Title: CA $228 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 $228 Cheap Flights from Toronto (YYZ) to Chicago (ORD) [View CA $228 flight on Mon, Oct 27, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YYZ,to:ORD,departure:27/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:227.92&airProductToken=AQqcAQozCMGCARIENTA0NRiYzgEg4poBKJLB-wIwmcL7AjhCQABYAWoFQkFTSUNyCE9XQUNaTkJWCjIIwYIBEgQxNTAyGOKaASChAyj0wvsCMNnD-wI4QkABWAFqBUJBU0lDcghPV0FDWk5CVgoxCMGCARIENDkxNRihAyCuHCikx_sCMJLI-wI4QkABWAFqBUJBU0lDcghPVkFJWFNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) - [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) - ![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:29/09/2025TANYT&leg2=from:ord,to:yyz,departure:06/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) - ![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:29/09/2025TANYT&leg2=from:ord,to:yyz,departure:06/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) - ![Flair Airlines](https://a.travel-assets.com/air/airlines/f8_sq.svg) Flair Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:yyz,to:ord,departure:29/09/2025TANYT&leg2=from:ord,to:yyz,departure:06/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F8"}}]) - ![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:29/09/2025TANYT&leg2=from:ord,to:yyz,departure:06/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![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:29/09/2025TANYT&leg2=from:ord,to:yyz,departure:06/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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:29/09/2025TANYT&leg2=from:ord,to:yyz,departure:06/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:29/09/2025TANYT&leg2=from:ord,to:yyz,departure:06/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"PD"}}]) - ## Plan, book, fly with confidence - ### Be in the know Get alerts if flight prices drop or rise\* - ### Book smarter Save up to 30% on select hotels after you book a flight\* - ### 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 $228 for one-way flights and CA $296 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) Wed, Oct 15 - Mon, Dec 1 YYZ Toronto ORD Chicago CA $296 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:15/10/2025TANYT&leg2=from:ORD,to:YYZ,departure:01/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:295.16&airProductToken=AQplCjEIwYYBEgM0ODAYmM4BIJhdKIe0-gIw27T6AjhHQABYAWoFQkFTSUNyCEdOQTJBMkJBCjAIwYYBEgM1MjEYmF0grhwohLX6AjCbtvoCOEdAAVgBagVCQVNJQ3IIR05BMkEyQkEKMwoxCMGGARIDNTA4GK4cIJjOASijyv4CMIbL_gI4R0AAWAFqBUJBU0lDcghHTkEyQTJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sun, Oct 12 - Sun, Nov 30 YYZ Toronto ORD Chicago CA $296 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:12/10/2025TANYT&leg2=from:ORD,to:YYZ,departure:30/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:295.16&airProductToken=AQojCiEI1YIBEgQxNTM4GJjOASCuHCjMk_oCML-U-gI4TkAAWAEKIwohCNWCARIEMzQ0MBiuHCCYzgEo9rr-AjDiu_4COE5AAFgBEgoIARABGAEqAlVBGAEiBAgBEAEoBDAB) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Fri, May 1 - Tue, May 5 YYZ Toronto ORD