Title: CA $90 Cheap Flights from Boston (BOS) to Chicago (ORD) - Expedia.ca ![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) # CA $90 Cheap Flights from Boston (BOS) to Chicago (ORD) [View CA $90 flight on Wed, Apr 22, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:BOS,to:ORD,departure:22/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:89.78&airProductToken=AQpdCi0IzpYBEgQzOTI5GMGTASDlWijwiIsDML2KiwM4V0AAWAFqAlJQcgZXQTE0TlIKLAjOlgESBDIyMDQY5Vogrhwo-Y2LAzDMj4sDOFdAAVgBagJSUHIGV0ExNE5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ## Popular airlines from Logan International Airport (BOS) to Chicago O'Hare International Airport (ORD) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.ca/Flights-Search?leg1=from:BOS,to:ORD,departure:22/04/2026TANYT&leg2=from:ORD,to:BOS,departure:29/04/2026TANYT&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_F9.svg) Frontier Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:BOS,to:ORD,departure:22/04/2026TANYT&leg2=from:ORD,to:BOS,departure:29/04/2026TANYT&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_AA.svg) American Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:BOS,to:ORD,departure:22/04/2026TANYT&leg2=from:ORD,to:BOS,departure:29/04/2026TANYT&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_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:BOS,to:ORD,departure:22/04/2026TANYT&leg2=from:ORD,to:BOS,departure:29/04/2026TANYT&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_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:BOS,to:ORD,departure:22/04/2026TANYT&leg2=from:ORD,to:BOS,departure:29/04/2026TANYT&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_NK.svg) Spirit Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:BOS,to:ORD,departure:22/04/2026TANYT&leg2=from:ORD,to:BOS,departure:29/04/2026TANYT&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_WN.svg) Southwest Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:BOS,to:ORD,departure:22/04/2026TANYT&leg2=from:ORD,to:BOS,departure:29/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](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 rewards [Sign in](https://www.expedia.ca/login) ## Cheap flights from Boston (BOS) to Chicago (ORD) Prices were available within the past 7 days and start at CA $90 for one-way flights and CA $217 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Apr 28 - Wed, May 6 BOS Boston ORD Chicago CA $217 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:28/04/2026TANYT&leg2=from:ORD,to:BOS,departure:06/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:216.10&airProductToken=AQojCiEIxJgBEgQyODA0GMGTASCuHCiHzIsDMLXNiwM4RUAAWAEKIwohCMSYARIEMjU3MBiuHCDBkwEok6KMAzCfo4wDOEVAAFgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, May 9 - Wed, May 27 BOS Boston ORD Chicago CA $233 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:09/05/2026TANYT&leg2=from:ORD,to:BOS,departure:27/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:232.20&airProductToken=AQohCh8IwmwSAzgxMRjBkwEgrhwot8eMAzDxyIwDOExAAFgBCiIKIAjCbBIEMTAxMhiuHCDBkwEompOOAzCvlI4DOExAAFgBEgoIARABGAEqAkI2GAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Apr 29 - Sun, May 3 BOS Boston ORD Chicago CA $233 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:29/04/2026TANYT&leg2=from:ORD,to:BOS,departure:03/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:232.85&airProductToken=AQo4CjYIxJgBEgQyNTcwGMGTASCuHCi-0YsDMPfSiwM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWV1gyQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Apr 28 - Sat, May 2 BOS Boston ORD Chicago CA $239 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:28/04/2026TANYT&leg2=from:ORD,to:BOS,departure:02/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:238.70&airProductToken=AQojCiEIxJgBEgQyODA0GMGTASCuHCiHzIsDMLXNiwM4RUAAWAEKIwohCMSYARIEMjgyOBiuHCDBkwEolPOLAzCm9IsDOEVAAFgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Apr 29 - Sun, May 3 BOS Boston ORD Chicago CA $240 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:29/04/2026TANYT&leg2=from:ORD,to:BOS,departure:03/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:239.70&airProductToken=AQo0CjIIwYIBEgQyODE1GMGTASCuHCiv1osDMPTXiwM4QkAAWAFqBUJBU0lDcghRVkFKVVNCWAozCjEIwYIBEgM5NjYYrhwgwZMBKLT-iwMwx_-LAzhCQABYAWoFQkFTSUNyCFFWQUpaU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Aug 27 - Wed, Sep 2 BOS Boston ORD Chicago CA $241 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:27/08/2026TANYT&leg2=from:ORD,to:BOS,departure:02/09/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:240.52&airProductToken=AQo0CjIIwYIBEgQzMDQ4GMGTASCuHCiymZYDMOGalgM4QkAAWAFqBUJBU0lDcghRVkFKWFNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Apr 28 - Thu, Apr 30 BOS Boston ORD Chicago CA $246 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:28/04/2026TANYT&leg2=from:ORD,to:BOS,departure:30/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:245.10&airProductToken=AQojCiEIxJgBEgQyODA0GMGTASCuHCiHzIsDMLXNiwM4RUAAWAEKIwohCMSYARIEMjU3MBiuHCDBkwEo096LAzDf34sDOEVAAFgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, May 2 - Sat, May 16 BOS Boston ORD Chicago CA $247 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:02/05/2026TANYT&leg2=from:ORD,to:BOS,departure:16/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:246.20&airProductToken=AQohCh8IwmwSAzgxMRjBkwEgrhwoh_mLAzC8-osDOExAAFgBCiIKIAjCbBIEMTAxMhiuHCDBkwEopJGNAzC2ko0DOExAAFgBEgoIARABGAEqAkI2GAEiBAgBEAEoBDAB) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Thu, Apr 23 - Mon, May 4 BOS Boston ORD Chicago CA $271 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:23/04/2026TANYT&leg2=from:ORD,to:BOS,departure:04/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:270.34&airProductToken=AQpdCi0IzpYBEgQzOTI5GMGTASDlWiiQlIsDMN2ViwM4R0AAWAFqAlJQcgZHQTE0TlIKLAjOlgESBDIyMDQY5VogrhwomZmLAzDsmosDOEdAAVgBagJSUHIGR0ExNE5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, Apr 