Title: $27 Cheap flights from Winchester, MA - 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) # $27 Cheap flights from Winchester, MA [View $27 flight on Wed, Mar 11, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:BOS,to:MIA,departure:3/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:26.88&airProductToken=AQoxCi8IzpYBEgQzMDMzGMGTASCMAiier4cDMPywhwM4UEAAWAFqAlJQcghQMjFTWUJWMhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) - [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 [Winchester Travel Guide](https://expedia.com/Winchester.dx175481)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d175481.Travel-Guide-Hotels)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d175481.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d175481.Destination-Travel-Guides) ## Popular airlines from Winchester - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta - ![](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_NK.svg) Spirit Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines - ![](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) ## Today's featured flight deals from Winchester Nonstop Carry-on included Lower price than typical - Boston (BOS)London (LHR) Tue, Feb 10 Sat, Feb 14 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 3-day trip found 11 hours ago 55% less than typical $510 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:LHR,departure:2/10/2026TANYT&leg2=from:LHR,to:BOS,departure:2/14/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-af6de5db511c4b0783cc82cc9d3aa1bb-754-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gBmNTrW6IBAU6qAQcKA0JPUxAAsgEHCgNMSFIQAA~AQpBCj8IyYQBEgQ0MDI3GMGTASDriQEoj-qEAzCk7YQDOE9AAFgBagVCQVNJQ3IIT0xOMEMyQlZ6CgjBggESBDAxMDgKZgoxCMmEARIDNzI2GOuJASCMGCj8lIUDMI2WhQM4T0AAWAFqBUJBU0lDcghPTE4wQzJCVgoxCMmEARIDMzQ3GIwYIMGTASiynIUDML-ghQM4T0ABWAFqBUJBU0lDcghPTE4wQzJCVhIKCAEQARgBKgJJQhgBIgQIARABKAIoAygEMA0&medianPrice=1476.00&displayPrice=509.33&src=dflp) - Boston (BOS)London (LHR) Wed, Feb 11 Mon, Feb 16 ![Delta](https://a.travel-assets.com/air/airlines/dl_sq.svg)Delta • Nonstop --- 4-day trip found 15 hours ago 50% less than typical $522 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:LHR,departure:2/11/2026TANYT&leg2=from:LHR,to:BOS,departure:2/16/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-834948ef2e194a5086b8250989522018-1845-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gB_PHqW6oBBwoDQk9TEACyAQcKA0xIUhAA~AQo3CjUIxJgBEgI1OBjBkwEg64kBKK_1hAMwuviEAzhFQABYAWoJTUFJTkJBU0lDcghWTE4wMk5CNwp9CkMIxJgBEgQ5NTg4GOuJASCAkwEopqWFAzD2pYUDOEVAAFgBaglNQUlOQkFTSUNyCFZMTjAyTkI3egoIy5gBEgQxMDAwCjYIxJgBEgMyNTcYgJMBIMGTASiMp4UDMPGqhQM4RUABWAFqCU1BSU5CQVNJQ3IIVkxOMDJOQjcSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB&medianPrice=1406.00&displayPrice=521.13&src=dflp) - Boston (BOS)London (LHR) Wed, Feb 11 Sun, Feb 22 ![Delta](https://a.travel-assets.com/air/airlines/dl_sq.svg)Delta • Nonstop --- 10-day trip found 15 hours ago 50% less than typical $537 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:LHR,departure:2/11/2026TANYT&leg2=from:LHR,to:BOS,departure:2/22/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-c0bfe1f2188247579b05d5e7cb2a226f-1462-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gB2OnqW6oBBwoDQk9TEACyAQcKA0xIUhAA~AQo3CjUIxJgBEgI1OBjBkwEg64kBKK_1hAMwuviEAzhFQABYAWoJTUFJTkJBU0lDcghWTE4wMk5CNwptCjQIxJgBEgIzNxjriQEg4Fwolu2FAzDp8YUDOEVAAFgBaglNQUlOQkFTSUNyCFZMTjAyTkI3CjUIxJgBEgM5ODcY4FwgwZMBKOn2hQMwhviFAzhFQAFYAWoJTUFJTkJBU0lDcghWTE4wMk5CNxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE&medianPrice=1349.00&displayPrice=536.93&src=dflp) - Boston (BOS)Phoenix (PHX) Sun, Mar 15 Sat, Mar 21 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 6-day trip found 15 hours ago 55% less than typical $282 