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Madison

$154+ Cheap flights from Westchester County to Madison (MSN)

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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MSN
Jan 20 — Jan 271
Tue 1/20
Tue 1/27
1 adult, Economy
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Cheap flight deals from Westchester County to Madison

Cheapest flights from Westchester County to Madison
Explore the most affordable flight options available from Westchester County to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 21, 2025.

This Delta deal was found by Cheapflights users on 12/19. 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 12/263:15 pmHPN - MSN
1 stop7h 54mDelta
Fri 1/29:45 amMSN - HPN
1 stop5h 04mDelta
Deal found 12/19$743
This American Airlines deal was found by Cheapflights users on 12/18. 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.
Sat 12/2712:00 pmHPN - MSN
1 stop8h 40mAmerican Airlines
Sun 12/288:10 pmMSN - HPN
1 stop14h 19mAmerican Airlines
Deal found 12/18$810
This Delta deal was found by Cheapflights users on 12/19. 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.
Mon 12/224:29 pmHPN - MSN
1 stop5h 52mDelta
Tue 12/2310:50 amMSN - HPN
1 stop4h 46mDelta
Deal found 12/19$939
This American Airlines deal was found by Cheapflights users on 12/19. 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 12/2311:04 amHPN - MSN
1 stop5h 17mAmerican Airlines
Tue 12/238:10 pmMSN - HPN
1 stop18h 49mAmerican Airlines
Deal found 12/19$1,011

Find flight deals from Westchester County to Madison

Keep the following information in mind while searching for Westchester County to Madison flight deals. Data was last updated December 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$307
(American Airlines)

One-way from

$154
(American Airlines)

Popular in

August

Cheapest in

February

Average price

$471
Provider with most accurate pricing for New York (NYC)-Madison Truax Field flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Madison Truax Field flights.
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From Westchester County to Madison Truax Field
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One-way flight from Westchester County to Madison Truax Field
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Highest demand for flights based on searches. 4% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County to Madison 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 December 21, 2025.
Use the filters below to find and compare flights from Westchester County to Madison that are best for you.

Fly from

Westchester County

Fly to

Madison

Route

Depart

Return

Price

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Thu 2/12

11:00 am-3:30 pm

1 stop5h 30m

Madison Truax Field

Sun 2/15

6:00 am-2:30 pm

1 stop7h 30m

$307

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Fri 2/20

3:00 pm-9:44 pm

1 stop7h 44m

Madison Truax Field

Mon 2/23

10:45 am-6:25 pm

1 stop6h 40m

$307

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Fri 2/20

3:00 pm-9:44 pm

1 stop7h 44m

Madison Truax Field

Sun 2/22

2:55 pm-9:59 pm

1 stop6h 04m

$307

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Thu 5/28

3:15 pm-9:57 pm

1 stop7h 42m

Madison Truax Field

Sun 5/31

5:45 am-12:14 pm

1 stop5h 29m

$393

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Fri 1/2

3:15 pm-10:09 pm

1 stop7h 54m

Madison Truax Field

Sun 1/4

7:00 am-11:59 am

1 stop3h 59m

$413

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Thu 5/7

11:12 am-3:52 pm

1 stop5h 40m

Madison Truax Field

Sun 5/10

5:09 am-11:12 am

1 stop5h 03m

$622

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Thu 2/26

12:36 pm-4:59 pm

1 stop5h 23m

Madison Truax Field

Sun 3/1

10:59 am-4:32 pm

1 stop4h 33m

$662

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Wed 1/14

6:30 am-10:11 am

1 stop4h 41m

$154

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Thu 3/26

6:30 am-10:06 am

1 stop4h 36m

$234

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Fri 1/2

5:16 pm-8:45 pm

1 stop4h 29m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

Showing 1-10 of 14 results
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Best time to book a flight from Westchester County to Madison

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

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

Currently, March is the cheapest month in which you can book a flight from Westchester County to Madison (average of $164). Flying from Westchester County to Madison in January is currently the most expensive (average of $480). 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 Madison

Get insights into the airlines that provide service to Madison. 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 Madison. Reviews last updated December 21, 2025.
Get a feel of what it's like to fly with American Airlines from Westchester County to Madison by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,050 reviews

Overall

7.2

Comfort

7.2

Crew

8.0

Entertainment

6.9

Food

6.5

Boarding

7.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,050 reviews
American Airlines
7.2
Good
11,050 reviews

Overall

7.2

Comfort

7.2

Crew

8.0

Entertainment

6.9

Food

6.5

Boarding

7.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

Related info for your journey

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

    For a flight from Westchester County to Madison, you will be flying into Truax Field. Madison Truax Field (MSN) is just 5.4 mi from the center of the city.

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

    Airlines like American Airlines and Delta fly from Westchester County to Madison in about 7h 42m. The time it takes to get you to your destination can typically vary by up to 02m. The distance between Westchester County and Madison is about 812 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

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

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

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

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

    Currently, March is the cheapest month in which you can book a flight from Westchester County to Madison (average of $164). Flying from Westchester County to Madison in January is currently the most expensive (average of $480). 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

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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Alternative routes for Westchester County to Madison

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Westchester County to Madison

Discover the top airline that operate flights from Westchester County to Madison. 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 December 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$328Average$485FlexibilityNo cancel feeOn-time71%

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