Title: $38 Cheap flights from Chesterfield, 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) # $38 Cheap flights from Chesterfield, MA [View $38 flight on Mon, May 4, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:BDL,to:MCO,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:37.98&airProductToken=AQowCi4IxnISBDI3NjkY4VggzHAoipCMAzDHkYwDOEVAAFgBagRQQ18xcgdLMjFEWFMyEgoIARABGAEqAkY5GAEiBAgBEAEoAigDMA0) [Chesterfield Travel Guide](https://expedia.com/Chesterfield.dx89029)[Hotels in Chesterfield](https://expedia.com/Chesterfield-Hotels.d89029.Travel-Guide-Hotels)[Car Rentals in Chesterfield](https://expedia.com/Car-Rentals-In-Chesterfield.d89029.Car-Rental-Guide)[Chesterfield Vacation Packages](https://expedia.com/Chesterfield.d89029.Destination-Travel-Guides) ## Popular airlines from Chesterfield - ![](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_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_WN.svg) Southwest Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AC.svg) Air Canada - ![](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 Chesterfield 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 ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Thu, Apr 30 - Mon, May 4 BDL Hartford ATL Atlanta $80 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BDL,to:ATL,departure:4/30/2026TANYT&leg2=from:ATL,to:BDL,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:79.96&airProductToken=AQowCi4IxnISBDEzMDUY4Vgg4Fwo5uCLAzCL4osDOEVAAFgBagRQQ18xcgdaMTRSWFM5CjAKLgjGchIEMTMwNhjgXCDhWCiZjIwDMKmNjAM4RUAAWAFqBFBDXzFyB1oxNE5YUzkSCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Sun, Apr 26 - Sat, May 2 BDL Hartford MCO Orlando $92 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BDL,to:MCO,departure:4/26/2026TANYT&leg2=from:MCO,to:BDL,departure:5/2/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:91.96&airProductToken=AQowCi4IxnISBDI3NjkY4VggzHAoiraLAzDHt4sDOEVAAFgBagRQQ18xcgdLMjFEWFMyEgwIARABGAEqAkY5MgAYASIECAEQASgCKAMwDQ) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Sat, Apr 4 - Thu, Apr 9 BOS Boston MCO Orlando $98 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MCO,departure:4/4/2026TANYT&leg2=from:MCO,to:BOS,departure:4/9/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:97.97&airProductToken=AQoxCi8IxnISBDMzNDcYwZMBIMxwKLK6iQMw_ruJAzhFQABYAWoEUENfMXIHWjA3U1hTMhIKCAEQARgBKgJGORgBIgQIARABKAIoAzAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Tue, Apr 14 - Tue, Apr 21 BOS Boston MIA Miami $102 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MIA,departure:4/14/2026TANYT&leg2=from:MIA,to:BOS,departure:4/21/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:101.98&airProductToken=AQovCi0IzpYBEgQzMDMzGMGTASCMAiiZqIoDMO6pigM4R0AAWAFqAlJQcgZHQTE0TlIKLwotCM6WARIEMTc0NBiMAiDBkwEokvmKAzDZ-ooDOEdAAFgBagJSUHIGR0ExNE5SEgwIARABGAEqAk5LMgAYASIECAEQASgCKAMoBDAN) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Thu, Jun 11 - Sat, Jun 13 PSM Portsmouth MCO Orlando $109 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:PSM,to:MCO,departure:6/11/2026TANYT&leg2=from:MCO,to:PSM,departure:6/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:108.80&airProductToken=AQotCisIzbABEgQyODU1GM9kIMxwKLS6jwMw07yPAzhCQABYAWoCRVpyBUJFWjAwCiwKKgjNsAESAzg0NhjMcCDPZCj6zo8DMLTQjwM4QkAAWAFqAkVacgVCRVowMBIMCAEQARgBKgJNWDIAGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Mon, Apr 13 - Tue, Apr 14 BOS Boston FLL Fort Lauderdale $111 Roundtrip found 7 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:FLL,departure:4/13/2026TANYT&leg2=from:FLL,to:BOS,departure:4/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:110.10&airProductToken=AQovCi0IzpYBEgQxNzQwGMGTASDlWijpnIoDMLSeigM4R0AAWAFqAlJQcgZHQTE0TlIKLgosCM6WARIDMTAyGOVaIMGTASjqrooDMKiwigM4R0AAWAFqAlJQcgZHQTE0TlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Mon, Apr 13 - Thu, Apr 