$64 Cheap Flights to Westchester County
One-way
Departing from
United States
Going to
Westchester County, United States
Westchester County (HPN)
United States • May, 2026
85% AI deal score
$1,043 $183
Westchester County (HPN)
United States • February, 2026
83% AI deal score
$245 $64
Westchester County (HPN)
United States • June, 2026
83% AI deal score
$430 $133
Top Cheap Flight Deals from United States to Westchester County
Recent round-trip flight deals to Westchester County
Fri, Mar 6 - Mon, Mar 16
Cheapest
Orlando (MCO) - Westchester County (HPN)
Breeze Airways airlines • 1 stop • Raleigh (RDU)
Westchester County (HPN) - Orlando (MCO)
Breeze Airways airlines • 1 stop • Raleigh (RDU)
$348
$109
-$239
69%
Tue, Apr 28 - Mon, May 11
Orlando (MCO) - Westchester County (HPN)
Breeze Airways airlines • 1 stop • Charleston (CHS)
Westchester County (HPN) - Orlando (MCO)
Breeze Airways airlines • 1 stop • Raleigh (RDU)
$348
$112
-$236
68%
Fri, May 1 - Mon, May 11
Orlando (MCO) - Westchester County (HPN)
Breeze Airways airlines • 1 stop • Raleigh (RDU)
Westchester County (HPN) - Orlando (MCO)
Breeze Airways airlines • 1 stop • Raleigh (RDU)
$348
$119
-$229
66%
Thu, Mar 12 - Tue, Mar 17
Orlando (MCO) - Westchester County (HPN)
Breeze Airways airlines • 1 stop • Charleston (CHS)
Westchester County (HPN) - Orlando (MCO)
Breeze Airways airlines • 1 stop • Charleston (CHS)
$348
$125
-$223
64%
Thu, Aug 20 - Sat, Aug 22
Charleston (CHS) - Westchester County (HPN)
Breeze Airways airlines • Direct
Westchester County (HPN) - Charleston (CHS)
Breeze Airways airlines • Direct
$153
$128
-$25
16%
Wed, Apr 29 - Sat, May 2
Daytona Beach (DAB) - Westchester County (HPN)
Breeze Airways airlines • Direct
Westchester County (HPN) - Daytona Beach (DAB)
Breeze Airways airlines • Direct
$265
$128
-$137
52%
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):
Last-Minute Flights from United States to Westchester County
Need to get to Westchester County ASAP? Even if you're booking a flight on short notice, there are often last-minute deals available:
Next 2 weeks deals
Last Minute Flight Deals!
In the next two weeks, fly to Westchester County from just $131!
⌛ Last-Minute
Orlando - HPN
A great last-minute steal for a cross-country flight.
Found 5 days ago
$133
round-trip
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
Sat, Sun
Based on the data provided, Tuesday is the day with the most deals for flights from Westchester County airport. Wednesday, Friday, and Thursday also show a higher chance of deals compared to Saturday, Sunday, and Monday.
Avg. deal survival time
9.4 hours
Deals from Westchester County Airport typically survive for 9.4 hours. This means that the average flight deal is likely to disappear in under 10 hours.
Rare deal frequency
16 deals
We found 16 rare deals for Westchester County Airport in the past month, thanks to our advanced AI constantly monitoring airfares. These rare deals had an AI Deal Score of 90+, and usually consist of mistake fares, special promotions, or ultra-discounts.
Average price drop
-1%
The average price drop for flights from Westchester County Airport is 0.9%, indicating a slight decrease in airfare costs from this location. This could mean travelers might find marginally better deals on flights originating from this airport compared to the initial listed prices.
Next 4 weeks: deal forecast
Westchester County Airport Next Month Forecast
Based on current trends, flight prices to Westchester County Airport are expected to remain relatively stable next month. There might be a slight increase due to the approaching spring break, but no significant price drops are anticipated.
Top 5 biggest price drops (last 3 months)
Found on February 16
Victoria - HPN
$1,260 → $358
72%
Found on February 16
Brasília - HPN
$2,510 → $1,690
33%
Found on February 21
Vilnius - HPN
$1,350 → $933
31%
Found on February 21
Tokyo - HPN
$1,305 → $921
29%
Found on February 16
Montreal - HPN
$755 → $385
49%
Check these nearby airports too
Looking for more options? These airports near HPN sometimes drop rare deals too:
Westchester County (HPN)
~4 rare deals/month
John F. Kennedy International (JFK)
~7 rare deals/month
LaGuardia (LGA)
~13 rare deals/month
If you’re flexible with departure cities, it’s worth keeping an eye on nearby airports — especially HPN 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
storytime with swe and author jamila h. lindo
Join the Society of Women Engineers for a reading and discussion with author Jamila H. Lindo as she presents her book, "Girls Can Be Engineers: Hannah's Dream." This event promises to inspire and encourage young girls to pursue careers in engineering.
capital city go-go at westchester knicks
Experience the excitement as the Westchester Knicks take on the Capital City Go-Go at the Westchester County Center in White Plains, NY. Get ready for an action-packed basketball game!
prelude to the revolution in a new york border town — rye historical society
Learn about the events leading up to the American Revolution in a New York border town. On July 11, 1776, Rye resident John Thomas Jr. publicly read the Declaration of Independence from the White Plains Courthouse, marking a pivotal moment in local history.
westchester comedy club @ white plains: saturday night laughs - feb 2026
Enjoy a night of laughter at the Westchester Comedy Club in White Plains, featuring five talented professional comedians from New York City. Stay tuned for the full lineup announcement and be sure to get your tickets early!
Westchester County Weather
Weather in Westchester County
Sun, Feb 22
45%
1° -2°
45%
Mon, Feb 23
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.
