Title: $51 Cheap Flights to Cheshire, MA - Expedia.com ![An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $51 Cheap Flights to Cheshire, MA [View $51 flight on Tue, Mar 31, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:RDU,to:ALB,departure:3/31/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:50.61&airProductToken=AQotCisIzbABEgM3NDQY8aABIOAKKLyMiQMwpY2JAzhBQABYAWoCTk9yBUFOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ) [Cheshire Travel Guide](https://expedia.com/Cheshire.dx6005398)[Hotels in Cheshire](https://expedia.com/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[Car Rentals in Cheshire](https://expedia.com/Car-Rentals-In-Cheshire.d6005398.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.com/Cheshire.d6005398.Destination-Travel-Guides) ## Popular airlines to Cheshire - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Cheshire, Massachusetts, United States of America,departure:3/17/2026TANYT&leg2=from:Cheshire, Massachusetts, United States of America,to:CMH,departure:3/24/2026TANYT&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_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Cheshire, Massachusetts, United States of America,departure:3/17/2026TANYT&leg2=from:Cheshire, Massachusetts, United States of America,to:CMH,departure:3/24/2026TANYT&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_UA.svg) United [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Cheshire, Massachusetts, United States of America,departure:3/17/2026TANYT&leg2=from:Cheshire, Massachusetts, United States of America,to:CMH,departure:3/24/2026TANYT&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_WN.svg) Southwest Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Cheshire, Massachusetts, United States of America,departure:3/17/2026TANYT&leg2=from:Cheshire, Massachusetts, United States of America,to:CMH,departure:3/24/2026TANYT&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_B6.svg) JetBlue Airways [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Cheshire, Massachusetts, United States of America,departure:3/17/2026TANYT&leg2=from:Cheshire, Massachusetts, United States of America,to:CMH,departure:3/24/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Cheshire, Massachusetts, United States of America,departure:3/17/2026TANYT&leg2=from:Cheshire, Massachusetts, United States of America,to:CMH,departure:3/24/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/30/landing_airline_sq_logo_MX.svg) Breeze Airways [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Cheshire, Massachusetts, United States of America,departure:3/17/2026TANYT&leg2=from:Cheshire, Massachusetts, United States of America,to:CMH,departure:3/24/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"MX"}}]) - ![](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) ## How much is the cheapest flight to Cheshire? Prices were available within the past 7 days and start at $51 for one-way flights and $97 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sun, Sep 6 - Fri, Sep 11 RDU Raleigh ALB Albany $97 Roundtrip found 17 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:RDU,to:ALB,departure:9/6/2026TANYT&leg2=from:ALB,to:RDU,departure:9/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:96.22&airProductToken=AQotCisIzbABEgM4NTQY8aABIOAKKJmJlwMwgoqXAzhCQABYAWoCTk9yBUJOTzAwCi0KKwjNsAESAzM3NxjgCiDxoAEoscaXAzCox5cDOEFAAFgBagJOT3IFQU5PMDASCggBEAEYASoCTVgYASIECAEQASgCKAMoBDAN) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Wed, May 13 - Tue, May 19 MCO Orlando ALB Albany $147 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ALB,departure:5/13/2026TANYT&leg2=from:ALB,to:MCO,departure:5/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:146.79&airProductToken=AQovCi0IwmwSBDI5MTkYzHAg4AoolPWMAzDA9owDOExAAFgBagJETnIIUEkyUVVFTDEKLwotCMJsEgQyOTIwGOAKIMxwKMiyjQMw_7ONAzhMQABYAWoCRE5yCFBJMlFVRUwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Fri, May 1 - Mon, May 18 MCO Orlando ALB Albany $147 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ALB,departure:5/1/2026TANYT&leg2=from:ALB,to:MCO,departure:5/18/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:146.79&airProductToken=AQowCi4I15wBEgQzMDY5GMxwIOAKKOftiwMwjO-LAzhWQABYAWoDV0dBcgdWTE5WSDJGCi8KLQjXnAESAzE3OBjgCiDMcCiKrI0DML6tjQM4VkAAWAFqA1dHQXIHVkxOVkgyRhIMCAEQARgBKgJXTjIAGAEiBAgBEAEoAigDKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Jun 2 - Wed, Jun 3 MCO Orlando ALB Albany $177 Roundtrip found 20 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ALB,departure:6/2/2026TANYT&leg2=from:ALB,to:MCO,departure:6/3/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:176.39&airProductToken=AQpkCjAIwYIBEgQyNzQ1GMxwIEMo68-OAzD70I4DOEJAAFgBagVCQVNJQ3IIT1ZBSlpTQlYKMAjBggESBDIzNDcYQyDgCijb0o4DMKvTjgM4QkABWAFqBUJBU0lDcghPVkFKWlNCVgpoCjIIwYIBEgQzMjk0GOAKIOKaASj-4I4DMIjijgM4QkAAWAFqBUJBU0lDcghPVkFKWlNCVgoyCMGCARIEMTg3ORjimgEgzHAotOKOAzCd444DOEJAAVgBagVCQVNJQ3IIT1ZBSlpTQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Jun 