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$212+ Cheap flights from New Windsor to Lexington (SWF - LEX)

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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — LEX
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Stewart to Lexington

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Lexington (LEX). 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$337
(Kiwi.com)

One-way from

$212
(Kiwi.com)

Popular in

October

Cheapest in

January

Average price

$512
Provider with most accurate pricing for New Windsor Stewart-Lexington Blue Grass flight deals.
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Provider most trusted by Cheapflights users for New Windsor Stewart-Lexington Blue Grass flights.
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From New Windsor Stewart to Lexington Blue Grass
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One-way flight from New Windsor Stewart to Lexington Blue Grass
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Highest demand for flights based on searches. 7% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Stewart to Lexington

Cheapest flights from Stewart to Lexington
Explore the most affordable flight options available from Stewart to Lexington. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/125:44 pmSWF - LEX
1 stop17h 27mAllegiant Air
Mon 12/159:01 amLEX - SWF
1 stop7h 29mAllegiant Air
Deal found 10/30$337
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:28 pmSWF - LEX
1 stop14h 42mAllegiant Air
Tue 12/309:23 pmLEX - SWF
1 stop19h 21mAllegiant Air
Deal found 10/29$362
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:50 pmSWF - LEX
1 stop12h 20mAllegiant Air
Tue 12/309:23 pmLEX - SWF
1 stop19h 21mAllegiant Air
Deal found 10/29$376
This Mytrip deal was found by Cheapflights users on 10/30. 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.
Sat 12/207:50 pmSWF - LEX
1 stop12h 20mAllegiant Air
Sun 12/289:48 pmLEX - SWF
1 stop14h 14mAllegiant Air
Deal found 10/30$423
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/267:25 pmSWF - LEX
1 stop19h 57mAllegiant Air
Thu 12/49:22 pmLEX - SWF
1 stop21h 18mAllegiant Air
Deal found 10/30$430
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/125:44 pmSWF - LEX
1 stop17h 27mAllegiant Air
Fri 12/199:09 amLEX - SWF
1 stop7h 29mAllegiant Air
Deal found 10/28$435
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/216:28 pmSWF - LEX
2 stops44h 04mMultiple Airlines
Tue 12/309:23 pmLEX - SWF
1 stop19h 21mMultiple Airlines
Deal found 10/29$473
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/198:11 pmSWF - LEX
1 stop19h 06mAllegiant Air
Sun 12/289:48 pmLEX - SWF
1 stop14h 14mAllegiant Air
Deal found 10/29$475
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:28 pmSWF - LEX
1 stop14h 42mAllegiant Air
Sun 12/289:48 pmLEX - SWF
1 stop14h 14mAllegiant Air
Deal found 10/29$486
This Mytrip deal was found by Cheapflights users on 10/27. 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.
Sun 11/2311:06 amSWF - LEX
1 stop8h 45mAllegiant Air
Fri 12/199:09 amLEX - SWF
1 stop7h 29mAllegiant Air
Deal found 10/27$511
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/234:50 pmSWF - LEX
1 stop27h 05mAllegiant Air
Tue 12/309:23 pmLEX - SWF
1 stop19h 21mAllegiant Air
Deal found 10/29$531

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Lexington 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 October 30, 2025.
Use the filters below to find and compare flights from New Windsor to Lexington that are best for you.

Fly from

Stewart

Fly to

Lexington

Route

Depart

Return

Price

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

Mon 12/22

5:28 pm-8:10 am

1 stop14h 42m

Lexington Blue Grass

Tue 12/30

9:23 pm-4:44 pm

1 stop19h 21m

$362

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

Sat 12/20

7:50 pm-8:10 am

1 stop12h 20m

Lexington Blue Grass

Tue 12/30

9:23 pm-4:44 pm

1 stop19h 21m

$376

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

Wed 11/26

7:25 pm-3:22 pm

1 stop19h 57m

Lexington Blue Grass

Thu 12/4

9:22 pm-6:40 pm

1 stop21h 18m

$430

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

Fri 12/12

5:44 pm-11:11 am

1 stop17h 27m

Lexington Blue Grass

Fri 12/19

9:09 am-4:38 pm

1 stop7h 29m

$435

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

Sun 12/21

6:28 pm-2:32 pm

2 stops44h 04m

Lexington Blue Grass

Tue 12/30

9:23 pm-4:44 pm

1 stop19h 21m

$473

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

Fri 12/19

8:11 pm-3:17 pm

1 stop19h 06m

Lexington Blue Grass

Sun 12/28

9:48 pm-12:02 pm

1 stop14h 14m

$475

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

Mon 12/22

5:28 pm-8:10 am

1 stop14h 42m

Lexington Blue Grass

Sun 12/28

9:48 pm-12:02 pm

1 stop14h 14m

$486

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

Sun 11/23

11:06 am-7:51 pm

1 stop8h 45m

Lexington Blue Grass

Fri 12/19

9:09 am-4:38 pm

1 stop7h 29m

$511

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

Tue 12/23

4:50 pm-7:55 pm

1 stop27h 05m

Lexington Blue Grass

Tue 12/30

9:23 pm-4:44 pm

1 stop19h 21m

$531

New WindsorLexington

SWF - LEX

SWFLEX

New Windsor Stewart

Fri 11/21

7:28 pm-12:12 pm

1 stop16h 44m

Lexington Blue Grass

Sat 11/29

3:53 pm-9:22 am

1 stop17h 29m

$546

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 16 results
1
2

Compare providers for flights from Stewart to Lexington

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 Stewart to Lexington in October.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 New Windsor-Lexington flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on New Windsor-Lexington flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from New Windsor-Lexington flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Lexington flights, Cheapflights users trust eDreams the most. eDreams 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 New Windsor-Lexington 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 Stewart to Lexington

Have a flexible travel schedule? Discover the best time to fly to Lexington 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 Lexington

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

Currently, January is the cheapest month in which you can book a flight from New Windsor to Lexington (average of $46). Flying from New Windsor to Lexington in September is currently the most expensive (average of $152). 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 Lexington. 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 New Windsor to Lexington?

    For as low as $362, Allegiant Air can have you in Lexington from New Windsor in 14h 42m. Airlines will cover a distance of 606 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Stewart to Lexington 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 Lexington?

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Lexington (average of $46). Flying from New Windsor to Lexington in September is currently the most expensive (average of $152). 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 Lexington?

Book flights to Lexington if you plan to visit one of these locations
Georgetown
Berea
Frankfort

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