Kentucky

$98+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SDF
Mar 5 — Mar 121
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Cheap 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 February 3, 2026.

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.
Mon 3/2312:11 pm
SWF
-
BNA
2 stops23h 30m
Multiple Airlines
Wed 3/252:27 pm
BNA
-
SWF
1 stop18h 12m
Multiple Airlines
Deal found 2/3$213
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 5/2110:28 am
SWF
-
BNA
1 stop10h 10m
Multiple Airlines
Wed 5/276:54 pm
BNA
-
SWF
1 stop13h 44m
Multiple Airlines
Deal found 2/2$230
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 2/2611:52 am
SWF
-
BNA
1 stop8h 56m
Multiple Airlines
Sat 2/288:52 pm
BNA
-
SWF
1 stop13h 10m
Multiple Airlines
Deal found 2/1$240
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/711:45 am
SWF
-
BNA
1 stop7h 14m
Multiple Airlines
Sun 5/1010:55 am
BNA
-
SWF
1 stop23h 00m
Multiple Airlines
Deal found 1/31$252
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.
Fri 5/811:45 am
SWF
-
CVG
1 stop11h 35m
Multiple Airlines
Sun 5/105:20 pm
CVG
-
SWF
1 stop17h 35m
Multiple Airlines
Deal found 2/1$259
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 4/1611:45 am
SWF
-
BNA
1 stop12h 34m
Multiple Airlines
Sat 4/186:54 pm
BNA
-
SWF
1 stop15h 01m
Multiple Airlines
Deal found 2/2$259
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.
Wed 5/612:05 pm
SWF
-
BNA
2 stops11h 42m
Multiple Airlines
Sat 5/96:54 pm
BNA
-
SWF
1 stop15h 01m
Multiple Airlines
Deal found 2/1$270
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 6/1110:28 am
SWF
-
BNA
1 stop10h 07m
Multiple Airlines
Tue 6/165:58 pm
BNA
-
SWF
2 stops16h 27m
Multiple Airlines
Deal found 2/1$282
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 6/410:28 am
SWF
-
BNA
1 stop10h 07m
Multiple Airlines
Tue 6/95:58 pm
BNA
-
SWF
2 stops16h 27m
Multiple Airlines
Deal found 2/2$295
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.
Thu 5/2110:28 am
SWF
-
BNA
1 stop10h 10m
Multiple Airlines
Sun 5/245:58 pm
BNA
-
SWF
1 stop13h 53m
Multiple Airlines
Deal found 2/3$296
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 2/267:22 pm
SWF
-
TYS
1 stop28h 14m
Allegiant Air
Thu 3/124:54 pm
TYS
-
SWF
1 stop16h 08m
Allegiant Air
Deal found 2/1$332
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 5/711:45 am
SWF
-
CVG
1 stop9h 24m
Allegiant Air
Sun 5/108:15 am
CVG
-
SWF
1 stop10h 42m
Allegiant Air
Deal found 2/1$340

Find flight deals from Stewart to Kentucky

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

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$213
(Kiwi.com)

One-way from

$98
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$283
Provider with most accurate pricing for New York (NYC)-Louisville Intl flight deals.
Provider most trusted by Cheapflights users for New York (NYC)-Louisville Intl flights.
From New Windsor Stewart to Kentucky
One-way flight from New Windsor Stewart to Kentucky
Highest demand for flights based on searches. 10% potential increase in price ($39 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Average for round-trip flights in February 2026

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 February 3, 2026.
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 3/23

12:11 pm-10:41 am

2 stops23h 30m

Nashville Intl

Wed 3/25

2:27 pm-9:39 am

1 stop18h 12m

$213

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Thu 5/21

10:28 am-7:38 pm

1 stop10h 10m

Nashville Intl

Wed 5/27

6:54 pm-9:38 am

1 stop13h 44m

$230

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Thu 2/26

11:52 am-7:48 pm

1 stop8h 56m

Nashville Intl

Sat 2/28

8:52 pm-11:02 am

1 stop13h 10m

$240

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Fri 5/8

11:45 am-11:20 pm

1 stop11h 35m

Cincinnati Cinci./N. Kentucky

Sun 5/10

5:20 pm-10:55 am

1 stop17h 35m

$259

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Thu 4/16

11:45 am-11:19 pm

1 stop12h 34m

Nashville Intl

Sat 4/18

6:54 pm-10:55 am

1 stop15h 01m

$259

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Wed 5/6

12:05 pm-10:47 pm

2 stops11h 42m

Nashville Intl

Sat 5/9

6:54 pm-10:55 am

1 stop15h 01m

$270

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Thu 6/11

10:28 am-7:35 pm

1 stop10h 07m

Nashville Intl

Tue 6/16

5:58 pm-11:25 am

2 stops16h 27m

$282

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Thu 6/4

10:28 am-7:35 pm

1 stop10h 07m

Nashville Intl

Tue 6/9

5:58 pm-11:25 am

2 stops16h 27m

$295

New WindsorNashville

SWF - BNA

SWFBNA

New Windsor Stewart

Thu 5/21

10:28 am-7:38 pm

1 stop10h 10m

Nashville Intl

Sun 5/24

5:58 pm-8:51 am

1 stop13h 53m

$296

New WindsorCincinnati

SWF - CVG

SWFCVG

New Windsor Stewart

Thu 5/7

11:45 am-9:09 pm

1 stop9h 24m

Cincinnati Cinci./N. Kentucky

Sun 5/10

8:15 am-6:57 pm

1 stop10h 42m

$340

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/31

Showing 1-10 of 60 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, June is the cheapest month in which you can book a flight from New Windsor to Kentucky (average of $60). Flying from New Windsor to Kentucky in December is currently the most expensive (average of $220). 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 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.

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

    Allegiant Air can get you from New Windsor to Kentucky in just under 9h 24m. Your travel time can differ by up to . There are 581 mi between New Windsor and Kentucky.

  • What are the most popular routes from New Windsor to Kentucky?

  • 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, June is the cheapest month in which you can book a flight from New Windsor to Kentucky (average of $60). Flying from New Windsor to Kentucky in December is currently the most expensive (average of $220). 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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