Title: Boston to Chicago cheap flights from $70 (BOS to CHI) - Expedia.com ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $70 Cheap Flights from Boston (BOS) to Chicago (CHI) [View $70 flight on Wed, Apr 29, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:BOS,to:MDW,departure:4/29/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:69.98&airProductToken=AQpiCi8IxnISBDM1MTEYwZMBIOBcKJfUiwMw1NWLAzhFQABYAWoEUENfMXIHSzIxUFhQNAovCMZyEgQyMjkxGOBcIOywASji1osDMN_XiwM4RUAAWAFqBFBDXzFyB0syMVBYUDQSCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ## Popular airlines from Logan International Airport (BOS) to Chicago - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:CHI,departure:4/21/2026TANYT&leg2=from:CHI,to:BOS,departure:4/28/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![](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:BOS,to:CHI,departure:4/21/2026TANYT&leg2=from:CHI,to:BOS,departure:4/28/2026TANYT&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_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:CHI,departure:4/21/2026TANYT&leg2=from:CHI,to:BOS,departure:4/28/2026TANYT&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_AA.svg) American Airlines [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:CHI,departure:4/21/2026TANYT&leg2=from:CHI,to:BOS,departure:4/28/2026TANYT&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_UA.svg) United [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:CHI,departure:4/21/2026TANYT&leg2=from:CHI,to:BOS,departure:4/28/2026TANYT&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:BOS,to:CHI,departure:4/21/2026TANYT&leg2=from:CHI,to:BOS,departure:4/28/2026TANYT&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_NK.svg) Spirit Airlines [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:CHI,departure:4/21/2026TANYT&leg2=from:CHI,to:BOS,departure:4/28/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![](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) ## Cheap Flights from Boston to Chicago (BOS-CHI) Prices were available within the past 7 days and start at $70 for one-way flights and $135 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Wed, Apr 22 - Wed, Apr 29 BOS Boston ORD Chicago $135 Roundtrip found 15 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:4/22/2026TANYT&leg2=from:ORD,to:BOS,departure:4/29/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:134.36&airProductToken=AQpdCi0IzpYBEgQzOTI5GMGTASDlWijwiIsDML2KiwM4V0AAWAFqAlJQcgZXQTE0TlIKLAjOlgESBDIyMDQY5Vogrhwo-Y2LAzDMj4sDOFdAAVgBagJSUHIGV0ExNE5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Wed, Apr 29 - Tue, May 5 BOS Boston ORD Chicago $140 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:4/29/2026TANYT&leg2=from:ORD,to:BOS,departure:5/5/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:139.96&airProductToken=AQphCi8IxnISBDMwODUYwZMBIOBcKPjQiwMwvtKLAzhFQABYAWoEUENfMXIHSzIxUFhQNAouCMZyEgQxNTk1GOBcIK4cKLPViwMwyNaLAzhFQABYAWoEUENfMXIHSzIxUFhQNAphCi4IxnISBDIxOTgYrhwg4Fwo05iMAzDfmYwDOEVAAFgBagRQQ18xcgdLMjFQWFA0Ci8IxnISBDMwODYY4FwgwZMBKKCcjAMwxJ2MAzhFQABYAWoEUENfMXIHSzIxUFhQNBIKCAEQARgBKgJGORgBIgQIARABKAIoAzAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Wed, Apr 22 - Sat, May 2 BOS Boston ORD Chicago $148 Roundtrip found 13 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:4/22/2026TANYT&leg2=from:ORD,to:BOS,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:147.78&airProductToken=AQpdCi0IzpYBEgQzOTI5GMGTASDlWijwiIsDML2KiwM4V0AAWAFqAlJQcgZXQTE0TlIKLAjOlgESBDIyMDQY5Vogrhwo-Y2LAzDMj4sDOFdAAVgBagJSUHIGV0ExNE5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Tue, May 5 - Wed, May 13 BOS Boston MDW Chicago $150 Roundtrip found 16 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MDW,departure:5/5/2026TANYT&leg2=from:MDW,to:BOS,departure:5/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:149.97&airProductToken=AQpECiAIxnISBDMwODUYwZMBIOBcKLiUjAMw9JWMAzhLQABYAQogCMZyEgQyMjkxGOBcIOywASitlowDMKmXjAM4S0ABWAEKRAogCMZyEgQyNzgwGOywASDgXCjg8YwDMN7yjAM4S0AAWAEKIAjGchIEMzA4NhjgXCDBkwEooPaMAzDE94wDOEtAAVgBEgoIARABGAEqAkY5GAEiBAgBEAEoBDAB) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Tue, May 12 - Wed, May 13 BOS Boston ORD Chicago $150 Roundtrip found 8 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:5/12/2026TANYT&leg2=from:ORD,to:BOS,departure:5/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:149.97&airProductToken=AQpfCi4IxnISBDM1MTEYwZMBIOBcKOvkjAMwoeaMAzhLQABYAWoDRUNPcgdLMjFQWFA0Ci0IxnISBDMzOTcY4FwgrhwogemMAzCT6owDOEtAAVgBagNFQ09yB0syMVBYUDQKXwotCMZyEgQyMTk4GK4cIOBcKNPyjAMw3_OMAzhLQABYAWoDRUNPcgdLMjFQWFA0Ci4IxnISBDMwODYY4FwgwZMBKKD2jAMwxPeMAzhLQAFYAWoDRUNPcgdLMjFQWFA0EgoIARABGAEqAkY5GAEiBAgBEAEoAigDKAQwAQ) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Tue, Apr 