Title: CA $111 Cheap Flights from Windham County - 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 $111 Cheap Flights from Windham County [View CA $111 flight on Sun, Feb 15, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:LEB,to:BOS,departure:15/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:110.70&airProductToken=AQouCiwIwmwSBDUxNzEYiwkgwZMBKP2fhQMww6CFAzhaQABYAWoCQU5yBlpIMEJFThIKCAEQARgBKgJCNhgBIgQIARABKAIoAygEMAE) - [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 Add a place to stay Direct flights only [Windham County Hotels](https://expedia.ca/Destinations-In-Windham-County.d6057353.Hotel-Destinations)[Things to do in Windham County](https://expedia.ca/Things-To-Do-In-Windham-County.d6057353.Travel-Guide-Activities)[Windham County Car Rentals](https://expedia.ca/Destinations-In-Windham-County.d6057353.Car-Rental-Destinations)[Windham County Vacations](https://expedia.ca/Windham-County.d6057353.Destination-Travel-Guides) ## Popular airlines from Windham County - ![JetBlue Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways - ![Cape Air](https://a.travel-assets.com/air/airlines/9k_sq.svg) Cape Air ![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 Windham County 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 ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, Feb 14 - Mon, Feb 16 LEB Lebanon BOS Boston CA $217 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:LEB,to:BOS,departure:14/02/2026TANYT&leg2=from:BOS,to:LEB,departure:16/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:216.20&airProductToken=AQouCiwIwmwSBDUxNjcYiwkgwZMBKLiRhQMw_pGFAzhaQABYAWoCQU5yBlpIMEJFThIKCAEQARgBKgJCNhgBIgQIARABKAIoAygEMAE) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Sat, Feb 14 - Mon, Feb 16 LEB Lebanon BOS Boston CA $218 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:LEB,to:BOS,departure:14/02/2026TANYT&leg2=from:BOS,to:LEB,departure:16/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:217.30&airProductToken=AQosCioIuZYBEgQxODgwGIsJIMGTASjMlYUDMJKWhQM4QkAAWAFqAkVScgNCSVAKLAoqCLmWARIEMTg3ORjBkwEgiwkohauFAzDGq4UDOEJAAFgBagJFUnIDQklQEgoIARABGAEqAkhSGAEiBAgBEAEoAigDKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, Feb 14 - Mon, Feb 16 LEB Lebanon BOS Boston CA $223 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:LEB,to:BOS,departure:14/02/2026TANYT&leg2=from:BOS,to:LEB,departure:16/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:222.50&airProductToken=AQouCiwIwmwSBDUxNjcYiwkgwZMBKLiRhQMw_pGFAzhaQABYAWoCQU5yBlpIMEJFTgouCiwIwmwSBDUxNjgYwZMBIIsJKNyohQMwnamFAzhaQABYAWoCQU5yBlpIMEJFThIKCAEQARgBKgJCNhgBIgQIARABKAIoAygEMAE) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Tue, Oct 21 - Tue, Oct 28 RUT Rutland MIA Miami CA $676 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RUT,to:MIA,departure:21/10/2025TANYT&leg2=from:MIA,to:RUT,departure:28/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:675.60&airProductToken=AQpECiAIuZYBEgI2MBiRnQEgwZMBKPr5-gIwx_r6AjhRQABYAQogCMSYARIDNzc2GMGTASCMAiiq_PoCMID--gI4VUABWAEKZwogCMSYARIEMjM4NxiMAiDLASjUxvsCMIfI-wI4WEAAWAEKIQjEmAESBDU3NDUYywEgwZMBKMTI-wIwlsn7AjhYQAFYAQogCLmWARICNjMYwZMBIJGdASjbyfsCMKvK-wI4U0ABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Thu, Dec 18 - Mon, Dec 29 RUT Rutland RSW Fort Myers CA $676 