Title: $57 Cheap flights from Winchester - Expedia.com ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $57 Cheap flights from Winchester [View $57 flight on Fri, Jun 19, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:YOW,to:YYZ,departure:6/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:56.25&airProductToken=AQojCiEI16YBEgM4OTMY2LMBIJjOASiPj5ADMNCPkAM4QUAAWAESCggBEAEYASoCV1MYASIECAEQASgEMAE) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travelers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only [Hotels in Winchester](https://expedia.com/Winchester-Hotels.d6344696.Travel-Guide-Hotels)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d6344696.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d6344696.Destination-Travel-Guides) ## Popular airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AC.svg) Air Canada - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WS.svg) WestJet - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_PD.svg) Porter Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_TS.svg) Air Transat - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_LH.svg) Lufthansa - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_LX.svg) Swiss International Air Lines - ![](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 OneKeyCash [Learn about One Key](https://www.expedia.com/welcome-one-key) ## Cheapest flights from Winchester These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Tue, May 26 - Fri, May 29 YOW Ottawa YYZ Toronto $117 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:YOW,to:YYZ,departure:5/26/2026TANYT&leg2=from:YYZ,to:YOW,departure:5/29/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:116.61&airProductToken=AQo0CjII16YBEgM4OTMY2LMBIJjOASiPgY4DMNCBjgM4QUAAWAFqBUJBU0lDcghBQVVEMFpCVwo0CjII16YBEgM1ODgYmM4BINizASiup44DMO-njgM4QUAAWAFqBUJBU0lDcghBQVVEMFpCVxIMCAEQARgBKgJXUzIAGAEiBAgBEAEoAigDKAQwAQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Tue, Mar 17 - Thu, Mar 19 YOW Ottawa YYZ Toronto $126 Roundtrip found 5 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:YOW,to:YYZ,departure:3/17/2026TANYT&leg2=from:YYZ,to:YOW,departure:3/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:125.04&airProductToken=AQojCiEI16YBEgM1ODkY2LMBIJjOASiE7YcDMNXthwM4QUAAWAEKIwohCNemARIDNTg4GJjOASDYswEo8ouIAzC3jIgDOEFAAFgBEgoIARABGAEqAldTGAEiBAgBEAEoBDAB) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Sun, May 3 - Thu, May 7 YOW Ottawa YYZ Toronto $132 Roundtrip found 4 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:YOW,to:YYZ,departure:5/3/2026TANYT&leg2=from:YYZ,to:YOW,departure:5/7/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:131.19&airProductToken=AQo0CjII16YBEgM4OTMY2LMBIJjOASiv_osDMPD-iwM4RUAAWAFqBUJBU0lDcghMQVVEMExCVwo0CjII16YBEgM1ODgYmM4BINizASjur4wDMK-wjAM4QUAAWAFqBUJBU0lDcghBQVVEMFpCVxIMCAEQARgBKgJXUzIAGAEiBAgBEAEoAigDKAQwAQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Sat, Jun 27 - Sat, Jul 11 YOW Ottawa YYZ Toronto $135 Roundtrip found 8 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:YOW,to:YYZ,departure:6/27/2026TANYT&leg2=from:YYZ,to:YOW,departure:7/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:134.68&airProductToken=AQojCiEI16YBEgM4OTMY2LMBIJjOASiP6ZADMNDpkAM4QUAAWAEKIwohCNemARIDNTg4GJjOASDYswEojouSAzDPi5IDOEFAAFgBEgoIARABGAEqAldTGAEiBAgBEAEoBDAB) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Mon, Apr 27 - Sun, May 3 YOW Ottawa YYZ Toronto $136 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:YOW,to:YYZ,departure:4/27/2026TANYT&leg2=from:YYZ,to:YOW,departure:5/3/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:135.89&airProductToken=AQojCiEI16YBEgM4OTMY2LMBIJjOASjvuosDMLC7iwM4QUAAWAEKIwohCNemARIDNTg4GJjOASDYswEo7oKMAzCvg4wDOEFAAFgBEgoIARABGAEqAldTGAEiBAgBEAEoBDAB) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Sat, Apr 18 - Sun, May 17 YOW Ottawa YYZ Toronto $144 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:YOW,to:YYZ,departure:4/18/2026TANYT&leg2=from:YYZ,to:YOW,departure:5/17/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:143.54&airProductToken=AQo0CjII16YBEgM1ODkY2LMBIJjOASiE1YoDMNXVigM4QUAAWAFqBUJBU0lDcghBQVVEMFpCSgo0CjII16YBEgM4OTIYmM4BINizASjDo40DMISkjQM4RUAAWAFqBUJBU0lDcghMQVVEMExCSxIKCAEQARgBKgJXUxgBIgQIARABKAIoAygEMAE) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Wed, Mar 18 - Wed, Apr 1 YOW Ottawa FLL Fort Lauderdale $175 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:YOW,to:FLL,departure:3/18/2026TANYT&leg2=from:FLL,to:YOW,departure:4/1/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:174.82&airProductToken=AQojCiEIwYYBEgQxMjU2GNizASDlWijH-IcDMLD6hwM4R0AAWAEKIwohCMGGARIEMTI1NxjlWiDYswEouJiJAzD_mYkDOEdAAFgBEgoIARABGAEqAkFDGAEiBAgBEAEoCCgEMAE) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Thu, Mar 19 - Wed, Apr 1 YOW Ottawa FLL Fort Lauderdale $175 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:YOW,to:FLL,departure:3/19/2026TANYT&leg2=from:FLL,to:YOW,departure:4/1/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:174.82&airProductToken=AQoiCiAI0IgBEgM1MTcY2LMBIOVaKL-IiAMwm4qIAzhNQABYAQoiCiAI0IgBEgM1MTIY5Vog2LMBKNOZiQMwpZuJAzhNQABYARIKCAEQARgBKgJQRBgBIgQIARABKAQwAQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Fri, May 1 - Sun, May 10 YOW Ottawa RSW Fort Myers $197 