Title: CA $55 Cheap Flights from Winchester - Expedia.ca ![](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium) # CA $55 Cheap Flights from Winchester [View CA $55 flight on Fri, Dec 5, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:BWI,to:MIA,departure:05/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:54.28&airProductToken=AQouCiwIzpYBEgQxMDI3GMFFIIwCKNT3_gIwgPn-AjhXQABYAWoCUlByBldBMjFOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers 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.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 from Winchester - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines - ![Frontier Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines - ![Spirit Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines - ![Alaska Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines ![notification illustration](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\* ![deals illustration](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\* ![trophy illustration](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) ## Cheapest flights from Winchester These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Sat, Oct 18 - Sat, Oct 25 BWI Baltimore FLL Fort Lauderdale CA $88 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BWI,to:FLL,departure:18/10/2025TANYT&leg2=from:FLL,to:BWI,departure:25/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:87.10&airProductToken=AQotCisIzpYBEgM5MDEYwUUg5Voo5Nv6AjCB3foCOFdAAFgBagJSUHIGV1RSR0cxCi4KLAjOlgESBDEyNzAY5VogwUUo9KT7AjCOpvsCOFdAAFgBagJSUHIGV1RSR0cxEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Fri, Dec 5 - Fri, Dec 12 BWI Baltimore MIA Miami CA $109 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BWI,to:MIA,departure:05/12/2025TANYT&leg2=from:MIA,to:BWI,departure:12/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:108.56&airProductToken=AQouCiwIzpYBEgQxMDI3GMFFIIwCKNT3_gIwgPn-AjhXQABYAWoCUlByBldBMjFOUgouCiwIzpYBEgQxMDI4GIwCIMFFKJfI_wIwv8n_AjhXQABYAWoCUlByBldBMjFOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Mon, Nov 3 - Thu, Nov 6 BWI Baltimore MCO Orlando CA $112 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BWI,to:MCO,departure:03/11/2025TANYT&leg2=from:MCO,to:BWI,departure:06/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:111.46&airProductToken=AQotCisIzpYBEgM3MTEYwUUgzHAo3Yz8AjDvjfwCOFdAAFgBagJSUHIGV0EyMU5SCi0KKwjOlgESAzcxMhjMcCDBRSiQsPwCMJux_AI4V0AAWAFqAlJQcgZXQTIxTlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Mon, Oct 13 - Fri, Oct 17 BWI Baltimore TPA Tampa CA $117 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BWI,to:TPA,departure:13/10/2025TANYT&leg2=from:TPA,to:BWI,departure:17/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:116.07&airProductToken=AQouCiwIzpYBEgQyMTk1GMFFIPMDKNyj-gIw9KT6AjhXQABYAWoCUlByBldUUkdCMQouCiwIzpYBEgQyMTk2GPMDIMFFKJzP-gIwpdD6AjhHQABYAWoCUlByBkdBMTROUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Tue, Oct 21 - Wed, Oct 22 BWI Baltimore LAS Las Vegas CA $145 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BWI,to:LAS,departure:21/10/2025TANYT&leg2=from:LAS,to:BWI,departure:22/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:144.75&airProductToken=AQpfCi0IzpYBEgQxNTkxGMFFIIu4ASif9_oCMPX5-gI4UEAAWAFqAlJQcgZQQTE0TlIKLgjOlgESBDI1OTIYi7gBIIuQASi2-voCMIX7-gI4UEABWAFqAlJQcgZQQTE0TlIKLwotCM6WARIEMTYwMhiLkAEgwUUogYv7AjCejfsCOEdAAFgBagJSUHIGR0EyMU5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Sun, Oct 26 - Wed, Oct 29 BWI Baltimore ATL Atlanta CA $147 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BWI,to:ATL,departure:26/10/2025TANYT&leg2=from:ATL,to:BWI,departure:29/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:146.28&airProductToken=AQouCiwIzpYBEgQyNzYzGMFFIOBcKLyy-wIws7P7AjhXQABYAWoCUlByBldBMjFOUgpbCisIzpYBEgMxMzEY4Fwg5VooktH7AjD70fsCOFdAAFgBagJSUHIGV0EyMU5SCiwIzpYBEgQxMjcwGOVaIMFFKM7S-wIw5dP7AjhXQAFYAWoCUlByBldBMjFOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, Oct 11 - Sat, Oct 18 DCA Washington MIA Miami CA $162 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:DCA,to:MIA,departure:11/10/2025TANYT&leg2=from:MIA,to:DCA,departure:18/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:161.90&airProductToken=AQoyCjAIwYIBEgQxNTMzGEMgjAIo3o36AjD6jvoCOEJAAFgBagVCQVNJQ3IIT1VBSlpTQlgKMgowCMGCARIEMjY0OBiMAiBDKNvb-gIw99z6AjhCQABYAWoFQkFTSUNyCE9VQUpaU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Mon, Nov 24 - Tue, Dec 2 DCA Washington BOS Boston CA $170 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:DCA,to:BOS,departure:24/11/2025TANYT&leg2=from:BOS,to:DCA,departure:02/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:169.50&airProductToken=AQohCh8IwmwSBDExNTQYQyDBkwEo8Pb9AjDJ9_0COExAAFgBCiEKHwjCbBIEMTM1NRjBkwEgQyio1P4CMIzV_gI4TEAAWAESCggBEAEYASoCQjYYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Nov 15 - Wed, Nov 19 DCA Washington ATL Atlanta CA $218 