HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Westchester County

$184+ Cheap flights from Madison (MSN) to Westchester County

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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — HPN
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to Westchester County with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Madison to Westchester County

Keep the following information in mind while searching for Madison to Westchester County flight deals. Data was last updated August 18, 2025.

Round-trip from

$298
(Delta)

One-way from

$184
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$399
From Madison Truax Field to Westchester County
Search Deals
One-way flight from Madison Truax Field to Westchester County
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

Find flight deals from Madison to Westchester County

Cheapest flights from Madison to Westchester County
Explore the most affordable flight options available from Madison to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/271:20 pmMSN - HPN
1 stop7h 18mDelta
Tue 12/95:10 pmHPN - MSN
1 stop4h 34mDelta
Deal found 8/17$298
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/271:20 pmMSN - HPN
1 stop7h 18mDelta
Sun 12/76:00 amHPN - MSN
1 stop5h 15mDelta
Deal found 8/17$303
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/29:25 amMSN - HPN
1 stop6h 09mDelta
Tue 12/96:00 amHPN - MSN
1 stop5h 15mDelta
Deal found 8/17$319
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/271:20 pmMSN - HPN
1 stop7h 18mDelta
Wed 12/106:00 amHPN - MSN
1 stop5h 15mDelta
Deal found 8/17$322
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/83:47 pmMSN - HPN
1 stop6h 42mAmerican Airlines
Sun 10/126:00 amHPN - MSN
1 stop5h 15mAmerican Airlines
Deal found 8/17$324
This American Airlines deal was found by Cheapflights users on 8/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/272:14 pmMSN - HPN
1 stop6h 45mAmerican Airlines
Wed 10/2911:29 amHPN - MSN
1 stop4h 45mAmerican Airlines
Deal found 8/18$328
This Delta deal was found by Cheapflights users on 8/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/55:40 amMSN - HPN
1 stop7h 49mDelta
Mon 9/86:50 pmHPN - MSN
1 stop5h 12mDelta
Deal found 8/15$329
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/29:25 amMSN - HPN
1 stop6h 09mDelta
Wed 12/106:00 amHPN - MSN
1 stop5h 15mDelta
Deal found 8/17$343
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/271:20 pmMSN - HPN
1 stop7h 18mDelta
Fri 12/55:10 pmHPN - MSN
1 stop4h 34mDelta
Deal found 8/17$358
This American Airlines deal was found by Cheapflights users on 8/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/29:41 amMSN - HPN
1 stop5h 18mAmerican Airlines
Sat 9/64:30 pmHPN - MSN
1 stop4h 26mAmerican Airlines
Deal found 8/18$367
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/163:46 pmMSN - HPN
1 stop6h 43mAmerican Airlines
Sun 10/196:00 amHPN - MSN
1 stop5h 15mAmerican Airlines
Deal found 8/17$368

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Westchester County 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 August 18, 2025.
Use the filters below to find and compare flights from Madison to Westchester County that are best for you.

