- Must visit
Shenandoah Valley Civil War Museum
Museum in the historic Frederick County Courthouse with exhibits on the Civil War in the lower Shenandoah Valley and the region’s wartime history.
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Journey information
Overview: New York, NY to Winchester, VA flight
USAUSA
Flights from New York, NY to Winchester, VA depart on average 65 times per day, taking around 1h 31m. Cheap flight tickets for this journey start at $69 (€57) but you can travel from only $57 (€47) by train.
There are 19 flights per day. The earliest flight runs at 05:00, the last at 22:45. The fastest flight covers the 244 miles (393 km) distance in 1h 14m. June is the cheapest month to fly.
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Train from $57 (€47)
Distance 244 miles (393 km) |
Average flight duration 1h 31m |
Cheapest ticket price $69 (€57) |
Flights per day 65 |
Direct flights 19 |
Fastest flight 1h 14m |
First flight 5:00 AM |
Last flight 10:45 PM |
Cheapest Month Jun |
Cheapest Day Sun |
High Season Jan - Mar |
Low Season Oct - Dec |
Best time to book 35 days |
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Train from $57 (€47)
The cheapest and fastest flights from New York, NY to Winchester, VA
Showing times and prices for Jul 11
Cheapest price
$139
Average price
$185
Fastest journey
1 h 14 m
Average duration
1 h 18 m
Flights per day
2
Distance
393 km
Cheap tickets
The best way to find a cheap flight ticket from New York, NY to Winchester, VA is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from New York, NY to Winchester, VA will cost around $185 if you buy it on the day, but the cheapest tickets can be found for only $139.
Fast flights
Of the 2 flights that leave New York, NY for Winchester, VA onSat, Jul 11, 2 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sat, Jul 11 the direct flights cover the 393 km distance in an average of 1 h 18 m but if you time it right, some flights will get you there in just 1 h 14 m .
On Sat, Jul 11 the longest flights will take 1 h 21 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.
2:45 AM1h14New York, NY3:59 AMWinchester, VA$1391One-way0 transfers- 1:38 AM1h21New York, NY2:59 AMWinchester, VA$2311One-way0 transfers
- 2:45 AM1h14New York, NY3:59 AMWinchester, VA$1391One-way0 transfers
- 1:38 AM1h21New York, NY2:59 AMWinchester, VA$2311One-way0 transfers
Travel Information
Compare flight and train for New York, NY to Winchester, VA
Omio recommends booking the train as it is the most popular option from New York, NY to Winchester, VA among Omio's users. If you are prioritising price take the flight with prices starting from $69. For those with little time consider booking a flight which can get you there in 1h 31m. The ticket price range depends on the travel mode: a flight costs an average of $69, and a train costs an average of $57.
Distance: 244 miles (393 km)
Compare flight with
| Flight | Most popular Train | Driving |
|---|---|---|
$191 Average price Cheapest | $220 Average price | $67 Average price (fuel + tolls) |
4h 31m Average total duration Fastest 1h 31m Onboard + 3h 0m Additional time* | 5h 33m Average total duration 5h 3m Onboard + 30m Additional time* | 4h 19m Average total duration (door-to-door) |
 Most popular airline |  Most popular train company | Your own car or car rental |
Direct Options | Direct Options | Direct Options |
The cheapest way to travel from New York, NY to Winchester, VA is a flight with an average price of $191 (€157).
This is compared to other travel options from New York, NY to Winchester, VA:
A flight is $28 (€23) less than a train for this route with tickets for a train from New York, NY to Winchester, VA costing on average $220 (€180).
The fastest way to travel from New York, NY to Winchester, VA is by flight with an average journey time of 1h 31m.
Other travel options to Winchester, VA take longer:
Train takes on average 5h 3m.
It's helpful to compare your options as there are 2 ways to travel between New York, NY and Winchester, VA including taking a flight and train.
We recommend using the train as it is the most popular way to get from New York, NY to Winchester, VA among Omio's users.
Live departures
New York, NY to Winchester, VA flight times
The table below shows live departures for New York, NY to Winchester, VA flights for tomorrow, Friday, July 10. You can also manually refresh the results below to see updated flight journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 1:38 AM New York, NY | 1h21 | 2:59 AM Winchester, VA | 0 transfersDirect | |
| 2:45 AM New York, NY | 1h14 | 3:59 AM Winchester, VA | 0 transfersDirect | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets New York, NY to Winchester, VA by flight or train
Compare flight and train prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
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Jul 11
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Airlines: Republic Airlines from New York, NY to Winchester, VAFind the best flights between New York, NY to Winchester, VA with Omio's travel partners Republic Airlines from $57 (€47). We can find you the best deals, schedules and tickets when comparing and booking the best trip.
Republic Airlines
About
Republic Airways is a major regional airline in the United States, operating as a subsidiary of Republic Airways Holdings. It provides scheduled passenger service for American Airlines (as American Eagle), Delta Air Lines (as Delta Connection), and United Airlines (as United Express) using a fleet of Embraer 170 and 175 regional jets. Headquartered in Indianapolis, Indiana, Republic Airways operates over 900 daily flights to more than 80 cities across the U.S. and Canada. The company is known for its large fleet of Embraer E-Jets and its state-of-the-art training facilities. In April 2025, Republic Airways Holdings announced its acquisition of Mesa Air Group, which is expected to create the second-largest regional carrier in the U.S.