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:DCA,to:ATL,departure:15/11/2025TANYT&leg2=from:ATL,to:DCA,departure:19/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:217.60&airProductToken=AQogCh4IxJgBEgMzODAYQyDgXCijlP0CMJeV_QI4RUAAWAEKIAoeCMSYARIDMzc4GOBcIEMol8X9AjD9xf0COEVAAFgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, Jan 20 - Tue, Jan 27 IAD Washington MCO Orlando CA $247 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:IAD,to:MCO,departure:20/01/2026TANYT&leg2=from:MCO,to:IAD,departure:27/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:246.90&airProductToken=AQoiCiAI1YIBEgQyNDYzGIgYIMxwKPf8ggMwjP6CAzhHQABYAQoiCiAI1YIBEgQyNDgyGMxwIIgYKOjHgwMw6siDAzhHQABYARIKCAEQARgBKgJVQRgBIgQIARABKAQwAQ) ## Flights from Winchester: Essential Travel Information | Cheapest flight from Winchester | CA $88 (roundtrip) | | --- | --- | | Best airlines to fly from Winchester | Spirit Airlines, American Airlines, JetBlue Airways, Delta, United | | Cheapest month to fly from Winchester | October | | Winchester IATA code | DCA | | Winchester Country/State | Virginia | | Airline ticket deals from Winchester | CA $88 - CA $247 | ## How to find cheap flights from Winchester #### How much is a flight from Winchester? Flights from Winchester are available at a range of prices. Attractive deals include one-way fares from CA $55 and roundtrip fares from CA $88. You'll often find the best deals in October. With Expedia, explore offers from multiple airlines and plan your journey effortlessly, ensuring you secure the perfect flight at a competitive price. #### How can I find cheap flights from Winchester? Discovering affordable flights from Winchester has never been easier, thanks to Expedia. We present a simple solution for comparing fares to a multitude of destinations, with one-way deals from CA $55 and roundtrip offers from CA $88. After choosing an enticing deal, enhance your search with our filters and sort by 'Price (Lowest)' to find the most economical and suitable options. Begin your journey with us today and relish the simplicity of securing cost-effective flights. #### How can I get the best deal on flights from Winchester? For the best deal on flights from Winchester, flexibility is key. Utilize our 'Show flexible dates' feature on Expedia to compare prices for different dates, and you may find deals when such offers are present. Remember, direct flights from Winchester could come with a higher price tag, and different airlines' baggage policies might affect the total cost. Stay tuned with our latest offers to make the most of your travel budget. #### What is the best airline to fly with from Winchester? With Expedia, finding the best airline for your journey from Winchester is a breeze. We offer options from 20 different airlines, including Spirit Airlines, American Airlines, JetBlue Airways, Delta, United. Whether you prioritize price, comfort, or loyalty programs, we have a fit for your travel needs. #### What is the best month to fly from Winchester? The best month to fly from Winchester is typically October, as it often offers great deals. If you're looking to save on your journey, start your search with Expedia. We provide options to filter for the lowest possible prices, including those from one-way from CA $55 and roundtrip from CA $88 fares. However, remember that airfare can fluctuate based on the time of year and ticket availability. #### When is the best time to book/buy flights from Winchester? Secure the best savings with Expedia. Data suggests that booking flights from Winchester three weeks in advance can save you up to 20%. Also, consider flying in October for the best rates. Stay updated with us for the latest data and savings advice. #### Are there any last-minute flights from Winchester? With Expedia, finding last-minute flights from Winchester has never been easier. We offer you a chance to explore the best deals from 20 airlines. Even if you're planning to travel immediately, you can access a variety of options, including one-way from CA $55 and roundtrip from CA $88 fares. Start exploring now and seize the top offers available over the next two weeks. Rest assured, you can find a perfect flight even at the last minute. #### Why book with Expedia? Choose Expedia for unbeatable prices, exceptional value, and substantial savings. We offer a wide selection of routes from Winchester, with flight options from 20 airlines, including one-way deals from CA $55. Customize your journey to suit your needs and achieve even more savings by bundling your flight with a hotel or car hire. Start planning your trip with us today and earn rewards points with every booking. #### Can I change/cancel my flight? Absolutely, at Expedia, you can change or cancel your flight. However, fees and refund policies depend on your flight agreement, as each airline has distinct rules for exchanges and refunds. For detailed information, check your itinerary or visit our customer service portal. 