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$93+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SDF
Mar 31 — Apr 71
Mon 3/31
Mon 4/7
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 March 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$214
(Mytrip)

One-way from

$93
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$303
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. 7% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 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 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 March 26, 2025.

This Mytrip deal was found by Cheapflights users on 3/25. 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 5/28:39 pmSWF - TYS
1 stop24h 29mAllegiant Air
Mon 5/56:00 amTYS - SWF
1 stop13h 49mAllegiant Air
Deal found 3/25$214
This Mytrip deal was found by Cheapflights users on 3/25. 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 4/210:51 amSWF - CVG
1 stop12h 19mAllegiant Air
Thu 4/36:30 amCVG - SWF
1 stop26h 50mAllegiant Air
Deal found 3/25$216
This Mytrip deal was found by Cheapflights users on 3/25. 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 5/911:50 amSWF - BNA
1 stop21h 30mMultiple Airlines
Sun 5/116:00 amBNA - SWF
1 stop28h 00mMultiple Airlines
Deal found 3/25$218
This Mytrip deal was found by Cheapflights users on 3/25. 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 4/2511:50 amSWF - SDF
1 stop10h 27mMultiple Airlines
Mon 4/289:27 pmSDF - SWF
1 stop12h 35mMultiple Airlines
Deal found 3/25$225
This Mytrip deal was found by Cheapflights users on 3/25. 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 6/1311:21 amSWF - BNA
1 stop25h 07mAllegiant Air
Sun 6/152:37 pmBNA - SWF
1 stop26h 51mAllegiant Air
Deal found 3/25$240
This Mytrip deal was found by Cheapflights users on 3/23. 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 5/162:45 pmSWF - LEX
1 stop26h 24mAllegiant Air
Sun 5/184:47 pmLEX - SWF
1 stop18h 18mAllegiant Air
Deal found 3/23$247
This Mytrip deal was found by Cheapflights users on 3/25. 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 5/18:04 pmSWF - SDF
1 stop24h 33mAllegiant Air
Sun 5/49:05 amSDF - SWF
1 stop24h 06mAllegiant Air
Deal found 3/25$256
This Mytrip deal was found by Cheapflights users on 3/25. 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 5/1611:55 amSWF - CVG
1 stop8h 36mMultiple Airlines
Sun 5/189:15 amCVG - SWF
2 stops25h 50mMultiple Airlines
Deal found 3/25$289
This Mytrip deal was found by Cheapflights users on 3/24. 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 5/2211:23 amSWF - TYS
1 stop11h 24mMultiple Airlines
Sun 5/259:30 amTYS - SWF
2 stops25h 35mMultiple Airlines
Deal found 3/24$432

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 March 26, 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 WindsorKnoxville

SWF - TYS

SWFTYS

New Windsor Stewart

Fri 5/2

8:39 pm-9:08 pm

1 stop24h 29m

Knoxville McGhee Tyson

Mon 5/5

6:00 am-7:49 pm

1 stop13h 49m

$214

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Fri 5/9

11:50 am-8:20 am

1 stop21h 30m

Nashville Intl

Sun 5/11

6:00 am-11:00 am

1 stop28h 00m

$218

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Fri 4/25

11:50 am-10:17 pm

1 stop10h 27m

Louisville Intl

Mon 4/28

9:27 pm-10:02 am

1 stop12h 35m

$225

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Thu 5/1

8:04 pm-6:11 pm

1 stop22h 07m

Cincinnati Cinci./N. Kentucky

Sun 5/4

6:30 am-11:00 am

1 stop28h 30m

$228

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Fri 6/13

11:21 am-11:28 am

1 stop25h 07m

Nashville Intl

Sun 6/15

2:37 pm-6:28 pm

1 stop26h 51m

$240

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

Thu 5/1

8:04 pm-8:37 pm

1 stop24h 33m

Louisville Intl

Sun 5/4

9:05 am-9:11 am

1 stop24h 06m

$256

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Fri 5/16

11:55 am-8:31 pm

1 stop8h 36m

Cincinnati Cinci./N. Kentucky

Sun 5/18

9:15 am-11:05 am

2 stops25h 50m

$289

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

Fri 4/25

10:01 am-8:38 pm

1 stop10h 37m

Lexington Blue Grass

Sun 4/27

5:07 pm-11:00 am

1 stop17h 53m

$328

New WindsorKnoxville

SWF - TYS

SWFTYS

New Windsor Stewart

Thu 5/22

11:23 am-10:47 pm

1 stop11h 24m

Knoxville McGhee Tyson

Sun 5/25

9:30 am-11:05 am

2 stops25h 35m

$432

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Fri 5/30

11:55 am-11:08 pm

1 stop11h 13m

$93

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 18 results
1
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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 March 26, 2025.
Breeze Airways
8.0
Very good
156 reviews

Overall

8.0

Comfort

8.2

Food

6.7

Crew

8.8

Boarding

8.3

Entertainment

6.6

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
8.0
Very good
156 reviews
Breeze Airways
8.0
Very good
156 reviews

Overall

8.0

Comfort

8.2

Food

6.7

Crew

8.8

Boarding

8.3

Entertainment

6.6

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
730 reviews
Breeze Airways
8.0
Very good
156 reviews

Overall

8.0

Comfort

8.2

Food

6.7

Crew

8.8

Boarding

8.3

Entertainment

6.6

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 - Cincinnati Cinci./N. Kentucky or New Windsor Stewart - Knoxville McGhee Tyson 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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