Title: CA $163 Cheap Flights from Toronto (YYZ) 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 $163 Cheap Flights from Toronto (YYZ) to Chicago (ORD) [View CA $163 flight on Tue, Feb 10, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YYZ,to:ORD,departure:10/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:162.84&airProductToken=AQozCjEIwYYBEgM1MDkYmM4BIK4cKPHphAMw6eqEAzhHQABYAWoFQkFTSUNyCEdOQTJBMkJBEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwAQ) - [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 Toronto Pearson Intl. Airport (YYZ) to Chicago O'Hare International Airport (ORD) - ![Porter Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_PD.svg) Porter Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:ORD,departure:26/12/2025TANYT&leg2=from:ORD,to:YYZ,departure:02/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"PD"}}]) - ![WestJet](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WS.svg) WestJet [](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:ORD,departure:26/12/2025TANYT&leg2=from:ORD,to:YYZ,departure:02/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) - ![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:YYZ,to:ORD,departure:26/12/2025TANYT&leg2=from:ORD,to:YYZ,departure:02/01/2026TANYT&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:YYZ,to:ORD,departure:26/12/2025TANYT&leg2=from:ORD,to:YYZ,departure:02/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![Air Canada](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AC.svg) Air Canada [](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:ORD,departure:26/12/2025TANYT&leg2=from:ORD,to:YYZ,departure:02/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) - ![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:YYZ,to:ORD,departure:26/12/2025TANYT&leg2=from:ORD,to:YYZ,departure:02/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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 Toronto (YYZ) to Chicago (ORD) Prices were available within the past 7 days and start at CA $163 for one-way flights and CA $256 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Thu, Feb 12 - Sat, Feb 28 YYZ Toronto ORD Chicago CA $256 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:12/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:28/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:255.64&airProductToken=AQozCjEIwYYBEgM1MDcYmM4BIK4cKKP-hAMwlv-EAzhHQABYAWoFQkFTSUNyCEdOQTJBMkJBCjMKMQjBhgESAzUxMBiuHCCYzgEo4LWGAzDDtoYDOEdAAFgBagVCQVNJQ3IIR05BMkEyQkESCggBEAEYASoCQUMYASIECAEQASgCKAMoBDAN) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, Feb 18 - Sat, Feb 28 YYZ Toronto ORD Chicago CA $256 Roundtrip found 19 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:18/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:28/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:255.69&airProductToken=AQo5CjcI1YIBEgQzNjQwGJjOASCuHCj4xIUDMPTFhQM4TkAAWAFqCjFfYmFzaWNlY29yCEdOQTJBMkJOCjkKNwjVggESBDUyNzgYrhwgmM4BKIK2hgMw67aGAzhOQABYAWoKMV9iYXNpY2Vjb3IIR05BMkEyQk4SCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Feb 19 - Sun, Feb 22 YYZ Toronto ORD Chicago CA $263 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:19/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:22/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:262.12&airProductToken=AQo0CjIIwYIBEgQzNjA4GJjOASCuHCiXzoUDMI_PhQM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWAplCjAIwYIBEgQyMzQ1GK4cIEMol-uFAzCK7IUDOEJAAFgBagVCQVNJQ3IIT1ZBQ1pTQlgKMQjBggESBDU2NjUYQyCYzgEo5OyFAzDS7YUDOEJAAVgBagVCQVNJQ3IIT1ZBQ1pTQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Feb 19 - Sun, Feb 22 YYZ Toronto ORD Chicago CA $270 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:19/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:22/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:269.92&airProductToken=AQpnCjIIwYIBEgQ0NTU2GJjOASDLASjdzYUDMMbOhQM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWAoxCMGCARIEMjA0MRjLASCuHCiVz4UDMMTQhQM4QkABWAFqBUJBU0lDcghPVkFDWlNCWAplCjAIwYIBEgQyMzQ1GK4cIEMol-uFAzCK7IUDOEJAAFgBagVCQVNJQ3IIT1ZBQ1pTQlgKMQjBggESBDU2NjUYQyCYzgEo5OyFAzDS7YUDOEJAAVgBagVCQVNJQ3IIT1ZBQ1pTQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Thu, Feb 12 - Sat, Feb 28 YYZ Toronto ORD Chicago CA $272 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:12/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:28/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:271.46&airProductToken=AQozCjEIwYYBEgM1MDkYmM4BIK4cKLGAhQMwqYGFAzhHQABYAWoFQkFTSUNyCEdOQTJBMkJBEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwDQ) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Tue, Feb 17 - Fri, Feb 27 YYZ Toronto ORD Chicago CA $272 Roundtrip found 19 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:17/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:27/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:271.51&airProductToken=AQozCjEIwYYBEgM1MDcYmM4BIK4cKMO2hQMwtreFAzhHQABYAWoFQkFTSUNyCEdOQTJBMkJBEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Feb 11 - Thu, Feb 12 YYZ Toronto ORD Chicago CA $275 Roundtrip found 1 hour ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:11/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:12/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:274.79&airProductToken=AQo0CjIIwYIBEgQzNjA0GJjOASCuHCje8YQDMNHyhAM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Thu, Feb 19 - Sun, Feb 22 YYZ Toronto ORD Chicago CA $276 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:19/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:22/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:275.73&airProductToken=AQozCjEIwYYBEgM1MDkYmM4BIK4cKJHPhQMwidCFAzhHQABYAWoFQkFTSUNyCEdOQTJBMkJBEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwDQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Feb 19 - Sun, Feb 22 