Title: Cheap Flights to Winchester , VA from CA $202 - Expedia.ca ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap Flights to Winchester , VA from CA $202 [View CA $202 flight on Wed, Jul 15, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YTZ,to:IAD,departure:15/07/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:201.38&airProductToken=AQpnCjIIwYYBEgQ3OTYyGPjMASCYXSietpIDMOu2kgM4R0AAWAFqBUJBU0lDcghHTkEyQTlCQQoxCMGGARIEODcyNRiYXSCIGCixuJIDMKW5kgM4R0ABWAFqBUJBU0lDcghHTkEyQTlCQRIKCAIQARgCKgJBQxgBIgQIARABKAIoAygEMA0) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Flight 1 Leaving from Going to Departing Flight 2 Leaving from Going to Departing [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d6056879.Destination-Travel-Guides) ## Popular airlines to Winchester - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winchester, Virginia, United States of America,departure:22/02/2026TANYT&leg2=from:Winchester, Virginia, United States of America,to:CMH,departure:01/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winchester, Virginia, United States of America,departure:22/02/2026TANYT&leg2=from:Winchester, Virginia, United States of America,to:CMH,departure:01/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winchester, Virginia, United States of America,departure:22/02/2026TANYT&leg2=from:Winchester, Virginia, United States of America,to:CMH,departure:01/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winchester, Virginia, United States of America,departure:22/02/2026TANYT&leg2=from:Winchester, Virginia, United States of America,to:CMH,departure:01/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winchester, Virginia, United States of America,departure:22/02/2026TANYT&leg2=from:Winchester, Virginia, United States of America,to:CMH,departure:01/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winchester, Virginia, United States of America,departure:22/02/2026TANYT&leg2=from:Winchester, Virginia, United States of America,to:CMH,departure:01/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winchester, Virginia, United States of America,departure:22/02/2026TANYT&leg2=from:Winchester, Virginia, United States of America,to:CMH,departure:01/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## How much is the cheapest flight to Winchester? Prices were available within the past 7 days and start at CA $202 for one-way flights and CA $311 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Thu, Feb 19 - Tue, Mar 31 YYZ Toronto IAD Washington CA $311 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:IAD,departure:19/02/2026TANYT&leg2=from:IAD,to:YYZ,departure:31/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:310.03&airProductToken=AQpyCjEIwYYBEgM0MDgYmM4BIJhdKMDLhQMwksyFAzhHQABYAWoFQkFTSUNyCEdOQTRBOUJBCj0IwYYBEgQ0NjcyGJhdIIgYKIHNhQMwgc6FAzhHQAFYAWoFQkFTSUNyCEdOQTRBOUJBegoI1YIBEgQ0NjcyCnQKPgjBhgESBDQxNjEYiBgg2LMBKN-LiQMwy4yJAzhHQABYAWoFQkFTSUNyCEdOQTJBOUJBegoI1YIBEgQ0MTYxCjIIwYYBEgM0NTEY2LMBIJjOASjAjYkDMIaOiQM4R0ABWAFqBUJBU0lDcghHTkEyQTlCQRIKCAIQARgCKgJBQxgBIgQIARABKAIoAygEMA0) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sat, May 2 - Tue, May 12 YYC Calgary IAD Washington CA $323 Roundtrip found 16 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:IAD,departure:02/05/2026TANYT&leg2=from:IAD,to:YYC,departure:12/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:322.62&airProductToken=AQpECiAI1YIBEgQxOTUzGJgWIINpKI_3iwMwq_iLAzhOQABYAQogCNWCARIEMjQwOBiDaSCIGCif-YsDMPb6iwM4TkABWAEKQgofCNWCARIDMzY3GIgYILJxKOLqjAMw0O2MAzhOQABYAQofCNWCARIDMjkxGLJxIJgWKPvwjAMwq_KMAzhOQAFYARIKCAEQARgBKgJVQRgBIgQIARABKAQwAQ) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Tue, Apr 7 - Wed, Apr 8 YUL Montreal IAD Washington CA $375 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:IAD,departure:07/04/2026TANYT&leg2=from:IAD,to:YUL,departure:08/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:374.46&airProductToken=AQpGCiEI0IgBEgQyNDcyGJhdIPjMASiE3YkDMNndiQM4VkAAWAEKIQjQiAESBDI3MjMY-MwBIIgYKIHeiQMw2t6JAzhWQAFYAQpGCiEI0IgBEgQyNzI0GIgYIPjMASjG6okDMKDriQM4VkAAWAEKIQjQiAESBDI0ODcY-MwBIJhdKPrriQMwxeyJAzhWQAFYARIKCAEQARgBKgJQRBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, May 1 - Tue, May 5 YYC Calgary DCA Washington CA $378 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:DCA,departure:01/05/2026TANYT&leg2=from:DCA,to:YYC,departure:05/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:377.03&airProductToken=AQptCjUIxJgBEgQyNDkyGJgWIMx8KNjoiwMw_emLAzhFQABYAWoJTUFJTkJBU0lDcghWQVZOQTBCUQo0CMSYARIEMjk2MxjMfCBDKPXriwMwiu2LAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZOQTBCUQqiAQozCMSYARIDMzQzGEMg4Fwor5WMAzChlowDOEVAAFgBaglNQUlOQkFTSUNyCFZBVk5BMEJRCjQIxJgBEgM0MjMY4Fwg8hIompiMAzCQmowDOEVAAVgBaglNQUlOQkFTSUNyCFZBVk5BMEJRCjUIxJgBEgQ0MTEzGPISIJgWKKqcjAMwrJ2MAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZOQTBCURIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Feb 24 - Tue, Mar 3 YVR Vancouver DCA Washington CA $382 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:DCA,departure:24/02/2026TANYT&leg2=from:DCA,to:YVR,departure:03/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:381.22&airProductToken=AQpoCjMIwYIBEgQxMDk5GLiNASCjsQEorYOGAzCuhYYDOEJAAFgBagVCQVNJQ3IIT1ZBQ1VTQlYKMQjBggESBDI3NTIYo7EBIEMogIiGAzCwiYYDOEJAAVgBagVCQVNJQ3IIT1ZBQ1VTQlYKaAoxCMGCARIEMTE3NxhDIKOxASiC1IYDMN_VhgM4QkAAWAFqBUJBU0lDcghPVkFDVVNCVgozCMGCARIEMTQzNBijsQEguI0BKM3WhgMw4diGAzhCQAFYAWoFQkFTSUNyCE9WQUNVU0JWEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ## Find the cheapest month to fly from Columbus (CMH) to Baltimore (BWI) ### March is typically the cheapest month to fly From CA $176 - CA $569 per traveller. Expedia.ca gives you the best tools to secure great deals on flights to Winchester. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Winchester. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Winchester. Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Winchester flights with full confidence knowing that you've found the best deal online. Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Winchester. Looking to save even more? Get additional savings by bundling your Winchester flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Winchester trip! ## Frequently asked questions ### What is the name of Winchester's airport? ### What airport is best to fly into Winchester? ### How many airlines fly to Winchester? ### Which airlines fly to Winchester? ### How many nonstop flights are there to Winchester? ### Where are the most popular flights to Winchester departing from? ### How long is the flight to Winchester Airport? ### How to book the cheapest flight to Winchester? ### Do you have any tips for my flight to Winchester? > - The secret to having a worry-free travel experience is to pack in advance. Start with the essentials: passport, official ID, credit cards and vital medications. Next, take on board items that'll help keep you occupied, like your laptop or a magazine. It's also smart to bring your chargers, a neck pillow and a pair of earphones. Finally, don't forget to chuck in toiletry items like a toothbrush, facial wipes and a fresh change of clothes. > > > Do not pack the following items in your hand luggage: > > > - Check carefully that you don't have sharp or pointed objects hiding in the bottom of your hand luggage. Other banned items include explosive or flammable products, like aerosols and matches, and gels and liquids in containers with a capacity of more than 3.4 ounces (100 millilitres). > > > What to wear on a flight: > > > - The aisles of a plane are no place for a fashion parade. Layer up with comfortable clothing and go for shoes that are enclosed, flat and easy to slip on and off. > - Deep vein thrombosis (DVT) is a risk on long-distance flights. It results from blood clotting due to poor circulation, so do some gentle leg and foot exercises in your seat and consider wearing compression tights or socks. ### How to get through airport security fast when flying to Winchester? > - Be sure to have your ID and travel documents within easy reach. They're the first things you'll be asked to show at security. > - Next up is the X-ray machine. Empty your pockets and remove anything that is likely to beep. This includes items like earphones or headphones, as well as your coat or jacket. They'll all need to go on the X-ray conveyor belt. > - For just a few moments, you'll have to unplug from the digital world. Your laptop, phone and any other electronics must also go through the scanner. > - Remove all liquids and gels from your hand luggage. They usually need to be sent through the X-ray separately. Each product should be no larger than 3.4 ounces (100 millilitres) and everything must fit inside a quart-size (one litre), clear zip-lock bag. > - There's a good chance you'll be required to take your shoes off for scanning, so wearing lightweight sneakers is always a smart idea. > - Airlines will not allow any sharp objects in your hand luggage. If you need to bring these kinds of items, pack them in your checked baggage. __Flights to Winchester information__ | Destination airport | Washington Dulles Intl. | | ----------------------------- | ----------------------- | | Destination airport IATA code | IAD | | Destination city name | Washington | | Roundtrip price | CA $310 | ## Trending flights to Winchester Prices were available within the past 7 days and start at CA $202 for one-way flights and CA $311 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Thu, Feb 19 - Tue, Mar 31 YYZ Toronto IAD Washington CA $311 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:IAD,departure:19/02/2026TANYT&leg2=from:IAD,to:YYZ,departure:31/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:310.03&airProductToken=AQpyCjEIwYYBEgM0MDgYmM4BIJhdKMDLhQMwksyFAzhHQABYAWoFQkFTSUNyCEdOQTRBOUJBCj0IwYYBEgQ0NjcyGJhdIIgYKIHNhQMwgc6FAzhHQAFYAWoFQkFTSUNyCEdOQTRBOUJBegoI1YIBEgQ0NjcyCnQKPgjBhgESBDQxNjEYiBgg2LMBKN-LiQMwy4yJAzhHQABYAWoFQkFTSUNyCEdOQTJBOUJBegoI1YIBEgQ0MTYxCjIIwYYBEgM0NTEY2LMBIJjOASjAjYkDMIaOiQM4R0ABWAFqBUJBU0lDcghHTkEyQTlCQRIKCAIQARgCKgJBQxgBIgQIARABKAIoAygEMA0) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - [3 Star Hotels in Old Town Winchester ](https://www.expedia.ca/3Star-Old-Town-Winchester-Winchester-Hotels.s30-n6164092-0.Travel-Guide-Filter-Hotels) - 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