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:PHX,departure:3/15/2026TANYT&leg2=from:PHX,to:BOS,departure:3/21/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-d4b84773f7d849f79a01482bd982d75f-2630-1-st-v5-sos-d4b84773f7d849f79a01482bd982d75f-2435-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAb7x6luQAQCQARKqAQcKA0JPUxAAsgEHCgNQSFgQAA~AQo1CjMIwYIBEgQyMjYwGMGTASDvuQEo59aHAzDV2YcDOEJAAFgBagVCQVNJQ3IIT1VBSlpUQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL.AQphCi4I15wBEgM4OTMY77kBIKEDKJCbiAMwzpyIAzhHQABYAWoDV0dBcgdHTEFVVzJGCi8I15wBEgQxOTEzGKEDIMGTASiCnogDMJifiAM4R0ABWAFqA1dHQXIHR0xBVVcyRhIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE&medianPrice=784.00&displayPrice=281.60&src=dflp) - Boston (BOS)Phoenix (PHX) Sun, Mar 8 Sun, Mar 15 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 7-day trip found 23 hours ago 50% less than typical $282 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:PHX,departure:3/8/2026TANYT&leg2=from:PHX,to:BOS,departure:3/15/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-947a17f78a9d48689e7e52976b02f23f-2747-1-st-v5-sos-947a17f78a9d48689e7e52976b02f23f-2740-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAf-L6VuqAQcKA0JPUxAAsgEHCgNQSFgQAA~AQo1CjMIwYIBEgQyMjYwGMGTASDvuQEoh4iHAzD1iocDOEJAAFgBagVCQVNJQ3IIT1VBSlpUQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL.AQpoCjIIwYIBEgQzMjA1GO-5ASCuHCi74IcDMJHihwM4QkAAWAFqBUJBU0lDcghRVUFIWk5CWAoyCMGCARIENDc1NhiuHCDBkwEoguOHAzCW5IcDOEJAAVgBagVCQVNJQ3IIUVVBSFpOQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=779.00&displayPrice=281.59&src=dflp) - Boston (BOS)Phoenix (PHX) Sun, Mar 15 Sat, Mar 21 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 6-day trip found 8 hours ago 50% less than typical $314 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:PHX,departure:3/15/2026TANYT&leg2=from:PHX,to:BOS,departure:3/21/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-42b0b52e10ef4934beeabd0cabb74b7a-2870-1-st-v5-sos-42b0b52e10ef4934beeabd0cabb74b7a-2668-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAcCv7FuQAQ6QAQCqAQcKA0JPUxAAsgEHCgNQSFgQAA~AQo1CjMIwYIBEgQyMjYwGMGTASDvuQEo59aHAzDV2YcDOEJAAFgBagVCQVNJQ3IIUVdBSFpOQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL.AQphCi4I15wBEgM4OTMY77kBIKEDKJCbiAMwzpyIAzhHQABYAWoDV0dBcgdHTEFVVzJGCi8I15wBEgQxOTEzGKEDIMGTASiCnogDMJifiAM4R0ABWAFqA1dHQXIHR0xBVVcyRhIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE&medianPrice=784.00&displayPrice=313.60&src=dflp) - Boston (BOS)Nashville (BNA) Mon, Mar 16 Sat, Mar 21 ![Southwest Airlines](https://a.travel-assets.com/air/airlines/wn_sq.svg)Southwest Airlines • Nonstop --- 4-day trip found 21 hours ago 55% less than typical $177 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:BNA,departure:3/16/2026TANYT&leg2=from:BNA,to:BOS,departure:3/21/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-08f205c5890348adae059a04b1debc1d-3124-1-st-v5-sos-08f205c5890348adae059a04b1debc1d-3059-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAdLA6VuqAQcKA0JPUxAAsgEHCgNCTkEQAA~AQoxCi8I15wBEgQxMjQzGMGTASChAyid6IcDMMzphwM4REAAWAFqA1dHQXIHRFpOVUgyRRIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE.AQpeCi0IwmwSBDExNzQYoQMgqVEo_puIAzCKnYgDOExAAFgBagJETnIIT0kyQVVFTDEKLQjCbBIDNjE4GKlRIMGTASjmnogDMLSfiAM4TEABWAFqAkROcghPSTJBVUVMMRIKCAEQARgBKgJCNhgBIgQIARABKAIoBCgGMAE&medianPrice=502.00&displayPrice=176.71&src=dflp) - Boston (BOS)Nashville (BNA) Fri, Mar 6 Sun, Mar 15 ![Delta](https://a.travel-assets.com/air/airlines/dl_sq.svg)Delta • Nonstop --- 9-day trip found 11 hours ago 45% less than typical $208 