Title: CA $82 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 $82 Cheap Flights from Boston (BOS) to Chicago (ORD) [View CA $82 flight on Sun, Dec 7, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:BOS,to:ORD,departure:07/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:81.60&airProductToken=AQo0CjIIwYIBEgQ0NjE4GMGTASCuHCiQif8CMOSK_wI4QkAAWAFqBUJBU0lDcghPV0FKWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers 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 O'Hare International Airport (ORD) - ![JetBlue Airways](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:13/11/2025TANYT&leg2=from:ord,to:bos,departure:20/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![American Airlines](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:13/11/2025TANYT&leg2=from:ord,to:bos,departure:20/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![Delta](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:13/11/2025TANYT&leg2=from:ord,to:bos,departure:20/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![United](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:13/11/2025TANYT&leg2=from:ord,to:bos,departure:20/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![Spirit Airlines](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:13/11/2025TANYT&leg2=from:ord,to:bos,departure:20/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![Southwest Airlines](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:13/11/2025TANYT&leg2=from:ord,to:bos,departure:20/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![Frontier Airlines](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:13/11/2025TANYT&leg2=from:ord,to:bos,departure:20/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) ![notification illustration](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\* ![deals illustration](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\* ![trophy illustration](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 $82 for one-way flights and CA $128 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Wed, Dec 31 - Mon, Jan 5 BOS Boston ORD Chicago CA $128 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:31/12/2025TANYT&leg2=from:ORD,to:BOS,departure:05/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:127.60&airProductToken=AQpeCi0IwmwSAzUxNxjBkwEgqVEo35qBAzCtm4EDOExAAFgBagJETnIIUEkyUVVFTDEKLQjCbBIEMTMwNRipUSCuHCicnYEDMNOegQM4TEABWAFqAkROcghQSTJRVUVMMQowCi4IwmwSBDEwMTIYrhwgwZMBKOXVgQMw-taBAzhMQABYAWoCRE5yCFBJMlFVRUwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Dec 11 - Mon, Jan 5 BOS Boston ORD Chicago CA $128 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:11/12/2025TANYT&leg2=from:ORD,to:BOS,departure:05/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:127.90&airProductToken=AQo0CjIIwYIBEgQxMzI4GMGTASCuHCjUtf8CMJm3_wI4QkAAWAFqBUJBU0lDcghPVkFJWFNCWAo0CjIIwYIBEgQyNDQ5GK4cIMGTASiM1oEDMKPXgQM4QkAAWAFqBUJBU0lDcghPVkFJWFNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Dec 11 - Mon, Jan 5 BOS Boston ORD Chicago CA $147 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:11/12/2025TANYT&leg2=from:ORD,to:BOS,departure:05/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:146.05&airProductToken=AQo4CjYIxJgBEgQyNjc5GMGTASCuHCjuuP8CMJ-6_wI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFXU1g1QkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Dec 11 - Mon, Jan 5 BOS Boston ORD Chicago CA $160 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:11/12/2025TANYT&leg2=from:ORD,to:BOS,departure:05/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:159.65&airProductToken=AQo0CjIIwYIBEgQxMzI4GMGTASCuHCjUtf8CMJm3_wI4QkAAWAFqBUJBU0lDcghPVkFJWFNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Dec 3 - Mon, Dec 15 BOS Boston ORD Chicago CA $164 Roundtrip found 17 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:03/12/2025TANYT&leg2=from:ORD,to:BOS,departure:15/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:163.20&airProductToken=AQojCiEIxJgBEgQyNjc2GMGTASCuHCiU4v4CMMPj_gI4RUAAWAEKIgogCMSYARIDOTcyGK4cIMGTASje5_8CMO7o_wI4RUAAWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Dec 9 - Tue, Dec 16 BOS Boston ORD Chicago CA $165 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:09/12/2025TANYT&leg2=from:ORD,to:BOS,departure:16/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:164.32&airProductToken=AQo4CjYIxJgBEgQyNjc2GMGTASCuHCjUpf8CMIOn_wI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFXTlgwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Thu, Dec 11 - Mon, Jan 5 BOS Boston ORD Chicago CA $167 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:11/12/2025TANYT&leg2=from:ORD,to:BOS,departure:05/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:166.60&airProductToken=AQovCi0IwmwSAzMxMRjBkwEgrhwo6rb_AjCjuP8COExAAFgBagJETnIIU0kyUUJFTDEKMAouCMJsEgQxMDEyGK4cIMGTASjl1YEDMPrWgQM4TEAAWAFqAkROcghQSTJRVUVMMRIKCAEQARgBKgJCNhgBIgQIARABKAIoBCgGMAE) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Dec 3 - Thu, Dec 4 BOS Boston ORD Chicago CA $171 Roundtrip found 19 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:03/12/2025TANYT&leg2=from:ORD,to:BOS,departure:04/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:170.70&airProductToken=AQozCjEIwYIBEgM0ODgYwZMBIK4cKKXf_gIw4-D-AjhCQABYAWoFQkFTSUNyCE9XQUpaU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Tue, Dec 