Title: $41 Cheap Flights to Pittsfield, VT - Expedia.com ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $41 Cheap Flights to Pittsfield, VT [View $41 flight on Mon, May 4, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:BOS,to:LEB,departure:5/4/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:40.88&airProductToken=AQo6CjgIwmwSBDUxNzQYwZMBIIsJKNSOjAMwlY-MAzhQQABYAWoCQU5yBlBIMEJFTnoKCLmWARIEMTg4MRIKCAEQARgBKgJCNhgBIgQIARABKAIoAygEMAE) [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 to Pittsfield - ![](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:Pittsfield, Vermont, United States of America,departure:4/22/2026TANYT&leg2=from:Pittsfield, Vermont, United States of America,to:CMH,departure:4/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![](https://a.travel-assets.com/air/airlines/9k_sq.svg) Cape Air [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Pittsfield, Vermont, United States of America,departure:4/22/2026TANYT&leg2=from:Pittsfield, Vermont, United States of America,to:CMH,departure:4/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"9K"}}]) - ![](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 Pittsfield? Prices were available within the past 7 days and start at $41 for one-way flights and $125 for 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) Fri, Apr 17 - Tue, Apr 28 BOS Boston LEB Lebanon $125 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:LEB,departure:4/17/2026TANYT&leg2=from:LEB,to:BOS,departure:4/28/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:124.76&airProductToken=AQo6CjgIwmwSBDUxNzIYwZMBIIsJKPDNigMwsc6KAzhaQABYAWoCQU5yBlpIMEJFTnoKCLmWARIEMTg3OQo6CjgIwmwSBDUxNzEYiwkgwZMBKMHJiwMwhsqLAzhQQABYAWoCQU5yBlBIMEJFTnoKCLmWARIEMTg3NhIKCAEQARgBKgJCNhgBIgQIARABKAIoAygEMAE) ![Cape Air](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9k.gif) Fri, Apr 17 - Tue, Apr 28 BOS Boston LEB Lebanon $127 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:LEB,departure:4/17/2026TANYT&leg2=from:LEB,to:BOS,departure:4/28/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:126.23&airProductToken=AQosCioIuZYBEgQxODc5GMGTASCLCSjwzYoDMLHOigM4U0AAWAFqAkVScgNTSVASCggBEAEYASoCSFIYASIECAEQASgCKAMoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, Aug 29 - Wed, Sep 2 LGA New York RUT Rutland $394 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:LGA,to:RUT,departure:8/29/2026TANYT&leg2=from:RUT,to:LGA,departure:9/2/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:393.61&airProductToken=AQpeCjEIwYIBEgQ0NzY5GMsBIMGTASi0sJYDMP2wlgM4T0AAWAFqBE1BSU5yCE9WQUpaU00xCikIuZYBEgI3MRjBkwEgkZ0BKM-ylgMwp7OWAzhTQAFYAWoCRVJyA1NJUApeCikIuZYBEgI2MBiRnQEgwZMBKIXdlgMw2t2WAzhTQABYAWoCRVJyA1NJUAoxCMGCARIENDQzMBjBkwEgywEott-WAzCK4JYDOE9AAVgBagRNQUlOcghPVkFKWlNNMRIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Apr 17 - Fri, Apr 24 LGA New York LEB Lebanon $395 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:LGA,to:LEB,departure:4/17/2026TANYT&leg2=from:LEB,to:LGA,departure:4/24/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:394.91&airProductToken=AQpkCjYIxJgBEgQ1Njc3GMsBIMGTASiOy4oDMOLLigM4VkAAWAFqCU1BSU5DTEFTQ3IIVkFVU1gwTUwKKgi5lgESBDE4NzkYwZMBIIsJKPDNigMwsc6KAzhTQAFYAWoCRVJyA1NJUBIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Thu, Jun 4 - Tue, Jun 9 EWR New York RUT Rutland $404 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:EWR,to:RUT,departure:6/4/2026TANYT&leg2=from:RUT,to:EWR,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:403.61&airProductToken=AQpiCjUI1YIBEgQxMTEwGMSNASDBkwEoleeOAzDh544DOEtAAFgBagdFQ09OT01ZcghLQUE0SkhEUwopCLmWARICNzEYwZMBIJGdASiX644DMOfrjgM4U0ABWAFqAkVScgNTSVAKYgopCLmWARICNzAYkZ0BIMGTASjXoo8DMKyjjwM4U0AAWAFqAkVScgNTSVAKNQjVggESBDIwNjAYwZMBIMSNASj6pI8DMNeljwM4S0ABWAFqB0VDT05PTVlyCEtBQTRKSERTEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwAQ) ## Frequently asked questions ### What month is the cheapest to fly to Pittsfield? ### Which US cities have the cheapest flights to Pittsfield? ### Which US cities fly direct to Pittsfield? ### How to find a cheap flight to Pittsfield? ### How to get a cheap last-minute flight to Pittsfield? ### How far in advance should I book a flight to Pittsfield? ### Which day of the week is the cheapest day to buy a plane ticket to Pittsfield? ### Which airlines fly to Pittsfield? > - American Airlines > - United Airlines > - Delta Air Lines > - Breeze Airways ### Where do you fly into Pittsfield? ### How far is the airport from central Pittsfield? ### Can I save money by booking a Pittsfield trip package? ### Can I change or cancel my flight to Pittsfield? \*Flight schedules are subject to change. \*Available to One Key members. ## Travel information | Destination airport | Lebanon Municipal | | ----------------------------- | ----------------- | | Destination airport IATA code | LEB | | Destination city name | Lebanon | | Roundtrip price | $125 | ## Trending flights to Pittsfield Prices were available within the past 7 days and start at $41 for one-way flights and $125 for 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) Fri, Apr 17 - Tue, Apr 28 BOS Boston LEB Lebanon $125 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:LEB,departure:4/17/2026TANYT&leg2=from:LEB,to:BOS,departure:4/28/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:124.76&airProductToken=AQo6CjgIwmwSBDUxNzIYwZMBIIsJKPDNigMwsc6KAzhaQABYAWoCQU5yBlpIMEJFTnoKCLmWARIEMTg3OQo6CjgIwmwSBDUxNzEYiwkgwZMBKMHJiwMwhsqLAzhQQABYAWoCQU5yBlBIMEJFTnoKCLmWARIEMTg3NhIKCAEQARgBKgJCNhgBIgQIARABKAIoAygEMAE) ## 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) - 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