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$88+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SDF
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$173
(Mytrip)

One-way from

$88
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$325
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. 8% potential increase in price ($28 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 June 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 junio 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/10. 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.
lun. 7/287:56 pmSWF - BNA
1 stop20h 43mMultiple Airlines
vie. 8/17:00 amBNA - SWF
1 stop26h 13mMultiple Airlines
Deal found 6/10$173
This Mytrip deal was found by Cheapflights users on 6/11. 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.
vie. 8/17:56 pmSWF - CVG
1 stop12h 55mAllegiant Air
vie. 8/86:00 amCVG - SWF
1 stop13h 06mAllegiant Air
Deal found 6/11$186
This Mytrip deal was found by Cheapflights users on 6/12. 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.
mié. 8/67:00 pmSWF - LEX
1 stop19h 15mAllegiant Air
dom. 8/107:34 pmLEX - SWF
1 stop23h 32mAllegiant Air
Deal found 6/12$200
This Mytrip deal was found by Cheapflights users on 6/11. 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.
vie. 8/87:56 pmSWF - TYS
1 stop15h 06mAllegiant Air
dom. 8/108:54 pmTYS - SWF
1 stop22h 12mAllegiant Air
Deal found 6/11$202
This Mytrip deal was found by Cheapflights users on 6/10. 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.
jue. 9/117:12 pmSWF - SDF
1 stop20h 15mMultiple Airlines
lun. 9/155:32 pmSDF - SWF
1 stop16h 54mMultiple Airlines
Deal found 6/10$218
This Mytrip deal was found by Cheapflights users on 6/12. 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.
vie. 8/16:11 pmSWF - SDF
1 stop20h 35mAllegiant Air
dom. 8/311:34 amSDF - SWF
1 stop22h 55mAllegiant Air
Deal found 6/12$232
This Mytrip deal was found by Cheapflights users on 6/10. 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.
vie. 8/17:56 pmSWF - CVG
1 stop12h 55mMultiple Airlines
dom. 8/31:00 pmCVG - SWF
2 stops30h 06mMultiple Airlines
Deal found 6/10$233
This Mytrip deal was found by Cheapflights users on 6/10. 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.
lun. 6/167:18 pmSWF - BNA
1 stop22h 31mAllegiant Air
vie. 6/207:00 amBNA - SWF
1 stop26h 36mAllegiant Air
Deal found 6/10$300
This Mytrip deal was found by Cheapflights users on 6/10. 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.
dom. 8/246:50 pmSWF - TYS
2 stops15h 44mMultiple Airlines
jue. 8/289:12 pmTYS - SWF
1 stop15h 53mMultiple Airlines
Deal found 6/10$302
This Mytrip deal was found by Cheapflights users on 6/12. 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.
lun. 6/238:01 pmSWF - LEX
1 stop15h 23mMultiple Airlines
sáb. 6/289:17 pmLEX - SWF
2 stops20h 39mMultiple Airlines
Deal found 6/12$347
This FlightHub deal was found by Cheapflights users on 6/11. 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.
lun. 8/181:28 pmSWF - CVG
1 stop19h 23mBreeze Airways
dom. 8/248:45 pmCVG - SWF
1 stop16h 03mBreeze Airways
Deal found 6/11$562

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 junio 12, 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

lun. 7/28

7:56 pm-3:39 pm

1 stop20h 43m

Nashville Intl

vie. 8/1

7:00 am-10:13 am

1 stop26h 13m

$173

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

vie. 8/1

7:56 pm-8:51 am

1 stop12h 55m

Cincinnati Cinci./N. Kentucky

vie. 8/8

6:00 am-7:06 pm

1 stop13h 06m

$186

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

mié. 8/6

7:00 pm-2:15 pm

1 stop19h 15m

Lexington Blue Grass

dom. 8/10

7:34 pm-7:06 pm

1 stop23h 32m

$200

New WindsorKnoxville

SWF - TYS

SWFTYS

New Windsor Stewart

vie. 8/8

7:56 pm-11:02 am

1 stop15h 06m

Knoxville McGhee Tyson

dom. 8/10

8:54 pm-7:06 pm

1 stop22h 12m

$202

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

vie. 7/25

7:56 pm-7:28 pm

1 stop23h 32m

Louisville Intl

dom. 7/27

8:13 pm-7:06 pm

1 stop22h 53m

$224

New WindsorLouisville

SWF - SDF

SWFSDF

New Windsor Stewart

vie. 8/1

6:11 pm-2:46 pm

1 stop20h 35m

Louisville Intl

dom. 8/3

11:34 am-10:29 am

1 stop22h 55m

$232

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

vie. 8/1

7:56 pm-8:51 am

1 stop12h 55m

Cincinnati Cinci./N. Kentucky

dom. 8/3

1:00 pm-7:06 pm

2 stops30h 06m

$233

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

lun. 6/16

7:18 pm-4:49 pm

1 stop22h 31m

Nashville Intl

vie. 6/20

7:00 am-10:36 am

1 stop26h 36m

$300

New WindsorKnoxville

SWF - TYS

SWFTYS

New Windsor Stewart

dom. 8/24

6:50 pm-10:34 am

2 stops15h 44m

Knoxville McGhee Tyson

jue. 8/28

9:12 pm-1:05 pm

1 stop15h 53m

$302

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

lun. 6/23

8:01 pm-11:24 am

1 stop15h 23m

Lexington Blue Grass

sáb. 6/28

9:17 pm-5:56 pm

2 stops20h 39m

$347

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 24 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 junio 12, 2025.
Read reviews from past customers who have flown Breeze Airways and Allegiant Air from New Windsor to Kentucky. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
178 reviews

Entertainment

6.6

Overall

8.1

Boarding

8.3

Food

6.7

Crew

8.8

Comfort

8.2

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
178 reviews
Breeze Airways
8.1
Very good
178 reviews

Entertainment

6.6

Overall

8.1

Boarding

8.3

Food

6.7

Crew

8.8

Comfort

8.2

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
725 reviews
Breeze Airways
8.1
Very good
178 reviews

Entertainment

6.6

Overall

8.1

Boarding

8.3

Food

6.7

Crew

8.8

Comfort

8.2

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 - Cincinnati Cinci./N. Kentucky, New Windsor Stewart - Nashville Intl 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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