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 to Madison

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 R 7,046. Find the lowest prices on one-way and return tickets right here.

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 July.

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.

White Plains to Madison: Flight information

The things to know before you go.
Cheapest flight foundR 4,293
Cheapest month to flyJuly

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

The best price we found for a return flight from Westchester County to Madison is R 6,481. 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.
Currently, there are no airlines that fly direct from Westchester County to Madison. But we found flights with one or more stops from R 6,473.
As of June 2026, there are no flights flying from Westchester County to Madison.
The cheapest month to fly from Westchester County to Madison is usually July.
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, 30 July 2026.
No airlines currently offer direct flights between Westchester County Airport and Madison Airport. Most routes have one or more stops.
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.

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.

Currently, Breeze Airways offers the cheapest flight tickets to Madison.

Travelling from Westchester County Airport (HPN) to Madison Airport (MSN): what you need to know

  • To ensure you get on your HPN to MSN flight, leave enough time to navigate the airport and find your gate. Arriving two hours ahead of international departures and one hour before domestic flights is the general travel rule.

  • During popular months such as July, you'll want to get to the airport earlier than normal. Plan to arrive two hours before a domestic departure and four hours ahead for an international flight when you travel during a high season in general.

  • If you'd like to break up your flight, simply deselect 'Direct flights only' when searching for your ticket from Westchester County Airport to Madison Airport. These are the top stopovers between HPN and MSN:

    • Chicago O'Hare International Airport

    • Charlotte Douglas Airport

    • Detroit Wayne County Airport

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

  • The cheapest price we've seen for a one-way Westchester County Airport to Madison Airport flight is R 4,293. A return ticket is currently R 6,481. Depending on the availability and when you book, these fares may change.

  • It's often best to book in advance if you're hoping to get cheap tickets from HPN to MSN. That's because flight prices are based on demand, which tends to increase closer to departure.

  • Finding cheap flights from Westchester County Airport to Madison Airport is easy if you're flexible with your trip dates. Use the 'Whole month' tool to see the best prices across each month and score a great deal.

  • You won't have to check back in every day to see if fares have gone down when you set up a Price Alert. We'll notify you as soon as there's a new deal on cheap flights from HPN to MSN.

  • Choose your ideal departure and arrival times, airlines and number of stops with the filters. Or sort your results by 'Cheapest' to see the best deals on flights from Westchester County Airport to Madison Airport.

Handy information about Westchester County Airport (HPN)

  • HPN's address is 240 Airport Road, Suite 202.

  • 73% of flights that depart Westchester County Airport make it to their destination on time.

  • Central White Plains to Westchester County Airport is approximately 6 kilometres. Depending on traffic, it'll take you about 10 minutes to get there if you're catching a taxi, ride-sharing or driving.

  • You can expect a journey time of roughly 25 minutes on public transport.

  • Get your flight from Westchester County Airport to Madison Airport off to a relaxed start. Just a short ride from HPN, book a night at Sonesta White Plains Downtown and be well-rested for the trip ahead.

Arriving at Madison Airport (MSN)

Getting from Madison Airport (MSN) to central Madison

  • The street address for MSN is 4000 International Lane.

  • Madison Airport is approximately 13 kilometres from the centre of Madison. The drive time takes about 20 minutes.

  • It'll take around 40 minutes to get there using public transport.

When to fly to Madison Airport (MSN)

  • The quietest month for a flight from Westchester County Airport to Madison Airport is March, while August is the most popular. Choose the ideal time to go to Madison based on whether you prefer a laid-back vibe or a more bustling atmosphere.

  • When reserving your flight from Westchester County Airport to Madison Airport, consider the type of weather you like. July is the warmest month in Madison, with the temperature ranging from 13ºC (55ºF) to 29ºC (84ºF).

  • Look for cheap tickets from HPN to MSN in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -18ºC (0ºF) and 0ºC (32ºF) on average.

Explore more of the United States

  • Madison has its own special appeal, but there are so many other parts of the United States you'll want to see. About 193 kilometres south-east of Madison, a trip to Chicago will keep you on the move. Check out popular attractions like Millennium Park, Art Institute of Chicago and Willis Tower.

  • If there's time to check out another major stop in the United States, consider Indianapolis, about 451 kilometres south-east of Madison. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are among its highlights.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.