Title: CA $187 Cheap Flights from Toronto (YTZ) 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 $187 Cheap Flights from Toronto (YTZ) to Chicago (ORD) [View CA $187 flight on Tue, Nov 25, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YTZ,to:ORD,departure:25/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:186.13&airProductToken=AQpnCjIIwYYBEgQ3OTU4GPjMASCYXSjig_4CMK6E_gI4R0AAWAFqBUJBU0lDcghHTkE0QTJCQQoxCMGGARIEODk2MRiYXSCuHCiChf4CMKeG_gI4R0ABWAFqBUJBU0lDcghHTkE0QTJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) - [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 Billy Bishop Toronto City Airport (YTZ) to Chicago O'Hare International Airport (ORD) - ![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:ytz,to:ord,departure:20/11/2025TANYT&leg2=from:ord,to:ytz,departure:27/11/2025TANYT&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:ytz,to:ord,departure:20/11/2025TANYT&leg2=from:ord,to:ytz,departure:27/11/2025TANYT&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 (YTZ) to Chicago (ORD) Prices were available within the past 7 days and start at CA $187 for one-way flights and CA $311 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, Nov 27 - Sat, Nov 29 YTZ Toronto ORD Chicago CA $311 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:ORD,departure:27/11/2025TANYT&leg2=from:ORD,to:YTZ,departure:29/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:310.41&airProductToken=AQpnCjIIwYYBEgQ3OTU4GPjMASCYXSiimv4CMO6a_gI4R0AAWAFqBUJBU0lDcghHTkE0QTJCQQoxCMGGARIEODk2MRiYXSCuHCjCm_4CMOec_gI4R0ABWAFqBUJBU0lDcghHTkE0QTJCQQpnCjEIwYYBEgQ4OTU4GK4cIJhdKNGv_gIwzrD-AjhHQABYAWoFQkFTSUNyCEdOQTRBMkJBCjIIwYYBEgQ3OTY1GJhdIPjMASiWsv4CMOuy_gI4R0ABWAFqBUJBU0lDcghHTkE0QTJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Thu, Jan 15 - Mon, Jan 19 YTZ Toronto ORD Chicago CA $312 Roundtrip found 23 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:ORD,departure:15/01/2026TANYT&leg2=from:ORD,to:YTZ,departure:19/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:311.01&airProductToken=AQpnCjIIwYYBEgQ3OTU4GPjMASCYXSjCwYIDMI7CggM4R0AAWAFqBUJBU0lDcghHTkE0QTJCQQoxCMGGARIEODk2MRiYXSCuHCjiwoIDMIfEggM4R0ABWAFqBUJBU0lDcghHTkE0QTJCQQpnCjEIwYYBEgQ4OTYwGK4cIJhdKIrwggMwjfGCAzhHQABYAWoFQkFTSUNyCEdOQTRBMkJBCjIIwYYBEgQ3OTc1GJhdIPjMASii8oIDMPfyggM4R0ABWAFqBUJBU0lDcghHTkE0QTJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Fri, Dec 26 - Sun, Feb 1 YTZ Toronto ORD Chicago CA $347 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:ORD,departure:26/12/2025TANYT&leg2=from:ORD,to:YTZ,departure:01/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:346.35&airProductToken=AQpnCjIIwYYBEgQ3OTY4GPjMASCYXSju4oADMLrjgAM4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoxCMGGARIEODk2NxiYXSCuHCid5IADMMLlgAM4R0ABWAFqBUJBU0lDcghHTkEyQTJCQQpnCjEIwYYBEgQ4OTU4GK4cIJhdKNv_gwMw2ICEAzhHQABYAWoFQkFTSUNyCEdOQTRBMkJBCjIIwYYBEgQ3OTY1GJhdIPjMASj4gYQDMM2ChAM4R0ABWAFqBUJBU0lDcghHTkE0QTJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Wed, Jan 14 - Sun, Jan 18 YTZ Toronto ORD Chicago CA $373 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:ORD,departure:14/01/2026TANYT&leg2=from:ORD,to:YTZ,departure:18/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:372.69&airProductToken=AQpnCjIIwYYBEgQ3OTU4GPjMASCYXSiitoIDMO62ggM4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoxCMGGARIEODk2MRiYXSCuHCjCt4IDMOe4ggM4R0ABWAFqBUJBU0lDcghHTkEyQTJCQQpnCjEIwYYBEgQ4OTU4GK4cIJhdKJviggMwmOOCAzhHQABYAWoFQkFTSUNyCEdOQTRBMkJBCjIIwYYBEgQ3OTY1GJhdIPjMASjW5IIDMKvlggM4R0ABWAFqBUJBU0lDcghHTkE0QTJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Wed, Nov 19 - Wed, Nov 26 YTZ Toronto ORD Chicago CA $375 Roundtrip found 12 