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Stewart

$85+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SWF
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$206
(Mytrip)

One-way from

$85
(Booking.com)

Popular in

December

Cheapest in

February

Average price

$247
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. 10% potential increase in price ($32 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 July 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 July 31, 2025.

This Mytrip deal was found by Cheapflights users on 7/31. 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 10/36:30 amCVG - SWF
1 stop13h 01mAllegiant Air
Mon 10/611:01 amSWF - CVG
1 stop10h 36mAllegiant Air
Deal found 7/31$206
This Mytrip deal was found by Cheapflights users on 7/31. 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 8/88:01 pmTYS - SWF
1 stop14h 12mAllegiant Air
Fri 8/157:37 pmSWF - TYS
1 stop14h 27mAllegiant Air
Deal found 7/31$230
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 12/43:44 pmBNA - SWF
2 stops18h 53mMultiple Airlines
Sun 12/711:09 amSWF - BNA
1 stop12h 05mMultiple Airlines
Deal found 7/30$232
This Mytrip deal was found by Cheapflights users on 7/31. 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.
Thu 10/212:40 pmCVG - SWF
2 stops22h 41mMultiple Airlines
Mon 10/611:01 amSWF - CVG
1 stop10h 36mMultiple Airlines
Deal found 7/31$276
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 8/812:16 pmSDF - SWF
1 stop6h 50mMultiple Airlines
Sun 8/106:42 pmSWF - SDF
2 stops24h 26mMultiple Airlines
Deal found 7/30$337
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.
Sat 8/910:57 amSDF - SWF
1 stop6h 04mAllegiant Air
Sun 8/178:33 pmSWF - SDF
1 stop13h 35mAllegiant Air
Deal found 7/30$351
This Mytrip deal was found by Cheapflights users on 7/31. 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 8/88:01 pmTYS - SWF
1 stop14h 12mMultiple Airlines
Sun 8/107:52 pmSWF - TYS
1 stop14h 19mMultiple Airlines
Deal found 7/31$372
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/49:03 pmCVG - SWF
1 stop14h 41mBreeze Airways
Mon 9/812:24 pmSWF - CVG
1 stop20h 35mBreeze Airways
Deal found 7/29$436
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.
Sat 8/28:51 pmBNA - SWF
1 stop12h 32mAllegiant Air
Mon 8/411:19 amSWF - BNA
1 stop10h 51mAllegiant Air
Deal found 7/29$501
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.
Thu 7/3110:00 amLEX - SWF
1 stop7h 52mAllegiant Air
Mon 8/47:56 pmSWF - LEX
1 stop15h 27mAllegiant Air
Deal found 7/29$529
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/187:19 pmEVV - SWF
1 stop15h 37mBreeze Airways
Thu 8/287:52 pmSWF - EVV
1 stop23h 47mBreeze Airways
Deal found 7/30$592

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 July 31, 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

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Fri 10/3

6:30 am-7:31 pm

1 stop13h 01m

New Windsor Stewart

Mon 10/6

11:01 am-9:37 pm

1 stop10h 36m

$206

NashvilleNew Windsor

BNA - SWF

BNASWF

Nashville Intl

Thu 12/4

3:44 pm-11:37 am

2 stops18h 53m

New Windsor Stewart

Sun 12/7

11:09 am-10:14 pm

1 stop12h 05m

$232

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Thu 10/2

12:40 pm-11:21 am

2 stops22h 41m

New Windsor Stewart

Mon 10/6

11:01 am-9:37 pm

1 stop10h 36m

$276

KnoxvilleNew Windsor

TYS - SWF

TYSSWF

Knoxville McGhee Tyson

Fri 8/15

9:37 pm-10:13 am

1 stop12h 36m

New Windsor Stewart

Sun 8/17

8:33 pm-12:41 pm

1 stop16h 08m

$289

KnoxvilleNew Windsor

TYS - SWF

TYSSWF

Knoxville McGhee Tyson

Wed 8/13

8:30 am-6:16 pm

1 stop9h 46m

New Windsor Stewart

Tue 8/19

12:36 pm-10:04 am

2 stops21h 28m

$389

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Thu 9/4

9:03 pm-11:44 am

1 stop14h 41m

New Windsor Stewart

Mon 9/8

12:24 pm-8:59 am

1 stop20h 35m

$436

EvansvilleNew Windsor

EVV - SWF

EVVSWF

Evansville Dress Regional

Mon 8/18

7:19 pm-11:56 am

1 stop15h 37m

New Windsor Stewart

Thu 8/28

7:52 pm-6:39 pm

1 stop23h 47m

$592

LexingtonNew Windsor

LEX - SWF

LEXSWF

Lexington Blue Grass

Thu 8/7

10:00 am-5:52 pm

1 stop7h 52m

New Windsor Stewart

Mon 8/11

11:19 am-8:30 pm

1 stop9h 11m

$595

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Fri 12/5

6:00 am-6:40 pm

1 stop12h 40m

New Windsor Stewart

Sun 12/7

11:33 am-8:36 pm

1 stop9h 03m

$597

NashvilleNew Windsor

BNA - SWF

BNASWF

Nashville Intl

Fri 8/22

8:17 am-4:46 pm

1 stop7h 29m

$85

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 21 results
1
2
3

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 $206). 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 July 31, 2025.
Read reviews from past customers who have flown Breeze Airways and Allegiant Air from Kentucky to New Windsor. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.0
Very good
191 reviews

Overall

8.0

Comfort

8.1

Crew

8.7

Boarding

8.2

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

Overall

8.0

Comfort

8.1

Crew

8.7

Boarding

8.2

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
702 reviews
Breeze Airways
8.0
Very good
191 reviews

Overall

8.0

Comfort

8.1

Crew

8.7

Boarding

8.2

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 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 $206). 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 New Windsor?

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

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