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:YOW,to:RSW,departure:5/1/2026TANYT&leg2=from:RSW,to:YOW,departure:5/10/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:196.65&airProductToken=AQpuCjUI1YIBEgQzNDk3GNizASCIGCjA64sDMK7siwM4TkAAWAFqCEVDT0JBU0lDcghHTkEyQTRCTgo1CNWCARIEMTc0MhiIGCDRtAEog-2LAzCn7osDOE5AAVgBaghFQ09CQVNJQ3IIR05BMkE0Qk4KcAo2CNWCARIEMjYyOBjRtAEgxI0BKPfMjAMwqs6MAzhOQABYAWoIRUNPQkFTSUNyCEdOQTJBNEJOCjYI1YIBEgQzNjYwGMSNASDYswEo9tCMAzDW0YwDOE5AAVgBaghFQ09CQVNJQ3IIR05BMkE0Qk4SDAgBEAEYASoCVUEyABgBIgQIARABKAIoAygEMAE) ![Air Transat](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/TS.gif) Fri, Mar 27 - Sat, Mar 28 YOW Ottawa YYZ Toronto $258 Roundtrip found 7 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:YOW,to:YYZ,departure:3/27/2026TANYT&leg2=from:YYZ,to:YOW,departure:3/28/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:257.44&airProductToken=AQozCjEI1KYBEgQ3ODkyGNizASCYzgEo-eGIAzDE4ogDOE9AAFgBagNCR1RyCE8yQTBaRFpMCjMKMQjUpgESBDc4NjQYmM4BINizASjD6YgDMIfqiAM4T0AAWAFqA0JHVHIITzJBMFpEWkwSDAgBEAEYASoCVFMyABgBIgQIARABKAIoAygEMA0) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=FTG_SPRING_PROMO_) ## How to Find Cheap Flights from Winchester #### How much is a flight from Winchester? This week, flights from Winchester are available between $117 – $258\. #### How to find cheap flights from Winchester? Expedia makes it easy to compare cheap flights from Winchester to many destinations. Check out excellent deals on domestic and international flights from Winchester. Once you select an offer, use our filters and sort by “Price (Lowest)” to see some of the cheapest and suitable options. #### How can I get the best deal on flights from Winchester? On Expedia, you have some of best airline ticket deals at your fingertips. Whether it’s a beach escape with your partner, a family vacation with your kids, or business trip with colleagues, these low airline ticket prices mean more savings for you. An excellent strategy for finding some of the best deals on flights from Winchester is to be flexible with your dates. Within each offer, you can compare prices for similar timeframes using our “Show flexible dates” feature. Depending on your destination, direct flights from Winchester may be more expensive. Airlines with strict bag policies or fees can also impact your costs. #### What is the best airline to fly from Winchester? At Expedia, we give you all the available options from our reputable partners. Select the airline that best suits your preferences and membership loyalties. You can fly from Winchester with: WestJet, Porter Airlines, Air Canada, Air Transat, United. #### What is the best month to fly from Winchester? One of the cheapest times to fly from Winchester airport(s) is May, based on the current list of flights available now. Prices on plane tickets vary considerably throughout the year due to availability and seasonal demand. #### Are there any last-minute flights from Winchester? Expedia is the place to find last-minute flights from Winchester, making it easy for you to compare prices on flights in the near future for different combinations of travel dates and from multiple airlines. We source some of the best deals for you and display some of the best offers available over the next 2 weeks. #### Why book your ticket with Expedia? Booking flights from Winchester with Expedia is the obvious choice to get low prices, save money, and see more value from every dollar spent. We show you some of the best deals happening right now and provide a vast inventory of airlines and flight routes to choose from, so you can find some of the cheapest flights from Winchester. You can customize your journey to your timeline, route preferences, budget, rewards programs, and more. #### Can I change/cancel my flight? Some flights can be changed or canceled, but fees and refunds will depend on the unique terms of your flight agreement. Airlines have different rules and restrictions for exchanging or refunding flights. For more information, go to your itinerary or visit our [customer service portal](https://www.expedia.com/service/). We recommend choosing flights with no change fees for the most flexibility. Filter by “Flexible change policies” to see flights with no change fees. \*Data specialists from both ARC and Expedia Group analysed ARC's global flight data to distil actionable information to help people save money on travel. While it's impossible to guarantee when to find the lowest prices, after examining the variables, we were able to observe trends. Analysis based on ARC, round-trip flight data between 1 October 2017 - 30 September 2018 for Economy and Premium cabin ATPs on a global basis. ## Travel information ## Flights from Winchester: Essential Travel Information | Cheapest flight from Winchester | $117 (roundtrip) | | ------------------------------------- | --------------------------------------------------------- | | Best airlines to fly from Winchester | WestJet, Porter Airlines, Air Canada, Air Transat, United | | Cheapest month to fly from Winchester | May | | Winchester IATA code | YOW | | Winchester Country/State | North Dundas | | Airline ticket deals from Winchester | $117 - $258 | \*Flight schedules are subject to change. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Chesterville ](https://www.expedia.com/Chesterville-North-Dundas-Hotels.0-n3000434217-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Chesterville ](https://www.expedia.com/4Star-Chesterville-North-Dundas-Hotels.s40-n3000434217-0.Travel-Guide-Filter-Hotels) - 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