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Kentucky

$85+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SDF
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$170
(Mytrip)

One-way from

$85
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$313
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. 7% potential increase in price ($27 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 July 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 July 30, 2025.

This Mytrip deal was found by Cheapflights users on 7/30. 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 10/2411:31 amSWF - BNA
1 stop11h 46mMultiple Airlines
Mon 10/275:45 amBNA - SWF
1 stop7h 26mMultiple Airlines
Deal found 7/30$170
This Mytrip deal was found by Cheapflights users on 7/30. 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 10/1711:31 amSWF - SDF
1 stop8h 04mMultiple Airlines
Sun 10/198:40 pmSDF - SWF
1 stop13h 31mMultiple Airlines
Deal found 7/30$204
This Mytrip deal was found by Cheapflights users on 7/29. 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 10/312:11 pmSWF - CVG
1 stop11h 28mAllegiant Air
Sun 10/55:32 pmCVG - SWF
1 stop16h 39mAllegiant Air
Deal found 7/29$216
This Mytrip deal was found by Cheapflights users on 7/28. 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 11/147:05 pmSWF - SDF
1 stop14h 49mAllegiant Air
Mon 11/179:33 pmSDF - SWF
1 stop12h 53mAllegiant Air
Deal found 7/28$232
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Mon 8/117:56 pmSWF - TYS
1 stop14h 06mAllegiant Air
Fri 8/159:37 pmTYS - SWF
1 stop12h 36mAllegiant Air
Deal found 7/29$240
This Mytrip deal was found by Cheapflights users on 7/30. 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 8/2112:13 pmSWF - LEX
1 stop7h 24mAllegiant Air
Sun 8/249:20 pmLEX - SWF
1 stop12h 52mAllegiant Air
Deal found 7/30$285
This Mytrip deal was found by Cheapflights users on 7/29. 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 10/2411:31 amSWF - CVG
2 stops11h 32mMultiple Airlines
Mon 10/277:30 amCVG - SWF
1 stop11h 46mMultiple Airlines
Deal found 7/29$307
This Mytrip deal was found by Cheapflights users on 7/28. 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 10/3112:24 pmSWF - TYS
2 stops10h 42mMultiple Airlines
Mon 11/38:31 pmTYS - SWF
1 stop13h 55mMultiple Airlines
Deal found 7/28$339
This Mytrip deal was found by Cheapflights users on 7/30. 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 8/2112:13 pmSWF - LEX
1 stop7h 24mMultiple Airlines
Sun 8/249:20 pmLEX - SWF
2 stops15h 28mMultiple Airlines
Deal found 7/30$373
This Gotogate deal was found by Cheapflights users on 7/28. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/111:28 pmSWF - CVG
1 stop19h 23mBreeze Airways
Thu 8/148:45 pmCVG - SWF
1 stop16h 03mBreeze Airways
Deal found 7/28$565

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 July 30, 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 10/24

11:31 am-10:17 pm

1 stop11h 46m

Nashville Intl

Mon 10/27

5:45 am-2:11 pm

1 stop7h 26m

$170

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Fri 10/17

11:31 am-7:35 pm

1 stop8h 04m

Louisville Intl

Sun 10/19

8:40 pm-10:11 am

1 stop13h 31m

$204

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Fri 10/3

12:11 pm-11:39 pm

1 stop11h 28m

Cincinnati Cinci./N. Kentucky

Sun 10/5

5:32 pm-10:11 am

1 stop16h 39m

$216

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Fri 11/14

7:05 pm-9:54 am

1 stop14h 49m

Louisville Intl

Mon 11/17

9:33 pm-10:26 am

1 stop12h 53m

$232

New WindsorKnoxville

SWF - TYS

SWFTYS

New Windsor Stewart

Mon 8/11

7:56 pm-10:02 am

1 stop14h 06m

Knoxville McGhee Tyson

Fri 8/15

9:37 pm-10:13 am

1 stop12h 36m

$240

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

Thu 8/21

12:13 pm-7:37 pm

1 stop7h 24m

Lexington Blue Grass

Sun 8/24

9:20 pm-10:12 am

1 stop12h 52m

$285

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Fri 10/24

11:31 am-11:03 pm

2 stops11h 32m

Cincinnati Cinci./N. Kentucky

Mon 10/27

7:30 am-7:16 pm

1 stop11h 46m

$307

New WindsorKnoxville

SWF - TYS

SWFTYS

New Windsor Stewart

Fri 10/31

12:24 pm-11:06 pm

2 stops10h 42m

Knoxville McGhee Tyson

Mon 11/3

8:31 pm-10:26 am

1 stop13h 55m

$339

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

Thu 8/21

12:13 pm-7:37 pm

1 stop7h 24m

Lexington Blue Grass

Sun 8/24

9:20 pm-12:48 pm

2 stops15h 28m

$373

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Mon 8/11

1:28 pm-8:51 am

1 stop19h 23m

Cincinnati Cinci./N. Kentucky

Thu 8/14

8:45 pm-12:48 pm

1 stop16h 03m

$565

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 22 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.

Reviews of airlines servicing Kentucky

Get insights into the airlines that provide service to Kentucky. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kentucky. Reviews last updated July 30, 2025.
See what other customers who have flown with Breeze Airways and Allegiant Air from New Windsor to Kentucky have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.0
Very good
191 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.0

Food

6.7

Entertainment

6.5

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.0
Very good
191 reviews
Breeze Airways
8.0
Very good
191 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.0

Food

6.7

Entertainment

6.5

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Allegiant Air
7.2
Good
703 reviews
Breeze Airways
8.0
Very good
191 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.0

Food

6.7

Entertainment

6.5

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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.

  • 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, 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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