HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$154+ Cheap flights from Madison to New Windsor (MSN - SWF)

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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SWF
Feb 8 — Feb 151
Sun 2/8
Sun 2/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to Stewart 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 Madison to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$990
(Kiwi.com)

One-way from

$154
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$402
Provider with most accurate pricing for Madison Truax Field-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-New Windsor Stewart flights.
Search Deals
From Madison Truax Field to New Windsor Stewart
Search Deals
One-way flight from Madison Truax Field to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Find flight deals from Madison to Stewart

Cheapest flights from Madison to Stewart
Explore the most affordable flight options available from Madison to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 9, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/8. 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.
Wed 2/116:36 pmMSN - SWF
1 stop15h 32mBreeze Airways
Fri 2/1312:11 pmSWF - MSN
2 stops30h 45mBreeze Airways
Deal found 1/8$990
This Gotogate deal was found by Cheapflights users on 1/7. 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.
Wed 1/146:16 pmMSN - SWF
1 stop16h 17mBreeze Airways
Fri 1/1612:11 pmSWF - MSN
2 stops30h 25mBreeze Airways
Deal found 1/7$1,301

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Stewart 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 January 9, 2026.
Use the filters below to find and compare flights from Madison to New Windsor that are best for you.

Fly from

Madison

Fly to

Stewart

Route

Depart

Return

Price

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 2/11

6:36 pm-11:08 am

1 stop15h 32m

New Windsor Stewart

Fri 2/13

12:11 pm-5:56 pm

2 stops30h 45m

$990

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 1/28

6:16 pm-11:33 am

1 stop16h 17m

$154

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 1/14

6:16 pm-11:33 am

1 stop16h 17m

$204

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Sat 1/31

6:16 pm-11:31 am

2 stops40h 15m

$237

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 6/24

6:05 pm-8:58 am

1 stop13h 53m

$266

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Sat 1/17

6:16 pm-11:33 am

1 stop16h 17m

$300

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 6/24

9:54 am-9:38 am

2 stops22h 44m

$309

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Sat 6/20

7:55 pm-8:58 am

1 stop12h 03m

$423

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Sun 3/22

7:56 pm-11:31 am

3 stops14h 35m

$443

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Sat 6/20

7:55 pm-5:43 pm

2 stops20h 48m

$483

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

  • Most accurate provider: When it comes to deals on Madison-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-New Windsor flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Madison-New Windsor flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Madison to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Madison 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 Madison to New Windsor

What is the cheapest month to book a flight from Madison to New Windsor?

Currently, April is the cheapest month in which you can book a flight from Madison to New Windsor (average of $75). Flying from Madison to New Windsor in September is currently the most expensive (average of $228). 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.

Related info for your journey

Find useful and relevant information for your journey from Madison to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Madison to New Windsor?

    Airlines like Breeze Airways fly from Madison to New Windsor in about 15h 32m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 785 mi.

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

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

  • How can I find direct flights from Madison to Stewart?

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

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

    Yes. Cheapflights offers flight deals from Madison to Stewart 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 Madison to New Windsor?

    Currently, April is the cheapest month in which you can book a flight from Madison to New Windsor (average of $75). Flying from Madison to New Windsor in September is currently the most expensive (average of $228). 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 New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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 Madison to Stewart

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

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.
Site
Cookie settings©2026 Cheapflights