Title: $40 Cheap flights from Pittsfield, VT - 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) # $40 Cheap flights from Pittsfield, VT [View $40 flight on Sun, May 17, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:LEB,to:BOS,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:39.10&airProductToken=AQouCiwIwmwSBDUzOTkYiwkgwZMBKNidjQMwnp6NAzhQQABYAWoCQU5yBlBIMEJFThIMCAEQARgBKgJCNjIAGAEiBAgBEAEoAigDKAQwAQ) [Pittsfield Travel Guide](https://expedia.com/Pittsfield.dx184066)[Hotels in Pittsfield](https://expedia.com/Pittsfield-Hotels.d184066.Travel-Guide-Hotels)[Car Rentals in Pittsfield](https://expedia.com/Car-Rentals-In-Pittsfield.d184066.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.com/Pittsfield.d184066.Destination-Travel-Guides) ## Popular airlines from Pittsfield - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways - ![](https://a.travel-assets.com/air/airlines/9k_sq.svg) Cape Air - ![](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 Pittsfield 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 ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Wed, Mar 18 - Mon, Mar 23 LEB Lebanon BOS Boston $82 Roundtrip found 8 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:LEB,to:BOS,departure:3/18/2026TANYT&leg2=from:BOS,to:LEB,departure:3/23/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:81.76&airProductToken=AQoiCiAIwmwSBDUxNjcYiwkgwZMBKPT4hwMwuvmHAzhQQABYAQoiCiAIwmwSBDUxNzAYwZMBIIsJKOeziAMwqLSIAzhQQABYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, Mar 7 - Wed, Apr 15 LEB Lebanon BOS Boston $99 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:LEB,to:BOS,departure:3/7/2026TANYT&leg2=from:BOS,to:LEB,departure:4/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:98.20&airProductToken=AQoiCiAIwmwSBDUxNzEYiwkgwZMBKP2AhwMwwoGHAzhVQABYAQoiCiAIwmwSBDUxNzAYwZMBIIsJKMe2igMwiLeKAzhQQABYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Fri, Mar 13 - Mon, Mar 23 LEB Lebanon BOS Boston $104 Roundtrip found 8 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:LEB,to:BOS,departure:3/13/2026TANYT&leg2=from:BOS,to:LEB,departure:3/23/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:103.26&airProductToken=AQoiCiAIwmwSBDUxNzEYiwkgwZMBKIHEhwMwxsSHAzhVQABYAQoiCiAIwmwSBDUxNzAYwZMBIIsJKOeziAMwqLSIAzhQQABYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Wed, Mar 11 - Sun, Mar 15 LEB Lebanon BOS Boston $119 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:LEB,to:BOS,departure:3/11/2026TANYT&leg2=from:BOS,to:LEB,departure:3/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:118.20&airProductToken=AQo6CjgIwmwSBDUxNjcYiwkgwZMBKJSqhwMw2qqHAzhVQABYAWoCQU5yBlVIMEJFTnoKCLmWARIEMTg3MAo6CjgIwmwSBDUxNzIYwZMBIIsJKNDahwMwkduHAzhVQABYAWoCQU5yBlVIMEJFTnoKCLmWARIEMTg3ORIKCAEQARgBKgJCNhgBIgQIARABKAIoAygEMAE) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Wed, Mar 11 - Sun, Mar 15 LEB Lebanon BOS Boston $125 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:LEB,to:BOS,departure:3/11/2026TANYT&leg2=from:BOS,to:LEB,departure:3/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:124.45&airProductToken=AQo6CjgIwmwSBDUxNjcYiwkgwZMBKJSqhwMw2qqHAzhVQABYAWoCQU5yBlVIMEJFTnoKCLmWARIEMTg3MBIKCAEQARgBKgJCNhgBIgQIARABKAIoAygEMAE) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, Mar 7 - Sun, Mar 15 RUT Rutland BOS Boston $131 Roundtrip found 23 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:RUT,to:BOS,departure:3/7/2026TANYT&leg2=from:BOS,to:RUT,departure:3/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:130.51&airProductToken=AQojCiEIwmwSBDUxMDQYkZ0BIMGTASjPgYcDMJ-ChwM4VUAAWAEKIwohCMJsEgQ1MTAzGMGTASCRnQEoq9qHAzD72ocDOFVAAFgBEgoIARABGAEqAkI2GAEiBAgBEAEoBDAB) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Thu, Mar 5 - Sun, Mar 8 LEB Lebanon BOS Boston $136 Roundtrip found 3 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:LEB,to:BOS,departure:3/5/2026TANYT&leg2=from:BOS,to:LEB,departure:3/8/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:135.20&airProductToken=AQosCioIuZYBEgQxODcwGIsJIMGTASiQ54YDMNbnhgM4VkAAWAFqAkVScgNWSVAKLAoqCLmWARIEMTg3NRjBkwEgiwkoh4uHAzDIi4cDOFZAAFgBagJFUnIDVklQEgwIARABGAEqAkhSMgAYASIECAEQASgCKAMoBDAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Wed, Mar 