28 - Wed, Apr 29 BOS Boston ORD Chicago $151 Roundtrip found 8 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:4/28/2026TANYT&leg2=from:ORD,to:BOS,departure:4/29/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:150.56&airProductToken=AQpfCi4IxnISBDMwODUYwZMBIOBcKNjFiwMwnseLAzhLQABYAWoDRUNPcgdLMjFQWFA0Ci0IxnISBDE1OTUY4Fwgrhwok8qLAzCoy4sDOEtAAVgBagNFQ09yB0syMVBYUDQSCggBEAEYASoCRjkYASIECAEQASgCKAMoBDAB) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Wed, Apr 22 - Mon, May 11 BOS Boston ORD Chicago $153 Roundtrip found 4 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:4/22/2026TANYT&leg2=from:ORD,to:BOS,departure:5/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:152.78&airProductToken=AQpdCi0IzpYBEgQzOTI5GMGTASDlWijwiIsDML2KiwM4V0AAWAFqAlJQcgZXQTE0TlIKLAjOlgESBDIyMDQY5Vogrhwo-Y2LAzDMj4sDOFdAAVgBagJSUHIGV0ExNE5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Apr 14 - Wed, Apr 15 BOS Boston RFD Rockford $157 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:RFD,departure:4/14/2026TANYT&leg2=from:RFD,to:BOS,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:156.10&airProductToken=AQpnCjIIwYIBEgQ0NDg2GMGTASCuHCioqooDMOSrigM4QkAAWAFqBUJBU0lDcghPVUFKWlNCVgoxCMGCARIENjU3NhiuHCCxGSiMrIoDMOasigM4QkABWAFqBUJBU0lDcghPVUFKWlNCVhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Tue, Apr 28 - Thu, Apr 30 BOS Boston MDW Chicago $157 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MDW,departure:4/28/2026TANYT&leg2=from:MDW,to:BOS,departure:4/30/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:156.79&airProductToken=AQoxCi8I15wBEgM4OTgYwZMBIOywASjRyYsDMPHKiwM4VkAAWAFqA1dHQXIHVkxOVUgyRgoyCjAI15wBEgQyMzkyGOywASDBkwEo4OKLAzDs44sDOFZAAFgBagNXR0FyB1ZMTlVIMkYSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, May 2 - Mon, May 4 BOS Boston ORD Chicago $159 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:5/2/2026TANYT&leg2=from:ORD,to:BOS,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:158.38&airProductToken=AQovCi0IwmwSAzgxMRjBkwEgrhwoh_mLAzC8-osDOExAAFgBagJETnIIUEkyUVVPTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB) ## Alternative airports near Chicago Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:ORD,departure:4/21/2026TANYT&leg2=from:ORD,to:BOS,departure:4/28/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. Cheapest 23 min [Flights from $152 ](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:ORD,departure:4/21/2026TANYT&leg2=from:ORD,to:BOS,departure:4/28/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:MDW,departure:4/21/2026TANYT&leg2=from:MDW,to:BOS,departure:4/28/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) MDW Midway Intl. Closest 16 min [Flights from $330 ](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:MDW,departure:4/21/2026TANYT&leg2=from:MDW,to:BOS,departure:4/28/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:RFD,departure:4/21/2026TANYT&leg2=from:RFD,to:BOS,departure:4/28/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) RFD Greater Rockford 1 h 30 min [Flights from $409 ](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:RFD,departure:4/21/2026TANYT&leg2=from:RFD,to:BOS,departure:4/28/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Frequently asked questions ### How much is a flight from Logan Intl. Airport (BOS) to Chicago, IL (CHI-All Airports)? ### Do I need to pay a cancellation fee if I cancel my flight from Logan Intl. Airport to Chicago, IL (CHI-All Airports)? ### How do I find cheap flights from Logan Intl. Airport (BOS) to Chicago, IL (CHI-All Airports) that have flexible change policies? ### How far is the flight from Logan Intl. Airport (BOS) to Chicago, IL (CHI-All Airports)? ### Which airlines fly direct from BOS to Chicago, IL (CHI-All Airports)? > - American Airlines - (AA) with 230 monthly flights > - United Airlines - (UA) with 178 monthly flights > - Delta Air Lines - (DL) with 139 monthly flights > - Southwest Airlines - (WN) with 121 monthly flights ### Are BOS to Chicago, IL (CHI-All Airports) flight tickets cheaper when they're purchased at the last minute? ## Travel information | Origin airport | Logan Intl. | | ------------------- | ------------ | | Destination airport | O'Hare Intl. | | Roundtrip price | $134 | | Distance | 863 mi | \*Flight schedules are subject to change. \*Available to One Key members. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Garden Prairie Hotels ](https://www.expedia.com/Garden-Prairie-Hotels.d3000346277.Travel-Guide-Hotels) - [5 Star Hotels in Garden Prairie ](https://www.expedia.com/5Star-Garden-Prairie-Hotels.s50-0-d3000346277.Travel-Guide-Filter-Hotels) - 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