2 - Tue, Jun 9 MCO Orlando ALB Albany $197 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ALB,departure:6/2/2026TANYT&leg2=from:ALB,to:MCO,departure:6/9/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:196.40&airProductToken=AQpuCjUIxJgBEgQyNTY0GMxwIMsBKIbUjgMwr9WOAzhFQABYAWoJTUFJTkJBU0lDcghWQVVTQTBCQwo1CMSYARIENTQ5MxjLASDgCijx1o4DMLfXjgM4RUABWAFqCU1BSU5CQVNJQ3IIVkFVU0EwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ## Find the cheapest month to fly from Columbus (CMH) to Albany (ALB) ### August is typically the cheapest month to fly From $194 - $526 per traveler. ![](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_) ## Frequently asked questions ### What month is the cheapest to fly to Cheshire? ### Which US cities have the cheapest flights to Cheshire? > - Baltimore (BWI) > - Norfolk (ORF) > - Orlando (MCO) > - West Palm Beach (PBI) > - Richmond (RIC) > > > with fares often starting from $29. ### Which US cities fly direct to Cheshire? > - Orlando (MCO) > - Chicago (MDW, ORD) > - Atlanta (ATL) > - Washington (DCA, IAD) > - Charlotte (CLT) > > > To ALB > - Chicago (MDW, ORD) > - Atlanta (ATL) > - Orlando (MCO) > - Washington (DCA, IAD) > - Charlotte (CLT) > > > To Manchester-Boston Regional (MHT) > - Orlando (MCO) > - Baltimore (BWI) > - Charlotte (CLT) > - Washington (DCA, IAD) > - Philadelphia (PHL) ### How to find a cheap flight to Cheshire? ### Which airlines fly to Cheshire? > - American Airlines > - Delta > - Delta Air Lines > - Frontier Airlines > - JetBlue Airways > - United > - United Airlines ### Where do you fly into Cheshire? > - The closest major airport is Hartford, CT (BDL-Bradley Intl.), about 55 miles from the city center, which is a hub for American Airlines, Delta, and United, with other airlines like WN, JetBlue Airways also operating here. > - Albany, NY (ALB-Albany Intl.) is another option, about 46 miles away, serving as a hub for American Airlines, United, and WN, with Delta, JetBlue Airways also operating here. > - Manchester, NH (MHT-Manchester-Boston Regional), about 122 miles away, serving as a hub for American Airlines, WN, and United, with JetBlue Airways, MX also operating here. > - Worcester, MA (ORH-Worcester Regional), about 92 miles away, serving as a hub for American Airlines, JetBlue Airways, and Delta, with PT also operating here. > - New Haven, CT (HVN-Tweed - New Haven Regional), about 91 miles away, serving as a hub for MX and XP. ### What is the cheapest airport to fly to in Cheshire? ### Which budget airlines fly to Cheshire? > - Southwest Airlines: serves Albany (ALB), Hartford (BDL), Manchester (MHT) > - JetBlue Airways: serves Albany (ALB), Hartford (BDL), Worcester (ORH), Manchester (MHT) > - Breeze: serves Albany (ALB), Hartford (BDL), New Haven (HVN), Manchester (MHT) > - Frontier Airlines: flies to Hartford (BDL) > - Spirit Airlines: flies to Hartford (BDL) > - WestJet: serves Albany (ALB), Hartford (BDL) > - Avelo Airlines: flies to New Haven (HVN) > - Sun Country Airlines: flies to Hartford (BDL) > - Azul: serves Hartford (BDL), Worcester (ORH) > - GOL Linhas Aereas Inteligentes: flies to Hartford (BDL) ### What is the best month to visit Cheshire? ### How far in advance should I book a flight to Cheshire? ### What day of the week is cheapest day to buy a plane ticket to Cheshire? ### What is the most expensive month to fly to Cheshire? ### How can I track flight prices to Cheshire? ### How to get a cheap last-minute flight to Cheshire? ### Can I earn miles booking a flight to Cheshire with Expedia? ### Can I save money by booking a Cheshire trip package? ### Can I change or cancel my flight to Cheshire? \*Flight schedules are subject to change. ## Book with confidence # Tips to find the cheapest flights to Cheshire **The cheapest day to fly** Get started finding a cheap flight to Cheshire on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you. **The cheapest month to fly** September is the cheapest month to fly to Cheshire. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Cheshire. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute. **The most affordable time to book a flight** Typically, a Sunday can be the cheapest time to book a flight to Cheshire, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation. **The cheapest round-trip tickets to Cheshire** The lowest price for round-trip flights to Cheshire in 2026 starts from from $97, while one-way tickets start from from $51\. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Cheshire. If you have a preferred departure time or airline, you can use the handy filters to customize your search. **The cheapest airlines flying to Cheshire** Breeze Airways, Southwest Airlines, JetBlue Airways, American Airlines, Delta are just some of the airlines that can typically offer cheap tickets to Cheshire. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Cheshire and countless more destinations worldwide. **The most affordable airports to fly into** To view the cheapest airports to fly into for Cheshire, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Cheshire. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia. **Save with a package** With Expedia's amazing [package deals](https://www.expedia.com/package-deals), you could save hundreds of dollars by booking your Cheshire plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving. **Date flexibility for the cheapest flights to Cheshire** If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Cheshire. **Stopover savings** The cheapest tickets to Cheshire are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Cheshire. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved. **Get Expedia's Price Drop Protection** Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference\*. This gives you peace of mind that you're getting one of the cheapest flights to Cheshire for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members. \*Terms apply. **Use our Price Tracking feature** Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Cheshire. Simply download the free Expedia app to your smart device and activate Cheshire flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices. **Book with Expedia** As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Cheshire. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too. Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. The percentages you see are averages. ## Travel information | Destination airport | Albany Intl. | | ----------------------------- | ------------ | | Destination airport IATA code | ALB | | Destination city name | Albany | | Roundtrip price | $96 | ## Trending flights to Cheshire Prices were available within the past 7 days and start at $51 for one-way flights and $97 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sun, Sep 6 - Fri, Sep 11 RDU Raleigh ALB Albany $97 Roundtrip found 17 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:RDU,to:ALB,departure:9/6/2026TANYT&leg2=from:ALB,to:RDU,departure:9/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:96.22&airProductToken=AQotCisIzbABEgM4NTQY8aABIOAKKJmJlwMwgoqXAzhCQABYAWoCTk9yBUJOTzAwCi0KKwjNsAESAzM3NxjgCiDxoAEoscaXAzCox5cDOEFAAFgBagJOT3IFQU5PMDASCggBEAEYASoCTVgYASIECAEQASgCKAMoBDAN) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near St Mary's of the Assumption Church ](https://www.expedia.com/St-Marys-Of-The-Assumption-Church-Hotels.0-l553248621532665539-0.Travel-Guide-Filter-Hotels) - [Hotels near Mount Greylock State Reservation Visitor Center ](https://www.expedia.com/Mount-Greylock-State-Reservation-Visitor-Center-Hotels.0-l6272782-0.Travel-Guide-Filter-Hotels) - [Lanesborough Hotels ](https://www.expedia.com/Lanesborough-Hotels.d6005408.Travel-Guide-Hotels) - [B&B in Lanesborough ](https://www.expedia.com/Lanesborough-Bed-And-Breakfast.d6005408-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Lanesborough ](https://www.expedia.com/Lanesborough-Hotels-Cheap-Hotels.0-0-d6005408-tCheapHotels.Travel-Guide-Filter-Hotels) - [Apartments in Lanesborough ](https://www.expedia.com/Lanesborough-Apartments.d6005408-aaApartments.Travel-Guide-Accommodation) - [Cottages in Lanesborough ](https://www.expedia.com/Lanesborough-Cottages.d6005408-aaCottages.Travel-Guide-Accommodation) - [Luxury Hotels in Lanesborough ](https://www.expedia.com/Lanesborough-Hotels-Luxury-Hotel.0-0-d6005408-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Cabin Rentals in Lanesborough ](https://www.expedia.com/Lanesborough-Cabins.d6005408-aaCabins.Travel-Guide-Accommodation) - [Resorts in Lanesborough ](https://www.expedia.com/Lanesborough-Resorts.d6005408-aaResorts.Travel-Guide-Accommodation) - [Motels in Lanesborough ](https://www.expedia.com/Lanesborough-Motels.d6005408-aaMotels.Travel-Guide-Accommodation) - [Aparthotels in Lanesborough ](https://www.expedia.com/Lanesborough-Apart-Hotels.d6005408-aaApartHotels.Travel-Guide-Accommodation) - [Condo Rentals in Lanesborough ](https://www.expedia.com/Lanesborough-Condos.d6005408-aaCondos.Travel-Guide-Accommodation) - [Vacation Homes in Lanesborough ](https://www.expedia.com/Lanesborough-Private-Vacation-Homes.d6005408-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Ski Hotels in Lanesborough ](https://www.expedia.com/Lanesborough-Hotels-Ski-Hotel.0-0-d6005408-tSkiHotel.Travel-Guide-Filter-Hotels) - [Hotels near Susan B. 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