Cheap Flights from Westchester County to Madison

Compare Westchester County to Madison flight deals

Find the cheapest month or even day of the year to fly to Madison

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Flight deals from Westchester County Airport to Madison Airport

Looking for a cheap last-minute deal or the best return flight from Westchester County Airport to Madison Airport? If you want to travel next month, return fares start from $718. Find the lowest prices on one-way and return tickets right here.

Madison.$640 per passenger.Departing Thu, 14 May, returning Tue, 19 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Westchester County on Thu, 14 May, arriving in Madison.Inbound indirect flight with Delta, departs from Madison on Tue, 19 May, arriving in Westchester County.Price includes taxes and charges.From $640, select.

Madison.$718 per passenger.Departing Mon, 20 Apr, returning Thu, 23 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Westchester County on Mon, 20 Apr, arriving in Madison.Inbound indirect flight with Delta, departs from Madison on Thu, 23 Apr, arriving in Westchester County.Price includes taxes and charges.From $718, select.

Madison.$719 per passenger.Departing Sun, 23 Aug, returning Thu, 3 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Westchester County on Sun, 23 Aug, arriving in Madison.Inbound indirect flight with Delta, departs from Madison on Thu, 3 Sep, arriving in Westchester County.Price includes taxes and charges.From $719, select.

Madison.$1,488 per passenger.Departing Thu, 2 Jul, returning Sun, 5 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Westchester County on Thu, 2 Jul, arriving in Madison.Inbound indirect flight with Delta, departs from Madison on Sun, 5 Jul, arriving in Westchester County.Price includes taxes and charges.From $1,488, select.

Find the cheapest month to fly from Westchester County to Madison

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Westchester County to Madison flights are currently cheapest in May.

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Westchester County to Madison: Alternative routes

Compare routes from Westchester County to Madison below. You may find an airport to fly into that's cheaper, faster, or easier than Madison.

Madison

9km from central Madison

ClosestCheapest

from $640

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White Plains to Madison: Flight information

The things to know before you go.

Cheapest flight found	$640
Cheapest month to fly	May

Finding cheap flights from Westchester County to Madison: Frequently asked questions

How much are return flights from Westchester County to Madison?

The best price we found for a return flight from Westchester County to Madison is $640. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

Which airlines fly direct from Westchester County to Madison?

Currently, there are no airlines that fly direct from Westchester County to Madison. But we found flights with one or more stops from $640.

How many flights are there a week from Westchester County to Madison?

As of March 2026, there are no flights flying from Westchester County to Madison.

When is the cheapest time to fly from Westchester County to Madison?

The cheapest month to fly from Westchester County to Madison is usually May.

Which upcoming date is cheapest to fly from Westchester County Airport to Madison Airport on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Westchester County Airport to Madison Airport on Thursday, 14 May 2026.

Can I get a direct flight from Westchester County Airport to Madison Airport?

No airlines currently offer direct flights between Westchester County Airport and Madison Airport. Most routes have one or more stops.

How can I find the best flight deal to Madison?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Madison but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Madison?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Madison is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly from Westchester County Airport to Madison with?

Currently, Delta offers the cheapest flight tickets to Madison.

Flying from Westchester County Airport (HPN) to Dane County Regional Airport (MSN): what you need to know

Get to the airport on time so you don't miss your HPN to MSN flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid any last-minute rush.
During popular months such as August, it's a good idea to get to the airport earlier. Plan to arrive two hours before a domestic departure and four hours ahead for international flights when you travel during a high season in general.
If you want to include a stop along the way, simply deselect 'Direct flights only' when searching for your ticket from Westchester County Airport to Dane County Regional Airport. Here are the top stopovers between HPN and MSN:
- Detroit Metropolitan Wayne County Airport
- Ronald Reagan National Airport
- O'Hare International Airport

How to find the cheapest flights from Westchester County Airport (HPN) to Dane County Regional Airport (MSN)

$788 is the best price for a one-way Westchester County Airport to Dane County Regional Airport flight. A return flight starts at $640. These prices can change based on availability.
It's a good idea to book in advance if you're hoping to get cheap tickets from HPN to MSN. That's because airlines change prices based on demand, which tends to increase closer to departure.
Finding cheap flights from Westchester County Airport to Dane County Regional Airport is easier if you can be flexible with your travel plans. Use the 'Whole month' tool to see the lowest prices across every month and score a great deal.
You don't need to check back in every day to find out if fares have gone down when you create a Price Alert. We'll update you the moment there's a change in price on cheap flights from HPN to MSN.
Choose your preferred arrival and departure times, airlines and number of stops with the filters. Alternatively, sort your results by 'Cheapest' to see the best deals on flights from Westchester County Airport to Dane County Regional Airport.

Handy information about Westchester County Airport (HPN)

The address for HPN is 240 Airport Road, Suite 202.
When it comes to the on-time performance of Westchester County Airport, 74.52% of flights meet their scheduled arrival time.

Arriving at Dane County Regional Airport (MSN)

If you're arriving on a late Westchester County Airport to Dane County Regional Airport flight, nothing tops the convenience of staying near the terminal. Pick up your bags from the carousel and then be showered and relaxing shortly after at one of these accommodation options near MSN:
Grab a Dane County Regional Airport rental car and explore Madison and beyond with your own wheels. Hertz, Alamo and Enterprise are top outlets to choose from here.
To get the best deal, book your vehicle from Dane County Regional Airport about two weeks before you travel.

Getting from Dane County Regional Airport (MSN) to central Madison

You'll find MSN at 4000 International Lane.
Dane County Regional Airport to the centre of Madison has a drive time of around 20 minutes. It's approximately 14 kilometres away.
When travelling on public transport, expect a journey of about 1 hour 10 minutes.

When to fly to Dane County Regional Airport (MSN)

The quietest month for a flight from Westchester County Airport to Dane County Regional Airport is January, while August is the busiest. Pick the best time to visit Madison based on whether you prefer a faster pace or a more relaxed vibe.
The warmest month in Madison is July, with temperatures ranging between 13ºC and 29ºC. Lock in your flights from Westchester County Airport to Dane County Regional Airport in this month if you enjoy this type of weather.
January sees average temperatures of between -18ºC and 0ºC. Look for cheap tickets from HPN to MSN sometime then if you'd rather travel in cooler conditions.

Explore more of United States

Chicago is just one of the many cities in United States waiting to be discovered after you've experienced Madison. Around 193 kilometres away to the south-east, well-known attractions include Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier.
If there's time to check out another great destination in United States, head for Indianapolis, roughly 451 kilometres south-east of Madison. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are the start of reasons to visit.