Title: Boston to Chicago cheap flights from $49 (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) # $49 Cheap Flights from Boston (BOS) to Chicago (CHI) [View $49 flight on Tue, Apr 28, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:BOS,to:MDW,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:48.40&airProductToken=AQoxCi8I15wBEgM5NjEYwZMBIOywASioxosDMM3HiwM4VkAAWAFqA1dHQXIHVkJOVkgyTBIMCAIQARgCKgJXTjIAGAEiBAgBEAEoAigDKAQwAQ) - [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 ## Popular airlines from Logan International Airport (BOS) to Chicago - ![](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:3/12/2026TANYT&leg2=from:CHI,to:BOS,departure:3/19/2026TANYT&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_B6.svg) JetBlue Airways [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:CHI,departure:3/12/2026TANYT&leg2=from:CHI,to:BOS,departure:3/19/2026TANYT&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_WN.svg) Southwest Airlines [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:CHI,departure:3/12/2026TANYT&leg2=from:CHI,to:BOS,departure:3/19/2026TANYT&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_AA.svg) American Airlines [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:CHI,departure:3/12/2026TANYT&leg2=from:CHI,to:BOS,departure:3/19/2026TANYT&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_NK.svg) Spirit Airlines [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:CHI,departure:3/12/2026TANYT&leg2=from:CHI,to:BOS,departure:3/19/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![](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:3/12/2026TANYT&leg2=from:CHI,to:BOS,departure:3/19/2026TANYT&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_F9.svg) Frontier Airlines [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:CHI,departure:3/12/2026TANYT&leg2=from:CHI,to:BOS,departure:3/19/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![](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 Logan International Airport (BOS) to Chicago Nonstop Carry-on included Lower price than typical - Boston (BOS)Chicago (MDW) Fri, Mar 6 Mon, Mar 9 ![Southwest Airlines](https://a.travel-assets.com/air/airlines/wn_sq.svg)Southwest Airlines • Nonstop --- 3-day trip found 5 hours ago 60% less than typical $145 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:MDW,departure:3/6/2026TANYT&leg2=from:ORD,to:BOS,departure:3/9/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-f8b9f667737e4830a1112a38f38136bb-3376-1-st-v5-sos-f8b9f667737e4830a1112a38f38136bb-3290-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAeq60lyQARiQARiqAQcKA0JPUxAAsgEHCgNDSEkQAA~AQoyCjAI15wBEgQxMjY2GMGTASDssAEo3feGAzCR-YYDOFZAAFgBagNQTFVyB1ZMVzNXNFESCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB.AQo0CjIIwYIBEgQxNDU3GK4cIMGTASjJmocDMNWbhwM4QkAAWAFqBUJBU0lDcghPM0FaWk5CWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs&medianPrice=454.00&displayPrice=144.80&src=dflp) - Boston (BOS)Chicago (MDW) Fri, Mar 6 Sun, Mar 15 ![Southwest Airlines](https://a.travel-assets.com/air/airlines/wn_sq.svg)Southwest Airlines • Nonstop --- 9-day trip found 6 hours ago 20% less than typical $271 