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RUT,to:RSW,departure:18/12/2025TANYT&leg2=from:RSW,to:RUT,departure:29/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:675.80&airProductToken=AQpFCiEIwmwSBDUxMDAYkZ0BIMGTASiEhYADMNGFgAM4WkAAWAEKIAjCbBIDNDY1GMGTASDRtAEoooiAAzD4iYADOFVAAVgBCkQKHwjCbBICNjYY0bQBIMGTASiMgYEDMMaCgQM4WkAAWAEKIQjCbBIENTEwMxjBkwEgkZ0BKNeDgQMwp4SBAzhaQAFYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sun, Dec 21 - Mon, Dec 29 RUT Rutland RSW Fort Myers CA $704 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RUT,to:RSW,departure:21/12/2025TANYT&leg2=from:RSW,to:RUT,departure:29/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:703.80&airProductToken=AQpGCiEIwmwSBDUxMDAYkZ0BIMGTASjkpoADMLGngAM4WkAAWAEKIQjCbBIEMTc2NRjBkwEg0bQBKLqqgAMwlayAAzhPQAFYAQpECh8IwmwSAjY2GNG0ASDBkwEojIGBAzDGgoEDOFpAAFgBCiEIwmwSBDUxMDMYwZMBIJGdASjXg4EDMKeEgQM4WkABWAESCggBEAEYASoCQjYYASIECAEQASgEMAE) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Mon, Mar 2 - Fri, Mar 6 RUT Rutland MCO Orlando CA $714 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RUT,to:MCO,departure:02/03/2026TANYT&leg2=from:MCO,to:RUT,departure:06/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:713.70&airProductToken=AQpfCi0IwmwSBDUxMDQYkZ0BIMGTASjNyYYDMJrKhgM4WkAAWAFqAkFOcgZaSDBCRU4KLgjCbBIEMTE1MRjBkwEgzHAonsuGAzDozIYDOFVAAVgBagJBTnIIVUkyQVJFWTUKXgotCMJsEgMzNTIYzHAgwZMBKPTxhgMwqPOGAzhVQABYAWoCQU5yCFVJMkFVRVk1Ci0IwmwSBDUxMDMYwZMBIJGdASi39YYDMIf2hgM4WkABWAFqAkFOcgZaSDBCRU4SCggBEAEYASoCQjYYASIECAEQASgCKAMoBDAB) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Sat, Feb 28 - Sat, Mar 7 RUT Rutland MCO Orlando CA $718 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RUT,to:MCO,departure:28/02/2026TANYT&leg2=from:MCO,to:RUT,departure:07/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:717.50&airProductToken=AQpaCikIuZYBEgI3MBiRnQEgwZMBKI2zhgMw2rOGAzhTQABYAWoCRVJyA1NJUAotCMJsEgM1NTIYwZMBIMxwKLi1hgMw_raGAzhVQAFYAWoCQU5yCFVJMkFSRVk1CokBCi0IwmwSBDE1ODQYzHAgqVEom_6GAzC7_4YDOFBAAFgBagJBTnIIUEMyQVVFWTUKLQjCbBIDNjE4GKlRIMGTASivgYcDMPqBhwM4UEABWAFqAkFOcghQQzJBVUVZNQopCLmWARICNzEYwZMBIJGdASjJgocDMJmDhwM4U0ABWAFqAkVScgNTSVASCggBEAEYASoCQjYYASIECAEQASgCKAMoBDAB) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Mon, Mar 2 - Fri, Mar 6 RUT Rutland MCO Orlando CA $722 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RUT,to:MCO,departure:02/03/2026TANYT&leg2=from:MCO,to:RUT,departure:06/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:721.20&airProductToken=AQpjCikIuZYBEgI1MhiRnQEgwZMBKMTFhgMwkcaGAzhTQABYAWoCRVJyA1NJUAo2CMSYARIEMTU3MBjBkwEgzHAozceGAzCayYYDOFRAAVgBaglNQUlOQ0xBU0NyCFRBVk5BME1FEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, Feb 28 - Sat, Mar 7 RUT Rutland MCO Orlando CA $724 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RUT,to:MCO,departure:28/02/2026TANYT&leg2=from:MCO,to:RUT,departure:07/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:723.80&airProductToken=AQpfCi0IwmwSBDUxMDIYkZ0BIMGTASj2sIYDMMOxhgM4WkAAWAFqAkFOcgZaSDBCRU4KLgjCbBIEMTE1MRjBkwEgzHAo3rSGAzCotoYDOFVAAVgBagJBTnIIVUkyQVJFWTUKjQEKLQjCbBIEMTU4NBjMcCCpUSib_oYDMLv_hgM4UEAAWAFqAkFOcghQQzJBVUVZNQotCMJsEgM2MTgYqVEgwZMBKK-BhwMw-oGHAzhQQAFYAWoCQU5yCFBDMkFVRVk1Ci0IwmwSBDUxMDUYwZMBIJGdASjJgocDMJmDhwM4WkABWAFqAkFOcgZaSDBCRU4SCggBEAEYASoCQjYYASIECAEQASgCKAMoBDAB) ## How to find cheap flights from Windham County #### How much is a flight from Windham County? Flights from Windham County are available at a range of prices. Attractive deals include one-way fares from CA $111 and roundtrip fares from CA $217. You'll often find the best deals in February. 