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Westchester County

$164+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — HPN
Apr 30 — May 71
Thu 4/30
Thu 5/7
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 March 31, 2026.

This American Airlines deal was found by Cheapflights users on 3/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:00 am
MSN
-
HPN
1 stop5h 29m
American Airlines
Tue 5/196:57 pm
HPN
-
MSN
1 stop4h 59m
American Airlines
Deal found 3/27$327
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Wed 5/66:05 pm
MSN
-
HPN
2 stops16h 22m
Breeze Airways
Sun 5/178:00 am
HPN
-
MSN
1 stop25h 25m
Breeze Airways
Deal found 3/28$365
This Delta deal was found by Cheapflights users on 3/26. 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 9/59:00 am
MSN
-
HPN
1 stop6h 40m
Delta
Tue 9/85:10 pm
HPN
-
MSN
1 stop4h 30m
Delta
Deal found 3/26$387
This American Airlines deal was found by Cheapflights users on 3/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/264:34 pm
MSN
-
HPN
1 stop5h 52m
American Airlines
Mon 6/295:29 pm
HPN
-
MSN
1 stop6h 50m
American Airlines
Deal found 3/27$396
This American Airlines deal was found by Cheapflights users on 3/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/62:18 pm
MSN
-
HPN
1 stop6h 41m
American Airlines
Sun 5/176:30 am
HPN
-
MSN
1 stop5h 44m
American Airlines
Deal found 3/28$397
This Delta deal was found by Cheapflights users on 3/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/159:29 am
MSN
-
HPN
1 stop5h 20m
Delta
Sat 5/166:00 am
HPN
-
MSN
1 stop5h 16m
Delta
Deal found 3/27$423
This American Airlines deal was found by Cheapflights users on 3/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/49:52 am
MSN
-
HPN
1 stop5h 07m
American Airlines
Tue 4/76:57 pm
HPN
-
MSN
1 stop5h 04m
American Airlines
Deal found 3/28$425
This Delta deal was found by Cheapflights users on 3/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/47:00 am
MSN
-
HPN
1 stop3h 43m
Delta
Thu 4/96:00 am
HPN
-
MSN
1 stop5h 31m
Delta
Deal found 3/28$463
This Delta deal was found by Cheapflights users on 3/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/211:26 am
MSN
-
HPN
1 stop5h 52m
Delta
Tue 4/76:00 am
HPN
-
MSN
1 stop5h 31m
Delta
Deal found 3/28$489
This Delta deal was found by Cheapflights users on 3/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:43 am
MSN
-
HPN
1 stop7h 46m
Delta
Sat 5/166:00 am
HPN
-
MSN
1 stop5h 16m
Delta
Deal found 3/27$491

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 March 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$327
(American Airlines)

Popular in

March

Cheapest in

January

Average price

$448
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.
Search Deals
From Madison Truax Field to Westchester County
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 31, 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
Quickest round-trip

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Sat 5/16

5:00 am-11:29 am

1 stop5h 29m

White Plains Westchester County

Tue 5/19

6:57 pm-10:56 pm

1 stop4h 59m

$327

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Sat 9/5

9:00 am-4:40 pm

1 stop6h 40m

White Plains Westchester County

Tue 9/8

5:10 pm-8:40 pm

1 stop4h 30m

$387

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Fri 6/26

4:34 pm-11:26 pm

1 stop5h 52m

White Plains Westchester County

Mon 6/29

5:29 pm-11:19 pm

1 stop6h 50m

$396

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Fri 5/15

9:29 am-3:49 pm

1 stop5h 20m

White Plains Westchester County

Sat 5/16

6:00 am-10:16 am

1 stop5h 16m

$423

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Thu 5/14

5:43 am-2:29 pm

1 stop7h 46m

White Plains Westchester County

Sat 5/16

6:00 am-10:16 am

1 stop5h 16m

$491

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Fri 5/15

6:29 pm-11:50 am

2 stops16h 21m

White Plains Westchester County

Sun 5/17

12:30 pm-5:26 pm

1 stop5h 56m

$646

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Fri 5/15

6:29 pm-11:50 am

2 stops16h 21m

White Plains Westchester County

Mon 5/18

12:30 pm-5:26 pm

1 stop5h 56m

$646
Cheapest one-way
Quickest one-way

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Sat 4/25

2:18 pm-9:59 pm

1 stop6h 41m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

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, 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 December is currently the most expensive (average of $335). 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 March 31, 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
7.9
Good
8,364 reviews

Comfort

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

7.9

Boarding

8.1

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
8,364 reviews
Delta
7.9
Good
8,364 reviews

Comfort

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

7.9

Boarding

8.1

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
11,543 reviews
Delta
7.9
Good
8,364 reviews

Comfort

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

7.9

Boarding

8.1

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 $327, American Airlines can have you in Westchester County from Madison in 5h 29m. 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 December is currently the most expensive (average of $335). 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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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 March 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$258Average$394FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$323Average$385FlexibilityNo cancel feeOn-time71%

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