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Winchester Flights from C$129

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

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Flight deals to Winchester

Looking for a cheap last-minute deal or the best roundtrip flight to Winchester? Find our lowest prices on one-way and roundtrip tickets to the most convenient airport right here.
Washington, D.C..C$129 per passenger.Departing Mon, Oct 6.One-way flight with WestJet.Outbound indirect flight with WestJet, departing from Vancouver International on Mon, Oct 6, arriving in Washington Dulles.Price includes taxes and charges.From C$129, select.
Washington, D.C..C$144 per passenger.Departing Tue, Sep 9.One-way flight with United.Outbound indirect flight with United, departing from Halifax International on Tue, Sep 9, arriving in Washington Dulles.Price includes taxes and charges.From C$144, select.
Washington, D.C..C$152 per passenger.Departing Sat, Nov 15.One-way flight with United.Outbound indirect flight with United, departing from Halifax International on Sat, Nov 15, arriving in Washington Dulles.Price includes taxes and charges.From C$152, select.
Washington, D.C..C$158 per passenger.Departing Mon, Oct 6.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departing from Toronto Island on Mon, Oct 6, arriving in Washington Dulles.Price includes taxes and charges.From C$158, select.
Washington, D.C..C$158 per passenger.Departing Thu, Sep 18.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departing from Toronto Island on Thu, Sep 18, arriving in Washington Dulles.Price includes taxes and charges.From C$158, select.
Washington, D.C..C$159 per passenger.Departing Thu, Nov 6.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departing from Toronto Island on Thu, Nov 6, arriving in Washington Dulles.Price includes taxes and charges.From C$159, select.
Washington, D.C..C$163 per passenger.Departing Mon, Dec 8.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departing from Toronto Island on Mon, Dec 8, arriving in Washington Dulles.Price includes taxes and charges.From C$163, select.
Washington, D.C..C$182 per passenger.Departing Fri, Aug 29.One-way flight with Air Canada.Outbound indirect flight with Air Canada, departing from Halifax International on Fri, Aug 29, arriving in Washington Dulles.Price includes taxes and charges.From C$182, select.
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Flying to Winchester

The things to know before you go.
Fly intoWashington Dulles Airport
Distance to Winchester66.9 km
Average flight time2 hrs, 35 mins
Most popular airlineUnited
Cheapest flight foundC$129
Cheapest month to flyOctober

Find the cheapest time to fly to Winchester

Flexible on travel dates? Find the cheapest month – or even day – to catch a flight to Winchester.
Aug
from C$182
Sep
from C$144
Oct
from C$129
Nov
from C$152
Dec
from C$163
Jan
from C$202
Feb
from C$259
Mar
from C$263
Apr
from C$320
May
from C$256
Jun
from C$325
Jul
from C$303

Frequently asked questions

The average flight time to Winchester is 1 hour and 51 minutes. We've calculated this based on journeys to Washington Dulles Airport.
There are two (2) airports near Winchester: Washington Dulles Airport and Hagerstown Airport.
United, Air Canada, Republic Airways, Copa, Jazz Air, Avianca, Porter Airlines, and Porter Airlines Inc all offer direct flights to Washington Dulles Airport.
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 Winchester 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.
Yes – you can fly direct to Washington Dulles Airport and the average flight time is 2 hours and 35 minutes.
The best price we found for a roundtrip flight to Winchester is C$208. This is an estimate based on information collected from different airlines and travel providers flying to Washington Dulles Airport over the last four (4) days and is subject to change and availability.
The cheapest airport near Winchester is Washington Dulles – which is 66.9 km away from the center of Winchester. We've found flights to this airport from C$208.
After crunching the numbers on our flight calendar, we found that the cheapest date to fly to Washington Dulles Airport, the closest airport to Winchester, is Wednesday, October 29, 2025.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Winchester is around 40 days in advance, so don’t leave your flight to the last minute.
Washington Dulles Airport is 66.9km from Winchester, Hagerstown Airport is 69.0km from Winchester, and Manassas Airport is 76.0km from Winchester.
The average temperature in Winchester in August is around 24°C. The warmest month in Winchester is typically July, which averages 31°C. The coolest month is January, with temperatures averaging -6°C. The rainiest month is May, and it usually rains the least in February.
Currently, the cheapest airline that flies to Washington Dulles Airport – the closest airport to Winchester – is Porter Airlines.
Washington Dulles Airport is 66.9km from Winchester which is approximately 1 hour and 9 minutes driving time. Check out the options for car rental at Washington Dulles Airport.