Title: $28 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) # $28 Cheap flights from Chesterfield, MA [View $28 flight on Sun, Mar 15, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:BDL,to:MCO,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:27.98&airProductToken=AQowCi4IxnISBDE2ODMY4VggzHAoqN2HAzDq3ocDOEVAAFgBagRQQ18xcgdLMjFEWFMyEgwIARABGAEqAkY5MgAYASIECAEQASgCKAMwDQ) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travelers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only [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_NK.svg) Spirit Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines - ![](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) ## Today's featured flight deals from Chesterfield Nonstop Carry-on included Lower price than typical - Boston (BOS)London (LHR) Sat, Feb 14 Fri, Feb 20 ![Delta](https://a.travel-assets.com/air/airlines/dl_sq.svg)Delta • Nonstop --- 5-day trip found 1 hour ago 55% less than typical $521 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:LHR,departure:2/14/2026TANYT&leg2=from:LHR,to:BOS,departure:2/20/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-a13501dbae7f476f811aa604183441a6-986-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gBtK6AXJABG6oBBwoDQk9TEACyAQcKA0xIUhAA~AQo3CjUIxJgBEgI1OBjBkwEg64kBKI-XhQMwmpqFAzhFQABYAWoJTUFJTkJBU0lDcghWTE4wMk5CNwp9CkMIxJgBEgQ5NTg4GOuJASCAkwEoptKFAzD20oUDOEVAAFgBaglNQUlOQkFTSUNyCFZMTjAyTkI3egoIy5gBEgQxMDAwCjYIxJgBEgMyNTcYgJMBIMGTASiM1IUDMPHXhQM4RUABWAFqCU1BSU5CQVNJQ3IIVkxOMDJOQjcSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB&medianPrice=1518.00&displayPrice=520.33&src=dflp) - Boston (BOS)London (LHR) Sat, Feb 14 Fri, Feb 20 ![Delta](https://a.travel-assets.com/air/airlines/dl_sq.svg)Delta • Nonstop --- 5-day trip found 5 hours ago 50% less than typical $526 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:LHR,departure:2/14/2026TANYT&leg2=from:LHR,to:BOS,departure:2/20/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-8f1ae3719ccb4a719dd2b7e9c58eb52b-172-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gBprf_W6oBBwoDQk9TEACyAQcKA0xIUhAA~AQpACj4I1qYBEgQ0MDEyGMGTASDriQEoj5eFAzCamoUDOFRAAFgBagVMSUdIVHIIT0xOMDJOQjd6CQjEmAESAzA1OApACj4I1qYBEgQ0MDExGOuJASDBkwEo5NOFAzC614UDOFRAAFgBagVMSUdIVHIIT0xOMDJOQjd6CQjEmAESAzA1ORIKCAEQARgBKgJWUxgBIgQIARABKAIoAygEMAE&medianPrice=1445.00&displayPrice=525.93&src=dflp) - Boston (BOS)London (LHR) Sat, Feb 14 Sun, Feb 22 ![Delta](https://a.travel-assets.com/air/airlines/dl_sq.svg)Delta • Nonstop --- 7-day trip found 3 hours ago 50% less than typical $537 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:LHR,departure:2/14/2026TANYT&leg2=from:LHR,to:BOS,departure:2/22/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-ac64edd0162b46608310682a8b13dffd-820-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gBse7_W6oBBwoDQk9TEACyAQcKA0xPThAA~AQo3CjUIxJgBEgI1OBjBkwEg64kBKI-XhQMwmpqFAzhFQABYAWoJTUFJTkJBU0lDcghWTE4wMk5CNwptCjMIxJgBEgE0GOuJASCpUSiq7YUDMK3xhQM4RUAAWAFqCU1BSU5CQVNJQ3IIVkxOMDJOQjcKNgjEmAESBDU3NjUYqVEgwZMBKJT2hQMw7vaFAzhFQAFYAWoJTUFJTkJBU0lDcghWTE4wMk5CNxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE&medianPrice=1444.00&displayPrice=536.03&src=dflp) - Boston (BOS)Nashville (BNA) Sun, Mar 8 Sun, Mar 15 ![Delta](https://a.travel-assets.com/air/airlines/dl_sq.svg)Delta • Nonstop --- 7-day trip found 6 hours ago 50% less than typical $218 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:BNA,departure:3/8/2026TANYT&leg2=from:BNA,to:BOS,departure:3/15/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-bc6990de17034d769ffd1e45402195c5-4302-1-st-v5-sos-bc6990de17034d769ffd1e45402195c5-4305-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAZyK_1uQAQOQAQCqAQcKA0JPUxAAsgEHCgNCTkEQAA~AQo4CjYIxJgBEgQ1Nzc4GMGTASChAyidiYcDMNOKhwM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB.AQpgCi0I15wBEgM1ODUYoQMgwUUoz96HAzC434cDOEZAAFgBagNXR0FyB0ZMQVVXMkUKLwjXnAESBDIyMjkYwUUgwZMBKKDihwMw-uKHAzhGQAFYAWoDV0dBcgdGTEFVVzJFEgoIARABGAEqAldOGAEiBAgBEAEoAigDKAQwAQ&medianPrice=578.00&displayPrice=217.20&src=dflp) - Boston (BOS)Nashville (BNA) Sun, Mar 22 Sat, Mar 28 ![JetBlue Airways](https://a.travel-assets.com/air/airlines/b6_sq.svg)JetBlue Airways • Nonstop --- 5-day trip found 3 hours ago 50% less than typical $202 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:BNA,departure:3/22/2026TANYT&leg2=from:BNA,to:BOS,departure:3/28/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-cd06a8fb315e4a3786f16f0edcb02c3c-3145-1-st-v5-sos-cd06a8fb315e4a3786f16f0edcb02c3c-3086-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAfXv_1uQAROQAQCqAQcKA0JPUxAAsgEHCgNCTkEQAQ~AQovCi0IwmwSAzMwNxjBkwEgoQMo0ayIAzCGrogDOExAAFgBagJETnIIT0kyQVVFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB.AQppCjIIwYIBEgQzMDIyGKEDIOKaASi964gDMJbsiAM4QkAAWAFqBUJBU0lDcghRVUFKWFNCVgozCMGCARIEMTEyMBjimgEgwZMBKM7tiAMw0u6IAzhCQAFYAWoFQkFTSUNyCFFVQUpYU0JWEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw&medianPrice=539.00&displayPrice=201.70&src=dflp) - Boston (BOS)Nashville (BNA) Sun, Mar 22 Sat, Mar 28 ![JetBlue Airways](https://a.travel-assets.com/air/airlines/b6_sq.svg)JetBlue Airways • Nonstop --- 6-day trip found 3 hours ago 50% less than typical $202 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:BNA,departure:3/22/2026TANYT&leg2=from:BNA,to:BOS,departure:3/28/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-8aa45096892f434b811a7aa1e8deaefb-787-1-st-v5-sos-8aa45096892f434b811a7aa1e8deaefb-772-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAZzv_1uQAQGQAQGqAQcKA0JPUxAAsgEHCgNCTkEQAQ~AQowCi4IwmwSBDEwMDcYwZMBIKEDKP2liAMwsqeIAzhMQABYAWoCRE5yCE9JMkFVRUwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ.AQppCjIIwYIBEgQzMTY5GKEDIOKaASjh7IgDMLvtiAM4QkAAWAFqBUJBU0lDcghRVUFKWFNCVgozCMGCARIEMjgxMxjimgEgwZMBKKbviAMwrfCIAzhCQAFYAWoFQkFTSUNyCFFVQUpYU0JWEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw&medianPrice=539.00&displayPrice=201.70&src=dflp) - Hartford (BDL)San Juan (SJU) Mon, Mar 16 Fri, Mar 20 ![JetBlue Airways](https://a.travel-assets.com/air/airlines/b6_sq.svg)JetBlue Airways • Nonstop --- 3-day trip found 3 hours ago 40% less than typical $416 [](https://www.expedia.com/Flights-Search?leg1=from:BDL,to:SJU,departure:3/16/2026TANYT&leg2=from:SJU,to:BDL,departure:3/20/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-1c73c4cdf096480ab1d8b2cb1f6d1dfb-1310-1-st-v5-sos-1c73c4cdf096480ab1d8b2cb1f6d1dfb-1286-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAZrp_1uQARCQAQGqAQcKA0hGRBACsgEHCgNTSlUQAA~AQowCi4IwmwSBDE0NzUY4VggsqIBKNfohwMwvuqHAzhMQABYAWoCRE5yCFBJN1FVRUwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ.AQpmCjEIwYIBEgM5OTMYsqIBIIwCKN6QiAMwl5KIAzhCQABYAWoFQkFTSUNyCEdOVTJBQkJaCjEIwYIBEgQxMjU2GIwCIOFYKPSViAMwr5eIAzhCQAFYAWoFQkFTSUNyCEdOVTJBQkJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw&medianPrice=940.00&displayPrice=415.50&src=dflp) - Hartford (BDL)San Juan (SJU) Mon, Mar 16 Fri, Mar 20 ![JetBlue Airways](https://a.travel-assets.com/air/airlines/b6_sq.svg)JetBlue Airways • Nonstop --- 3-day trip found 13 hours ago 40% less than typical $416 [](https://www.expedia.com/Flights-Search?leg1=from:BDL,to:SJU,departure:3/16/2026TANYT&leg2=from:SJU,to:BDL,departure:3/20/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-a9e2d89f031742e097ca69a7639ecf63-1201-1-st-v5-sos-a9e2d89f031742e097ca69a7639ecf63-1179-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAdrC_VuQASCQASCqAQcKA0hGRBAAsgEHCgNTSlUQAA~AQowCi4IwmwSBDE0NzUY4VggsqIBKNfohwMwvuqHAzhMQABYAWoCRE5yCFBJN1FVRUwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ.AQpnCjIIwYIBEgQyMTQxGLKiASCMAijSkYgDMIqTiAM4QkAAWAFqBUJBU0lDcghHTlUyQUJCWgoxCMGCARIEMTI1NhiMAiDhWCj0lYgDMK-XiAM4QkABWAFqBUJBU0lDcghHTlUyQUJCWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs&medianPrice=940.00&displayPrice=415.50&src=dflp) - Hartford (BDL)San Juan (SJU) Sun, Mar 15 Sat, Mar 21 ![JetBlue Airways](https://a.travel-assets.com/air/airlines/b6_sq.svg)JetBlue Airways • Nonstop --- 5-day trip found 12 hours ago 60% less than typical $275 [](https://www.expedia.com/Flights-Search?leg1=from:BDL,to:SJU,departure:3/15/2026TANYT&leg2=from:SJU,to:BDL,departure:3/21/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-47e3efa6357f4741811f1a9017262d1d-12-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gB_OD9W5ABDaoBBwoDSEZEEACyAQcKA1NKVRAA~AQowCi4IwmwSBDE0NzUY4VggsqIBKLfdhwMwnt-HAzhMQABYAWoCRE5yCFBJN1FSRUwxCjAKLgjCbBIEMjQ3NhiyogEg4Vgo4Z6IAzDZoIgDOExAAFgBagJETnIIUEk3UVJFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB&medianPrice=962.00&displayPrice=275.00&src=dflp) ## 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) Tue, Feb 24 - Thu, Feb 26 BDL Hartford MCO Orlando $56 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BDL,to:MCO,departure:2/24/2026TANYT&leg2=from:MCO,to:BDL,departure:2/26/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:55.96&airProductToken=AQowCi4IxnISBDI3NjkY4VggzHAomYOGAzDWhIYDOEVAAFgBagRQQ18xcgdLMTREWFMyCjAKLgjGchIEMTY4NBjMcCDhWCjYmIYDMImahgM4RUAAWAFqBFBDXzFyB0sxNERYUzISCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Tue, Mar 3 - Tue, Mar 10 BOS Boston MIA Miami $66 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MIA,departure:3/3/2026TANYT&leg2=from:MIA,to:BOS,departure:3/10/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:65.98&airProductToken=AQoxCi8IzpYBEgQzMDMzGMGTASCMAija1YYDMLjXhgM4V0AAWAFqAlJQcghXMjFTWUJOUgowCi4IzpYBEgMyNzIYjAIgwZMBKKWlhwMw76aHAzhXQABYAWoCUlByCFcyMVNZQk5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Wed, Mar 4 - Tue, Mar 10 BOS Boston FLL Fort Lauderdale $67 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:FLL,departure:3/4/2026TANYT&leg2=from:FLL,to:BOS,departure:3/10/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:66.22&airProductToken=AQoxCi8IzpYBEgQxNzQwGMGTASDlWiiT24YDMOjchgM4V0AAWAFqAlJQcghXMjFTWUJOUgowCi4IzpYBEgM3NDMY5VogwZMBKKClhwMw4KaHAzhXQABYAWoCUlByCFcyMVNZQlYyEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Thu, Feb 26 - Sun, Mar 1 BDL Hartford ATL Atlanta $80 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BDL,to:ATL,departure:2/26/2026TANYT&leg2=from:ATL,to:BDL,departure:3/1/2026TANYT&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=AQowCi4IxnISBDEzMDUY4Vgg4Fwo75uGAzCcnYYDOEVAAFgBagRQQ18xcgdaMDdRWFM5CjAKLgjGchIEMTMwNhjgXCDhWCiIvIYDMJi9hgM4RUAAWAFqBFBDXzFyB1owN1lYUzkSCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Sun, Apr 5 - Thu, Apr 9 BDL Hartford MIA Miami $82 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BDL,to:MIA,departure:4/5/2026TANYT&leg2=from:MIA,to:BDL,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:81.96&airProductToken=AQowCi4IxnISBDI2NTMY4VggjAIoxMmJAzCEy4kDOEVAAFgBagRQQ18xcgdaMDdEWFM5CjAKLgjGchIEMjY1NBiMAiDhWCjN9IkDMI32iQM4RUAAWAFqBFBDXzFyB0syMVJYUzISCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Wed, Mar 4 - Wed, Mar 11 BOS Boston RSW Fort Myers $92 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:RSW,departure:3/4/2026TANYT&leg2=from:RSW,to:BOS,departure:3/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:91.56&airProductToken=AQoyCjAIzpYBEgQzMjcxGMGTASDRtAEotNuGAzCR3YYDOEdAAFgBagJSUHIIRzIxU1lCTlIKLwotCM6WARIDMjY4GNG0ASDBkwEo9quHAzCzrYcDOEdAAFgBagJSUHIGR1RSR0QxEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sat, May 30 - Sat, Jun 6 PSM Portsmouth MCO Orlando $94 