$59 Cheap Flights to Westchester County
One-way
Departing from
United States
Going to
Westchester County, United States
Westchester County (HPN)
United States • February, 2026
97% AI deal score
$890 $118
Westchester County (HPN)
United States • January, 2026
97% AI deal score
$890 $118
Westchester County (HPN)
United States • February, 2026
92% AI deal score
$445 $59
Westchester County (HPN)
United States • February, 2026
92% AI deal score
$445 $60
Top Cheap Flight Deals from United States to Westchester County
Recent round-trip flight deals to Westchester County
Thu, Jan 22 - Tue, Feb 3
Cheapest
Orlando (MCO) - Westchester County (HPN)
Breeze Airways airlines • 1 stop • Charleston (CHS)
Westchester County (HPN) - Orlando (MCO)
Breeze Airways airlines • 1 stop • Charleston (CHS)
$250
$77
-$173
69%
Fri, Jan 30 - Tue, Feb 3
Orlando (MCO) - Westchester County (HPN)
Breeze Airways airlines • 1 stop • Raleigh (RDU)
Westchester County (HPN) - Orlando (MCO)
Breeze Airways airlines • 1 stop • Charleston (CHS)
$250
$81
-$169
68%
Fri, Jan 23 - Mon, Feb 9
Orlando (MCO) - Westchester County (HPN)
Breeze Airways airlines • 1 stop • Raleigh (RDU)
Westchester County (HPN) - Orlando (MCO)
Breeze Airways airlines • 1 stop • Raleigh (RDU)
$250
$82
-$168
67%
Thu, Jan 22 - Mon, Feb 9
Orlando (MCO) - Westchester County (HPN)
Breeze Airways airlines • 1 stop • Charleston (CHS)
Westchester County (HPN) - Orlando (MCO)
Breeze Airways airlines • 1 stop • Raleigh (RDU)
$250
$82
-$168
67%
Thu, Jan 15 - Tue, Feb 3
Orlando (MCO) - Westchester County (HPN)
Breeze Airways airlines • 1 stop • Charleston (CHS)
Westchester County (HPN) - Orlando (MCO)
Breeze Airways airlines • 1 stop • Charleston (CHS)
$250
$81
-$169
68%
Tue, Jan 13 - Tue, Feb 3
Orlando (MCO) - Westchester County (HPN)
Breeze Airways airlines • 1 stop • Charleston (CHS)
Westchester County (HPN) - Orlando (MCO)
Breeze Airways airlines • 1 stop • Charleston (CHS)
$250
$81
-$169
68%
The cheapest time to fly to Westchester County
Ready to jet to Westchester County on a budget? Check out these popular routes with surprisingly cheap fares (one-way prices):
Facts About Flights from United States to Westchester County
To help you plan your journey, here are some quick Westchester County flight facts and tips.
Westchester County city airports
Westchester County Airport (HPN) is a convenient and accessible option for travelers in the Lower Hudson Valley and the New York City metropolitan area. Located in White Plains, New York, HPN offers a more relaxed and less crowded alternative to the major NYC airports. While its flight options might be fewer compared to larger hubs, Westchester County Airport provides a range of domestic flights, with connections to various cities across the United States. This makes it ideal for both business and leisure travelers seeking a smoother travel experience. The airport boasts modern facilities, including comfortable waiting areas, dining options, and efficient security checkpoints. Ground transportation is readily available with taxis, ride-sharing services, and car rentals, ensuring easy access to and from the airport. For those prioritizing convenience and a stress-free travel day, Westchester County Airport is a solid choice.
Pro tip: search “Westchester County (Any)” to see fares to all Westchester County airports – sometimes one is cheaper than the others on your dates.
Insights for flights to Westchester County
Cheapest airport
Stewart International Airport (SWF)
Located in Newburgh, NY, Stewart International Airport (SWF) offers a more relaxed travel experience with fewer crowds, making it an attractive alternative to the busier NYC airports. Despite being smaller, it still provides a range of domestic and international flights, ensuring you can reach your destination with ease and maybe a little extra zen!