Luggage & cancellation policy
Average Duration
1h 19m
Cheapest Price
$64 (€52)
Republic Airlines frequency
9 a day
Luggage included
One carry-on bag (24 x 16 x 10) and one personal item
Additional luggage
Checked bags for a fee
Cancellation Policy
Tickets are non-refundable but may be cancelled for future flight credit minus applicable fees
Pregnant on board
Passengers can fly up to the end of their 36th week for single pregnancies and the end of their 32nd week for multiple pregnancies
Unaccompagned minor
Unaccompanied minor service is available for children ages 5-14. Must be booked directly with Republic Airlines
Amenities on board the airplane
USB plugs
Accessibility
Republic Airlines offers assistance for passengers with reduced mobility, including wheelchair services and priority boarding. Passengers are advised to request these services in advance to ensure availability and proper arrangements.
Complete guide to Winchester
Things to do in Winchester
Discover the best of Winchester — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Winchester trip today.
- Must visit
Museum Of The Shenandoah Valley
Regional art and history museum known for changing exhibitions, decorative arts, and landscaped grounds that make it one of Winchester’s signature cultural stops.
- Recommended
Shenandoah Valley Discovery Museum
Hands-on children’s museum in downtown Winchester with interactive science, art, and play exhibits, especially good for families.
- Must visit
Old Town Winchester
The city’s main walking district, centered on a pedestrian mall with shops, historic facades, seasonal events, and an active street scene.
- Must visit
Loudoun Street Mall
Pedestrian-friendly stretch through downtown Winchester, popular for strolling, people-watching, and experiencing the historic center.
- Recommended
Museum Of The Shenandoah Valley Gardens
Well-kept gardens and grounds surrounding the museum, popular for walks, photos, and seasonal blooms.
Virginia Ham Biscuits
Salt-cured Virginia country ham served in small biscuits is a classic regional snack tied to Shenandoah Valley and wider Virginia food traditions.
- Vegetarian
- Gluten-free
Fried Apples
A traditional Shenandoah Valley side dish of skillet-cooked apples with butter and spices, commonly served with country breakfasts and ham.
- Vegetarian
- Vegan
- Gluten-free
Apple Butter
Slow-cooked spiced apple spread that reflects the valley’s long apple-growing heritage and is commonly eaten on bread, biscuits, or pancakes.
Violino Ristorante Italiano
Established upscale Italian restaurant known for polished service, classic dishes, and a refined date-night atmosphere in Winchester.
Village Square Restaurant
Long-running local favorite for Southern breakfasts and comfort food, especially biscuits, gravy, and classic diner-style plates.
The Union Jack Pub & Restaurant
Popular established pub in Old Town with British and American fare, good beer selection, and a lively casual atmosphere.
United States Dollar
Prices are moderate for U.S. travelers. Dining and coffee are reasonable, while hotels vary by season and events.
Average meal costs
- Budget
- USD 10-15 for fast food or a simple lunch.
- Mid-range
- USD 20-35 per person at a casual restaurant.
- Fine dining
- USD 50+ per person at upscale restaurants.
- Coffee
- USD 3-6 for a regular coffee or latte.
Tipping culture
Tip 15-20% in restaurants before tax. Tip USD 1-2 per drink at bars, round up taxis, and tip hotel staff or delivery drivers.
FAQs: New York, NY to Winchester, VA Flight
Find answers to the most common questions about traveling from New York, NY to Winchester, VA by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Winchester, VA, this guide helps you travel smarter and with confidence.
Cheap plane tickets from New York, NY to Winchester, VA can start from as little as $69 (€57) when you book in advance. The average flight ticket price for New York, NY to Winchester, VA is $191 (€157) ; however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The average journey time by plane from New York, NY to Winchester, VA is 1h 14m to travel the 244 miles (393 km) long route. Journey times can vary on weekends and holidays, so use our Journey Planner to search for a specific date.
The earliest flight from New York, NY to Winchester, VA leaves at 5:00 AM. Plan your trip with the Journey Planner from Omio.
The latest flight from New York, NY to Winchester, VA leaves at 10:45 PM.
Yes, there are 19 direct flights a day from New York, NY to Winchester, VA with Republic Airlines. Schedules can vary on holidays or weekends with fewer direct flights.
When taking a flight from New York, NY to Winchester, VA, you can count on Republic Airlines for the best way to get you to Winchester, VA. You can also check all possible airlines who offer a service between New York, NY and Winchester, VA and compare the amenities they offer before buying a plane ticket.
The cheapest month for a flight from New York, NY to Winchester, VA is June.
It's helpful to compare your options as there are 2 ways to travel between New York, NY and Winchester, VA including taking a flight and train.
Since neither New York, NY nor Winchester, VA are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and United States. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
There is no time difference between New York, NY and Winchester, VA.
