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Westchester County

$328+ 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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — HPN
Aug 10 — Aug 171
Mon 8/10
Mon 8/17
1 adult, Economy
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Cheap 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 July 11, 2026.

This American Airlines deal was found by Cheapflights users on 7/8. 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 8/63:54 pm
MSN
-
HPN
1 stop6h 35m
American Airlines
Tue 8/116:30 am
HPN
-
MSN
1 stop6h 38m
American Airlines
Deal found 7/8$347
This American Airlines deal was found by Cheapflights users on 7/8. 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 7/239:18 am
MSN
-
HPN
1 stop6h 57m
American Airlines
Mon 7/275:26 pm
HPN
-
MSN
1 stop6h 53m
American Airlines
Deal found 7/8$415
This American Airlines deal was found by Cheapflights users on 7/9. 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 9/183:25 pm
MSN
-
HPN
2 stops7h 01m
American Airlines
Mon 9/285:23 pm
HPN
-
MSN
2 stops7h 54m
American Airlines
Deal found 7/9$423
This American Airlines deal was found by Cheapflights users on 7/8. 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 10/86:06 am
MSN
-
HPN
1 stop7h 40m
American Airlines
Sun 10/116:30 am
HPN
-
MSN
1 stop6h 24m
American Airlines
Deal found 7/8$447

Find 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 July 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$347
(American Airlines)

One-way from

$328
(Delta)

Popular in

June

Cheapest in

January

Average price

$439
Provider with most accurate pricing for Madison Truax Field-New York (NYC) flight deals.
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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
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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. 10% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in July 2026
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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 July 11, 2026.
Use the filters below to find and compare flights from Madison to Westchester County that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Fri 9/18

4:23 pm-11:26 pm

1 stop6h 03m

White Plains Westchester County

Mon 9/28

6:00 am-12:26 pm

1 stop7h 26m

$347
Quickest round-trip

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Thu 12/10

6:16 am-11:29 am

1 stop4h 13m

White Plains Westchester County

Mon 12/14

12:19 pm-6:35 pm

1 stop7h 16m

$347

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Thu 8/6

3:54 pm-11:29 pm

1 stop6h 35m

White Plains Westchester County

Tue 8/11

6:30 am-12:08 pm

1 stop6h 38m

$347
Cheapest one-way
Quickest one-way

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Sun 9/6

7:03 am-11:56 am

1 stop3h 53m

$328

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Sun 9/6

12:38 pm-6:28 pm

1 stop4h 50m

$328

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Wed 9/2

12:38 pm-6:21 pm

1 stop4h 43m

$328

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Mon 9/7

9:48 am-3:46 pm

1 stop4h 58m

$328

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Sat 7/18

5:48 am-12:08 pm

1 stop5h 20m

$388

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/6

Sorted by cheapest first

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, December is the cheapest month in which you can book a flight from Madison to Westchester County (average of $306). Flying from Madison to Westchester County in August is currently the most expensive (average of $407). 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 July 11, 2026.
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
7.8
Good
8,457 reviews

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Food

7.2

Crew

8.5

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
Delta
7.8
Good
8,457 reviews
Delta
7.8
Good
8,457 reviews

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Food

7.2

Crew

8.5

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
American Airlines
7.1
Good
11,806 reviews
Delta
7.8
Good
8,457 reviews

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Food

7.2

Crew

8.5

Overall

7.8

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 $347, American Airlines can have you in Westchester County from Madison in 6h 03m. 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, December is the cheapest month in which you can book a flight from Madison to Westchester County (average of $306). Flying from Madison to Westchester County in August is currently the most expensive (average of $407). 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

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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 July 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$323Average$405FlexibilityNo cancel feeOn-time71%
DeltaCheapest$324Average$394FlexibilityNo cancel feeOn-timeN/A

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