Nonstop vs. 1-stop
20+ cities
Westchester County Airport (HPN) offers a convenient gateway to the New York metropolitan area, though it's more of a secondary airport than a major hub. Popular routes include connections to Florida, with seasonal flights to various vacation destinations, and daily services to smaller cities up and down the East Coast!
HPN Airport Deal Stats
Current most discounted routes
Avg. most discounted routes (last 3 months)
HPN airport insights
Best days to catch a deal
Tue, Sat
Based on the provided data, Tuesday has the most deals for the Westchester County airport. Friday has the second highest number of deals, making it another potentially good day to find cheaper flights.
Avg. deal survival time
16.0 hours
Deals from Westchester County airport survive an average of 16.0 hours. This short survival time means you should book quickly when you find a deal you like.
Rare deal frequency
5 deals
In the past month, we've discovered 5 rare flight deals for Westchester County Airport. These exceptional deals, scoring 90+ on our AI Deal Score, typically arise from mistake fares, special promotions, or ultra-discounts.
Average price drop
-61%
The average price drop for flights departing from Westchester County Airport is 61.4%, indicating significant potential savings. Travelers flying from this airport have a high chance of securing a cheaper flight compared to the initial listed price.
Next 4 weeks: deal forecast
Westchester County Airport Flight Forecast (February 2026)
Based on current data, flight prices from Westchester County Airport are expected to remain relatively stable throughout February 2026, with a slight increase possible during the President's Day holiday weekend. No significant price drops are anticipated.
Top 5 biggest price drops (last 3 months)
Found on December 28
Inverness - HPN
$2,100 → $337
84%
Found on December 28
Innsbruck - HPN
$2,350 → $368
84%
Found on December 28
Montreal - HPN
$755 → $206
73%
Found on December 28
Waterloo - HPN
$750 → $214
71%
Found on December 31
Whangarei - HPN
$3,000 → $916
69%
Check these nearby airports too
Looking for more options? These airports near HPN sometimes drop rare deals too:
Newark Liberty International (EWR)
~6 rare deals/month
John F. Kennedy International (JFK)
~12 rare deals/month
LaGuardia (LGA)
~6 rare deals/month
If you’re flexible with departure cities, it’s worth keeping an eye on nearby airports — especially EWR and JFK for long-haul deal surprises.
When Is the Best Time to Fly from United States to Westchester County
Timing is everything when hunting for cheap flights. Here are data-backed insights on the best times to fly to Westchester County:
Cheapest month
January
Cheapest month
January is often the cheapest month to fly to Westchester County, offering budget-friendly travel options. Visiting during this time allows you to explore the region's attractions with fewer crowds and potentially lower accommodation costs. Plus, you might catch some beautiful winter scenery, making it a unique and affordable travel experience.
Best day to book
Tuesday
Best day to book
Booking your flight on a Tuesday could save you some serious cash! Airlines often release deals early in the week, so keep an eye out. You might snag a fantastic fare by being strategic with your booking day; happy travels!
Cheapest days to fly
Wednesday
Cheapest days to fly
Flying on a Wednesday can be lighter on your wallet. Mid-week flights tend to be less popular, leading to lower prices. Take advantage of this trend and enjoy a more affordable trip to Westchester County!
Advance booking sweet spot
2 months
Advance booking sweet spot
Booking around two months in advance is the sweet spot for flights to Westchester County. This timeframe typically offers a balance between availability and price, increasing your chances of securing a great deal. Plan ahead and watch those fares drop!
Westchester County Airports & Ground Transportation
One big question for travelers is which Westchester County airport to fly into. Here’s a quick guide to Westchester County’s airports and how to get to the city from each:
Westchester County Airport (HPN)
Westchester County Airport (HPN) is your local gateway to the skies, offering a convenient and stress-free alternative to the hustle and bustle of the larger NYC airports. Located just a few miles outside of White Plains, HPN provides a more relaxed flying experience, with shorter security lines and easier navigation. While amenities are more limited compared to larger airports, you'll find essential services like restaurants and shops. Getting to and from Westchester is a breeze with taxis, ride-sharing services, and car rentals readily available. For a scenic and budget-friendly option, consider the Bee-Line Bus System, which connects the airport to various points throughout the county.