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:PSM,to:MCO,departure:5/30/2026TANYT&leg2=from:MCO,to:PSM,departure:6/6/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:93.50&airProductToken=AQosCioIzbABEgM4NDcYz2QgzHAonLOOAzDqtI4DOEFAAFgBagJOT3IFQU5PMDAKLAoqCM2wARIDODQ2GMxwIM9kKJqAjwMw1IGPAzhBQABYAWoCTk9yBUFOTzAwEgwIARABGAEqAk1YMgAYASIECAEQASgCKAMoBDAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Wed, Feb 25 - Thu, Feb 26 BOS Boston SJU San Juan $109 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:SJU,departure:2/25/2026TANYT&leg2=from:SJU,to:BOS,departure:2/26/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:108.15&airProductToken=AQoxCi8IzpYBEgQzOTA4GMGTASCyogEonZOGAzCUlYYDOFdAAFgBagJSUHIHVzdTWUJOUgowCi4IzpYBEgQzMDEyGLKiASDBkwEo-pmGAzD_m4YDOFdAAFgBagJSUHIGV0ExNE5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, May 5 - Tue, May 12 BDL Hartford MIA Miami $147 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BDL,to:MIA,departure:5/5/2026TANYT&leg2=from:MIA,to:BDL,departure:5/12/2026TANYT&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=AQoyCjAIwYIBEgM0MTIY4VggjAIoqZSMAzDvlYwDOEJAAFgBagVCQVNJQ3IIT1ZBSlVTQlgKMwoxCMGCARIEMTI3MhiMAiDhWCiO6owDMM_rjAM4QkAAWAFqBUJBU0lDcghPVkFKVVNCWBIMCAEQARgBKgJBQTIAGAEiBAgBEAEoAigDKAQwCw) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Tue, May 12 - Sat, May 16 BDL Hartford MCO Orlando $147 Roundtrip found 9 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BDL,to:MCO,departure:5/12/2026TANYT&leg2=from:MCO,to:BDL,departure:5/16/2026TANYT&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=AQovCi0I15wBEgM0NzkY4VggzHAop-iMAzDb6YwDOFZAAFgBagNXR0FyB1ZETlZIMkYKLwotCNecARIDMjAyGMxwIOFYKMqQjQMw6pGNAzhWQABYAWoDV0dBcgdWRE5WSDJGEgoIARABGAEqAldOGAEiBAgBEAEoAigDKAQwAQ) ## Flights from Chesterfield: Essential Travel Information | Cheapest flight from Chesterfield | $56 (roundtrip) | | --------------------------------------- | ---------------------------------------------------------------------------------------------------------- | | Best airlines to fly from Chesterfield | Frontier Airlines, Spirit Airlines, Breeze Airways, Southwest Airlines, JetBlue Airways, American Airlines | | Cheapest month to fly from Chesterfield | February | | Chesterfield IATA code | CEF | | Chesterfield Country/State | Massachusetts | | Airline ticket deals from Chesterfield | $56 - $147 | ## How to Find Cheap Flights from Chesterfield, MA #### How much is a flight from Chesterfield? This week, flights from Chesterfield are available between $56 – $147\. #### 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, Spirit Airlines, Breeze Airways, Southwest Airlines, JetBlue Airways, American Airlines. #### What is the best month to fly from Chesterfield? One of the cheapest times to fly from Chesterfield airport(s) is February, 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. \*Flight schedules are subject to change. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals ### Lodging - [Western Massachusetts Hotels ](https://www.expedia.com/Western-Massachusetts-Hotels.d6234063.Travel-Guide-Hotels) - [Resorts & Hotels with Spas in Western Massachusetts ](https://www.expedia.com/Western-Massachusetts-Hotels-Spa-Hotel.0-0-d6234063-tSpaHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Western Massachusetts ](https://www.expedia.com/Western-Massachusetts-Hotels-Luxury-Hotel.0-0-d6234063-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Western Massachusetts ](https://www.expedia.com/Western-Massachusetts-Hotels-Romantic-Hotel.0-0-d6234063-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Western Massachusetts ](https://www.expedia.com/Western-Massachusetts-Hotels-Hotels-With-Indoor-Pool.0-0-d6234063-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - 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