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Madison

$327+ Cheap flights from Westchester County to Madison (MSN)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/20. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MSN
May 1 — May 81
Fri 5/1
Fri 5/8
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 April 1, 2026.

This American Airlines deal was found by Cheapflights users on 3/30. 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.
Mon 4/205:16 pm
HPN
-
MSN
1 stop5h 36m
American Airlines
Tue 4/2110:19 am
MSN
-
HPN
1 stop4h 29m
American Airlines
Deal found 3/30$327
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Mon 6/16:59 pm
HPN
-
MSN
1 stop6h 00m
American Airlines
Fri 6/54:34 pm
MSN
-
HPN
1 stop5h 52m
American Airlines
Deal found 3/30$376
This Delta deal was found by Cheapflights users on 3/31. 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 5/235:15 pm
HPN
-
MSN
1 stop4h 34m
Delta
Mon 5/257:00 am
MSN
-
HPN
1 stop3h 51m
Delta
Deal found 3/31$383
This American Airlines deal was found by Cheapflights users on 3/30. 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 4/145:16 pm
HPN
-
MSN
1 stop5h 36m
American Airlines
Sat 4/1810:19 am
MSN
-
HPN
1 stop4h 29m
American Airlines
Deal found 3/30$385
This American Airlines deal was found by Cheapflights users on 3/30. 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 5/235:59 pm
HPN
-
MSN
1 stop7h 00m
American Airlines
Mon 5/255:38 pm
MSN
-
HPN
1 stop4h 48m
American Airlines
Deal found 3/30$387
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.
Sun 6/76:59 pm
HPN
-
MSN
1 stop6h 00m
American Airlines
Thu 6/184:34 pm
MSN
-
HPN
1 stop5h 52m
American Airlines
Deal found 3/28$396
This American Airlines deal was found by Cheapflights users on 3/31. 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 5/85:59 pm
HPN
-
MSN
1 stop6h 55m
American Airlines
Sun 5/105:33 am
MSN
-
HPN
1 stop4h 56m
American Airlines
Deal found 3/31$402
This American Airlines deal was found by Cheapflights users on 3/30. 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 4/127:00 am
HPN
-
MSN
1 stop7h 48m
American Airlines
Mon 4/136:00 am
MSN
-
HPN
1 stop7h 31m
American Airlines
Deal found 3/30$405
This American Airlines deal was found by Cheapflights users on 3/31. 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 6/76:59 pm
HPN
-
MSN
1 stop6h 00m
American Airlines
Fri 6/124:34 pm
MSN
-
HPN
1 stop5h 52m
American Airlines
Deal found 3/31$406
This American Airlines deal was found by Cheapflights users on 3/31. 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 4/127:00 am
HPN
-
MSN
1 stop7h 48m
American Airlines
Tue 4/1410:19 am
MSN
-
HPN
1 stop6h 07m
American Airlines
Deal found 3/31$415
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 4/1612:30 pm
HPN
-
MSN
1 stop6h 06m
Delta
Sun 4/199:41 am
MSN
-
HPN
1 stop5h 08m
Delta
Deal found 3/28$452
This American Airlines deal was found by Cheapflights users on 3/30. 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 7/126:30 am
HPN
-
MSN
1 stop7h 00m
American Airlines
Sat 7/188:19 am
MSN
-
HPN
1 stop6h 40m
American Airlines
Deal found 3/30$456

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 April 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$327
(American Airlines)

Popular in

August

Cheapest in

February

Average price

$449
Provider with most accurate pricing for New York (NYC)-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Madison Truax Field flights.
Search Deals
From Westchester County to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

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 April 1, 2026.
Use the filters below to find and compare flights from Westchester County to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Sat 8/29

4:19 pm-10:35 pm

1 stop7h 16m

Madison Truax Field

Sat 9/12

9:00 am-4:40 pm

1 stop6h 40m

$327

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Thu 7/23

5:26 pm-11:19 pm

1 stop6h 53m

Madison Truax Field

Mon 7/27

4:31 pm-11:27 pm

1 stop5h 56m

$327

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Mon 6/1

6:59 pm-11:59 pm

1 stop6h 00m

Madison Truax Field

Fri 6/5

4:34 pm-11:26 pm

1 stop5h 52m

$376
Quickest round-trip

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Sat 5/23

5:15 pm-8:49 pm

1 stop4h 34m

Madison Truax Field

Mon 5/25

7:00 am-11:51 am

1 stop3h 51m

$383

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Sat 5/23

5:59 pm-11:59 pm

1 stop7h 00m

Madison Truax Field

Mon 5/25

5:38 pm-11:26 pm

1 stop4h 48m

$387

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Sun 4/12

7:00 am-1:48 pm

1 stop7h 48m

Madison Truax Field

Tue 4/14

10:19 am-5:26 pm

1 stop6h 07m

$415

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Thu 4/16

12:30 pm-5:36 pm

1 stop6h 06m

Madison Truax Field

Sun 4/19

9:41 am-3:49 pm

1 stop5h 08m

$452

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Thu 7/2

6:30 am-12:30 pm

1 stop7h 00m

Madison Truax Field

Sun 7/5

7:13 am-1:13 pm

1 stop5h 00m

$486

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Fri 5/8

5:59 pm-11:54 pm

1 stop6h 55m

Madison Truax Field

Sun 5/10

8:24 pm-11:29 am

1 stop14h 05m

$553

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Wed 8/19

11:00 am-5:15 pm

2 stops7h 15m

Madison Truax Field

Sat 8/22

6:00 am-11:28 am

1 stop4h 28m

$814

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/28

Sorted by cheapest first

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, June is the cheapest month in which you can book a flight from Westchester County to Madison (average of $188). Flying from Westchester County to Madison in January is currently the most expensive (average of $389). 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 April 1, 2026.
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
7.1
Good
11,545 reviews

Comfort

7.2

Crew

7.9

Food

6.4

Boarding

7.5

Overall

7.1

Entertainment

6.9

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.
American Airlines
7.1
Good
11,545 reviews
American Airlines
7.1
Good
11,545 reviews

Comfort

7.2

Crew

7.9

Food

6.4

Boarding

7.5

Overall

7.1

Entertainment

6.9

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

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 Delta and American Airlines fly from Westchester County to Madison in about 6h 53m. The time it takes to get you to your destination can typically vary by up to 23m. 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, June is the cheapest month in which you can book a flight from Westchester County to Madison (average of $188). Flying from Westchester County to Madison in January is currently the most expensive (average of $389). 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

Browse thousands of different options on Cheapflights for your next trip

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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 April 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$307Average$488FlexibilityNo cancel feeOn-time71%

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