Title: CA $166 Cheap American Airlines fights from Toronto to Chicago - 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 $166 Cheap American Airlines fights from Toronto (YYZ) to Chicago (ORD) [View CA $166 flight on Thu, Feb 5, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YYZ,to:ORD,departure:05/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:165.89&airProductToken=AQo0CjIIwYIBEgQzNjA0GJjOASCuHCijroQDMJavhAM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) - [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 - ![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) ## American Airlines flights from Toronto to Chicago (YYZ→ORD) Prices were available within the past 7 days and start at CA $166 for one-way flights and CA $262 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Feb 10 - Thu, Feb 12 YYZ Toronto ORD Chicago CA $262 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:10/02/2026TANYT&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:261.80&airProductToken=AQo0CjIIwYIBEgQzNjA4GJjOASCuHCj46IQDMPDphAM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWAo0CjIIwYIBEgQzNjA0GK4cIJjOASj2-4QDMNz8hAM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Feb 10 - Thu, Feb 12 YYZ Toronto ORD Chicago CA $270 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:10/02/2026TANYT&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:269.50&airProductToken=AQppCjMIwYIBEgQ1MDIwGJjOASDimgEo1eaEAzDl54QDOEJAAFgBagVCQVNJQ3IIT1ZBQ1pTQlgKMgjBggESBDIyOTgY4poBIK4cKPbohAMwgeqEAzhCQAFYAWoFQkFTSUNyCE9WQUNaU0JYCmcKMQjBggESBDIyMjMYrhwg71komPuEAzCN_IQDOEJAAFgBagVCQVNJQ3IIT1ZBQ1pTQlgKMgjBggESBDU4NjQY71kgmM4BKPT-hAMw5P-EAzhCQAFYAWoFQkFTSUNyCE9WQUNaU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, Jan 31 - Mon, Feb 2 YYZ Toronto ORD Chicago CA $291 Roundtrip found 1 hour ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:31/01/2026TANYT&leg2=from:ORD,to:YYZ,departure:02/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:290.15&airProductToken=AQo0CjIIwYIBEgQzNjA4GJjOASCuHCi4-IMDMLD5gwM4QkAAWAFqBUJBU0lDcghPVUFDWlNCWAo0CjIIwYIBEgQzNDU2GK4cIJjOASifkIQDMI-RhAM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Feb 10 - Thu, Feb 12 YYZ Toronto ORD Chicago CA $294 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:10/02/2026TANYT&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:293.69&airProductToken=AQo0CjIIwYIBEgQzNjA0GJjOASCuHCi-5oQDMLHnhAM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, Jan 31 - Mon, Feb 2 YYZ Toronto ORD Chicago CA $298 Roundtrip found 1 hour ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:31/01/2026TANYT&leg2=from:ORD,to:YYZ,departure:02/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:297.85&airProductToken=AQplCjEIwYIBEgQ1NjY3GJjOASBDKNf4gwMwzvmDAzhCQABYAWoFQkFTSUNyCE9VQUNaU0JYCjAIwYIBEgQzMjk2GEMgrhwoxfqDAzDS-4MDOEJAAVgBagVCQVNJQ3IIT1VBQ1pTQlgKZwoxCMGCARIENDUxMhiuHCDLASjZi4QDMOOMhAM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWAoyCMGCARIENDQzOBjLASCYzgEoj4-EAzCAkIQDOEJAAVgBagVCQVNJQ3IIT1ZBQ1pTQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Feb 10 - Thu, Feb 12 YYZ Toronto ORD Chicago CA $302 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:10/02/2026TANYT&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:301.39&airProductToken=AQplCjEIwYIBEgQ1NjY4GJjOASBDKJ_mhAMwjeeEAzhCQABYAWoFQkFTSUNyCE9WQUNaU0JYCjAIwYIBEgQ0NzMxGEMgrhwoxOeEAzDd6IQDOEJAAVgBagVCQVNJQ3IIT1ZBQ1pTQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ## 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:29/12/2025TANYT&leg2=from:MDW,to:YYZ,departure:05/01/2026TANYT&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 CA $805 ](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:MDW,departure:29/12/2025TANYT&leg2=from:MDW,to:YYZ,departure:05/01/2026TANYT&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 | | Popular airline | American Airlines | | Distance | 697 km | | 0 | | ## Frequently asked questions ### How much is an American Airlines flight from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD)? ### What is the cheapest month to fly from YYZ to ORD with American Airlines? ### Does American Airlines fly nonstop from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD)? ### How long does it take to fly from YYZ to ORD with American Airlines? ### Which day of the week has the most American Airlines flights from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD)? ### What airports does American Airlines fly into in Chicago? ### What type of plane does American Airlines fly from Pearson Intl. Airport (YYZ) to O'Hare Intl. Airport (ORD)? ### Can I change or cancel my American Airlines flight from Pearson Intl. Airport (YYZ) to O'Hare Intl. 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