Title: Cheap Flights from Toronto (YYZ) to Chicago (PWK) - 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) # Cheap Flights from Toronto (YYZ) to Chicago (PWK) - [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, IL (PWK-Chicago Executive) - ![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:pwk,departure:15/11/2025TANYT&leg2=from:pwk,to:yyz,departure:22/11/2025TANYT&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:pwk,departure:15/11/2025TANYT&leg2=from:pwk,to:yyz,departure:22/11/2025TANYT&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:pwk,departure:15/11/2025TANYT&leg2=from:pwk,to:yyz,departure:22/11/2025TANYT&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:pwk,departure:15/11/2025TANYT&leg2=from:pwk,to:yyz,departure:22/11/2025TANYT&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:pwk,departure:15/11/2025TANYT&leg2=from:pwk,to:yyz,departure:22/11/2025TANYT&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:pwk,departure:15/11/2025TANYT&leg2=from:pwk,to:yyz,departure:22/11/2025TANYT&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:pwk,departure:15/11/2025TANYT&leg2=from:pwk,to:yyz,departure:22/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"PD"}}]) - ![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) ## 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:ORD,departure:15/11/2025TANYT&leg2=from:ORD,to:YYZ,departure:18/11/2025TANYT&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 $320](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:ORD,departure:15/11/2025TANYT&leg2=from:ORD,to:YYZ,departure:18/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) [](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:MDW,departure:15/11/2025TANYT&leg2=from:MDW,to:YYZ,departure:18/11/2025TANYT&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 $328](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:MDW,departure:15/11/2025TANYT&leg2=from:MDW,to:YYZ,departure:18/11/2025TANYT&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 Toronton Pearson to Chicago Executive Airport (PWK)? > If you're travelling from Pearson Intl. Airport (YYZ) to Chicago Executive Airport, round-trip flights start from . This price is based on fares available within the last 7 days on Expedia for flights departing within the next year, so don't let a good deal slip through your fingers. Book now and save yourself both money and time. 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 Chicago Executive Airport (PWK)? > Each air carrier has a different set of terms and conditions. If you decide to cancel your vacation, visit our [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from YYZ to PWK that have flexible change policies? > Plenty of carriers offer the option to move your flight without charging a fee. All you pay is any additional cost for the new flight. When looking for Toronto Pearson Airport to PWK flights, you'll find a "No change fees" filter for you to pick. ### How far is the flight from YYZ to Chicago Executive Airport (PWK)? > The distance from Pearson Intl. Airport (YYZ) (YYZ) to Chicago Executive Airport (PWK) is 700 kilometres. You'll be disembarking the plane and collecting your baggage from the carousel in no time. ### Which airlines fly direct from Toronto Pearson Airport to Chicago Executive Airport (PWK)? > Unfortunately, there are no airlines that directly fly between Toronton Pearson and Chicago Executive Airport. You'll have to book a flight with at least one stop. ### Are Pearson Intl. Airport (YYZ) to PWK flight tickets cheaper when they're purchased at the last minute? > Booking last minute from Toronton Pearson to PWK can be hit-or-miss. It is possible to score a bargain, but then again, you could miss out! If you'd prefer to start your travel planning early, Expedia compares flight deals up to 12 months in advance. Just bear in mind that not all airlines issue their prices so far in advance. Our suggestion? Check back often as prices are updated frequently. ## Travel information | Origin airport | Pearson Intl. | | --- | --- | | Destination airport | Chicago Executive | | Distance | 692 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 airlines that cover this route. There are nonstop flights to Chicago Executive, 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 Chicago Executive, PWK**  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 rising to .   Here are more money-saving tips:  - Fly in 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. 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