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$87+ 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 6/14. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SDF
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$195
(Mytrip)

One-way from

$87
(Mytrip)

Popular in

December

Cheapest in

August

Average price

$308
Provider with most accurate pricing for New York (NYC)-Louisville Intl flight deals.
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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. 9% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 29, 2025.

This Mytrip deal was found by Cheapflights users on 4/29. 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 6/97:18 pmSWF - BNA
1 stop22h 31mAllegiant Air
Fri 6/137:00 amBNA - SWF
1 stop26h 11mAllegiant Air
Deal found 4/29$196
This Mytrip deal was found by Cheapflights users on 4/29. 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 6/278:01 pmSWF - BNA
1 stop13h 25mMultiple Airlines
Tue 7/19:00 amBNA - SWF
1 stop25h 00mMultiple Airlines
Deal found 4/29$198
This Mytrip deal was found by Cheapflights users on 4/29. 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 6/67:18 pmSWF - CVG
1 stop18h 35mAllegiant Air
Sun 6/87:30 amCVG - SWF
1 stop27h 01mAllegiant Air
Deal found 4/29$220
This Mytrip deal was found by Cheapflights users on 4/29. 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 5/3011:55 amSWF - TYS
1 stop20h 25mAllegiant Air
Sun 6/18:35 pmTYS - SWF
1 stop14h 30mAllegiant Air
Deal found 4/29$231
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Wed 6/46:35 pmSWF - SDF
1 stop15h 43mMultiple Airlines
Sun 6/811:34 amSDF - SWF
1 stop22h 57mMultiple Airlines
Deal found 4/29$246
This Mytrip deal was found by Cheapflights users on 4/28. 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 6/2011:21 amSWF - LEX
1 stop9h 12mAllegiant Air
Sun 6/228:39 pmLEX - SWF
1 stop22h 32mAllegiant Air
Deal found 4/28$257
This Mytrip deal was found by Cheapflights users on 4/28. 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.
Wed 7/211:50 amSWF - CVG
1 stop24h 20mMultiple Airlines
Sun 7/61:00 pmCVG - SWF
1 stop23h 48mMultiple Airlines
Deal found 4/28$299
This Mytrip deal was found by Cheapflights users on 4/29. 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 6/137:18 pmSWF - TYS
1 stop13h 16mMultiple Airlines
Mon 6/166:00 amTYS - SWF
2 stops11h 06mMultiple Airlines
Deal found 4/29$331
This Mytrip deal was found by Cheapflights users on 4/27. 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.
Fri 5/236:07 pmSWF - SDF
1 stop21h 50mAllegiant Air
Tue 5/273:28 pmSDF - SWF
1 stop26h 24mAllegiant Air
Deal found 4/27$335
This Mytrip deal was found by Cheapflights users on 4/28. 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 6/201:28 pmSWF - LEX
2 stops18h 26mMultiple Airlines
Sun 6/228:39 pmLEX - SWF
1 stop22h 32mMultiple Airlines
Deal found 4/28$384
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/261:28 pmSWF - CVG
1 stop19h 23mBreeze Airways
Thu 5/298:45 pmCVG - SWF
1 stop16h 03mBreeze Airways
Deal found 4/29$567

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 April 29, 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

Mon 6/9

7:18 pm-4:49 pm

1 stop22h 31m

Nashville Intl

Fri 6/13

7:00 am-10:11 am

1 stop26h 11m

$196

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Fri 6/27

8:01 pm-8:26 am

1 stop13h 25m

Nashville Intl

Tue 7/1

9:00 am-11:00 am

1 stop25h 00m

$198

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Fri 6/6

7:18 pm-1:53 pm

1 stop18h 35m

Cincinnati Cinci./N. Kentucky

Sun 6/8

7:30 am-10:31 am

1 stop27h 01m

$220

New WindsorKnoxville

SWF - TYS

SWFTYS

New Windsor Stewart

Fri 5/30

11:55 am-8:20 am

1 stop20h 25m

Knoxville McGhee Tyson

Sun 6/1

8:35 pm-11:05 am

1 stop14h 30m

$231

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Wed 6/4

6:35 pm-10:18 am

1 stop15h 43m

Louisville Intl

Sun 6/8

11:34 am-10:31 am

1 stop22h 57m

$246

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

Fri 6/20

11:21 am-8:33 pm

1 stop9h 12m

Lexington Blue Grass

Sun 6/22

8:39 pm-7:11 pm

1 stop22h 32m

$257

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Wed 7/2

11:50 am-12:10 pm

1 stop24h 20m

Cincinnati Cinci./N. Kentucky

Sun 7/6

1:00 pm-12:48 pm

1 stop23h 48m

$299

New WindsorKnoxville

SWF - TYS

SWFTYS

New Windsor Stewart

Fri 6/13

7:18 pm-8:34 am

1 stop13h 16m

Knoxville McGhee Tyson

Mon 6/16

6:00 am-5:06 pm

2 stops11h 06m

$331

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Fri 5/23

6:07 pm-3:57 pm

1 stop21h 50m

Louisville Intl

Tue 5/27

3:28 pm-5:52 pm

1 stop26h 24m

$335

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

Fri 6/20

1:28 pm-7:54 am

2 stops18h 26m

Lexington Blue Grass

Sun 6/22

8:39 pm-7:11 pm

1 stop22h 32m

$384

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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.

Rainfall in Kentucky by month

Plan your trip to Kentucky by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kentucky ranges from 3.1 - 5.3 inches per month. May is typically the wettest month, when rainfall can reach 5.3 in. September is typically the driest time to visit Kentucky when rainfall is around 3.1 in.

Temperature in Kentucky by month

Plan your trip to Kentucky by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kentucky, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 35.6 F).

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 April 29, 2025.
Breeze Airways
8.1
Very good
160 reviews

Comfort

8.2

Food

6.7

Crew

8.8

Overall

8.1

Entertainment

6.6

Boarding

8.3

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
160 reviews
Breeze Airways
8.1
Very good
160 reviews

Comfort

8.2

Food

6.7

Crew

8.8

Overall

8.1

Entertainment

6.6

Boarding

8.3

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
734 reviews
Breeze Airways
8.1
Very good
160 reviews

Comfort

8.2

Food

6.7

Crew

8.8

Overall

8.1

Entertainment

6.6

Boarding

8.3

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 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 - Louisville Intl or New Windsor Stewart - Cincinnati Cinci./N. Kentucky 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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