HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MSN
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Westchester County to Madison with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 15, 2025.

Round-trip from

$307
(Delta)

One-way from

$154
(American Airlines)

Popular in

August

Cheapest in

February

Average price

$389
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. 6% potential increase in price ($29 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 September 2025
Search Deals

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 September 15, 2025.

This Delta deal was found by Cheapflights users on 9/15. 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 10/115:20 pmHPN - MSN
1 stop4h 01mDelta
Sat 10/187:00 amMSN - HPN
1 stop3h 59mDelta
Deal found 9/15$307
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/56:00 amHPN - MSN
1 stop4h 59mAmerican Airlines
Fri 10/103:46 pmMSN - HPN
1 stop6h 43mAmerican Airlines
Deal found 9/13$355
This American Airlines deal was found by Cheapflights users on 9/13. 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 9/286:00 amHPN - MSN
1 stop4h 59mAmerican Airlines
Thu 10/25:00 amMSN - HPN
1 stop5h 29mAmerican Airlines
Deal found 9/13$365
This Delta deal was found by Cheapflights users on 9/15. 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 9/246:40 pmHPN - MSN
1 stop5h 18mDelta
Sat 10/45:40 amMSN - HPN
1 stop5h 20mDelta
Deal found 9/15$384
This Delta deal was found by Cheapflights users on 9/15. 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 10/116:40 pmHPN - MSN
1 stop5h 05mDelta
Wed 10/155:30 amMSN - HPN
1 stop5h 30mDelta
Deal found 9/15$392
This Delta deal was found by Cheapflights users on 9/15. 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 10/146:00 amHPN - MSN
1 stop5h 32mDelta
Wed 10/155:30 amMSN - HPN
1 stop5h 30mDelta
Deal found 9/15$408
This Delta deal was found by Cheapflights users on 9/15. 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 10/116:40 pmHPN - MSN
1 stop5h 05mDelta
Fri 10/179:34 amMSN - HPN
2 stops25h 25mDelta
Deal found 9/15$412
This Delta deal was found by Cheapflights users on 9/15. 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 10/116:40 pmHPN - MSN
1 stop5h 05mDelta
Thu 10/165:30 amMSN - HPN
1 stop5h 30mDelta
Deal found 9/15$422
This Delta deal was found by Cheapflights users on 9/15. 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 10/156:40 pmHPN - MSN
2 stops15h 00mDelta
Sat 10/187:00 amMSN - HPN
1 stop3h 59mDelta
Deal found 9/15$426
This Delta deal was found by Cheapflights users on 9/15. 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 10/146:00 amHPN - MSN
1 stop5h 32mDelta
Thu 10/165:30 amMSN - HPN
1 stop5h 30mDelta
Deal found 9/15$438
This Delta deal was found by Cheapflights users on 9/15. 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 10/115:20 pmHPN - MSN
1 stop4h 01mDelta
Tue 10/149:20 amMSN - HPN
1 stop25h 39mDelta
Deal found 9/15$441

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 September 15, 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

Wed 10/15

6:00 am-10:32 am

1 stop5h 32m

Madison Truax Field

Sat 10/18

7:00 am-11:59 am

1 stop3h 59m

$307

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Mon 10/6

5:57 pm-10:03 pm

1 stop5h 06m

Madison Truax Field

Mon 10/20

8:25 am-3:59 pm

1 stop6h 34m

$355

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Sun 10/5

6:00 am-9:59 am

1 stop4h 59m

Madison Truax Field

Fri 10/10

3:46 pm-11:29 pm

1 stop6h 43m

$355

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Sun 9/28

6:00 am-9:59 am

1 stop4h 59m

Madison Truax Field

Thu 10/2

5:00 am-11:29 am

1 stop5h 29m

$365

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Tue 10/14

6:00 am-10:32 am

1 stop5h 32m

Madison Truax Field

Wed 10/15

5:30 am-12:00 pm

1 stop5h 30m

$408

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Wed 10/15

6:00 am-10:32 am

1 stop5h 32m

Madison Truax Field

Fri 10/17

9:34 am-11:59 am

2 stops25h 25m

$412

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Sat 10/11

6:40 pm-10:45 pm

1 stop5h 05m

Madison Truax Field

Fri 10/17

9:34 am-11:59 am

2 stops25h 25m

$412

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Tue 10/14

6:00 am-10:32 am

1 stop5h 32m

Madison Truax Field

Fri 10/17

9:34 am-11:59 am

2 stops25h 25m

$412

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Sat 10/11

6:40 pm-10:45 pm

1 stop5h 05m

Madison Truax Field

Thu 10/16

5:30 am-12:00 pm

1 stop5h 30m

$422

White PlainsMadison

HPN - MSN

HPNMSN

White Plains Westchester County

Tue 10/14

6:00 am-10:32 am

1 stop5h 32m

Madison Truax Field

Thu 10/16

5:30 am-12:00 pm

1 stop5h 30m

$438

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 16 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, 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 September 15, 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
10,000 reviews

Crew

8.0

Comfort

7.2

Overall

7.2

Entertainment

6.9

Boarding

7.5

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Comfort

7.2

Overall

7.2

Entertainment

6.9

Boarding

7.5

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 5h 06m. The time it takes to get you to your destination can typically vary by up to 26m. 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.

  • What are the cheapest airlines to fly from Westchester County to Madison one-way?

    $154 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Delta and Breeze Airways, with prices starting from $183 and $470, respectively.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Westchester County to Madison

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
John F Kennedy Intl to Minneapolis flights
LaGuardia to Minneapolis flights
Newark to Minneapolis flights
LaGuardia to Milwaukee flights
John F Kennedy Intl to Milwaukee flights
White Plains to O'Hare Intl flights
LaGuardia to Madison flights
Newark to Milwaukee flights
Newark to Madison flights
Syracuse to O'Hare Intl flights
John F Kennedy Intl to Madison flights
Rochester to O'Hare Intl flights
Buffalo to O'Hare Intl flights
Syracuse to Minneapolis flights
Albany to O'Hare Intl flights
Newark to Appleton flights
John F Kennedy Intl to Appleton flights
LaGuardia to Green Bay flights
Albany to Minneapolis flights
LaGuardia to Appleton flights
White Plains to Minneapolis flights
Rochester to Minneapolis flights
Newark to Green Bay flights
John F Kennedy Intl to Green Bay flights
Ithaca to O'Hare Intl flights
Buffalo to Minneapolis flights
White Plains to Madison flights
Elmira to O'Hare Intl flights
Syracuse to Madison flights
Albany to Milwaukee flights
Islip to O'Hare Intl flights
Buffalo to Milwaukee flights
White Plains to Milwaukee flights
Stewart to O'Hare Intl flights
Albany to Madison flights
John F Kennedy Intl to Wausau flights
Newark to Wausau flights
Syracuse to Milwaukee flights
Binghamton to O'Hare Intl flights
LaGuardia to Wausau flights
LaGuardia to Duluth flights
Rochester to Madison flights
White Plains to Green Bay flights
Buffalo to Green Bay flights
Newark to Duluth flights
John F Kennedy Intl to Duluth flights
Rochester to Milwaukee flights

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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$328Average$475FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.