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Madison

$168+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MSN
Aug 6 — Aug 131
Mi 8/6
Mi 8/13
1 adult, Economy
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Cheap 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 August 1, 2025.

Round-trip from

$329
(American Airlines)

One-way from

$168
(American Airlines)

Popular in

July

Cheapest in

February

Average price

$518
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. 11% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 1, 2025.

This American Airlines deal was found by Cheapflights users on 7/31. 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.
Fr 9/196:50 pmHPN - MSN
1 stop5h 20mAmerican Airlines
Mo 9/222:54 pmMSN - HPN
1 stop7h 05mAmerican Airlines
Deal found 7/31$329
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 9/116:00 amHPN - MSN
1 stop4h 58mDelta
Sa 9/135:40 amMSN - HPN
1 stop7h 49mDelta
Deal found 7/30$384
This Gotogate deal was found by Cheapflights users on 7/31. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 8/228:00 amHPN - MSN
2 stops25h 01mBreeze Airways
Sa 8/2310:19 amMSN - HPN
2 stops24h 06mBreeze Airways
Deal found 7/31$798

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 August 1, 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

Fr 9/19

6:50 pm-11:10 pm

1 stop5h 20m

Madison Truax Field

Mo 9/22

2:54 pm-10:59 pm

1 stop7h 05m

$329

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Do 9/11

6:00 am-9:58 am

1 stop4h 58m

Madison Truax Field

Sa 9/13

5:40 am-2:29 pm

1 stop7h 49m

$384

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Di 9/9

12:09 pm-5:28 pm

2 stops30h 19m

Madison Truax Field

Sa 9/13

6:08 pm-11:29 am

2 stops16h 21m

$758

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Fr 8/22

8:00 am-8:01 am

2 stops25h 01m

Madison Truax Field

Sa 8/23

6:25 pm-8:59 pm

3 stops25h 34m

$942

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Sa 9/13

4:30 pm-7:54 pm

1 stop4h 24m

$168

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Do 8/21

5:15 pm-10:50 pm

2 stops6h 35m

$637

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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, January is the cheapest month in which you can book a flight from Westchester County to Madison (average of $338). Flying from Westchester County to Madison in March is currently the most expensive (average of $422). 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 August 1, 2025.
Get a feel of what it's like to fly with Delta, Breeze Airways, and 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.
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Breeze Airways
8.0
Very good
191 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

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.

  • 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, January is the cheapest month in which you can book a flight from Westchester County to Madison (average of $338). Flying from Westchester County to Madison in March is currently the most expensive (average of $422). 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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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 August 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$306Average$449FlexibilityNo cancel feeOn-time71%

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