Tip: Arrive early to allow ample time for parking and security, especially during peak travel seasons.
LaGuardia Airport (LGA)
LaGuardia Airport (LGA), one of the major airports serving the New York metropolitan area, is located in Queens, New York City. Although it is not in Westchester County, it is easily accessible and commonly used by residents in the southern part of the county. LGA offers a wide range of domestic flights and a growing number of international destinations, making it a popular choice for travelers. The airport boasts numerous shops, restaurants, and lounges to keep you entertained while you wait for your flight. Transportation options from LGA to Westchester include taxis, ride-sharing services, and public transportation via the MTA bus and subway system, followed by a Metro-North train ride.
What to Do in Westchester County
Westchester County isn’t just about getting there – it’s about enjoying the country once you arrive! Here are some top things to do in Westchester County, organized by interest:
Sightseeing & landmarks
Westchester County is steeped in history and offers a plethora of landmarks to explore! From the stunning Lyndhurst Mansion overlooking the Hudson River to the historic Philipsburg Manor, you'll be transported back in time.
Arts & culture
Immerse yourself in Westchester's vibrant arts scene! Catch a Broadway-caliber show at the Westchester Broadway Theatre or explore contemporary art at the Neuberger Museum of Art. The options are endless!
Food & nightlife
Get ready to tantalize your taste buds! Westchester County boasts a diverse culinary scene, from farm-to-table restaurants to cozy pubs. As the sun sets, the nightlife comes alive with live music venues and trendy bars.
Shopping & fashion
Shop 'til you drop in Westchester County! Discover upscale boutiques and department stores at The Westchester or uncover unique finds in the charming downtowns of towns like Bronxville and Katonah. You're sure to find something special.
Nearby getaways
Need a change of scenery? Westchester County is the perfect jumping-off point for exploring the Hudson Valley! Head north to discover charming towns, scenic hiking trails, and breathtaking views.
No matter your interest – be it art, food, nightlife, or nature – Westchester County has something for everyone. And the best part? Many events and attractions refresh throughout the year, so there’s always something new to experience each visit.
Events in Westchester County This Month
finding neverland
Based on the movie, Finding Neverland tells the story of J.M. Barrie, the playwright who created ‘Peter Pan’. As Barrie struggles to find inspiration for his next play, his life takes a turn when he meets a widow and her children, who inspire him to create the magical world of Neverland. Experience the wonder of this heartwarming story.
westchester comedy club new years laughs
Laugh in the new year at Westchester Comedy Club with four professional comedians from New York City: Paul Ollinger from The New York Comedy Festival and SiriusXM, Phil Hunt from BET and SiriusXM, and other hilarious acts. Enjoy a night of stand-up comedy to celebrate the start of the year.
champagne resolutions new year's eve 2026 at the dean nyc
Ring in the New Year at The Dean with "Champagne Resolutions" NYE. Enjoy a 5-hour top-shelf open bar, a champagne toast at midnight, a wide variety of delicious passed hors d'oeuvres, and NYC's most festive party crowd as we welcome 2026.
nye at bar sprezzatura
Celebrate 2026 high above the city at Bar Sprezzatura, New York’s premier Italian rooftop lounge. Our multi-level enclosed rooftop offers stunning Midtown views and a chic contemporary atmosphere, making it the perfect setting for an unforgettable New Year's Eve celebration.
Westchester County Weather
Weather in Westchester County
Sat, Jan 3
10%
-2° -7°
10%
Sun, Jan 4
Frequently Asked Questions About Flights to Westchester County
Pro Tips for Finding Cheap Flights to Westchester County
Finally, to wrap up, here’s a cheat sheet of pro tips that experienced travelers use to save on Westchester County flights:
Be Flexible with Dates: Flying on Tuesdays and Wednesdays is often cheaper than weekends. Consider shifting your travel dates by a day or two to snag a better deal. Who knows, you might discover a hidden gem during your extended stay!
Consider Nearby Airports: Don't limit yourself to just one airport! Check out flights into neighboring airports like LaGuardia or Newark. The slightly longer commute to Westchester County might save you a bundle, leaving you with more cash for pizza.