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:MDW,departure:3/6/2026TANYT&leg2=from:ORD,to:BOS,departure:3/15/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-9779acf7043b4c809717f76b47270002-3314-1-st-v5-sos-9779acf7043b4c809717f76b47270002-3229-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAcmT0lyQAQCQAQaqAQcKA0JPUxAAsgEHCgNDSEkQAA~AQoyCjAI15wBEgQxMjY2GMGTASDssAEo3feGAzCR-YYDOFZAAFgBagNQTFVyB1ZMVzNXNFESCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB.AQo0CjIIwYIBEgQxNDU3GK4cIMGTASiJ3ocDMJXfhwM4QkAAWAFqBUJBU0lDcghMVUFKWlNCWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs&medianPrice=450.00&displayPrice=270.80&src=dflp) - Boston (BOS)Chicago (ORD) Sun, Mar 8 Sat, Mar 14 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 6-day trip found 21 hours ago 40% less than typical $201 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:ORD,departure:3/8/2026TANYT&leg2=from:ORD,to:BOS,departure:3/14/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-187e7e224076423ab71caca7bab89ae8-2823-1-st-v5-sos-187e7e224076423ab71caca7bab89ae8-2775-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAfDkzlyQAQCQAR-qAQcKA0JPUxAAsgEHCgNDSEkQAA~AQo0CjIIwYIBEgQxMzI4GMGTASCuHCisiIcDMOuJhwM4QkAAWAFqBUJBU0lDcghPM0FaWk5CWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs.AQplCjAIwYIBEgQyMzQ1GK4cIEMo_MuHAzDrzIcDOEJAAFgBagVCQVNJQ3IITlVBSlpTQlgKMQjBggESBDQ0MDAYQyDBkwEow86HAzCmz4cDOEJAAVgBagVCQVNJQ3IITlVBSlpTQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=445.00&displayPrice=200.60&src=dflp) - Boston (BOS)Chicago (ORD) Fri, Mar 6 Sat, Mar 14 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 7-day trip found 4 hours ago 40% less than typical $217 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:ORD,departure:3/6/2026TANYT&leg2=from:ORD,to:BOS,departure:3/14/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-3020a409d3bc483fa7e894c9d6ceb767-3341-1-st-v5-sos-3020a409d3bc483fa7e894c9d6ceb767-3213-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAYXG0lyQAQGQAQGqAQcKA0JPUxAAsgEHCgNPUkQQAA~AQo0CjIIwYIBEgQxMjgzGMGTASCuHCjl9IYDMJ_2hgM4QkAAWAFqBUJBU0lDcghRN0FaWk5CWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs.AQplCjAIwYIBEgQyMzQ1GK4cIEMo_MuHAzDrzIcDOEJAAFgBagVCQVNJQ3IITlVBSlpTQlgKMQjBggESBDQ0MDAYQyDBkwEow86HAzCmz4cDOEJAAVgBagVCQVNJQ3IITlVBSlpTQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=452.00&displayPrice=216.60&src=dflp) - Boston (BOS)Chicago (ORD) Sun, Mar 15 Sun, Mar 22 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 7-day trip found 14 hours ago 20% less than typical $282 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:ORD,departure:3/15/2026TANYT&leg2=from:ORD,to:BOS,departure:3/22/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-e13af4577beb49b7ab629c47b9906672-532-1-st-v5-sos-e13af4577beb49b7ab629c47b9906672-511-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAfiw0FyQAQGQAQGqAQcKA0JPUxAAsgEHCgNPUkQQAA~AQo0CjIIwYIBEgQxMzI4GMGTASCuHCiM14cDMMvYhwM4QkAAWAFqBUJBU0lDcghOVUFKWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs.AQpnCjEIwYIBEgQzMzUzGK4cIII7KLCmiAMwkKeIAzhCQABYAWoFQkFTSUNyCFY3QUpaTkJYCjIIwYIBEgQ0Mzg5GII7IMGTASjIqIgDMMCpiAM4QkABWAFqBUJBU0lDcghWN0FKWk5CWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs&medianPrice=467.00&displayPrice=281.60&src=dflp) - Boston (BOS)Chicago (ORD) Thu, Mar 5 Sun, Mar 8 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 3-day trip just found 45% less than typical $181 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:ORD,departure:3/5/2026TANYT&leg2=from:ORD,to:BOS,departure:3/8/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-4de52e5f3740453ba8b89811860c8a08-405-1-st-v5-sos-4de52e5f3740453ba8b89811860c8a08-427-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAZ3O01yQAQGQARaqAQcKA0JPUxAAsgEHCgNPUkQQAA~AQo0CjIIwYIBEgQxMzI4GMGTASCuHCiI54YDMMfohgM4QkAAWAFqBUJBU0lDcghPM0FaWk5CWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs.AQo4CjYIxJgBEgQ1NjMzGK4cIMGTASjwiIcDMIGKhwM4RUAAWAFqCU1BSU5CQVNJQ3IIVEEzTlgwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB&medianPrice=426.00&displayPrice=180.80&src=dflp) - Boston (BOS)Chicago (ORD) Sun, Mar 8 Fri, Mar 13 ![United](https://a.travel-assets.com/air/airlines/ua_sq.svg)United • Nonstop --- 4-day trip just found 20% less than typical $286 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:ORD,departure:3/8/2026TANYT&leg2=from:LAX,to:BOS,departure:3/13/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-e94f0f389371464784b6e0c69781c486-867-1-st-v5-sos-e94f0f389371464784b6e0c69781c486-840-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAdm101yQAQ6QAQCqAQcKA0JPUxAAsgEHCgNMQVgQAA~AQo2CjQI1YIBEgQyNDg4GMGTASCuHCjEiIcDMP6JhwM4R0AAWAFqB0VDT05PTVlyCEdBQTNQRkROEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwAQ.AQpqCjMIwYIBEgQyMDU2GIu4ASCjsQEogr-HAzC5wIcDOEJAAFgBagVCQVNJQ3IIT1VBS1pTQlgKMwjBggESBDEyMDYYo7EBIMGTASibwYcDMPrChwM4QkABWAFqBUJBU0lDcghPVUFLWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs&medianPrice=461.00&displayPrice=285.60&src=dflp) - Boston (BOS)Chicago (ORD) Wed, Mar 4 Sun, Mar 8 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 3-day trip just found 45% less than typical $181 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:ORD,departure:3/4/2026TANYT&leg2=from:ORD,to:BOS,departure:3/8/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-ba863104f7e546fc8b5ddf358ec02354-802-1-st-v5-sos-ba863104f7e546fc8b5ddf358ec02354-767-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAYXE01yQAQaQAQGqAQcKA0JPUxAAsgEHCgNPUkQQAA~AQo0CjIIwYIBEgQ0NTgyGMGTASCuHCjz3YYDMLLfhgM4QkAAWAFqBUJBU0lDcghPM0FaWk5CWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs.AQo4CjYIxJgBEgQ1NjMzGK4cIMGTASjwiIcDMIGKhwM4RUAAWAFqCU1BSU5CQVNJQ3IIVEEzTlgwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB&medianPrice=424.00&displayPrice=180.80&src=dflp) - Boston (BOS)Chicago (ORD) Sun, Mar 8 Wed, Mar 11 ![JetBlue Airways](https://a.travel-assets.com/air/airlines/b6_sq.svg)JetBlue Airways • Nonstop --- 3-day trip found 20 hours ago 55% less than typical $145 [](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:ORD,departure:3/8/2026TANYT&leg2=from:RFD,to:BOS,departure:3/11/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-7822bf15f675465f8983785c7598530b-2392-1-st-v5-sos-7822bf15f675465f8983785c7598530b-2372-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAfyFz1yQAQCQASyqAQcKA0JPUxAAsgEHCgNDSEkQAg~AQovCi0IwmwSAzMxMRjBkwEgrhwotIiHAzDyiYcDOFVAAFgBagJBTnIIVUkzQUJFWTUSCggBEAEYASoCQjYYASIECAEQASgCKAMoBDAB.AQpnCjEIwYIBEgQ2NTcyGLEZIK4cKJSqhwMw7qqHAzhCQABYAWoFQkFTSUNyCE9VQUhaTkJWCjIIwYIBEgQyNDg5GK4cIMGTASiWq4cDMKCshwM4QkABWAFqBUJBU0lDcghPVUFIWk5CVhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs&medianPrice=422.00&displayPrice=144.49&src=dflp) ## Cheap Flights from Boston to Chicago (BOS-CHI) Prices were available within the past 7 days and start at $49 for one-way flights and $97 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, Apr 29 - Tue, May 5 BOS Boston ORD Chicago $97 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:96.80&airProductToken=AQo4CjYI1YIBEgM1MDMYwZMBIK4cKKTTiwMw19SLAzhOQABYAWoKMV9iYXNpY2Vjb3IIR0FVMkFYQlMSCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Apr 29 - Tue, May 5 BOS Boston ORD Chicago $97 