9 - Tue, Dec 16 BOS Boston ORD Chicago CA $233 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:09/12/2025TANYT&leg2=from:ORD,to:BOS,departure:16/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:232.55&airProductToken=AQpbCiwIzpYBEgM4OTEYwZMBIMxwKLyh_wIwgaP_AjhHQABYAWoCUlByBkdBMjFZNAorCM6WARIDODk3GMxwIK4cKMyl_wIwhKf_AjhHQAFYAWoCUlByBkdBMjFZNApbCisIzpYBEgMzMDIYrhwg5Voo5vL_AjCt9P8COFdAAFgBagJSUHIGV0EyMU8xCiwIzpYBEgMzNjMY5VogwZMBKOj0_wIwqPb_AjhXQAFYAWoCUlByBldBMjFPMRIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, Dec 3 - Thu, Dec 4 BOS Boston ORD Chicago CA $262 Roundtrip found 19 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:03/12/2025TANYT&leg2=from:ORD,to:BOS,departure:04/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:261.10&airProductToken=AQo0CjII1YIBEgQxNDE0GMGTASCuHCjU2_4CMIjd_gI4R0AAWAFqBTJfZWNvcghHQUE1QUhEUwo0CjII1YIBEgQxMjY5GK4cIMGTASj36P4CMIfq_gI4R0AAWAFqBTJfZWNvcghHQUE1QUhEUxIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAs) ## Find the cheapest month to fly from Boston (BOS) to Chicago (ORD) ### September is typically the cheapest month to fly From CA $127 - CA $190 per traveller. ## Alternative airports near Chicago Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.ca/Flights-Search?leg1=from:BOS,to:ORD,departure:13/11/2025TANYT&leg2=from:ORD,to:BOS,departure:27/11/2025TANYT&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 CA $217](https://www.expedia.ca/Flights-Search?leg1=from:BOS,to:ORD,departure:13/11/2025TANYT&leg2=from:ORD,to:BOS,departure:27/11/2025TANYT&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 to O'Hare Airport? > Pack your bags, because round-trip journeys between BOS and ORD start from CA $128. That's based on fares listed within the last 7 days on Expedia for flights departing within the next year. Prices can go up quickly, so book now to secure the best deal. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Logan Intl. Airport to O'Hare Airport? > Every airline has a different set of terms and conditions. If you decide to cancel your escape, visit our [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from Logan Intl. Airport to O'Hare Intl. Airport (ORD) that have flexible change policies? > Flights from BOS to O'Hare Intl. Airport (ORD) offering flexible change policies are available with many airlines. Simply use our "No change fees" filter while searching. You'll only need to pay the cost difference between flights, without any added fees to worry about. ### How many hours is the flight from BOS to ORD? > Consider bringing your own in-flight entertainment, as it takes around 3 hours and 2 minutes to touch down in O'Hare Airport from Logan Intl. Airport (BOS). A pair of noise-cancelling earphones will be useful too. ### How far is the flight from Logan Intl. Airport to O'Hare Intl. Airport (ORD)? > A flight distance of just 1,400 kilometres separates Boston and Chicago. Once you're in the air, you won't get a chance to do much more than listen to a few songs on your travel playlist. ### Which airlines fly direct from Logan Intl. Airport (BOS) to O'Hare Airport? > With a nice range of airlines to take your pick of, you'll be able to find your perfect flight from Logan Intl. Airport to O'Hare Airport in a few easy clicks. Here are some of the top carriers that fly directly between these airports: > > > > - 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? > Booking last minute from Logan Intl. Airport to O'Hare Intl. Airport (ORD) can be hit-or-miss. It is possible to score a bargain, but then again, you could miss out! If you'd prefer to play it safe and start planning your trip early, Expedia compares flight deals up to 12 months in advance. Just remember that not all airlines list their prices that far in advance. Our suggestion? Check back often as prices are updated frequently. ## Travel information | Origin airport | Logan Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Airlines serving | American Airlines, Delta, JetBlue Airways, Spirit Airlines | | Roundtrip price | CA $128 | | Distance | 1381 km | | Average flight time | 1 hour 57 mins | ## Book with confidence ### Boston to Chicago Flights **The easy way to book your flights from Boston to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Boston whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to O'Hare Intl., too.   Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Boston to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Logan Intl., BOS to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from Boston to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Boston currently is just CA $128 rising to CA $262.   Here are more money-saving tips:  - Fly in December when flight prices are normally at their lowest  - Book about a month to 6 weeks before you travel for the best prices to Chicago   - Avoid peak season and weekends when flights can cost more - Early morning and late-night flights are sometimes cheaper, so try varying your travel times  - One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!  **Reasons to choose Expedia for your flight to Chicago from Boston**  Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. 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