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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 11/28. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — HPN
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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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 November 6, 2025.

This American Airlines deal was found by Cheapflights users on 11/6. 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.
Fri 11/214:32 pmMSN - HPN
1 stop5h 57mAmerican Airlines
Tue 11/256:00 amHPN - MSN
1 stop4h 24mAmerican Airlines
Deal found 11/6$386
This Delta deal was found by Cheapflights users on 11/5. 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 11/125:29 amMSN - HPN
1 stop5h 31mDelta
Thu 11/136:00 amHPN - MSN
1 stop5h 38mDelta
Deal found 11/5$413
This Delta deal was found by Cheapflights users on 11/6. 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 12/66:59 amMSN - HPN
1 stop4h 00mDelta
Wed 12/106:10 amHPN - MSN
1 stop5h 49mDelta
Deal found 11/6$428
This Delta deal was found by Cheapflights users on 11/5. 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 12/911:44 amMSN - HPN
1 stop5h 16mDelta
Thu 12/116:10 amHPN - MSN
1 stop5h 49mDelta
Deal found 11/5$468
This Delta deal was found by Cheapflights users on 11/4. 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 11/205:29 amMSN - HPN
1 stop5h 31mDelta
Sun 11/234:29 pmHPN - MSN
1 stop7h 03mDelta
Deal found 11/4$501
This American Airlines deal was found by Cheapflights users on 11/6. 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.
Sat 12/67:00 amMSN - HPN
2 stops10h 17mAmerican Airlines
Wed 12/105:19 pmHPN - MSN
1 stop5h 37mAmerican Airlines
Deal found 11/6$531
This Delta deal was found by Cheapflights users on 11/5. 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.
Sun 11/95:29 amMSN - HPN
1 stop5h 31mDelta
Sun 11/95:14 pmHPN - MSN
1 stop4h 12mDelta
Deal found 11/5$587
This Delta deal was found by Cheapflights users on 11/4. 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 12/410:55 amMSN - HPN
1 stop4h 42mDelta
Thu 12/116:10 amHPN - MSN
1 stop5h 49mDelta
Deal found 11/4$610
This American Airlines deal was found by Cheapflights users on 11/4. 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 11/233:37 pmMSN - HPN
1 stop6h 10mAmerican Airlines
Mon 12/15:21 pmHPN - MSN
1 stop6h 03mAmerican Airlines
Deal found 11/4$676
This Delta deal was found by Cheapflights users on 11/5. 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 11/136:59 amMSN - HPN
1 stop4h 00mDelta
Thu 11/135:14 pmHPN - MSN
1 stop4h 12mDelta
Deal found 11/5$811

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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$305
(American Airlines)

One-way from

$154
(Delta)

Popular in

March

Cheapest in

February

Average price

$381
Provider with most accurate pricing for Madison Truax Field-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-New York (NYC) flights.
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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 ($33 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 November 2025
Search Deals

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 November 6, 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

Wed 1/7

10:41 am-6:08 pm

1 stop6h 27m

White Plains Westchester County

Sun 1/11

5:15 pm-10:40 pm

1 stop6h 25m

$305

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Tue 3/10

10:55 am-4:40 pm

1 stop4h 45m

White Plains Westchester County

Thu 3/12

3:15 pm-10:08 pm

1 stop7h 53m

$307

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Tue 3/10

10:55 am-4:40 pm

1 stop4h 45m

White Plains Westchester County

Sat 3/14

3:15 pm-10:08 pm

1 stop7h 53m

$333

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Fri 11/21

4:32 pm-11:29 pm

1 stop5h 57m

White Plains Westchester County

Tue 11/25

6:00 am-9:24 am

1 stop4h 24m

$386

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Sat 12/6

6:59 am-11:59 am

1 stop4h 00m

White Plains Westchester County

Wed 12/10

6:10 am-10:59 am

1 stop5h 49m

$428

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Thu 1/8

7:00 am-11:56 am

1 stop3h 56m

White Plains Westchester County

Sun 1/18

3:10 pm-10:19 am

1 stop20h 09m

$457

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Fri 1/9

7:00 am-11:56 am

1 stop3h 56m

White Plains Westchester County

Sun 1/18

3:10 pm-10:19 am

1 stop20h 09m

$457

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Fri 11/28

5:40 am-2:28 pm

1 stop7h 48m

$154

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Thu 11/20

5:29 am-12:00 pm

1 stop5h 31m

$183

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Sun 11/23

6:59 am-11:59 am

1 stop4h 00m

$183

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

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, April is the cheapest month in which you can book a flight from Madison to Westchester County (average of $148). Flying from Madison to Westchester County in February is currently the most expensive (average of $378). 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 November 6, 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
7.9
Good
8,001 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
Delta
7.9
Good
8,001 reviews
Delta
7.9
Good
8,001 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Food

7.3

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
11,040 reviews
Delta
7.9
Good
8,001 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Food

7.3

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, American Airlines can have you in Westchester County from Madison in 4h 45m. The distance from Madison to Westchester County is about 812 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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, April is the cheapest month in which you can book a flight from Madison to Westchester County (average of $148). Flying from Madison to Westchester County in February is currently the most expensive (average of $378). 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$258Average$562FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$326Average$516FlexibilityNo cancel feeOn-time71%

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