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Stewart

$88+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SWF
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$177
(Mytrip)

One-way from

$88
(Mytrip)

Popular in

December

Cheapest in

August

Average price

$283
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. 12% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/10. 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 8/17:00 amBNA - SWF
1 stop26h 13mMultiple Airlines
Mon 8/47:56 pmSWF - BNA
1 stop20h 43mMultiple Airlines
Deal found 6/10$177
This Mytrip deal was found by Cheapflights users on 6/10. 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 7/186:00 amCVG - SWF
1 stop13h 06mAllegiant Air
Mon 7/217:56 pmSWF - CVG
1 stop18h 10mAllegiant Air
Deal found 6/10$196
This Mytrip deal was found by Cheapflights users on 6/10. 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 9/59:47 amSDF - SWF
1 stop8h 27mAllegiant Air
Sun 9/77:12 pmSWF - SDF
1 stop21h 40mAllegiant Air
Deal found 6/10$198
This Mytrip deal was found by Cheapflights users on 6/10. 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 8/110:05 pmTYS - SWF
1 stop12h 08mAllegiant Air
Mon 8/47:56 pmSWF - TYS
1 stop20h 09mAllegiant Air
Deal found 6/10$216
This Mytrip deal was found by Cheapflights users on 6/11. 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 7/1812:16 pmSDF - SWF
1 stop6h 50mMultiple Airlines
Mon 7/217:56 pmSWF - SDF
1 stop23h 12mMultiple Airlines
Deal found 6/11$217
This Mytrip deal was found by Cheapflights users on 6/10. 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 7/253:00 pmLEX - SWF
1 stop19h 13mAllegiant Air
Fri 8/17:56 pmSWF - LEX
1 stop20h 21mAllegiant Air
Deal found 6/10$225
This Mytrip deal was found by Cheapflights users on 6/10. 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 7/257:00 amBNA - SWF
1 stop26h 13mAllegiant Air
Fri 8/111:19 amSWF - BNA
1 stop10h 51mAllegiant Air
Deal found 6/10$236
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Sun 7/201:00 pmCVG - SWF
2 stops30h 06mMultiple Airlines
Fri 7/257:56 pmSWF - CVG
1 stop12h 55mMultiple Airlines
Deal found 6/11$249
This Mytrip deal was found by Cheapflights users on 6/10. 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 8/110:05 pmTYS - SWF
1 stop12h 08mMultiple Airlines
Mon 8/46:11 pmSWF - TYS
2 stops19h 35mMultiple Airlines
Deal found 6/10$280
This Mytrip deal was found by Cheapflights users on 6/12. 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 7/43:00 pmLEX - SWF
1 stop21h 18mMultiple Airlines
Mon 7/76:11 pmSWF - LEX
2 stops17h 12mMultiple Airlines
Deal found 6/12$363
This FlightHub deal was found by Cheapflights users on 6/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/189:03 pmCVG - SWF
1 stop14h 41mBreeze Airways
Mon 9/2212:24 pmSWF - CVG
1 stop20h 35mBreeze Airways
Deal found 6/11$460

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 June 12, 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

Fri 8/1

7:00 am-10:13 am

1 stop26h 13m

New Windsor Stewart

Mon 8/4

7:56 pm-3:39 pm

1 stop20h 43m

$177

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Fri 7/18

6:00 am-7:06 pm

1 stop13h 06m

New Windsor Stewart

Mon 7/21

7:56 pm-2:06 pm

1 stop18h 10m

$196

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Fri 9/5

9:47 am-6:14 pm

1 stop8h 27m

New Windsor Stewart

Sun 9/7

7:12 pm-4:52 pm

1 stop21h 40m

$198

KnoxvilleNew Windsor

TYS - SWF

TYSSWF

Knoxville McGhee Tyson

Fri 8/1

10:05 pm-10:13 am

1 stop12h 08m

New Windsor Stewart

Mon 8/4

7:56 pm-4:05 pm

1 stop20h 09m

$216

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Fri 7/18

12:16 pm-7:06 pm

1 stop6h 50m

New Windsor Stewart

Mon 7/21

7:56 pm-7:08 pm

1 stop23h 12m

$217

LexingtonNew Windsor

LEX - SWF

LEXSWF

Lexington Blue Grass

Fri 7/25

3:00 pm-10:13 am

1 stop19h 13m

New Windsor Stewart

Fri 8/1

7:56 pm-4:17 pm

1 stop20h 21m

$225

NashvilleNew Windsor

BNA - SWF

BNASWF

Nashville Intl

Fri 7/25

7:00 am-10:13 am

1 stop26h 13m

New Windsor Stewart

Fri 8/1

11:19 am-9:10 pm

1 stop10h 51m

$236

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Sun 7/20

1:00 pm-7:06 pm

2 stops30h 06m

New Windsor Stewart

Fri 7/25

7:56 pm-8:51 am

1 stop12h 55m

$249

KnoxvilleNew Windsor

TYS - SWF

TYSSWF

Knoxville McGhee Tyson

Fri 8/1

10:05 pm-10:13 am

1 stop12h 08m

New Windsor Stewart

Mon 8/4

6:11 pm-1:46 pm

2 stops19h 35m

$280

LexingtonNew Windsor

LEX - SWF

LEXSWF

Lexington Blue Grass

Fri 7/4

3:00 pm-12:18 pm

1 stop21h 18m

New Windsor Stewart

Mon 7/7

6:11 pm-11:23 am

2 stops17h 12m

$363

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 23 results
1
2
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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 August is currently the most expensive (average of $219). 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 Stewart

Get insights into the airlines that provide service to Stewart. 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 Stewart. Reviews last updated June 12, 2025.
Get a feel of what it's like to fly with Breeze Airways and Allegiant Air from Kentucky to New Windsor by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
178 reviews

Entertainment

6.6

Crew

8.8

Overall

8.1

Comfort

8.2

Boarding

8.3

Food

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
178 reviews
Breeze Airways
8.1
Very good
178 reviews

Entertainment

6.6

Crew

8.8

Overall

8.1

Comfort

8.2

Boarding

8.3

Food

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Allegiant Air
7.3
Good
725 reviews
Breeze Airways
8.1
Very good
178 reviews

Entertainment

6.6

Crew

8.8

Overall

8.1

Comfort

8.2

Boarding

8.3

Food

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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.

  • 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 Louisville Intl - 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 August is currently the most expensive (average of $219). 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 Kentucky?

Book flights to Kentucky if you plan to visit one of these locations
Kingston

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