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Madison

$158+ 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 3/13. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MSN
Mar 8 — Mar 151
Sun 3/8
Sun 3/15
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 February 6, 2026.

This American Airlines deal was found by Cheapflights users on 2/6. 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 4/196:30 am
HPN
-
MSN
1 stop5h 44m
American Airlines
Wed 4/222:18 pm
MSN
-
HPN
1 stop6h 41m
American Airlines
Deal found 2/6$315
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Thu 5/78:00 am
HPN
-
MSN
1 stop25h 25m
Breeze Airways
Mon 5/116:50 pm
MSN
-
HPN
1 stop16h 43m
Breeze Airways
Deal found 2/3$320
This American Airlines deal was found by Cheapflights users on 2/5. 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 2/206:54 pm
HPN
-
MSN
1 stop5h 46m
American Airlines
Tue 2/244:45 pm
MSN
-
HPN
1 stop5h 14m
American Airlines
Deal found 2/5$355
This American Airlines deal was found by Cheapflights users on 2/5. 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 3/66:54 pm
HPN
-
MSN
1 stop5h 46m
American Airlines
Sun 3/86:15 am
MSN
-
HPN
1 stop4h 14m
American Airlines
Deal found 2/5$356
This American Airlines deal was found by Cheapflights users on 2/3. 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 2/165:29 pm
HPN
-
MSN
1 stop4h 27m
American Airlines
Thu 2/196:00 am
MSN
-
HPN
1 stop7h 30m
American Airlines
Deal found 2/3$381
This Delta deal was found by Cheapflights users on 2/3. 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 3/126:00 am
HPN
-
MSN
1 stop5h 31m
Delta
Sat 3/1410:56 am
MSN
-
HPN
1 stop4h 39m
Delta
Deal found 2/3$387
This Delta deal was found by Cheapflights users on 2/4. 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 9/36:00 am
HPN
-
MSN
1 stop5h 11m
Delta
Tue 9/89:00 am
MSN
-
HPN
1 stop6h 40m
Delta
Deal found 2/4$405
This Delta deal was found by Cheapflights users on 2/5. 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.
Tue 4/712:35 pm
HPN
-
MSN
1 stop5h 49m
Delta
Wed 4/87:00 am
MSN
-
HPN
1 stop3h 53m
Delta
Deal found 2/5$427
This American Airlines deal was found by Cheapflights users on 2/6. 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 2/126:30 am
HPN
-
MSN
1 stop4h 31m
American Airlines
Sun 2/157:00 am
MSN
-
HPN
1 stop5h 07m
American Airlines
Deal found 2/6$460
This Delta deal was found by Cheapflights users on 2/6. 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.
Wed 2/184:29 pm
HPN
-
MSN
1 stop6h 55m
Delta
Sat 2/217:00 am
MSN
-
HPN
1 stop3h 56m
Delta
Deal found 2/6$471
This Delta deal was found by Cheapflights users on 2/4. 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 5/83:15 pm
HPN
-
MSN
1 stop7h 12m
Delta
Sun 5/109:06 am
MSN
-
HPN
1 stop6h 30m
Delta
Deal found 2/4$472

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 February 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$315
(American Airlines)

One-way from

$158
(American Airlines)

Popular in

August

Cheapest in

February

Average price

$377
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
One-way flight from Westchester County to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 6, 2026.
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

Sun 4/19

6:30 am-11:14 am

1 stop5h 44m

Madison Truax Field

Wed 4/22

2:18 pm-9:59 pm

1 stop6h 41m

$315

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Fri 2/20

6:54 pm-11:40 pm

1 stop5h 46m

Madison Truax Field

Tue 2/24

4:45 pm-10:59 pm

1 stop5h 14m

$355

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Mon 2/16

5:29 pm-8:56 pm

1 stop4h 27m

Madison Truax Field

Thu 2/19

6:00 am-2:30 pm

1 stop7h 30m

$381

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Thu 3/12

6:00 am-10:31 am

1 stop5h 31m

Madison Truax Field

Sat 3/14

10:56 am-4:35 pm

1 stop4h 39m

$387

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Wed 4/8

12:35 pm-5:24 pm

1 stop5h 49m

Madison Truax Field

Thu 4/9

7:00 am-11:53 am

1 stop3h 53m

$427

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Tue 4/7

12:35 pm-5:24 pm

1 stop5h 49m

Madison Truax Field

Wed 4/8

7:00 am-11:53 am

1 stop3h 53m

$427

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Fri 5/8

3:15 pm-9:27 pm

1 stop7h 12m

Madison Truax Field

Sun 5/10

9:06 am-4:36 pm

1 stop6h 30m

$472

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Fri 5/8

7:49 am-12:30 pm

1 stop5h 41m

Madison Truax Field

Sun 5/10

6:00 am-11:27 am

1 stop4h 27m

$486

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Thu 2/19

5:30 pm-9:58 pm

1 stop5h 28m

Madison Truax Field

Sat 2/21

5:00 am-11:29 am

1 stop5h 29m

$516

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Sun 4/19

6:00 am-10:32 am

1 stop5h 32m

Madison Truax Field

Wed 4/22

5:30 am-12:02 pm

1 stop5h 32m

$542

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

Showing 1-10 of 17 results
1
2

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 $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 February 6, 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
7.2
Good
11,246 reviews

Comfort

7.2

Crew

8.0

Food

6.4

Overall

7.2

Entertainment

6.9

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,246 reviews
American Airlines
7.2
Good
11,246 reviews

Comfort

7.2

Crew

8.0

Food

6.4

Overall

7.2

Entertainment

6.9

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 5h 31m. The time it takes to get you to your destination can typically vary by up to 13m. 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 $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

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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 February 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$307Average$478FlexibilityNo cancel feeOn-time71%

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