Chicago CA $363 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:01/05/2026TANYT&leg2=from:ORD,to:YYZ,departure:05/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:362.91&airProductToken=AQo0CjIIwYYBEgQ4OTA5GJjOASCuHCiu7IsDMKPtiwM4S0AAWAFqBUJBU0lDcghLTkEyQTJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Mon, Oct 6 - Tue, Oct 7 YYZ Toronto ORD Chicago CA $363 Roundtrip found 1 hour ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:06/10/2025TANYT&leg2=from:ORD,to:YYZ,departure:07/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:362.98&airProductToken=AQqcAQozCMGCARIEMTg3NhiYzgEg4poBKKHT-QIwo9T5AjhCQABYAWoFQkFTSUNyCE9VQUNaTkJWCjIIwYIBEgQxNTAyGOKaASChAyjU1vkCMLnX-QI4QkABWAFqBUJBU0lDcghPVUFDWk5CVgoxCMGCARIEMjQ4ORihAyCuHCib2vkCMI7b-QI4QkABWAFqBUJBU0lDcghPVkFJWFNCWAqcAQoxCMGCARIEMjU1NhiuHCChAyiI4vkCMOTi-QI4QkAAWAFqBUJBU0lDcghPVkFJWFNCWAoyCMGCARIEMjY5MhihAyDimgEokOb5AjDs5vkCOEJAAVgBagVCQVNJQ3IIT1VBQ1pOQlYKMwjBggESBDE4NzYY4poBIJjOASi86PkCMLPp-QI4QkABWAFqBUJBU0lDcghPVUFDWk5CVhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Nov 19 - Sat, Dec 6 YYZ Toronto ORD Chicago CA $369 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:19/11/2025TANYT&leg2=from:ORD,to:YYZ,departure:06/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:368.60&airProductToken=AQojCiEIwYIBEgQzNjA0GJjOASCuHCjgwP0CMNPB_QI4T0AAWAEKIwohCMGCARIEMzYwNBiuHCCYzgEo8v7-AjDc__4COE9AAFgBEgoIARABGAEqAkFBGAEiBAgBEAEoCCgEMAE) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Sun, Nov 2 - Tue, Nov 4 YYZ Toronto ORD Chicago CA $388 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:02/11/2025TANYT&leg2=from:ORD,to:YYZ,departure:04/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:387.13&airProductToken=AQppCjMI16YBEgQ2MzQyGJjOASDjtAEog__7AjDg__sCOExAAFgBagVFQ09OT3IITE9VRDBaRVMKMgjXpgESBDcwODkY47QBIK4cKLyA_AIwj4H8AjhMQAFYAWoFRUNPTk9yCExPVUQwWkVTCmkKMgjXpgESBDY4OTkYrhwg47QBKLaW_AIwhZf8AjhMQABYAWoFRUNPTk9yCExPVUQwWkVTCjMI16YBEgQ2MzA1GOO0ASCYzgEop5f8AjD0l_wCOExAAVgBagVFQ09OT3IITE9VRDBaRVMSCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sun, Nov 2 - Tue, Nov 4 YYZ Toronto ORD Chicago CA $391 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:02/11/2025TANYT&leg2=from:ORD,to:YYZ,departure:04/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:390.80&airProductToken=AQpnCjIIwYIBEgQ1NDExGJjOASDvWSj-gfwCMNmC_AI4QkAAWAFqBUJBU0lDcghRVkFDWlNCWAoxCMGCARIEMTMzMxjvWSCuHCiQhvwCMKeH_AI4QkABWAFqBUJBU0lDcghRVkFDWlNCWAqcAQoxCMGCARIENjM0MRiuHCChAyjHnPwCMLid_AI4QkAAWAFqBUJBU0lDcghPVkFJWFNCWAoyCMGCARIEMTc5NBihAyDimgEo6qD8AjDCofwCOEJAAVgBagVCQVNJQ3IIT1dBQ1pOQlYKMwjBggESBDMxMzUY4poBIJjOASiXovwCMI6j_AI4QkABWAFqBUJBU0lDcghPV0FDWk5CVhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Sun, Nov 2 - Tue, Nov 4 YYZ Toronto ORD Chicago CA $400 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:02/11/2025TANYT&leg2=from:ORD,to:YYZ,departure:04/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:399.89&airProductToken=AQppCjMI16YBEgQ2MzQyGJjOASDjtAEog__7AjDg__sCOExAAFgBagVFQ09OT3IITE9VRDBaRVMKMgjXpgESBDcwODkY47QBIK4cKLyA_AIwj4H8AjhMQAFYAWoFRUNPTk9yCExPVUQwWkVTEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Mon, Nov 