We recommend using the train as it is the most popular way to get from New York, NY to Winchester, VA among Omio's users.
For domestic flights we recommend to arrive 1.5 to 2 hours before departure. Please check the website of your departure airport if in doubt. Some airports may offer booking time slots for security checks or offer additional information on when to get there based on time of day.
Most airlines permit carry-on bags that fit within specific dimensions (e.g., 22 x 14 x 9 inches or 56 x 36 x 23 cm), including handles and wheels. Bags must fit in the overhead bin or under the seat in front of you.
Many airlines impose weight limits, commonly ranging between 7 kg (15 lbs) and 12 kg (26 lbs). Typically, passengers are allowed one carry-on bag and one personal item (for example a purse, laptop bag, or backpack). Personal items must fit under the seat in front of you. Budget Airlines (like Ryanair or Wizz Air) have stricter size and weight limits, often requiring fees for larger carry-ons. Full-Service Airlines have more lenient policies, sometimes including more spacious dimensions or higher weight limits depending on your ticket class.
The list of items prohibited on an airplane varies by country and airline, but in general, the following items are not allowed in carry-on or checked baggage: Weapons and self-defence items, sharp objects, flammable materials, explosives, toxic substances, or liquids over 100ml (except for medications and baby essentials). In checked baggage, firearms (without authorization), explosives, large lithium batteries, and hazardous chemicals are prohibited. Electronic cigarettes must be in carry-on bags, while alcohol and dry ice have restrictions. Always check with your airline for specific regulations.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Winchester, VA, travelers should be cautious of pickpocketing and petty theft, especially in crowded areas and during events like the Shenandoah Apple Blossom Festival. Common scams include overcharging by unlicensed taxi or ride-share drivers and fraudulent ticket sales for local attractions. Staying aware of surroundings and using official transportation services helps ensure a safe visit.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
popular airports
Popular airports from New York, NY to Winchester, VA
Most New York, NY to Winchester, VA flights use the Newark Liberty International Airport to Albemarle Airport airport pair. Use this guide to compare New York, NY and Winchester, VA airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
Departure airports in New York
Arrival airports in Winchester
Which New York, NY airport do flights to Winchester, VA leave from?
Flights from New York, NY to Winchester, VA depart from Newark Liberty International Airport. The airport is 2 miles (4 km) from New York, NY city centre at 3 Brewster Rd, Newark, NJ 07114, USA.
LaGuardia Airport (LGA)Queens, NY 11371, USA
City-centre transport
Getting to LaGuardia Airport from New York city centre
LaGuardia Airport is 13 km from New York city centre. Public transport options include:
BusM60-Sbs · 42m · $11 · every ~16 min
M60-Sbs · 57m · $11 · every ~16 min
M60-Sbs · 1h 8m · $11 · every ~16 min
M101 · 1h 33m · $16 · every ~14 min
ShuttleLa Guardia Airport Shuttle · 49m · $37
LaGuardia Airport airport facilities and services
LaGuardia Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Lounge, Lost and Found Office, and Car Rental.
Food and drink
Food options include: Restaurants in all terminals, including fast food and sit-down options like Shake Shack and La Chula.
Wi-Fi and ATMs
Free Wi-Fi available throughout the airport. ATMs are located in all terminals, near main entrances and exits.
Luggage and lost property
Lost and found is available at the station.
Parking, taxis and toilets
Available at LaGuardia Airport: Parking, Taxis, WC.
Bike and car services
Available at LaGuardia Airport: Car Rental.
Accessibility
Accessibility facilities are available at LaGuardia Airport: Elevators, ramps, assistance.
Shops, hotels and contact
Nearby hotels include Hotels nearby, including LaGuardia Plaza Hotel and Aloft New York LaGuardia Airport..
John F. Kennedy International Airport (JFK)Queens, NY 11430, USA
City-centre transport
Getting to John F. Kennedy International Airport from New York city centre
John F. Kennedy International Airport is 3 km from New York city centre. Public transport options include:
TrainPort Jefferson Branch, Long Beach Branch, Babylon Branch, Ronkonkoma Branch, Hempstead Branch, City Terminal Zone, Far Rockaway Branch, West Hempstead Branch, Montauk Branch, Oyster Bay Branch · 33m · $18 · every ~19 min
SubwayA · 54m · $13 · every ~10 min
ShuttleJFK Airport Shuttle · 47m · $45
John F. Kennedy International Airport airport facilities and services
John F. Kennedy International Airport has practical services for this route, including Wifi, Shopping, Parking, ATM, Taxis, Accessibility, WC, Shower, Lounge, and Lost and Found Office.
Wi-Fi and ATMs
Free Wi-Fi available throughout the airport. ATMs are located in all terminals, near gates and check-inas.
Luggage and lost property
Lost and found is available at the station.
Parking, taxis and toilets
Available at John F. Kennedy International Airport: Parking, Taxis, WC.
Accessibility
Accessibility facilities are available at John F. Kennedy International Airport: Ramps, assistance.
Most popular flights from New York, NY
More options for your journey from New York, NY to Winchester, VA
Here are some other resources that might have the information you need
Most popular flights to and from Winchester, VA and New York, NY
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