29 - Sun, May 3 BOS Boston ORD Chicago CA $279 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:29/04/2026TANYT&leg2=from:ORD,to:BOS,departure:03/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:278.37&airProductToken=AQo0CjII1YIBEgQxMzQ5GMGTASCuHCjA0osDMPTTiwM4R0AAWAFqBTJfZWNvcghHQVUyQUhEUxIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAs) ## Frequently asked questions ### How much is a flight from Logan Intl. Airport to O'Hare Airport? ### Do I need to pay a cancellation fee if I cancel my flight from Logan Intl. Airport to O'Hare Airport? ### How do I find cheap flights from Logan Intl. Airport to O'Hare Intl. Airport (ORD) that have flexible change policies? ### How many hours is the flight from BOS to ORD? ### How far is the flight from Logan Intl. Airport to O'Hare Intl. Airport (ORD)? ### Which airlines fly direct from Logan Intl. Airport (BOS) to O'Hare Airport? > - American Airlines - (AA) with 178 monthly flights > - United Airlines - (UA) with 165 monthly flights > - Delta - (DL) with 117 monthly flights > - JetBlue - (B6) with 30 monthly flights ### Are BOS to O'Hare Airport flight tickets cheaper when they're purchased at the last minute? ## Travel information | Origin airport | Logan Intl. | | ------------------- | --------------------------------------------------------------------------------------------------------- | | Destination airport | O'Hare Intl. | | Airlines serving | Alaska Airlines, American Airlines, Delta, JetBlue Airways, Spirit Airlines, Sun Country Airlines, United | | Roundtrip price | CA $216 | | Distance | 1381 km | | Average flight time | 1 hour 57 mins | ## Explore a world of travel with Expedia - Flights - [Flights from Calgary to Rosemont ](https://www.expedia.ca/lp/flights/178245/7581/calgary-to-rosemont) - [Flights from Denver to Northwest Chicago ](https://www.expedia.ca/lp/flights/178254/6350697/denver-to-northwest-chicago) - 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[Flights from Sydney (SYD) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/syd/mdw/sydney-to-chicago) - [Flights from Syracuse (SYR) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/syr/mdw/syracuse-to-chicago) - [Flights from Fort Leonard Wood (TBN) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/tbn/mdw/fort-leonard-wood-to-chicago) - [Flights from Ua Pou (UAP) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/uap/chi/ua-pou-to-chicago) - [Flights from Fort Frances (YAG) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yag/chi/fort-frances-to-chicago) - [Flights from Brandon (YBR) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ybr/mdw/brandon-to-chicago) - [Flights from Nanaimo (YCD) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ycd/chi/nanaimo-to-chicago) - [Flights from St. Catharines (YCM) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ycm/chi/st-catharines-to-chicago) - [Flights from Edmonton (YEA) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yea/chi/edmonton-to-chicago) - [Flights from Edmonton (YEG) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yeg/chi/edmonton-to-chicago) - [Flights from Edmonton (YEG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yeg/mdw/edmonton-to-chicago) - [Flights from Flin Flon (YFO) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yfo/chi/flin-flon-to-chicago) - [Flights from Hamilton (YHM) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yhm/mdw/hamilton-to-chicago) - [Flights from Kamloops (YKA) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yka/chi/kamloops-to-chicago) - [Flights from Kelowna (YLW) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ylw/mdw/kelowna-to-chicago) - [Flights from Montreal (YMQ) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ymq/chi/montreal-to-chicago) - [Flights from Ottawa (YOW) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yow/mdw/ottawa-to-chicago) - [Flights from Peterborough (YPQ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ypq/mdw/peterborough-to-chicago) - [Flights from Québec (YQB) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yqb/mdw/quebec-to-chicago) - [Flights from Regina (YQR) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yqr/chi/regina-to-chicago) - [Flights from Regina (YQR) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yqr/mdw/regina-to-chicago) - [Flights from Gander (YQX) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yqx/chi/gander-to-chicago) - [Flights from Sudbury (YSB) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ysb/mdw/sudbury-to-chicago) - [Flights from Timmins (YTS) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yts/mdw/timmins-to-chicago) - [Flights from Toronto (YTZ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago) - [Flights from Montreal (YUL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yul/mdw/montreal-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ywg/mdw/winnipeg-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (PWK) ](https://www.expedia.ca/lp/flights/ywg/pwk/winnipeg-to-chicago) - [Flights from Whitehorse (YXY) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yxy/chi/whitehorse-to-chicago) - [Flights from Calgary (YYC) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yyc/mdw/calgary-to-chicago) - [Flights from Victoria (YYJ) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yyj/chi/victoria-to-chicago) - [Flights from St. John's (YYT) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yyt/chi/st-johns-to-chicago) - [Flights from Toronto (YYZ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yyz/mdw/toronto-to-chicago) - [Flights from Toronto (YYZ) to Chicago (PWK) ](https://www.expedia.ca/lp/flights/yyz/pwk/toronto-to-chicago) \*Available to Expedia members.