24 - Tue, Nov 25 YYZ Toronto ORD Chicago CA $411 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:24/11/2025TANYT&leg2=from:ORD,to:YYZ,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:410.79&airProductToken=AQo5CjcI1YIBEgQxNTM4GJjOASCuHCjo9_0CMOX4_QI4TkAAWAFqCjFfYmFzaWNlY29yCEdOQTJBMkJOCjkKNwjVggESBDE3NTYYrhwgmM4BKKiJ_gIwi4r-AjhOQABYAWoKMV9iYXNpY2Vjb3IIR05BMkEyQk4SCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Oct 23 - Mon, Oct 27 YYZ Toronto ORD Chicago CA $416 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:23/10/2025TANYT&leg2=from:ORD,to:YYZ,departure:27/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:415.79&airProductToken=AQpvCjYIxJgBEgQ1MDY2GJjOASCpUSj4jfsCMO-O-wI4RUAAWAFqCU1BSU5CQVNJQ3IIWEFWU0EwQlEKNQjEmAESBDUwMTcYqVEgrhwohZD7AjCukfsCOEVAAVgBaglNQUlOQkFTSUNyCFhBVlNBMEJREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ## Find the cheapest month to fly from Toronto (YYZ) to Chicago (ORD) ### November is typically the cheapest month to fly From CA $225 - CA $398 per traveller. 0 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, United, WestJet | | Roundtrip price | CA $295 | | Distance | 697 km | ## 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 American Airlines, Qatar Airways, JAL, Air Canada, EgyptAir, Copa Airlines, Air New Zealand, United Airlines, Alaska Airlines, Qantas, Royal Jordanian, Iberia, ANA, British Airways 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 $296 rising to CA $416.   Here are more money-saving tips:  - Fly in October 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? > Round-trip flights from Toronton Pearson to O'Hare Intl. Airport (ORD) start from CA $296. This figure is based on fares listed within the last 7 days on Expedia for flights departing within the next year — book now to avoid missing out. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Pearson Intl. Airport (YYZ) to O'Hare Airport? > This can differ from airline to airline, as each has its own terms and conditions. Visit the [Customer Service Portal](https://www.expedia.ca/helpcenter), where you'll find easy-to-follow instructions on how to cancel your flight online. ### How do I find cheap flights from Pearson Intl. Airport (YYZ) to O'Hare Airport that have flexible change policies? > Use our "No change fees" filter to find flexible travel options for your flight from Toronto Pearson Airport to ORD. This allows you to snag a good price ahead of time and still have the freedom to make changes without any extra fees. Keep in mind that you'll need to cover the fare difference. ### How many hours is the flight from Pearson Intl. Airport (YYZ) to O'Hare Airport? > The flight from YYZ to O'Hare Airport is around 2 hours and 5 minutes, so don't get too comfortable. There's a good chance the next time you glance out the window you'll be arriving in Chicago. ### How far is the flight from Toronton Pearson to O'Hare Airport? > Forget about a movie marathon on this flight — it's just 700 kilometres from Mississauga to Chicago. Sit down, order some food and you'll be there in no