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Stewart

$167+ Cheap flights from Louisville to New Windsor (SDF - 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SWF
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap flight deals from Louisville to Stewart

Cheapest flights from Louisville to Stewart
Explore the most affordable flight options available from Louisville to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/53:53 pm
SDF
-
SWF
1 stop26h 53m
Allegiant Air
Mon 3/97:36 pm
SWF
-
SDF
1 stop20h 49m
Allegiant Air
Deal found 1/25$380
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/219:41 am
SDF
-
SWF
1 stop23h 10m
Allegiant Air
Thu 6/48:04 pm
SWF
-
SDF
1 stop17h 58m
Allegiant Air
Deal found 1/25$403
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/199:12 pm
SDF
-
SWF
2 stops14h 19m
Multiple Airlines
Mon 2/237:37 pm
SWF
-
SDF
1 stop20h 51m
Multiple Airlines
Deal found 1/26$411
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/119:23 pm
SDF
-
SWF
1 stop11h 26m
Multiple Airlines
Mon 6/1512:15 pm
SWF
-
SDF
2 stops8h 33m
Multiple Airlines
Deal found 1/24$414
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/199:12 pm
SDF
-
SWF
1 stop13h 02m
Allegiant Air
Mon 2/237:37 pm
SWF
-
SDF
1 stop20h 51m
Allegiant Air
Deal found 1/26$427
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:31 pm
SDF
-
SWF
1 stop12h 27m
Multiple Airlines
Thu 6/48:04 pm
SWF
-
SDF
1 stop17h 58m
Multiple Airlines
Deal found 1/25$441
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:28 pm
SDF
-
SWF
2 stops13h 57m
Multiple Airlines
Thu 6/48:04 pm
SWF
-
SDF
1 stop17h 58m
Multiple Airlines
Deal found 1/25$463
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:18 am
SDF
-
SWF
1 stop9h 33m
Allegiant Air
Thu 6/48:04 pm
SWF
-
SDF
1 stop17h 58m
Allegiant Air
Deal found 1/25$507
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/58:27 pm
SDF
-
SWF
1 stop20h 45m
Allegiant Air
Sun 2/810:48 am
SWF
-
SDF
1 stop23h 19m
Allegiant Air
Deal found 1/26$585
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/128:57 pm
SDF
-
SWF
1 stop13h 17m
Allegiant Air
Sun 2/1511:42 am
SWF
-
SDF
1 stop20h 58m
Allegiant Air
Deal found 1/25$594

Find flight deals from Louisville to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Louisville (SDF) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$380
(Kiwi.com)

One-way from

$167
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$278
Provider with most accurate pricing for Louisville Intl-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-New Windsor Stewart flights.
Search Deals
From Louisville Intl to New Windsor Stewart
Search Deals
One-way flight from Louisville Intl 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 ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Louisville 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 January 26, 2026.
Use the filters below to find and compare flights from Louisville to New Windsor that are best for you.

Fly from

Louisville

Fly to

Stewart

Route

Depart

Return

Price

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Thu 3/5

3:53 pm-6:46 pm

1 stop26h 53m

New Windsor Stewart

Mon 3/9

7:36 pm-4:25 pm

1 stop20h 49m

$380

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Thu 5/21

9:41 am-8:51 am

1 stop23h 10m

New Windsor Stewart

Thu 6/4

8:04 pm-2:02 pm

1 stop17h 58m

$403

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Thu 2/19

9:12 pm-11:31 am

2 stops14h 19m

New Windsor Stewart

Mon 2/23

7:37 pm-4:28 pm

1 stop20h 51m

$411

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Thu 6/11

9:23 pm-8:49 am

1 stop11h 26m

New Windsor Stewart

Mon 6/15

12:15 pm-8:48 pm

2 stops8h 33m

$414

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Thu 2/19

9:12 pm-10:14 am

1 stop13h 02m

New Windsor Stewart

Mon 2/23

7:37 pm-4:28 pm

1 stop20h 51m

$427

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Sat 5/23

8:31 pm-8:58 am

1 stop12h 27m

New Windsor Stewart

Thu 6/4

8:04 pm-2:02 pm

1 stop17h 58m

$441

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Fri 5/22

9:28 pm-11:25 am

2 stops13h 57m

New Windsor Stewart

Thu 6/4

8:04 pm-2:02 pm

1 stop17h 58m

$463

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Fri 5/22

9:18 am-6:51 pm

1 stop9h 33m

New Windsor Stewart

Thu 6/4

8:04 pm-2:02 pm

1 stop17h 58m

$507

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Thu 2/5

8:27 pm-5:12 pm

1 stop20h 45m

New Windsor Stewart

Sun 2/8

10:48 am-10:07 am

1 stop23h 19m

$585

LouisvilleNew Windsor

SDF - SWF

SDFSWF

Louisville Intl

Thu 2/12

8:57 pm-10:14 am

1 stop13h 17m

New Windsor Stewart

Sun 2/15

11:42 am-8:40 am

1 stop20h 58m

$594

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 19 results
1
2

Compare providers for flights from Louisville to Stewart

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Louisville to Stewart in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Louisville-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Louisville-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Louisville-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Louisville-New Windsor flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Louisville-New Windsor flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Louisville to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Louisville 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 Louisville to New Windsor

What is the cheapest month to book a flight from Louisville to New Windsor?

Currently, May is the cheapest month in which you can book a flight from Louisville to New Windsor (average of $71). Flying from Louisville to New Windsor in January is currently the most expensive (average of $139). 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 Louisville to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    For as low as $380, Allegiant Air can have you in New Windsor from Louisville in 26h 53m. Louisville and New Windsor are separated by a distance of 658 mi.

  • Can I find deals for flights from Louisville to Stewart that include hotel bookings?

    Yes. In addition to deals on Louisville to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Louisville to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Louisville to Stewart.

  • Can I find deals for business class flights from Louisville to Stewart?

    Yes. Cheapflights offers flight deals from Louisville 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 Louisville to New Windsor?

    Currently, May is the cheapest month in which you can book a flight from Louisville to New Windsor (average of $71). Flying from Louisville to New Windsor in January is currently the most expensive (average of $139). 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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