16 BOS Boston ATL Atlanta $122 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ATL,departure:4/13/2026TANYT&leg2=from:ATL,to:BOS,departure:4/16/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:121.46&airProductToken=AQoxCi8IxnISBDMwODUYwZMBIOBcKNCcigMwjZ6KAzhFQABYAWoEUENfMXIHWjE0TlhTORIKCAEQARgBKgJGORgBIgQIARABKAIoAzAN) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Thu, Apr 9 - Sat, Apr 11 BOS Boston SJU San Juan $124 Roundtrip found 2 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:SJU,departure:4/9/2026TANYT&leg2=from:SJU,to:BOS,departure:4/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:123.48&airProductToken=AQoyCjAIxnISBDMwMDEYwZMBILKiASi28okDMKX0iQM4RUAAWAFqBFBDXzFyB1owN1JQTjISCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, May 1 - Mon, May 4 BDL Hartford ATL Atlanta $159 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BDL,to:ATL,departure:5/1/2026TANYT&leg2=from:ATL,to:BDL,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:158.80&airProductToken=AQo3CjUIxJgBEgQyNzM1GOFYIOBcKMXtiwMw6O6LAzhFQABYAWoJTUFJTkJBU0lDcghWRlZRQTBCRwo3CjUIxJgBEgQxMDExGOBcIOFYKMiQjAMwz5GMAzhFQABYAWoJTUFJTkJBU0lDcghWRlZRQTBCRxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Thu, Jun 4 - Wed, Jun 10 BDL Hartford TPA Tampa $167 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BDL,to:TPA,departure:6/4/2026TANYT&leg2=from:TPA,to:BDL,departure:6/10/2026TANYT&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=AQouCiwIwmwSAzUzMxjhWCDzAyi36o4DMPLrjgM4TEAAWAFqAkROcghQSTJRUkVMMQouCiwIwmwSAzUzNBjzAyDhWCiXrI8DML-tjwM4TEAAWAFqAkROcghQSTJRUkVMMRIKCAEQARgBKgJCNhgBIgQIARABKAIoBCgGMAE) ## How to Find Cheap Flights from Chesterfield, MA #### How much is a flight from Chesterfield? This week, flights from Chesterfield are available between $80 – $167\. #### How to find cheap flights from Chesterfield? Expedia makes it easy to compare cheap flights from Chesterfield to many destinations. Check out excellent deals on domestic and international flights from Chesterfield. 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 Chesterfield? 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 Chesterfield 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 Chesterfield may be more expensive. Airlines with strict bag policies or fees can also impact your costs. #### What is the best airline to fly from Chesterfield? 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 Chesterfield with: Frontier Airlines, Breeze Airways, Spirit Airlines, JetBlue Airways, Southwest Airlines, Delta. #### What is the best month to fly from Chesterfield? One of the cheapest times to fly from Chesterfield airport(s) is April, 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 Chesterfield? Expedia is the place to find last-minute flights from Chesterfield, 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 Chesterfield 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 Chesterfield. 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 Chesterfield: Essential Travel Information | Cheapest flight from Chesterfield | $80 (roundtrip) | | --------------------------------------- | ---------------------------------------------------------------------------------------------- | | Best airlines to fly from Chesterfield | Frontier Airlines, Breeze Airways, Spirit Airlines, JetBlue Airways, Southwest Airlines, Delta | | Cheapest month to fly from Chesterfield | April | | Chesterfield IATA code | CEF | | Chesterfield Country/State | Massachusetts | | Airline ticket deals from Chesterfield | $80 - $167 | \*Flight schedules are subject to change. \*Available to One Key members. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Western Massachusetts Hotels ](https://www.expedia.com/Western-Massachusetts-Hotels.d6234063.Travel-Guide-Hotels) - 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