time. ### Which airlines fly direct from Toronto Pearson Airport to O'Hare Intl. Airport (ORD)? > A popular airline that services the route from YYZ to O'Hare Intl. Airport (ORD) is United Airlines (UA). It offers 178 flights a month. Operating 121 flights every month on this route, Air Canada (AC) is another traveller favourite. ### Are Pearson Intl. Airport (YYZ) to O'Hare Airport flight tickets cheaper when they're purchased at the last minute? > It is possible to nab a great last-minute deal from Toronto Pearson Airport to O'Hare Airport, but it can also be hit-or-miss. As many airlines release prices up to a year in advance, it's worth keeping an eye on fares early and being ready to pounce when you see a bargain. Expedia compares carrier prices and updates flight deals frequently, so you can feel confident knowing you're always seeing the latest offers. ## Explore a world of travel with Expedia - Trending Routes - Trending Flights - Top Flights Destinations - Other Airlines - Main Airports for Flights - Cheap Flights from Other Airports - Expedia's Latest Trends ### Top Routes from Toronto - [Toronto to Mumbai (YYZ - BOM)](https://expedia.ca/lp/flights/yyz/bom/toronto-to-mumbai) - [Toronto to Newark Liberty Intl. Airport (YYZ - EWR)](https://expedia.ca/lp/flights/yyz/ewr/toronto-to-newark-liberty-intl-airport) - [Toronto to Calgary (YYZ - YYC)](https://expedia.ca/lp/flights/yyz/yyc/toronto-to-calgary) - [Toronto to Miami (YYZ - MIA)](https://expedia.ca/lp/flights/yyz/mia/toronto-to-miami) - [Toronto to Hong Kong (YYZ - HKG)](https://expedia.ca/lp/flights/yyz/hkg/toronto-to-hong-kong) - [Toronto to Fort Lauderdale (YYZ - FLL)](https://expedia.ca/lp/flights/yyz/fll/toronto-to-fort-lauderdale) - [Toronto to New York (YYZ - LGA)](https://expedia.ca/lp/flights/yyz/lga/toronto-to-new-york) - [Toronto to Delhi (YYZ - DEL)](https://expedia.ca/lp/flights/yyz/del/toronto-to-delhi) - [Toronto to Manila (YYZ - MNL)](https://expedia.ca/lp/flights/yyz/mnl/toronto-to-manila) - [Toronto to New York (YYZ - JFK)](https://expedia.ca/lp/flights/yyz/jfk/toronto-to-new-york) - [Toronto to Tokyo (YYZ - NRT)](https://expedia.ca/lp/flights/yyz/nrt/toronto-to-tokyo) - [Toronto to Vancouver (YYZ - YVR)](https://expedia.ca/lp/flights/yyz/yvr/toronto-to-vancouver) ### Top Routes to Chicago - [Ottawa to Chicago (YOW - ORD)](https://expedia.ca/lp/flights/yow/ord/ottawa-to-chicago) - [Calgary to Chicago (YYC - ORD)](https://expedia.ca/lp/flights/yyc/ord/calgary-to-chicago) - [Kelowna to Chicago (YLW - ORD)](https://expedia.ca/lp/flights/ylw/ord/kelowna-to-chicago) - [Detroit to Chicago (DTW - ORD)](https://expedia.ca/lp/flights/dtw/ord/detroit-to-chicago) - [Saskatoon to Chicago (YXE - ORD)](https://expedia.ca/lp/flights/yxe/ord/saskatoon-to-chicago) - [Winnipeg to Chicago (YWG - ORD)](https://expedia.ca/lp/flights/ywg/ord/winnipeg-to-chicago) - [Halifax to Chicago (YHZ - ORD)](https://expedia.ca/lp/flights/yhz/ord/halifax-to-chicago) - [Québec to Chicago (YQB - ORD)](https://expedia.ca/lp/flights/yqb/ord/quebec-to-chicago) - [Victoria to Chicago (YYJ - ORD)](https://expedia.ca/lp/flights/yyj/ord/victoria-to-chicago) - [Seattle to Chicago (SEA - ORD)](https://expedia.ca/lp/flights/sea/ord/seattle-to-chicago) - [Montreal to Chicago (YUL - ORD)](https://expedia.ca/lp/flights/yul/ord/montreal-to-chicago) - [Buffalo to Chicago (BUF - ORD)](https://expedia.ca/lp/flights/buf/ord/buffalo-to-chicago) ### Top Routes from Toronto - [WestJet Toronto to Calgary](https://expedia.ca/lp/flight-routes/westjet-from-pearson-intl-to-calgary-intl/ws/yyz/yyc) - [Cathay Pacific Toronto to Hong Kong](https://expedia.ca/lp/flight-routes/cathay-pacific-from-pearson-intl-to-hong-kong-intl/cx/yyz/hkg) - [Ethiopian Airlines Toronto to Delhi](https://expedia.ca/lp/flight-routes/ethiopian-airlines-from-pearson-intl-to-indira-gandhi-intl/et/yyz/del) - [American Airlines Toronto to New York](https://expedia.ca/lp/flight-routes/american-airlines-from-pearson-intl-to-john-f-kennedy-intl/aa/yyz/jfk) - [WestJet Toronto to Tokyo](https://expedia.ca/lp/flight-routes/westjet-from-pearson-intl-to-narita-intl/ws/yyz/nrt) - [WestJet Toronto to Vancouver](https://expedia.ca/lp/flight-routes/westjet-from-pearson-intl-to-vancouver-intl/ws/yyz/yvr) - [Air Canada Toronto to London](https://expedia.ca/lp/flight-routes/air-canada-from-pearson-intl-to-heathrow/ac/yyz/lhr) - [TAP Portugal Toronto to Lisbon](https://expedia.ca/lp/flight-routes/tap-portugal-from-pearson-intl-to-humberto-delgado/tp/yyz/lis) - [Flair Airlines Toronto to Abbotsford](https://expedia.ca/lp/flight-routes/flair-airlines-from-pearson-intl-to-abbotsford-intl/f8/yyz/yxx) ### Top Routes to Chicago - [Delta Detroit to Chicago](https://expedia.ca/lp/flight-routes/delta-from-detroit-metropolitan-wayne-county-to-ohare-intl/dl/dtw/ord) - [Alaska Airlines Seattle to Chicago](https://expedia.ca/lp/flight-routes/alaska-airlines-from-seattle-tacoma-intl-to-ohare-intl/as/sea/ord) ### Top Flight Destinations - [Flights to Las Vegas](https://expedia.ca/Cheap-Flights-To-Las-Vegas.d178276.Travel-Guide-Flights) - [Flights to New York](https://expedia.ca/Cheap-Flights-To-New-York.d178293.Travel-Guide-Flights) - [Flights to Orlando](https://expedia.ca/Cheap-Flights-To-Orlando.d178294.Travel-Guide-Flights) - [Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights to San Diego](https://expedia.ca/Cheap-Flights-To-San-Diego.d3073.Travel-Guide-Flights) - [Flights to San Francisco](https://expedia.ca/Cheap-Flights-To-San-Francisco.d178305.Travel-Guide-Flights) - [Flights to Los Angeles](https://expedia.ca/Cheap-Flights-To-Los-Angeles.d178280.Travel-Guide-Flights) - [Flights to Boston](https://expedia.ca/Cheap-Flights-To-Boston.d178239.Travel-Guide-Flights) - [Flights to Miami](https://expedia.ca/Cheap-Flights-To-Miami.d178286.Travel-Guide-Flights) - [Flights to Houston](https://expedia.ca/Cheap-Flights-To-Houston.d178265.Travel-Guide-Flights) - [Flights to Pigeon Forge](https://expedia.ca/Cheap-Flights-To-Pigeon-Forge.d8264.Travel-Guide-Flights) - [Flights to Nashville](https://expedia.ca/Cheap-Flights-To-Nashville.d178291.Travel-Guide-Flights) - [Flights to Myrtle Beach](https://expedia.ca/Cheap-Flights-To-Myrtle-Beach.d601685.Travel-Guide-Flights) - [Flights