11 - Wed, Mar 18 LEB Lebanon PHL Philadelphia $284 Roundtrip found 5 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:LEB,to:PHL,departure:3/11/2026TANYT&leg2=from:PHL,to:LEB,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:283.80&airProductToken=AQppCjgIwmwSBDUxNzMYiwkgwZMBKLCuhwMw9q6HAzhVQABYAWoCQU5yBlVIMEJFTnoKCLmWARIEMTg4MAotCMJsEgMzNTkYwZMBIO9ZKNuwhwMwvLGHAzhQQAFYAWoCQU5yCFBJNEFCRVk1CmkKLQjCbBIDMjYwGO9ZIMGTASi4-IcDMIX5hwM4UEAAWAFqAkFOcghQSTRBQkVZNQo4CMJsEgQ1MTcyGMGTASCLCSiw_IcDMPH8hwM4VUABWAFqAkFOcgZVSDBCRU56Cgi5lgESBDE4NzkSCggBEAEYASoCQjYYASIECAEQASgCKAMoBDAB) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Tue, Mar 24 - Tue, Mar 31 LEB Lebanon JFK New York $300 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:LEB,to:JFK,departure:3/24/2026TANYT&leg2=from:JFK,to:LEB,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:299.30&airProductToken=AQpECiEIuZYBEgQxODgwGIsJIMGTASjQwIgDMJbBiAM4VkAAWAEKHwjCbBIDNzE3GMGTASCpUSjIwYgDMJvCiAM4UEABWAEKRAofCMJsEgMzMTgYqVEgwZMBKMOMiQMwk42JAzhQQABYAQohCLmWARIEMTg3NRjBkwEgiwko542JAzCojokDOFZAAVgBEgoIARABGAEqAkI2GAEiBAgBEAEoBDAB) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Mon, Mar 16 - Tue, Mar 17 RUT Rutland JFK New York $344 Roundtrip found 3 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:RUT,to:JFK,departure:3/16/2026TANYT&leg2=from:JFK,to:RUT,departure:3/17/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:343.60&airProductToken=AQpDCiAIuZYBEgI3MBiRnQEgwZMBKLPmhwMwg-eHAzhCQABYAQofCMJsEgM3MTcYwZMBIKlRKMjnhwMwm-iHAzhQQAFYAQpDCh8IwmwSAzExOBipUSDBkwEotu2HAzD_7YcDOFBAAFgBCiAIuZYBEgI1NRjBkwEgkZ0BKMruhwMwmu-HAzhCQAFYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![](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 Pittsfield, VT #### How much is a flight from Pittsfield? This week, flights from Pittsfield are available between $82 – $344\. #### How to find cheap flights from Pittsfield? Expedia makes it easy to compare cheap flights from Pittsfield to many destinations. Check out excellent deals on domestic and international flights from Pittsfield. 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 Pittsfield? 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 Pittsfield 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 Pittsfield may be more expensive. Airlines with strict bag policies or fees can also impact your costs. #### What is the best airline to fly from Pittsfield? 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 Pittsfield with: JetBlue Airways, Cape Air. #### What is the best month to fly from Pittsfield? One of the cheapest times to fly from Pittsfield 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 Pittsfield? Expedia is the place to find last-minute flights from Pittsfield, 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 Pittsfield 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 Pittsfield. 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 Pittsfield: Essential Travel Information | Cheapest flight from Pittsfield | $82 (roundtrip) | | ------------------------------------- | ------------------------- | | Best airlines to fly from Pittsfield | JetBlue Airways, Cape Air | | Cheapest month to fly from Pittsfield | March | | Pittsfield IATA code | VSF | | Pittsfield Country/State | Vermont | | Airline ticket deals from Pittsfield | $82 - $344 | \*Flight schedules are subject to change. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Stockbridge Hotels ](https://www.expedia.com/Stockbridge-Hotels.d6357893.Travel-Guide-Hotels) - [B&B in Stockbridge ](https://www.expedia.com/Stockbridge-Bed-And-Breakfast.d6357893-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Stockbridge ](https://www.expedia.com/Stockbridge-Chalets.d6357893-aaChalets.Travel-Guide-Accommodation) - 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