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[Spa Hotels in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Spa-Hotel.0-n918789051029594112-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotels near Winchester Medical Center](https://www.expedia.ca/Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels) ### Flights - [Flights to Boyce](https://www.expedia.ca/Cheap-Flights-To-Boyce.d184084.Travel-Guide-Flights) - [Flights from Winchester Regional](https://www.expedia.ca/lp/airports/wgo/flights-from-winchester-regional-airport) - [Flights from Reston](https://www.expedia.ca/lp/flights/10437/flights-from-reston) - [Flights from Boston](https://www.expedia.ca/lp/flights/177514/flights-from-boston) - [Flights from Upperville](https://www.expedia.ca/lp/flights/184116/flights-from-upperville) - [Flights from Broad Run](https://www.expedia.ca/lp/flights/3000355036/flights-from-broad-run) - [Flights from Loudoun County](https://www.expedia.ca/lp/flights/3000391184/flights-from-loudoun-county) - [Flights from Bristow](https://www.expedia.ca/lp/flights/3000459833/flights-from-bristow) - [Flights from Gore](https://www.expedia.ca/lp/flights/3000460015/flights-from-gore) - [Flights from Star Tannery](https://www.expedia.ca/lp/flights/3000460674/flights-from-star-tannery) - [Flights from The Plains](https://www.expedia.ca/lp/flights/3000460694/flights-from-the-plains) - [Flights from Lowes Island](https://www.expedia.ca/lp/flights/553248634999279056/flights-from-lowes-island) - [Flights from Markham](https://www.expedia.ca/lp/flights/553248635975848092/flights-from-markham) - [Flights from Clear Brook](https://www.expedia.ca/lp/flights/553248635975870250/flights-from-clear-brook) - [Flights from Cross Junction](https://www.expedia.ca/lp/flights/553248635975978078/flights-from-cross-junction) - [Flights from Sully](https://www.expedia.ca/lp/flights/553248635976006627/flights-from-sully) - [Flights from Blue Ridge](https://www.expedia.ca/lp/flights/553248635976006713/flights-from-blue-ridge) - [Flights from Middleburg](https://www.expedia.ca/lp/flights/55837/flights-from-middleburg) - [Flights from Washington](https://www.expedia.ca/lp/flights/56034/flights-from-washington) - [Flights from Centreville](https://www.expedia.ca/lp/flights/603264/flights-from-centreville) - [Flights from Ashburn](https://www.expedia.ca/lp/flights/6035055/flights-from-ashburn) - [Flights from Luray](https://www.expedia.ca/lp/flights/6056892/flights-from-luray) - [Flights from Northern Virginia](https://www.expedia.ca/lp/flights/6057018/flights-from-northern-virginia) - [Flights from Nokesville](https://www.expedia.ca/lp/flights/6136847/flights-from-nokesville) - [Flights from Haymarket](https://www.expedia.ca/lp/flights/6155337/flights-from-haymarket) - [Flights from Hamilton](https://www.expedia.ca/lp/flights/6319482/flights-from-hamilton) - [Flights from Purcellville](https://www.expedia.ca/lp/flights/6338641/flights-from-purcellville) - [Flights from Fort Valley](https://www.expedia.ca/lp/flights/6353682/flights-from-fort-valley) - [Flights from Herndon](https://www.expedia.ca/lp/flights/7596/flights-from-herndon) - [Flights from Chantilly](https://www.expedia.ca/lp/flights/8638/flights-from-chantilly) - [Flights from New Market](https://www.expedia.ca/lp/flights/9037/flights-from-new-market) - [Flights from Sterling](https://www.expedia.ca/lp/flights/9843/flights-from-sterling) - [Flights from Blacksburg (BCB) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bcb/wgo/blacksburg-to-winchester) - [Flights from Hartford (BDL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bdl/wgo/hartford-to-winchester) - [Flights from Baltimore (BWI) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bwi/wgo/baltimore-to-winchester) - [Flights from Denver (DEN) to Winchester (WGO)](https://www.expedia.ca/lp/flights/den/wgo/denver-to-winchester) - [Flights from Dallas (DFW) to Winchester (WGO)](https://www.expedia.ca/lp/flights/dfw/wgo/dallas-to-winchester) - [Flights from El Paso (ELP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/elp/wgo/el-paso-to-winchester) - [Flights from Fort Lauderdale (FLL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/fll/wgo/fort-lauderdale-to-winchester) - [Flights from Greenville (GSP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/gsp/wgo/greenville-to-winchester) - [Flights from Jacksonville (JAX) to Winchester (WGO)](https://www.expedia.ca/lp/flights/jax/wgo/jacksonville-to-winchester) - [Flights from Melbourne (MEL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/mel/wgo/melbourne-to-winchester) - [Flights from Sarasota (SRQ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/srq/wgo/sarasota-to-winchester) - [Flights from Syracuse (SYR) to Winchester (WGO)](https://www.expedia.ca/lp/flights/syr/wgo/syracuse-to-winchester) - [Flights from Calgary (YYC) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyc/wgo/calgary-to-winchester) - [Flights from Toronto (YYZ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyz/wgo/toronto-to-winchester) ### Packages - [Appleland Sports Center](https://www.expedia.ca/Appleland-Sports-Center-Stephens-City.d553248621587477489.Vacation-Attraction) - [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) \*Available to Expedia members.