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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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SWF
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
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Cheap 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 February 3, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/1. 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 8/279:08 pm
CVG
-
SWF
1 stop14h 27m
Breeze Airways
Mon 8/3112:15 pm
SWF
-
CVG
1 stop20h 54m
Breeze Airways
Deal found 2/1$241
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 5/219:08 pm
CVG
-
SWF
1 stop14h 27m
Multiple Airlines
Mon 5/257:46 pm
SWF
-
CVG
1 stop19h 40m
Multiple Airlines
Deal found 2/2$318
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Wed 3/48:52 pm
BNA
-
SWF
1 stop11h 27m
Multiple Airlines
Fri 3/67:36 pm
SWF
-
BNA
1 stop18h 11m
Multiple Airlines
Deal found 2/2$318
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/141:54 pm
TYS
-
SWF
1 stop28h 44m
Allegiant Air
Mon 2/2311:04 am
SWF
-
TYS
1 stop5h 55m
Allegiant Air
Deal found 2/2$319
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Wed 5/271:01 pm
TYS
-
SWF
1 stop20h 37m
Allegiant Air
Mon 6/19:41 am
SWF
-
TYS
1 stop11h 32m
Allegiant Air
Deal found 2/2$324
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 5/299:18 am
SDF
-
SWF
1 stop9h 38m
Multiple Airlines
Sat 6/612:05 pm
SWF
-
SDF
2 stops30h 10m
Multiple Airlines
Deal found 2/3$330
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/148:52 pm
BNA
-
SWF
1 stop13h 00m
Multiple Airlines
Tue 2/1712:41 pm
SWF
-
BNA
2 stops19h 44m
Multiple Airlines
Deal found 2/3$332
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 6/67:15 pm
CVG
-
SWF
1 stop14h 23m
Allegiant Air
Mon 6/85:55 pm
SWF
-
CVG
1 stop5h 34m
Allegiant Air
Deal found 2/3$343
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Wed 5/278:00 am
CVG
-
SWF
1 stop25h 38m
Allegiant Air
Sun 6/710:28 am
SWF
-
CVG
1 stop26h 57m
Allegiant Air
Deal found 2/3$348
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 6/49:08 pm
CVG
-
SWF
1 stop14h 27m
Multiple Airlines
Mon 6/87:26 pm
SWF
-
CVG
1 stop20h 00m
Multiple Airlines
Deal found 2/2$350
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/52:51 pm
BNA
-
SWF
1 stop18h 28m
Multiple Airlines
Mon 2/911:09 am
SWF
-
BNA
1 stop21h 16m
Multiple Airlines
Deal found 2/2$358
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/75:50 pm
BNA
-
SWF
1 stop16h 18m
Multiple Airlines
Mon 2/911:09 am
SWF
-
BNA
1 stop21h 16m
Multiple Airlines
Deal found 2/3$360

Find flight deals from Kentucky to Stewart

Keep the following information in mind while searching for Kentucky to Stewart flight deals. Data was last updated February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$318
(Kiwi.com)

One-way from

$85
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$283
Provider with most accurate pricing for Louisville Intl-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-New York (NYC) flights.
Search Deals
From Kentucky to New Windsor Stewart
Search Deals
One-way flight from Kentucky to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 3, 2026.
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

Thu 5/21

9:08 pm-11:35 am

1 stop14h 27m

New Windsor Stewart

Mon 5/25

7:46 pm-3:26 pm

1 stop19h 40m

$318

NashvilleNew Windsor

BNA - SWF

BNASWF

Nashville Intl

Wed 3/4

8:52 pm-9:19 am

1 stop11h 27m

New Windsor Stewart

Fri 3/6

7:36 pm-12:47 pm

1 stop18h 11m

$318

KnoxvilleNew Windsor

TYS - SWF

TYSSWF

Knoxville McGhee Tyson

Sat 2/14

1:54 pm-6:38 pm

1 stop28h 44m

New Windsor Stewart

Mon 2/23

11:04 am-4:59 pm

1 stop5h 55m

$319

KnoxvilleNew Windsor

TYS - SWF

TYSSWF

Knoxville McGhee Tyson

Wed 5/27

1:01 pm-9:38 am

1 stop20h 37m

New Windsor Stewart

Mon 6/1

9:41 am-9:13 pm

1 stop11h 32m

$324

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Fri 5/29

9:18 am-6:56 pm

1 stop9h 38m

New Windsor Stewart

Sat 6/6

12:05 pm-6:15 pm

2 stops30h 10m

$330

NashvilleNew Windsor

BNA - SWF

BNASWF

Nashville Intl

Sat 2/14

8:52 pm-10:52 am

1 stop13h 00m

New Windsor Stewart

Tue 2/17

12:41 pm-7:25 am

2 stops19h 44m

$332

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Sat 6/6

7:15 pm-9:38 am

1 stop14h 23m

New Windsor Stewart

Mon 6/8

5:55 pm-11:29 pm

1 stop5h 34m

$343

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Wed 5/27

8:00 am-9:38 am

1 stop25h 38m

New Windsor Stewart

Sun 6/7

10:28 am-1:25 pm

1 stop26h 57m

$348

CincinnatiNew Windsor

CVG - SWF

CVGSWF

Cincinnati Cinci./N. Kentucky

Thu 6/4

9:08 pm-11:35 am

1 stop14h 27m

New Windsor Stewart

Mon 6/8

7:26 pm-3:26 pm

1 stop20h 00m

$350

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Fri 5/29

9:18 am-6:56 pm

1 stop9h 38m

New Windsor Stewart

Sun 5/31

8:10 pm-2:11 pm

1 stop18h 01m

$361

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 60 results
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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, May is the cheapest month in which you can book a flight from Kentucky to New Windsor (average of $71). Flying from Kentucky to New Windsor in April is currently the most expensive (average of $199). 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 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.

  • How long is the flight from Kentucky to New Windsor?

    For as low as $319, Allegiant Air can have you in New Windsor from Kentucky in 28h 44m. The distance from Kentucky to New Windsor is about 662 mi.

  • 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 Knoxville McGhee Tyson - 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, May is the cheapest month in which you can book a flight from Kentucky to New Windsor (average of $71). Flying from Kentucky to New Windsor in April is currently the most expensive (average of $199). 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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