In terms of precipitation, rainfall in Madison ranges from 1.2 - 4.5 inches per month. June is typically the wettest month, when rainfall can reach 4.5 in. January is typically the driest time to visit Madison when rainfall is around 1.2 in.

If weather is an important factor for your trip to Madison, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 71.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 19.4 F).

How far in advance should I book a flight from New Windsor to Madison?

Find a great deal and save up to 24% by booking at least 44 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from New Windsor to Madison within the next two weeks, with the cheapest ticket starting at $379.

What is the cheapest month to fly from New Windsor to Madison?

February is one of the best times of the year to fly to Madison from New Windsor. Prices for February average $445 per person but you can even find prices for as low as $228. The most expensive prices can be found in the month of August. Opting for a February flight can save you 16% on your journey compared to booking in August

What is the cheapest time of day to fly from SWF to MSN?

When flying from New Windsor to Madison, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

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

How can I find direct flights from Stewart to Madison?

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

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

Yes. Cheapflights offers flight deals from Stewart 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.

$289+ Flights from New Windsor to Madison

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Stewart 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 Stewart to Madison

Round-trip from	$593 (FlightHub)
One-way from	$289 (Booking.com)
Popular in	August
Cheapest in	February
Average price	$469

From New Windsor Stewart to Madison Truax Field

Search Deals

One-way flight from New Windsor Stewart to Madison Truax Field

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. 1% potential price decrease ($7 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in June 2025

Search Deals

Find flight deals from Stewart to Madison

Cheapest flights from Stewart to Madison
Explore the most affordable flight options available from Stewart to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2025.

Tue 9/212:36 pmSWF - MSN

1 stop29h 52mBreeze Airways

Sat 9/276:08 pmMSN - SWF

1 stop15h 45mBreeze Airways

Deal found 6/28

$593

Best flights from Stewart to Madison
Discover carefully curated flight deals from Stewart to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 30, 2025.

Tue 9/212:36 pmSWF - MSN

1 stop29h 52mBreeze Airways

Sat 9/276:08 pmMSN - SWF

1 stop15h 45mBreeze Airways

Deal found 6/28

$593

One-way flights from Stewart to Madison
Search for one-way flight options from Stewart to Madison. Find affordable one-way fares based on user searches. Data last updated June 30, 2025.

Tue 7/2912:36 pmSWF - MSN

1 stop22h 03mBreeze Airways

Deal found 6/28

$289

Fri 8/2212:17 pmSWF - MSN

2 stops22h 22mMultiple Airlines

Deal found 6/29

$294

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Windsor to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Tue 9/2

12:36 pm-5:28 pm

1 stop29h 52m

Madison Truax Field

Sat 9/27

6:08 pm-10:53 am

1 stop15h 45m

$593

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Tue 7/29

12:36 pm-9:39 am

1 stop22h 03m

$289

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Fri 8/22

12:17 pm-9:39 am

2 stops22h 22m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/28

Best time to book a flight from Stewart to Madison

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

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

Currently, January is the cheapest month in which you can book a flight from New Windsor to Madison (average of $338). Flying from New Windsor 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

Read reviews from past customers who have flown Breeze Airways from New Windsor to Madison. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Breeze Airways

8.1

Very good

182 reviews

Reviews

1 / 11

10.0

Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

Breeze Airways

8.1

Very good

182 reviews

Breeze Airways

8.1

Very good

182 reviews

Reviews

1 / 11

10.0

Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

Related info for your journey

Can I find deals for flights from Stewart to Madison that include hotel bookings?
Yes. In addition to deals on Stewart to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Stewart to Madison?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Madison.
Can I find deals for business class flights from Stewart to Madison?
Yes. Cheapflights offers flight deals from Stewart 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 New Windsor to Madison?
Currently, January is the cheapest month in which you can book a flight from New Windsor to Madison (average of $338). Flying from New Windsor 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

Portage

Middleton

Baraboo

Fitchburg

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Stewart to Madison

John F Kennedy Intl to O'Hare Intl flights

Newark to O'Hare Intl flights

LaGuardia to O'Hare Intl flights

Newark to Minneapolis flights

LaGuardia to Minneapolis flights

John F Kennedy Intl to Minneapolis flights

LaGuardia to Milwaukee flights

Newark to Milwaukee flights

John F Kennedy Intl to Milwaukee flights

Newark to Madison flights

Rochester to O'Hare Intl flights

Buffalo to O'Hare Intl flights

LaGuardia to Madison flights

White Plains to O'Hare Intl flights

John F Kennedy Intl to Madison flights

Syracuse to O'Hare Intl flights

Stewart to O'Hare Intl flights

Albany to O'Hare Intl flights

John F Kennedy Intl to Appleton flights

LaGuardia to Appleton flights

Buffalo to Minneapolis flights

Albany to Minneapolis flights

Islip to O'Hare Intl flights

Newark to Green Bay flights

White Plains to Milwaukee flights

Syracuse to Minneapolis flights

LaGuardia to Green Bay flights

Newark to Appleton flights

John F Kennedy Intl to Green Bay flights

Rochester to Minneapolis flights

White Plains to Minneapolis flights

Stewart to Milwaukee flights

Stewart to Minneapolis flights

Ithaca to O'Hare Intl flights

Rochester to Milwaukee flights

Albany to Milwaukee flights

Albany to Madison flights

John F Kennedy Intl to Duluth flights

Newark to Wausau flights

LaGuardia to Duluth flights

Newark to Duluth flights

Newark to Rhinelander flights

LaGuardia to Rhinelander flights

John F Kennedy Intl to Rhinelander flights

Buffalo to Milwaukee flights

John F Kennedy Intl to Wausau flights

Binghamton to O'Hare Intl flights

White Plains to Green Bay flights

White Plains to Madison flights

Syracuse to Milwaukee flights

Complete your trip

Madison car rentals

Milwaukee-Mitchell Airport car rentals

Madison Truax Field Airport car rentals

Appleton Intl Airport car rentals

Chicago Greater Rockford Airport car rentals

Dubuque Airport car rentals

Milwaukee car rentals

Green Bay car rentals

Appleton car rentals

Eau Claire car rentals

La Crosse car rentals

Other flights to Madison

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.

$289+ Cheap flights from New Windsor to Madison (SWF - 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Stewart to Madison with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Stewart to Madison

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Stewart to Madison

Cheapest flights from Stewart to MadisonExplore the most affordable flight options available from Stewart to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2025.

Explore the most affordable flight options available from Stewart to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Windsor to Madison that are best for you.

Best time to book a flight from Stewart to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Stewart with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from New Windsor to Madison

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

Reviews of airlines servicing Madison

Read reviews from past customers who have flown Breeze Airways from New Windsor to Madison. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

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

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

How can I find direct flights from Stewart to Madison?

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

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

Traveling to a place near New Windsor?

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 Stewart to Madison

See prices for flight routes from nearby airports that may be better suited for you.

100% Free

Book with Flexibility

Travel Smart

Cheapest flights from Stewart to Madison
Explore the most affordable flight options available from Stewart to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2025.