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:96.81&airProductToken=AQo4CjYIxJgBEgQyODA0GMGTASCuHCin14sDMNXYiwM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU1gyQkMKOAo2CMSYARIEMjU3MBiuHCDBkwEo85aMAzD_l4wDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNYMkJDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, Apr 29 - Tue, May 5 BOS Boston ORD Chicago $97 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:96.81&airProductToken=AQo5CjcI1YIBEgQxNzMyGMGTASCuHCj-04sDMLHViwM4TkAAWAFqCjFfYmFzaWNlY29yCEdBVTJBWEJTCjkKNwjVggESBDE2OTMYrhwgwZMBKM-YjAMw4pmMAzhOQABYAWoKMV9iYXNpY2Vjb3IIR0FVMkFYQlMSCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Wed, Apr 8 - Tue, Apr 14 BOS Boston ORD Chicago $97 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:4/8/2026TANYT&leg2=from:ORD,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:96.81&airProductToken=AQovCi0IwmwSAzMxMRjBkwEgrhwo3eSJAzCU5okDOExAAFgBagJETnIIUEkyUUJaTDEKLwotCMJsEgMzMTIYrhwgwZMBKLGqigMww6uKAzhMQABYAWoCRE5yCFBJMlFCWkwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, May 6 - Sat, May 9 BOS Boston ORD Chicago $98 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:5/6/2026TANYT&leg2=from:ORD,to:BOS,departure:5/9/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:97.80&airProductToken=AQo0CjIIwYIBEgQzMjA5GMGTASCuHCiEpIwDMMaljAM4QkAAWAFqBUJBU0lDcghPVkFJS1NCWAo0CjIIwYIBEgQzMjA5GK4cIMGTASibxIwDMLLFjAM4QkAAWAFqBUJBU0lDcghPVkFJWFNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Mon, May 4 - Sat, May 9 BOS Boston ORD Chicago $99 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:5/4/2026TANYT&leg2=from:ORD,to:BOS,departure:5/9/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:98.80&airProductToken=AQo0CjIIwYIBEgQxMDQwGMGTASCuHCiSjowDMNePjAM4QkAAWAFqBUJBU0lDcghPVkFJWFNCWAo0CjIIwYIBEgQzMjA5GK4cIMGTASibxIwDMLLFjAM4QkAAWAFqBUJBU0lDcghPVkFJWFNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Wed, May 6 - Fri, May 8 BOS Boston ORD Chicago $102 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:5/6/2026TANYT&leg2=from:ORD,to:BOS,departure:5/8/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:101.80&airProductToken=AQovCi0IwmwSAzgxMRjBkwEgrhwoh6aMAzC8p4wDOExAAFgBagJETnIIUEkyUUJaTDEKMAouCMJsEgQxMDEyGK4cIMGTASjUtowDMNu3jAM4TEAAWAFqAkROcghQSTJRQkhMMRIKCAEQARgBKgJCNhgBIgQIARABKAIoBCgGMAE) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Wed, Apr 1 - Sat, Apr 11 BOS Boston MDW Chicago $103 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MDW,departure:4/1/2026TANYT&leg2=from:MDW,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:102.80&airProductToken=AQoyCjAI15wBEgQzNTE0GMGTASDssAEo2JmJAzD9mokDOFZAAFgBagNXR0FyB1ZMTlZIMkUKMgowCNecARIEMTgwMBjssAEgwZMBKN2HigMw5IiKAzhWQABYAWoDV0dBcgdWSk5WSDJFEgoIAhABGAIqAldOGAEiBAgBEAEoAigDKAQwAQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sat, May 2 - Fri, May 8 BOS Boston ORD Chicago $103 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:5/2/2026TANYT&leg2=from:ORD,to:BOS,departure:5/8/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:102.80&airProductToken=AQo5CjcI1YIBEgQxODY5GMGTASCuHCjY8osDMIz0iwM4TkAAWAFqCjFfYmFzaWNlY29yCEdBRzJBWEJTCjkKNwjVggESBDE3NzkYrhwgwZMBKPa9jAMwi7-MAzhOQABYAWoKMV9iYXNpY2Vjb3IIR0FQMkFYQlMSCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Apr 29 - Tue, May 5 BOS Boston ORD Chicago $107 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:106.60&airProductToken=AQpxCjcIxJgBEgQxNzQ4GMGTASDjtAEoxdKLAzDQ04sDOEVAAFgBaglNQUlOQkFTSUNyCFZBVldYMkJDCjYIxJgBEgQxNzE2GOO0ASCuHCjx04sDMMnUiwM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWV1gyQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![](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_) ## 