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:ORD,departure:19/11/2025TANYT&leg2=from:ORD,to:YTZ,departure:26/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:374.08&airProductToken=AQpnCjIIwYYBEgQ3OTU4GPjMASCYXSiiwP0CMO7A_QI4R0AAWAFqBUJBU0lDcghHTkE0QTJCQQoxCMGGARIEODk2MRiYXSCuHCjCwf0CMOfC_QI4R0ABWAFqBUJBU0lDcghHTkE0QTJCQQpmCjAIwYYBEgM1MjIYrhwgmF0oypD-AjDJkf4COEdAAFgBagVCQVNJQ3IIR05BNEEyQkEKMgjBhgESBDc5NzkYmF0g-MwBKMaT_gIwm5T-AjhHQAFYAWoFQkFTSUNyCEdOQTRBMkJBEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwDQ) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Thu, Nov 27 - Sat, Nov 29 YTZ Toronto ORD Chicago CA $384 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:ORD,departure:27/11/2025TANYT&leg2=from:ORD,to:YTZ,departure:29/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:383.93&airProductToken=AQptCjUIwYYBEgQ3OTU4GPjMASCYXSiimv4CMO6a_gI4R0AAWAFqCFNUQU5EQVJEcghHTkE0QTJURwo0CMGGARIEODk2MRiYXSCuHCjCm_4CMOec_gI4R0ABWAFqCFNUQU5EQVJEcghHTkE0QTJURwp5CkAIwYYBEgQzNDU4GK4cIJhdKKax_gIwtLL-AjhHQABYAWoIU1RBTkRBUkRyCEdOQTRBMlRHegoI1YIBEgQzNDU4CjUIwYYBEgQ3OTY5GJhdIPjMASiOs_4CMOOz_gI4R0ABWAFqCFNUQU5EQVJEcghHTkE0QTJURxIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Wed, Nov 26 - Wed, Dec 3 YTZ Toronto ORD Chicago CA $385 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:ORD,departure:26/11/2025TANYT&leg2=from:ORD,to:YTZ,departure:03/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:384.72&airProductToken=AQp7CjYIwYYBEgQ3NzAyGPjMASDYswEono7-AjDWjv4COEdAAFgBaghTVEFOREFSRHIIR05BNEEyVEcKQQjBhgESBDQxMTMY2LMBIK4cKKqP_gIwy5D-AjhHQAFYAWoIU1RBTkRBUkRyCEdOQTRBMlRHegoI1YIBEgQ0MTEzCnkKQAjBhgESBDM0NTgYrhwgmF0opt7-AjC03_4COEdAAFgBaghTVEFOREFSRHIIR05BNEEyVEd6CgjVggESBDM0NTgKNQjBhgESBDc5NjkYmF0g-MwBKI7g_gIw4-D-AjhHQAFYAWoIU1RBTkRBUkRyCEdOQTRBMlRHEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwDQ) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Tue, Feb 24 - Tue, Mar 3 YTZ Toronto ORD Chicago CA $393 Roundtrip found 1 hour ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:ORD,departure:24/02/2026TANYT&leg2=from:ORD,to:YTZ,departure:03/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:392.06&airProductToken=AQpFCiEIwYYBEgQ3OTU4GPjMASCYXSjRg4YDMJ2EhgM4R0AAWAEKIAjBhgESBDg5NjEYmF0grhwo4oSGAzCHhoYDOEdAAVgBCkQKHwjBhgESAzUyMhiuHCCYXSjq04YDMOnUhgM4R0AAWAEKIQjBhgESBDc5NzUYmF0g-MwBKILWhgMw19aGAzhHQAFYARIKCAEQARgBKgJBQxgBIgQIARABKAgoBDAB) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sun, Dec 21 - Sat, Jan 10 YTZ Toronto ORD Chicago CA $409 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:ORD,departure:21/12/2025TANYT&leg2=from:ORD,to:YTZ,departure:10/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:408.38&airProductToken=AQpnCjIIwYYBEgQ3OTY4GPjMASCYXSjOqoADMJqrgAM4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoxCMGGARIEODk2NxiYXSCuHCj9q4ADMKKtgAM4R0ABWAFqBUJBU0lDcghHTkEyQTJCQQpnCjEIwYYBEgQ4OTYwGK4cIJhdKOqKggMw7YuCAzhHQABYAWoFQkFTSUNyCEdOQTJBMkJBCjIIwYYBEgQ3OTc1GJhdIPjMASiCjYIDMNeNggM4R0ABWAFqBUJBU0lDcghHTkEyQTJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sat, Jun 20 - Tue, Jun 23 YTZ Toronto ORD Chicago CA $574 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:ORD,departure:20/06/2026TANYT&leg2=from:ORD,to:YTZ,departure:23/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:573.23&airProductToken=AQpCCkAI1YIBEgQ4NjkxGPjMASCuHCiYoJADMIyhkAM4R0AAWAFqB0VDT05PTVlyCEdOQTVBMFRHegoIwYYBEgQ4NjkxCkIKQAjVggESBDg2NzgYrhwg-MwBKPS_kAMw2cCQAzhHQABYAWoHRUNPTk9NWXIIR05BNUEwVEd6CgjBhgESBDg2NzgSCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAB) ## Find the cheapest month to fly from Toronto (YTZ) to Chicago (ORD) ### September is typically the cheapest month to fly From CA $221 - CA $773 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:YTZ,to:MDW,departure:20/11/2025TANYT&leg2=from:MDW,to:YTZ,departure:23/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) MDW Midway Intl. CheapestClosest 16 min [Flights from CA $369](https://www.expedia.ca/Flights-Search?leg1=from:YTZ,to:MDW,departure:20/11/2025TANYT&leg2=from:MDW,to:YTZ,departure:23/11/2025TANYT&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 YTZ to ORD? > Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip journey from YTZ to O'Hare Airport was CA $311. Fares this cheap don't last long, so book yours today. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from YTZ to O'Hare Intl. Airport (ORD)? > Each air carrier has its own set of terms and conditions. If you do decide to cancel, follow the easy instructions on our [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from Billy Bishop Toronto City Airport (YTZ) to O'Hare Intl. Airport (ORD) that have flexible change policies? > Many airlines offer the option to reschedule your flight without charging a fee. All you pay is the fare difference. When looking for YTZ to O'Hare Intl. Airport (ORD) flights, you'll see a "No change fees" box for you to select. ### How many hours is the flight from Billy Bishop Toronto City Airport (YTZ) to ORD? > Consider bringing your own on-board entertainment (like some downloaded podcasts), as it takes an average of 3 hours and 51 minutes to jet to ORD from Billy Bishop Toronto City Airport (YTZ). A good set of noise-cancelling headphones will also be useful. ### How far is the flight from Billy Bishop Airport to O'Hare Airport? > Forget about a movie marathon on this flight — it's only 720 kilometres from Toronto to Chicago. Sit down, order a drink and you'll be in Chicago in no time. ### Which airlines fly direct from Billy Bishop Airport to ORD? > Flying directly between Billy Bishop Toronto City Airport (YTZ) and O'Hare Airport isn't possible at the moment. However, you'll still be able to find a flight to Chicago with at least one stop. ### Are YTZ to ORD flight tickets cheaper when they're purchased at the last minute? > Flight prices go up and down like a yo-yo, so not always. While last-minute flight deals between Billy Bishop Airport and O'Hare Airport are of course possible, it also makes sense to keep track of prices well before you fly. In fact, some air carriers publish their prices up to 12 months before the departure date. Expedia is constantly updating the biggest airfare bargains around, so keep checking and be ready to book when the price is right. ## Travel information | Origin airport | Billy Bishop Toronto City | | --- | --- | | Destination airport | O'Hare Intl. | | Airlines serving | Air Canada, United | | Roundtrip price | CA $310 | | Distance | 713 km | ## Book with confidence ### 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 Billy Bishop Toronto City, YTZ 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 $311 rising to CA $574.   Here are more money-saving tips:  - Fly in November 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. ## 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) - [Flights from Los Angeles to Evanston](https://www.expedia.ca/lp/flights/178280/8049/los-angeles-to-evanston) - [Flights from Mexico City to Northwest Chicago](https://www.expedia.ca/lp/flights/178285/6350697/mexico-city-to-northwest-chicago) - [Flights from New York to Evanston](https://www.expedia.ca/lp/flights/178293/8049/new-york-to-evanston) - [Flights from Ottawa to Evanston](https://www.expedia.ca/lp/flights/178296/8049/ottawa-to-evanston) - [Flights from Philadelphia to Rosemont](https://www.expedia.ca/lp/flights/178297/7581/philadelphia-to-rosemont) - [Flights from Portland to Rosemont](https://www.expedia.ca/lp/flights/178299/7581/portland-to-rosemont) - 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