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 Windham County? Discovering affordable flights from Windham County 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 $111 and roundtrip offers from CA $217. 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 Windham County? For the best deal on flights from Windham County, 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 Windham County 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 Windham County? With Expedia, finding the best airline for your journey from Windham County is a breeze. We offer options from 20 different airlines, including JetBlue Airways, Cape Air. Whether you prioritize price, comfort, or loyalty programs, we have a fit for your travel needs. #### What is the best month to fly from Windham County? The best month to fly from Windham County is typically February, 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 $111 and roundtrip from CA $217 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 Windham County? Secure the best savings with Expedia. Data suggests that booking flights from Windham County three weeks in advance can save you up to 20%. Also, consider flying in February for the best rates. Stay updated with us for the latest data and savings advice. #### Are there any last-minute flights from Windham County? With Expedia, finding last-minute flights from Windham County 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 $111 and roundtrip from CA $217 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 Windham County, with flight options from 20 airlines, including one-way deals from CA $111. 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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[Putney Hotels](https://www.expedia.ca/Putney-Hotels.d184069.Travel-Guide-Hotels) - [Resorts in Putney](https://www.expedia.ca/Putney-Resort-Hotels.d184069-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Tasha Tudor Museum](https://www.expedia.ca/Tasha-Tudor-Museum-Hotels.0-l553248621561865125-0.Travel-Guide-Filter-Hotels) - [Townshend Hotels](https://www.expedia.ca/Townshend-Hotels.d553248634998697337.Travel-Guide-Hotels) - [Cabin Rentals in Wardsboro](https://www.expedia.ca/Wardsboro-Cabins.d3000459767-aaCabins.Travel-Guide-Accommodation) - [Hostels in Wardsboro](https://www.expedia.ca/Wardsboro-Hostels.d3000459767-aaHostels.Travel-Guide-Accommodation) - [Wardsboro Hotels](https://www.expedia.ca/Wardsboro-Hotels.d3000459767.Travel-Guide-Hotels) - [Motels in Wardsboro](https://www.expedia.ca/Wardsboro-Motels.d3000459767-aaMotels.Travel-Guide-Accommodation) - [West Brattleboro Hotels](https://www.expedia.ca/West-Brattleboro-Hotels.d553248635976384457.Travel-Guide-Hotels) - [West Dummerston Hotels](https://www.expedia.ca/West-Dummerston-Brattleboro-Hotels.0-n3000459780-0.Travel-Guide-Filter-Hotels) - [Farmstay in West Townshend](https://www.expedia.ca/West-Townshend-Agritourism.d184080-aaAgritourism.Travel-Guide-Accommodation) - [Cheap Hotels in West Townshend](https://www.expedia.ca/West-Townshend-Hotels-Cheap-Hotels.0-0-d184080-tCheapHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in West Townshend](https://www.expedia.ca/West-Townshend-Hotels-Romantic-Hotel.0-0-d184080-tRomanticHotel.Travel-Guide-Filter-Hotels) - [West Townshend Hotels](https://www.expedia.ca/West-Townshend-Hotels.d184080.Travel-Guide-Hotels) - [West Townshend Hotels](https://www.expedia.ca/West-Townshend-Hotels.d553248635976474502.Travel-Guide-Hotels) - [Rv Parks in West