Fly from

Madison

Fly to

Westchester County

Route

Depart

Return

Price

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Thu 11/27

1:20 pm-9:38 pm

1 stop7h 18m

White Plains Westchester County

Tue 12/9

5:10 pm-8:44 pm

1 stop4h 34m

$298

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Thu 11/27

1:20 pm-9:38 pm

1 stop7h 18m

White Plains Westchester County

Sun 12/7

6:00 am-10:15 am

1 stop5h 15m

$303

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Thu 11/27

1:20 pm-9:38 pm

1 stop7h 18m

White Plains Westchester County

Sat 12/6

12:45 pm-4:36 pm

1 stop4h 51m

$303

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Tue 12/16

10:48 am-6:19 pm

1 stop6h 31m

White Plains Westchester County

Tue 1/6

6:08 pm-9:27 pm

1 stop4h 19m

$319

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Wed 12/3

7:00 am-11:46 am

1 stop3h 46m

White Plains Westchester County

Tue 12/9

12:45 pm-4:36 pm

1 stop4h 51m

$319

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Tue 12/2

9:25 am-4:34 pm

1 stop6h 09m

White Plains Westchester County

Tue 12/9

6:00 am-10:15 am

1 stop5h 15m

$319

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Thu 11/27

1:20 pm-9:38 pm

1 stop7h 18m

White Plains Westchester County

Wed 12/10

6:00 am-10:15 am

1 stop5h 15m

$322

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Wed 10/8

3:47 pm-11:29 pm

1 stop6h 42m

White Plains Westchester County

Sun 10/12

6:00 am-10:15 am

1 stop5h 15m

$324

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Wed 12/3

7:00 am-11:46 am

1 stop3h 46m

White Plains Westchester County

Sat 12/6

6:00 am-12:35 pm

1 stop7h 35m

$324

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Tue 12/2

9:25 am-4:34 pm

1 stop6h 09m

White Plains Westchester County

Sun 12/7

6:00 am-10:15 am

1 stop5h 15m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 17 results
1
2

Best time to book a flight from Madison to Westchester County

Have a flexible travel schedule? Discover the best time to fly to Westchester County from Madison 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 Madison to Westchester County

What is the cheapest month to book a flight from Madison to Westchester County?

Currently, January is the cheapest month in which you can book a flight from Madison to Westchester County (average of $276). Flying from Madison to Westchester County in March is currently the most expensive (average of $339). 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.

Reviews of airlines servicing Westchester County

Get insights into the airlines that provide service to Westchester County. 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 Westchester County. Reviews last updated August 18, 2025.
Peruse reviews from past customers who have flown with Delta and American Airlines from Madison to Westchester County to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!

Related info for your journey

Find useful and relevant information for your journey from Madison to Westchester County. 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 Madison to Westchester County?

    Madison Truax Field (MSN) is the airport you will fly out of if you book a flight from Madison to Westchester County. It is only a 5.4 mi journey to Truax Field (MSN) from Madison’s city center.

  • How long is the flight from Madison to Westchester County?

    For as low as $298, Delta can have you in Westchester County from Madison in 7h 18m. The distance from Madison to Westchester County is about 812 mi.

  • Can I find deals for flights from Madison to Westchester County that include hotel bookings?

    Yes. In addition to deals on Madison to Westchester County flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Westchester County?

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

  • Can I find deals for business class flights from Madison to Westchester County?

    Yes. Cheapflights offers flight deals from Madison to Westchester County 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 Madison to Westchester County?

    Currently, January is the cheapest month in which you can book a flight from Madison to Westchester County (average of $276). Flying from Madison to Westchester County in March is currently the most expensive (average of $339). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Westchester County

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
Minneapolis to John F Kennedy Intl flights
Minneapolis to LaGuardia flights
Minneapolis to Newark flights
Milwaukee to LaGuardia flights
Milwaukee to John F Kennedy Intl flights
Milwaukee to Newark flights
Madison to LaGuardia flights
Madison to Newark flights
Madison to John F Kennedy Intl flights
O'Hare Intl to Buffalo flights
O'Hare Intl to Albany flights
O'Hare Intl to Syracuse flights
O'Hare Intl to White Plains flights
O'Hare Intl to Rochester flights
Minneapolis to Buffalo flights
Appleton to John F Kennedy Intl flights
Appleton to Newark flights
Appleton to LaGuardia flights
Minneapolis to Syracuse flights
Green Bay to LaGuardia flights
O'Hare Intl to Stewart flights
Green Bay to Newark flights
Minneapolis to Albany flights
Green Bay to John F Kennedy Intl flights
Milwaukee to Buffalo flights
Minneapolis to Rochester flights
Minneapolis to White Plains flights
Madison to White Plains flights
Madison to Albany flights
Appleton to Buffalo flights
Duluth to LaGuardia flights
Milwaukee to White Plains flights
Milwaukee to Albany flights
Appleton to Syracuse flights
Green Bay to Buffalo flights
Eau Claire to Newark flights
O'Hare Intl to Islip flights
Duluth to John F Kennedy Intl flights
O'Hare Intl to Plattsburgh flights
Milwaukee to Syracuse flights
Madison to Buffalo flights
Green Bay to Albany flights
O'Hare Intl to Ithaca flights
Duluth to Newark flights
Madison to Rochester flights
Wausau to Newark flights
Escanaba to LaGuardia flights

Top 2 airlines flying from Madison to Westchester County

Discover the top 2 airlines that operate flights from Madison to Westchester County. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$258Average$532FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$296Average$378FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.