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:BNA,departure:3/6/2026TANYT&leg2=from:BNA,to:BOS,departure:3/15/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-644c307ab0e348cc849f4fa496285936-876-1-st-v5-sos-644c307ab0e348cc849f4fa496285936-825-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAdbl61uQAQGQAQGqAQcKA0JPUxAAsgEHCgNCTkEQAA~AQo4CjYIxJgBEgQ1NTk5GMGTASChAyiy-IYDMPP5hgM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB.AQpgCi0I15wBEgM1ODUYoQMgwUUoz96HAzC434cDOEZAAFgBagNXR0FyB0ZMQVVXMkUKLwjXnAESBDE0MzUYwUUgwZMBKP_ihwMw3uOHAzhGQAFYAWoDV0dBcgdGTEFVVzJFEgoIARABGAEqAldOGAEiBAgBEAEoAigDKAQwAQ&medianPrice=494.00&displayPrice=207.20&src=dflp) - Boston (BOS)Nashville (BNA) Wed, Mar 11 Sun, Mar 15 ![JetBlue Airways](https://a.travel-assets.com/air/airlines/b6_sq.svg)JetBlue Airways • Nonstop --- 4-day trip found 23 hours ago 45% less than typical $208 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:BNA,departure:3/11/2026TANYT&leg2=from:BNA,to:BOS,departure:3/15/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-af77ef7d6e9344eba04cb9513765af1d-3720-1-st-v5-sos-af77ef7d6e9344eba04cb9513765af1d-3640-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAfmM6VuQAQGQAQeqAQcKA0JPUxAAsgEHCgNCTkEQAA~AQovCi0IwmwSAzMwNxjBkwEgoQMo27CHAzCTsocDOExAAFgBagJETnIIVUkyUUJFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB.AQpgCi0I15wBEgM1ODUYoQMgwUUoz96HAzC434cDOEZAAFgBagNXR0FyB0ZMQVVXMkUKLwjXnAESBDE0MzUYwUUgwZMBKP_ihwMw3uOHAzhGQAFYAWoDV0dBcgdGTEFVVzJFEgoIARABGAEqAldOGAEiBAgBEAEoAigDKAQwAQ&medianPrice=482.00&displayPrice=207.29&src=dflp) ## 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 ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Tue, Mar 10 - Wed, Mar 18 BOS Boston MIA Miami $63 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MIA,departure:3/10/2026TANYT&leg2=from:MIA,to:BOS,departure:3/18/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:62.27&airProductToken=AQowCi4IzpYBEgMyNzMYwZMBIIwCKIqjhwMw5KSHAzhQQABYAWoCUlByCFAyMVNZQlYyCjEKLwjOlgESBDMwMzIYjAIgwZMBKM_6hwMwk_yHAzhXQABYAWoCUlByCFcyMVNZQk8xEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Tue, Mar 3 - Tue, Mar 10 BOS Boston MIA Miami $63 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MIA,departure:3/3/2026TANYT&leg2=from:MIA,to:BOS,departure:3/10/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:62.57&airProductToken=AQowCi4IzpYBEgMyNzMYwZMBIIwCKObUhgMwwNaGAzhQQABYAWoCUlByCFAyMVNZQlYyCi4KLAjOlgESAzI3MhiMAiDBkwEopaWHAzDvpocDOFdAAFgBagJSUHIGV0ExNE5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Wed, Mar 25 - Wed, Apr 1 BOS Boston MIA Miami $65 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MIA,departure:3/25/2026TANYT&leg2=from:MIA,to:BOS,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:64.77&airProductToken=AQoxCi8IzpYBEgQzMDMzGMGTASCMAiiZx4gDMO7IiAM4UEAAWAFqAlJQcghQMjFTWUJPMQoxCi8IzpYBEgQzMDMyGIwCIMGTASiPmIkDMNOZiQM4V0AAWAFqAlJQcghXMjFTWUJPMRIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Tue, Mar 3 - Thu, Mar 5 BOS Boston MIA Miami $67 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MIA,departure:3/3/2026TANYT&leg2=from:MIA,to:BOS,departure:3/5/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:66.87&airProductToken=AQoxCi8IzpYBEgQzMDMzGMGTASCMAija1YYDMLjXhgM4UEAAWAFqAlJQcghQMjFTWUJWMgovCi0IzpYBEgQzMDMyGIwCIMGTASiN6oYDMNnrhgM4V0AAWAFqAlJQcgZXQTE0TlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Wed, Mar 11 - Wed, Mar 18 BOS Boston FLL Fort Lauderdale $69 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:FLL,departure:3/11/2026TANYT&leg2=from:FLL,to:BOS,departure:3/18/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:68.78&airProductToken=AQoxCi8IzpYBEgQxNzQwGMGTASDlWii3qYcDMIyrhwM4V0AAWAFqAlJQcghXMjFTWUJWMgowCi4IzpYBEgM3NDMY5VogwZMBKLz_hwMw74CIAzhXQABYAWoCUlByCFcyMVNZQk8xEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Tue, Mar 17 - Wed, Mar 25 BOS Boston FLL Fort Lauderdale $71 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:FLL,departure:3/17/2026TANYT&leg2=from:FLL,to:BOS,departure:3/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:70.78&airProductToken=AQoxCi8IzpYBEgQxNzQwGMGTASDlWiiJ7YcDMNTuhwM4V0AAWAFqAlJQcghXMjFTWUJPMQowCi4IzpYBEgM3NDMY5VogwZMBKJzOiAMwz8-IAzhXQABYAWoCUlByCFcyMVNZQk8xEgwIARABGAEqAk5LMgAYASIECAEQASgCKAMoBDAN) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Wed, Apr 