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Stewart

$91+ 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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SWF
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$203
(Mytrip)

One-way from

$91
(Mytrip)

Popular in

December

Cheapest in

August

Average price

$272
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. 11% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 28, 2025.

This Mytrip deal was found by Cheapflights users on 3/27. 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 5/19:18 pmSDF - SWF
1 stop22h 31mMultiple Airlines
Mon 5/511:50 amSWF - SDF
1 stop10h 27mMultiple Airlines
Deal found 3/27$203
This Mytrip deal was found by Cheapflights users on 3/27. 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 5/87:36 pmTYS - SWF
1 stop24h 13mAllegiant Air
Wed 5/146:42 pmSWF - TYS
1 stop28h 15mAllegiant Air
Deal found 3/27$206
This Lucky2Go deal was found by Cheapflights users on 3/26. 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 Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/85:07 pmLEX - SWF
1 stop17h 53mAllegiant Air
Mon 5/1210:01 amSWF - LEX
1 stop10h 07mAllegiant Air
Deal found 3/26$229
This Mytrip deal was found by Cheapflights users on 3/26. 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 5/301:47 pmCVG - SWF
1 stop23h 15mAllegiant Air
Mon 6/211:55 amSWF - CVG
1 stop26h 13mAllegiant Air
Deal found 3/26$231
This Mytrip deal was found by Cheapflights users on 3/27. 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 5/87:15 amTYS - SWF
2 stops27h 45mMultiple Airlines
Wed 5/146:42 pmSWF - TYS
1 stop28h 15mMultiple Airlines
Deal found 3/27$262
This Mytrip deal was found by Cheapflights users on 3/27. 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.
Sat 5/246:10 pmBNA - SWF
1 stop15h 23mAllegiant Air
Sat 5/3111:03 amSWF - BNA
1 stop11h 18mAllegiant Air
Deal found 3/27$283
This Mytrip deal was found by Cheapflights users on 3/27. 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.
Tue 6/33:28 pmSDF - SWF
1 stop26h 17mAllegiant Air
Wed 6/116:35 pmSWF - SDF
1 stop19h 49mAllegiant Air
Deal found 3/27$317
This Mytrip deal was found by Cheapflights users on 3/27. 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.
Sat 5/246:10 pmBNA - SWF
1 stop15h 23mMultiple Airlines
Sat 5/311:52 pmSWF - BNA
3 stops29h 42mMultiple Airlines
Deal found 3/27$382
This Mytrip deal was found by Cheapflights users on 3/27. 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 4/174:17 pmTRI - SWF
1 stop16h 44mAllegiant Air
Sun 4/208:04 pmSWF - TRI
1 stop24h 40mAllegiant Air
Deal found 3/27$452
This Mytrip deal was found by Cheapflights users on 3/27. 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 3/307:00 amCVG - SWF
2 stops26h 20mMultiple Airlines
Tue 4/110:52 amSWF - CVG
1 stop9h 31mMultiple Airlines
Deal found 3/27$556
This FlightHub deal was found by Cheapflights users on 3/27. 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.
Sun 6/88:45 pmCVG - SWF
1 stop16h 03mBreeze Airways
Mon 6/161:28 pmSWF - CVG
1 stop19h 23mBreeze Airways
Deal found 3/27$709

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 March 28, 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

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Thu 5/1

9:18 pm-7:49 pm

1 stop22h 31m

New Windsor Stewart

Mon 5/5

11:50 am-10:17 pm

1 stop10h 27m

$203

KnoxvilleNew Windsor

TYS - SWF

TYSSWF

Knoxville McGhee Tyson

Thu 5/8

7:36 pm-7:49 pm

1 stop24h 13m

New Windsor Stewart

Wed 5/14

6:42 pm-10:57 pm

1 stop28h 15m

$206

LexingtonNew Windsor

LEX - SWF

LEXSWF

Lexington Blue Grass

Thu 5/8

5:07 pm-11:00 am

1 stop17h 53m

New Windsor Stewart

Mon 5/12

10:01 am-8:08 pm

1 stop10h 07m

$229

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Fri 5/30

1:47 pm-1:02 pm

1 stop23h 15m

New Windsor Stewart

Mon 6/2

11:55 am-2:08 pm

1 stop26h 13m

$231

KnoxvilleNew Windsor

TYS - SWF

TYSSWF

Knoxville McGhee Tyson

Thu 5/8

7:15 am-11:00 am

2 stops27h 45m

New Windsor Stewart

Wed 5/14

6:42 pm-10:57 pm

1 stop28h 15m

$262

NashvilleNew Windsor

BNA - SWF

BNASWF

Nashville Intl

Sat 5/24

6:10 pm-10:33 am

1 stop15h 23m

New Windsor Stewart

Sat 5/31

11:03 am-9:21 pm

1 stop11h 18m

$283

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Tue 6/3

3:28 pm-5:45 pm

1 stop26h 17m

New Windsor Stewart

Wed 6/11

6:35 pm-2:24 pm

1 stop19h 49m

$317

NashvilleNew Windsor

BNA - SWF

BNASWF

Nashville Intl

Sat 5/24

6:10 pm-10:33 am

1 stop15h 23m

New Windsor Stewart

Sat 5/31

1:52 pm-6:34 pm

3 stops29h 42m

$382

BlountvilleNew Windsor

TRI - SWF

TRISWF

Blountville Tri Cities TN/VA

Thu 4/17

4:17 pm-9:01 am

1 stop16h 44m

New Windsor Stewart

Sun 4/20

8:04 pm-8:44 pm

1 stop24h 40m

$452

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Sun 6/8

8:45 pm-12:48 pm

1 stop16h 03m

New Windsor Stewart

Mon 6/16

1:28 pm-8:51 am

1 stop19h 23m

$709

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 20 results
1
2

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 $224). 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 March 28, 2025.
Breeze Airways
8.1
Very good
157 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.8

Food

6.7

Comfort

8.2

Overall

8.1

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
157 reviews
Breeze Airways
8.1
Very good
157 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.8

Food

6.7

Comfort

8.2

Overall

8.1

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
731 reviews
Breeze Airways
8.1
Very good
157 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.8

Food

6.7

Comfort

8.2

Overall

8.1

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, Knoxville McGhee Tyson - New Windsor Stewart or Nashville 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 $224). 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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