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:3/12/2026TANYT&leg2=from:ORD,to:BOS,departure:3/19/2026TANYT&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 $156 ](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:ORD,departure:3/12/2026TANYT&leg2=from:ORD,to:BOS,departure:3/19/2026TANYT&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:3/12/2026TANYT&leg2=from:MDW,to:BOS,departure:3/19/2026TANYT&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 $291 ](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:MDW,departure:3/12/2026TANYT&leg2=from:MDW,to:BOS,departure:3/19/2026TANYT&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:3/12/2026TANYT&leg2=from:RFD,to:BOS,departure:3/24/2026TANYT&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 $192 ](https://www.expedia.com/Flights-Search?leg1=from:BOS,to:RFD,departure:3/12/2026TANYT&leg2=from:RFD,to:BOS,departure:3/24/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Find the cheapest month to fly from Boston (BOS) to Chicago (CHI) ### September is typically the cheapest month to fly From $84 - $183 per traveler. ## 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 | $97 | | Distance | 863 mi | ## Book with confidence # Boston to Chicago Flights The cheapest times to fly from Boston to Chicago On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Boston to Chicago are during the month of April. You can find some of the cheapest flights from Boston to Chicago with Expedia's search tool and vast selection of airlines. The best time to book a flight from Boston to Chicago Sunday is one of the best days to book for cheap flights from Boston to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance. How to find cheap round-trip tickets from Boston to Chicago Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Boston to Chicago in 2026\. You can also book with separate airlines for your outbound and return journeys, from $49 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference\*. This is available for a small fee, and is free to One Key Gold and Platinum tier members. Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Boston to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps. You could also save big by booking one of Expedia's [vacation packages](https://www.expedia.com/package-deals). Bundling together your Boston to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures. \*Terms apply. Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. The percentages you see are averages. \*Flight schedules are subject to change. ## 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) - [3 Star Hotels in Garden Prairie ](https://www.expedia.com/3Star-Garden-Prairie-Hotels.s30-0-d3000346277.Travel-Guide-Filter-Hotels) - [Kirkland Hotels ](https://www.expedia.com/Kirkland-Hotels.d553248634983555364.Travel-Guide-Hotels) - [Belvidere Hotels ](https://www.expedia.com/Belvidere-Hotels.d55583.Travel-Guide-Hotels) - [Marengo Hotels ](https://www.expedia.com/Marengo-Hotels.d553248634983534917.Travel-Guide-Hotels) - [Cheap Hotels in Belvidere ](https://www.expedia.com/Belvidere-Hotels-Cheap-Hotels.0-0-d55583-tCheapHotels.Travel-Guide-Filter-Hotels) - [Motels in Belvidere ](https://www.expedia.com/Belvidere-Motels.d55583-aaMotels.Travel-Guide-Accommodation) - 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