--- title: "Toronto to Chicago flights from - Expedia.ca" description: "Looking for cheap flights from Toronto (YYZ) to Chicago (PWK)? Discover one-way flights from and roundtrip from —compare prices in seconds!" canonical: "https://www.expedia.ca/lp/flights/yyz/pwk/toronto-to-chicago" language: en-CA market: CA currency: CAD prices_as_of: 2026-11-14T07:23:42Z --- # Cheap Flights from Toronto (YYZ) to Chicago (PWK) ![A city skyline with modern skyscrapers and a river with boats and people in the foreground.](https://images.trvl-media.com/place/178248/719a2712-bcc7-4b9d-86cc-997f107a7839.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ## Popular airlines from Toronto Pearson Intl. Airport (YYZ) to Chicago, IL (PWK-Chicago Executive) [Air Canada](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:PWK,departure:28/11/2026TANYT&leg2=from:PWK,to:YYZ,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) [WestJet](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:PWK,departure:28/11/2026TANYT&leg2=from:PWK,to:YYZ,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) [Flair Airlines](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:PWK,departure:28/11/2026TANYT&leg2=from:PWK,to:YYZ,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F8"}}]) [American Airlines](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:PWK,departure:28/11/2026TANYT&leg2=from:PWK,to:YYZ,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) [United](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:PWK,departure:28/11/2026TANYT&leg2=from:PWK,to:YYZ,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) [Delta](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:PWK,departure:28/11/2026TANYT&leg2=from:PWK,to:YYZ,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) [Porter Airlines](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:PWK,departure:28/11/2026TANYT&leg2=from:PWK,to:YYZ,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"PD"}}]) ### 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) Find the cheapest flights on Expedia from Toronto (YYZ) to Chicago (PWK). Flight ticket prices change frequently based on availability and demand. We send price‑drop alerts to make air travel simple and flexible. The lowest one-way fare found on Expedia for this route in the past 7 days starts at for travel on . ## Alternative airports near Chicago Prices were available within the past 7 days. Prices and availability are subject to change. [Select flight to O'Hare Intl. ORD. Average driving time to city centre is 23 minutes. Flights from CA $625](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:ORD,departure:28/11/2026TANYT&leg2=from:ORD,to:YYZ,departure:28/11/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 23 min [Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city centre is 16 minutes. Flights from CA $456](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:MDW,departure:28/11/2026TANYT&leg2=from:MDW,to:YYZ,departure:28/11/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 16 min ## 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. So book your flight to Chicago with Expedia today. ## Frequently Asked Questions ### How much does a flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (PWK-Chicago Executive) cost? You can find one-way and return flights from YYZ to PWK with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when YYZ to PWK ticket fares go up or down. ### What is the cheapest month to fly from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (PWK-Chicago Executive)? The cheapest months to fly from YYZ to PWK are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route. ### Which airlines fly direct from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (PWK-Chicago Executive)? Enter YYZ to PWK and your travel dates, then apply the 'Nonstop' filter to see only direct flights. ### How do I find cheap flights from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (PWK-Chicago Executive)? To find a cheap flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (PWK-Chicago Executive), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up [Price Tracking](https://www.expedia.ca/why/price-tracking) and receive alerts when fares go up or down. ### What is the best time to fly from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (PWK-Chicago Executive)? The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience. ### What is the earliest flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (PWK-Chicago Executive)? Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from YYZ to PWK. To compare more early flights, use the "Early Morning" and "Morning" filters in your search. ### Can you fly business or first class from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (PWK-Chicago Executive)? Select the "Business class" and "First class" filters when looking for YYZ to PWK flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip. ### How do I earn miles on a Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (PWK-Chicago Executive) flight with Expedia? It's easy to earn miles on a Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (PWK-Chicago Executive) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of [One Key™](https://www.expedia.ca/welcome-one-key), you can also earn OneKeyCash™\* on top of your airline miles when you book with Expedia. \*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands. ### Is it cheaper to buy a plane ticket from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (PWK-Chicago Executive) at the last minute? Typically, booking a last minute flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (PWK-Chicago Executive) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare. ### Is it cheaper to book a Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (PWK-Chicago Executive) flight and hotel package? Securing a Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (PWK-Chicago Executive) [flight and hotel package](https://www.expedia.ca/chicago.d178248.destination-travel-guides) is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars. ### Can I cancel or change the date of my flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (PWK-Chicago Executive)? If you booked your Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (PWK-Chicago Executive) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in [your itinerary](https://www.expedia.ca/trips) or confirmation email. Or, head to our [Customer Service portal](https://www.expedia.ca/helpcenter/) if you'd like more information. ## Travel information | Origin airport | Toronto Pearson Intl. 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