to Atlanta](https://expedia.ca/Cheap-Flights-To-Atlanta.d178232.Travel-Guide-Flights) - [Flights to San Antonio](https://expedia.ca/Cheap-Flights-To-San-Antonio.d178303.Travel-Guide-Flights) - [Flights to Denver](https://expedia.ca/Cheap-Flights-To-Denver.d178254.Travel-Guide-Flights) - [Flights to Honolulu](https://expedia.ca/Cheap-Flights-To-Honolulu.d1488.Travel-Guide-Flights) - [Flights to Gatlinburg](https://expedia.ca/Cheap-Flights-To-Gatlinburg.d7474.Travel-Guide-Flights) - [Flights to Panama City Beach](https://expedia.ca/Cheap-Flights-To-Panama-City-Beach.d8021.Travel-Guide-Flights) - [Flights to Atlantic City](https://expedia.ca/Cheap-Flights-To-Atlantic-City.d602179.Travel-Guide-Flights) ### Other Airlines - [Air Canada](https://expedia.ca/Air-Canada-Flights.cAC.Travel-Guide-Airlines) - [American Airlines](https://expedia.ca/American-Airlines-Flights.cAA.Travel-Guide-Airlines) - [Delta](https://expedia.ca/Delta-Flights.cDL.Travel-Guide-Airlines) - [WestJet](https://expedia.ca/WestJet-Flights.cWS.Travel-Guide-Airlines) - [Porter Airlines](https://expedia.ca/Porter-Airlines-Flights.cPD.Travel-Guide-Airlines) - [Air Transat](https://expedia.ca/Air-Transat-Flights.cTS.Travel-Guide-Airlines) - [British Airways](https://expedia.ca/British-Airways-Flights.cBA.Travel-Guide-Airlines) - [Lufthansa](https://expedia.ca/Lufthansa-Flights.cLH.Travel-Guide-Airlines) - [United](https://expedia.ca/United-Flights.cUA.Travel-Guide-Airlines) - [Qatar Airways](https://expedia.ca/Qatar-Airways-Flights.cQR.Travel-Guide-Airlines) - [Emirates](https://expedia.ca/Emirates-Flights.cEK.Travel-Guide-Airlines) - [Etihad Airways](https://expedia.ca/Etihad-Airways-Flights.cEY.Travel-Guide-Airlines) - [Flair Airlines](https://expedia.ca/Flair-Airlines-Flights.cF8.Travel-Guide-Airlines) - [Cathay Pacific](https://expedia.ca/Cathay-Pacific-Flights.cCX.Travel-Guide-Airlines) - [Virgin Atlantic](https://expedia.ca/Virgin-Atlantic-Flights.cVS.Travel-Guide-Airlines) - [Air India](https://expedia.ca/Air-India-Flights.cAI.Travel-Guide-Airlines) Chicago nearby Airports #### Chicago [Toronto to Midway Intl.](https://expedia.ca/lp/flights/yyz/mdw/toronto-to-chicago) CA $366.66 Toronto nearby Airports #### Kitchener [Region of Waterloo Intl. to Chicago](https://expedia.ca/lp/flights/ykf/ord/kitchener-to-chicago) CA $295.16 #### Hamilton [John C. Munro Hamilton Intl. to Chicago](https://expedia.ca/lp/flights/yhm/ord/hamilton-to-chicago) CA $372.74 #### Toronto [Billy Bishop Toronto City to Chicago](https://expedia.ca/lp/flights/ytz/ord/toronto-to-chicago) CA $401.84 ### Main Airports for Flights - [Billy Bishop Toronto City Airport (YTZ)](https://expedia.ca/lp/airports/ytz/flights-from-billy-bishop-toronto-city-airport) - [John C. Munro Hamilton Intl. Airport (YHM)](https://expedia.ca/lp/airports/yhm/flights-from-john-c-munro-hamilton-intl-airport) - [Region of Waterloo Intl. Airport (YKF)](https://expedia.ca/lp/airports/ykf/flights-from-region-of-waterloo-intl-airport) - [London Intl. Airport (YXU)](https://expedia.ca/lp/airports/yxu/flights-from-london-intl-airport) - [Muskoka