-9:54 am

1 stop14h 49m

Louisville Intl

Sun 11/16

8:53 pm-11:44 am

2 stops14h 51m

$281

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 60 results
1
2
3
...
6

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 $216). 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 20h 32m. 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 - Cincinnati Cinci./N. Kentucky 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 $216). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stewart to Kentucky

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Miami flights
Newark to Fort Lauderdale flights
Newark to Miami flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Los Angeles flights
LaGuardia to Fort Lauderdale flights
LaGuardia to Miami flights
John F Kennedy Intl to Dallas/Fort Worth flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to Dallas/Fort Worth flights
Newark to Los Angeles flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to West Palm Beach flights
Newark to Dallas/Fort Worth flights
John F Kennedy Intl to San Francisco flights
Newark to Orlando flights
Newark to West Palm Beach flights
Newark to Hobby flights
John F Kennedy Intl to Atlanta flights
LaGuardia to Hobby flights
LaGuardia to Orlando flights
Newark to San Francisco flights
John F Kennedy Intl to Tampa flights
LaGuardia to Tampa flights
Newark to Las Vegas flights
John F Kennedy Intl to Hobby flights
Newark to Tampa flights
LaGuardia to Los Angeles flights
LaGuardia to Atlanta flights
John F Kennedy Intl to Sky Harbor Intl flights
LaGuardia to West Palm Beach flights
LaGuardia to O'Hare Intl flights
John F Kennedy Intl to New Orleans flights
John F Kennedy Intl to Denver flights
Newark to Sky Harbor Intl flights
Newark to O'Hare Intl flights
Newark to George Bush Intcntl flights
Newark to New Orleans flights
John F Kennedy Intl to Seattle flights
Newark to Atlanta flights
John F Kennedy Intl to George Bush Intcntl flights
LaGuardia to Las Vegas flights
LaGuardia to New Orleans flights
LaGuardia to George Bush Intcntl flights
John F Kennedy Intl to Austin flights
John F Kennedy Intl to Nashville flights
LaGuardia to Denver flights
LaGuardia to San Francisco flights
Newark to Denver flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.