YYZ Toronto ORD Chicago CA $294 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:19/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:22/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:293.02&airProductToken=AQpvCjYIxJgBEgQ1MTgzGJjOASDLASiZyYUDMInKhQM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlEKNQjEmAESBDU3MzcYywEgrhwovsqFAzDty4UDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNBMEJRCnEKNgjEmAESBDIwMzkYrhwg47QBKM7rhQMwquyFAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTBCUQo3CMSYARIEMzkxMhjjtAEgmM4BKIXvhQMw1u-FAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCURIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Tue, Jan 6 - Wed, Jan 7 YYZ Toronto ORD Chicago CA $506 Roundtrip found 4 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:06/01/2026TANYT&leg2=from:ORD,to:YYZ,departure:07/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:505.72&airProductToken=AQpDCkEI0IgBEgQ2MDczGJjOASCuHCik4IEDMJzhgQM4TEAAWAFqCFNUQU5EQVJEcghMMk4xWk9aU3oKCMGCARIEMzYxMApDCkEI0IgBEgQ2MDYxGK4cIJjOASjN54EDML7ogQM4TEAAWAFqCFNUQU5EQVJEcghMMk4xWk9aU3oKCMGCARIEMzYwNhIKCAEQARgBKgJQRBgBIgQIARABKAIoAygEMAE) ## Find the cheapest month to fly from Toronto (YYZ) to Chicago (ORD) ### February is typically the cheapest month to fly From CA $213 - CA $361 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:YYZ,to:MDW,departure:26/12/2025TANYT&leg2=from:MDW,to:YYZ,departure:30/12/2025TANYT&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 CA $1,241 ](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:MDW,departure:26/12/2025TANYT&leg2=from:MDW,to:YYZ,departure:30/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) __Flight from Toronto to Chicago (YYZ - ORD) route information__ | Origin airport | Pearson Intl. | | ------------------- | ---------------------------------------------------------------------- | | Destination airport | O'Hare Intl. | | Airlines serving | Air Canada, American Airlines, Delta, Porter Airlines, United, WestJet | | Roundtrip price | CA $256 | | Distance | 697 km | | 0 | | ## Toronto to Chicago Flights **The easy way to book your flights from Toronto to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Toronto 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 Toronto to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Pearson Intl., YYZ to O'Hare Intl., ORD** Sort your search results by price to find great deals on your flight from Toronto to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Toronto currently is just CA $256 rising to CA $506\. Here are more money-saving tips: - Fly in February 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 Toronto** 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. So book your flight to Chicago with Expedia today. ## Frequently asked questions ### How much is a flight from Toronto Pearson Airport to O'Hare Airport? ### Do I need to pay a cancellation fee if I cancel my flight from Pearson Intl. Airport (YYZ) to O'Hare Airport? ### How do I find cheap flights from Pearson Intl. Airport (YYZ) to O'Hare Airport that have flexible change policies? ### How many hours is the flight from Pearson Intl. Airport (YYZ) to O'Hare Airport? ### How far is the flight from Toronton Pearson to O'Hare Airport? ### Which airlines fly direct from Toronto Pearson Airport to O'Hare Intl. Airport (ORD)? ### Are Pearson Intl. 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[Flights from Wilmington (ILM) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ilm/chi/wilmington-to-chicago) - [Flights from Indianapolis (IND) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ind/chi/indianapolis-to-chicago) - [Flights from Nakhon Phanom (KOP) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/kop/mdw/nakhon-phanom-to-chicago) - [Flights from Las Vegas (LAS) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/las/mdw/las-vegas-to-chicago) - [Flights from Los Angeles (LAX) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/lax/chi/los-angeles-to-chicago) - [Flights from Montego Bay (MBJ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/mbj/mdw/montego-bay-to-chicago) - [Flights from Orlando (MCO) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/mco/mdw/orlando-to-chicago) - [Flights from Michigan City (MGC) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/mgc/mdw/michigan-city-to-chicago) - [Flights from Muscle Shoals (MSL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/msl/mdw/muscle-shoals-to-chicago) - [Flights from Minneapolis (MSP) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/msp/chi/minneapolis-to-chicago) - [Flights from New York (NYC) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/nyc/chi/new-york-to-chicago) - [Flights from Omaha (OMA) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/oma/mdw/omaha-to-chicago) - [Flights from Chicago (ORD) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ord/chi/chicago-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/phl/mdw/philadelphia-to-chicago) - [Flights from Pueblo (PUB) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/pub/mdw/pueblo-to-chicago) - [Flights from Punta Cana (PUJ) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/puj/chi/punta-cana-to-chicago) - [Flights from Roanoke (ROA) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/roa/mdw/roanoke-to-chicago) - [Flights from Selinsgrove (SEG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/seg/mdw/selinsgrove-to-chicago) - [Flights from Sacramento (SMF) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/smf/mdw/sacramento-to-chicago) - [Flights from St. Louis (STL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/stl/mdw/st-louis-to-chicago) - [Flights from Newburgh (SWF) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/swf/mdw/newburgh-to-chicago) - [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.