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Westchester County

$154+ 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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — HPN
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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 September 15, 2025.

Round-trip from

$307
(Delta)

One-way from

$154
(Delta)

Popular in

March

Cheapest in

November

Average price

$399
From Madison Truax Field to Westchester County
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One-way flight from Madison Truax Field to Westchester County
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Highest demand for flights based on searches. 6% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 15, 2025.

This Delta deal was found by Cheapflights users on 9/15. 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.
Sat 11/111:00 amMSN - HPN
1 stop4h 38mDelta
Mon 11/35:20 pmHPN - MSN
1 stop4h 01mDelta
Deal found 9/15$307
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/1611:55 amMSN - HPN
1 stop4h 32mAmerican Airlines
Sun 10/196:00 amHPN - MSN
1 stop5h 15mAmerican Airlines
Deal found 9/14$355
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 9/305:40 amMSN - HPN
1 stop7h 49mDelta
Sat 10/44:29 pmHPN - MSN
1 stop7h 29mDelta
Deal found 9/15$365
This Delta deal was found by Cheapflights users on 9/14. 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 12/1110:55 amMSN - HPN
1 stop4h 42mDelta
Tue 12/166:00 amHPN - MSN
1 stop5h 40mDelta
Deal found 9/14$392
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/126:00 amMSN - HPN
1 stop4h 29mAmerican Airlines
Fri 10/176:59 pmHPN - MSN
1 stop5h 52mAmerican Airlines
Deal found 9/15$402
This Delta deal was found by Cheapflights users on 9/15. 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.
Sat 10/1110:58 amMSN - HPN
1 stop4h 40mDelta
Mon 10/205:20 pmHPN - MSN
1 stop16h 20mDelta
Deal found 9/15$421
This Delta deal was found by Cheapflights users on 9/15. 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.
Sat 10/115:30 amMSN - HPN
1 stop7h 59mDelta
Sat 10/186:40 pmHPN - MSN
2 stops15h 00mDelta
Deal found 9/15$426
This Delta deal was found by Cheapflights users on 9/15. 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.
Sat 10/115:30 amMSN - HPN
1 stop7h 59mDelta
Fri 10/176:40 pmHPN - MSN
2 stops16h 38mDelta
Deal found 9/15$432
This Delta deal was found by Cheapflights users on 9/15. 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.
Wed 10/155:30 amMSN - HPN
1 stop5h 30mDelta
Fri 10/176:40 pmHPN - MSN
1 stop5h 05mDelta
Deal found 9/15$439
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 10/149:20 amMSN - HPN
1 stop25h 39mDelta
Sat 10/186:00 amHPN - MSN
1 stop7h 26mDelta
Deal found 9/15$441
This Delta deal was found by Cheapflights users on 9/15. 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.
Wed 10/155:30 amMSN - HPN
1 stop5h 30mDelta
Wed 10/156:40 pmHPN - MSN
1 stop5h 05mDelta
Deal found 9/15$469
This Delta deal was found by Cheapflights users on 9/15. 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.
Sat 10/117:00 amMSN - HPN
2 stops14h 09mDelta
Tue 10/146:00 amHPN - MSN
1 stop5h 32mDelta
Deal found 9/15$471

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 September 15, 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

Sat 12/13

10:55 am-4:37 pm

1 stop4h 42m

White Plains Westchester County

Mon 12/15

6:00 am-10:40 am

1 stop5h 40m

$307

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Sat 11/1

4:29 pm-10:52 pm

1 stop5h 23m

White Plains Westchester County

Sun 11/2

5:59 pm-11:58 pm

1 stop6h 59m

$307

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Sat 12/13

1:30 pm-10:08 pm

1 stop7h 38m

White Plains Westchester County

Tue 12/16

5:17 pm-8:30 pm

1 stop4h 13m

$307

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Sat 10/11

10:58 am-4:38 pm

1 stop4h 40m

White Plains Westchester County

Tue 10/14

6:00 am-10:32 am

1 stop5h 32m

$307

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Sat 11/1

7:00 am-11:59 am

1 stop3h 59m

White Plains Westchester County

Mon 11/3

12:55 pm-4:36 pm

1 stop4h 41m

$307

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Fri 12/12

10:55 am-4:37 pm

1 stop4h 42m

White Plains Westchester County

Sun 12/14

6:00 am-10:40 am

1 stop5h 40m

$307

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Fri 12/12

10:55 am-4:37 pm

1 stop4h 42m

White Plains Westchester County

Tue 12/16

6:00 am-10:40 am

1 stop5h 40m

$307

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Sat 12/13

10:55 am-4:37 pm

1 stop4h 42m

White Plains Westchester County

Sun 12/14

6:00 am-10:40 am

1 stop5h 40m

$307

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Thu 10/16

11:55 am-5:27 pm

1 stop4h 32m

White Plains Westchester County

Sun 10/19

6:00 am-10:15 am

1 stop5h 15m

$355

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Fri 10/17

2:14 pm-9:59 pm

1 stop6h 45m

White Plains Westchester County

Sun 10/19

6:00 am-10:15 am

1 stop5h 15m

$355

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 21 results
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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 $338). 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 September 15, 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
7,954 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

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
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

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
7,954 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

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 $307, Delta can have you in Westchester County from Madison in 4h 42m. 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 $338). 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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Alternative routes for Madison to Westchester County

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$258Average$532FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$296Average$388FlexibilityNo cancel feeOn-time71%

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