29 - Tue, May 5 BOS Boston MCO Orlando $82 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MCO,departure:4/29/2026TANYT&leg2=from:MCO,to:BOS,departure:5/5/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:81.96&airProductToken=AQoxCi8IxnISBDMzNDcYwZMBIMxwKLTTiwMwgNWLAzhFQABYAWoEUENfMXIHWjIxWFhTMgoxCi8IxnISBDMzNDgYzHAgwZMBKPmUjAMwvZaMAzhFQABYAWoEUENfMXIHWjIxRVhTMhIKCAEQARgBKgJGORgBIgQIARABKAIoAzAN) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sat, May 30 - Sat, Jun 6 PSM Portsmouth MCO Orlando $94 Roundtrip found 22 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:PSM,to:MCO,departure:5/30/2026TANYT&leg2=from:MCO,to:PSM,departure:6/6/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:93.50&airProductToken=AQosCioIzbABEgM4NDcYz2QgzHAonLOOAzDqtI4DOEFAAFgBagJOT3IFQU5PMDAKLAoqCM2wARIDODQ2GMxwIM9kKJqAjwMw1IGPAzhBQABYAWoCTk9yBUFOTzAwEgwIARABGAEqAk1YMgAYASIECAEQASgCKAMoBDAN) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, Feb 28 - Thu, Mar 5 BOS Boston MIA Miami $167 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MIA,departure:2/28/2026TANYT&leg2=from:MIA,to:BOS,departure:3/5/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:166.80&airProductToken=AQo0CjIIwYIBEgQyNjEwGMGTASCMAiidtIYDMIG2hgM4QkAAWAFqBUJBU0lDcghRVUFKWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Feb 28 - Thu, Mar 5 BOS Boston MIA Miami $167 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MIA,departure:2/28/2026TANYT&leg2=from:MIA,to:BOS,departure:3/5/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:166.80&airProductToken=AQo4CjYIxJgBEgQxMjg5GMGTASCMAij7tIYDMOO2hgM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFVU0EwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ## Flights from Winchester: Essential Travel Information | Cheapest flight from Winchester | $63 (roundtrip) | | ------------------------------------- | ---------------------------------------------------------------------------- | | Best airlines to fly from Winchester | Spirit Airlines, Frontier Airlines, Breeze Airways, American Airlines, Delta | | Cheapest month to fly from Winchester | March | | Winchester IATA code | BOS | | Winchester Country/State | Boston | | Airline ticket deals from Winchester | $63 - $167 | ## How to Find Cheap Flights from Winchester, MA #### How much is a flight from Winchester? This week, flights from Winchester are available between $63 – $167\. #### 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: Spirit Airlines, Frontier Airlines, Breeze Airways, American Airlines, Delta. #### What is the best month to fly from Winchester? One of the cheapest times to fly from Winchester airport(s) is March, 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. \*Flight schedules are subject to change. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other ### Lodging - [Boston Hotels ](https://www.expedia.com/Boston-Hotels.d178239.Travel-Guide-Hotels) - [Hotels near Winchester Wedgemere Station ](https://www.expedia.com/Winchester-Wedgemere-Station-Hotels.d6209680.Travel-Guide-Hotels) - [Condo Rentals in Winchester Wedgemere Station ](https://www.expedia.com/Winchester-Wedgemere-Station-Condos.d6209680-aaCondos.Travel-Guide-Accommodation) - [B&B in Winchester Wedgemere Station ](https://www.expedia.com/Winchester-Wedgemere-Station-Bed-And-Breakfast.d6209680-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Woburn Hotels ](https://www.expedia.com/Woburn-Hotels.d10373.Travel-Guide-Hotels) - [Hotels near Horn Pond ](https://www.expedia.com/Horn-Pond-Hotels.0-l553248621561930457-0.Travel-Guide-Filter-Hotels) - 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