Airport (YQA)](https://expedia.ca/lp/airports/yqa/flights-from-muskoka-airport) - [Chris Hadfield Airport (YZR)](https://expedia.ca/lp/airports/yzr/flights-from-chris-hadfield-airport) - [Norman Rogers Airport (YGK)](https://expedia.ca/lp/airports/ygk/flights-from-norman-rogers-airport) - [Jack Garland Airport (YYB)](https://expedia.ca/lp/airports/yyb/flights-from-jack-garland-airport) - [Windsor Airport (YQG)](https://expedia.ca/lp/airports/yqg/flights-from-windsor-airport) ### Expedia's Latest Trends Flights - [YYZ to MCO flights](https://expedia.ca/lp/flights/yyz/mco/toronto-to-orlando) - [YYZ to YEG flights](https://expedia.ca/lp/flights/yyz/yeg/toronto-to-edmonton) - [YYZ to MNL flights](https://expedia.ca/lp/flights/yyz/mnl/toronto-to-manila) - [YVR to YYZ flights](https://expedia.ca/lp/flights/yvr/yyz/vancouver-to-toronto) - [YYZ to DXB flights](https://expedia.ca/lp/flights/yyz/dxb/toronto-to-dubai) - [YYZ to DEL flights](https://expedia.ca/lp/flights/yyz/del/toronto-to-delhi) - [YYZ to LHR flights](https://expedia.ca/lp/flights/yyz/lhr/toronto-to-london) - [YYZ to MIA flights](https://expedia.ca/lp/flights/yyz/mia/toronto-to-miami) - [YYZ to NYC flights](https://expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york) - [YYZ to YWG flights](https://expedia.ca/lp/flights/yyz/ywg/toronto-to-winnipeg) - [YEG to YYZ flights](https://expedia.ca/lp/flights/yeg/yyz/edmonton-to-toronto) - [YYZ to YXU flights](https://expedia.ca/lp/flights/yyz/yxu/toronto-to-london) - [YYZ to YVR flights](https://expedia.ca/lp/flights/yyz/yvr/toronto-to-vancouver) - [YYZ to YHZ flights](https://expedia.ca/lp/flights/yyz/yhz/toronto-to-halifax) - [YYZ to YYC flights](https://expedia.ca/lp/flights/yyz/yyc/toronto-to-calgary) - [YYZ to BOM flights](https://expedia.ca/lp/flights/yyz/bom/toronto-to-mumbai) - [YYZ to YUL flights](https://expedia.ca/lp/flights/yyz/yul/toronto-to-montreal) - [YYZ to ROM flights](https://expedia.ca/lp/flights/yyz/rom/toronto-to-rome) - [YYZ to CUN flights](https://expedia.ca/lp/flights/yyz/cun/toronto-to-cancun) - [YYZ to FLL flights](https://expedia.ca/lp/flights/yyz/fll/toronto-to-fort-lauderdale) - [YYZ to HKG flights](https://expedia.ca/lp/flights/yyz/hkg/toronto-to-hong-kong) - [DEL to YYZ flights](https://expedia.ca/lp/flights/del/yyz/delhi-to-toronto) - [YYZ to CDG flights](https://expedia.ca/lp/flights/yyz/cdg/toronto-to-paris) - [YYZ to LIS flights](https://expedia.ca/lp/flights/yyz/lis/toronto-to-lisbon) - [YYC to YYZ flights](https://expedia.ca/lp/flights/yyc/yyz/calgary-to-toronto) - [YYZ to LAS flights](https://expedia.ca/lp/flights/yyz/las/toronto-to-las-vegas) - [YUL to YYZ flights](https://expedia.ca/lp/flights/yul/yyz/montreal-to-toronto) - [YYZ to TYO flights](https://expedia.ca/lp/flights/yyz/tyo/toronto-to-tokyo) - [YYZ to LAX flights](https://expedia.ca/lp/flights/yyz/lax/toronto-to-los-angeles) - [YWG to YYZ flights](https://expedia.ca/lp/flights/ywg/yyz/winnipeg-to-toronto) \*Available to Expedia members. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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