Townshend](https://www.expedia.ca/West-Townshend-RV-Parks.d553248635976474502-aaRVParks.Travel-Guide-Accommodation) ### Flights - [Flights to Jamaica](https://www.expedia.ca/Cheap-Flights-To-Jamaica.d184052.Travel-Guide-Flights) - [Flights to Putney](https://www.expedia.ca/Cheap-Flights-To-Putney.d184069.Travel-Guide-Flights) - [Flights from Springfield](https://www.expedia.ca/lp/flights/10292/flights-from-springfield) - [Flights from Woodstock](https://www.expedia.ca/lp/flights/10868/flights-from-woodstock) - [Flights from Londonderry](https://www.expedia.ca/lp/flights/127228/flights-from-londonderry) - [Flights from Weston](https://www.expedia.ca/lp/flights/177460/flights-from-weston) - [Flights from Grafton](https://www.expedia.ca/lp/flights/184049/flights-from-grafton) - [Flights from Jamaica](https://www.expedia.ca/lp/flights/184052/flights-from-jamaica) - [Flights from Newfane](https://www.expedia.ca/lp/flights/184059/flights-from-newfane) - [Flights from Norwich](https://www.expedia.ca/lp/flights/184063/flights-from-norwich) - [Flights from Orwell](https://www.expedia.ca/lp/flights/184064/flights-from-orwell) - [Flights from West Halifax](https://www.expedia.ca/lp/flights/3000007842/flights-from-west-halifax) - [Flights from Mount Snow Valley](https://www.expedia.ca/lp/flights/3000458633/flights-from-mount-snow-valley) - [Flights from Proctor](https://www.expedia.ca/lp/flights/3000459714/flights-from-proctor) - [Flights from Readsboro](https://www.expedia.ca/lp/flights/3000459721/flights-from-readsboro) - [Flights from South Royalton](https://www.expedia.ca/lp/flights/3000459747/flights-from-south-royalton) - [Flights from Strafford](https://www.expedia.ca/lp/flights/3000459754/flights-from-strafford) - [Flights from Fair Haven](https://www.expedia.ca/lp/flights/55103/flights-from-fair-haven) - [Flights from Vernon](https://www.expedia.ca/lp/flights/553248634999176116/flights-from-vernon) - [Flights from Middletown Springs](https://www.expedia.ca/lp/flights/553248635975873537/flights-from-middletown-springs) - [Flights from Thetford](https://www.expedia.ca/lp/flights/553248635975876593/flights-from-thetford) - [Flights from South Strafford](https://www.expedia.ca/lp/flights/553248635976385080/flights-from-south-strafford) - [Flights from Central Vermont](https://www.expedia.ca/lp/flights/6057337/flights-from-central-vermont) - [Flights from Bennington](https://www.expedia.ca/lp/flights/6057349/flights-from-bennington) - [Flights from Pittsford](https://www.expedia.ca/lp/flights/6140713/flights-from-pittsford) - [Flights from Jacksonville](https://www.expedia.ca/lp/flights/6224642/flights-from-jacksonville) - [Flights from Windsor](https://www.expedia.ca/lp/flights/7881/flights-from-windsor) - [Flights from Bethel](https://www.expedia.ca/lp/flights/79405/flights-from-bethel) - [Flights from Brandon](https://www.expedia.ca/lp/flights/82420/flights-from-brandon) - [Flights from Ludlow](https://www.expedia.ca/lp/flights/8496/flights-from-ludlow) - [Flights from Chester](https://www.expedia.ca/lp/flights/89014/flights-from-chester) - [Flights from Brattleboro](https://www.expedia.ca/lp/flights/9636/flights-from-brattleboro) ### Packages - [Visit East Dover](https://www.expedia.ca/East-Dover.dx6060640) - [Landmark College](https://www.expedia.ca/Landmark-College-Putney.d553248635937215663.Vacation-Attraction) ### Vacation Rental - [Jamaica Vacation Rentals](https://www.expedia.ca/Jamaica-Vacation-Rentals.d184052.Travel-Guide-VacationRentals) \*Available to Expedia members.