Cheap Flights from Toronto (YYZ) to Chicago (DPA)

Popular airlines from Toronto Pearson Intl. Airport (YYZ) to Chicago, IL (DPA-Dupage)

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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. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $174
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $174
Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $223
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $223
Flights from Toronto (YYZ) to Chicago (DPA)
Origin airport
Pearson Intl.
Destination airport
Dupage
Distance
454 mi

Toronto to Chicago Flights

The cheapest times to fly from Toronto to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Toronto to Chicago are during the month of . You can find some of the cheapest flights from Toronto to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Toronto to Chicago

Sunday is one of the best days to book for cheap flights from Toronto to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Toronto to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Toronto to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Toronto to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Toronto to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Pearson Intl. Airport (YYZ) to Dupage Airport (DPA) cost?
Secure a cheap one-way flight or cheap return flight from Pearson Intl. Airport (YYZ) to Dupage Airport (DPA) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Pearson Intl. Airport (YYZ) to Dupage Airport (DPA)?
is the most affordable month to fly from YYZ to DPA. Traveling during an off-peak travel window is often the key to landing a great deal.
What is the cheapest airline that flies from Pearson Intl. Airport (YYZ) to Dupage Airport (DPA)?
To find the cheapest airline flying from YYZ to DPA, use Expedia's filter tool. Tailor your search based on your travel style, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Pearson Intl. Airport (YYZ) to Dupage Airport (DPA)?
There are no daily nonstop flights departing from Pearson Intl. Airport (YYZ) to Dupage Airport (DPA). But you can choose flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be on your way in no time at all.
What day of the week has the most flights from YYZ to DPA?
Usually you'll find the most flight options available on a Friday. Tuesdays tend to be the quietest.* But this can vary based on the season, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Pearson Intl. Airport (YYZ) to Dupage Airport (DPA)?
To avoid possible delays on the Pearson Intl. Airport (YYZ) to Dupage Airport (DPA) route, aim to fly before 3 PM. Departures after this hour are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Pearson Intl. Airport (YYZ)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Pearson Intl. Airport (YYZ). Consider the options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Pearson Intl. Airport (YYZ) to Dupage Airport (DPA) last-minute?
Booking your plane ticket from YYZ to DPA shortly before your journey is usually more expensive. But if you're flexible with your departure dates and times, you could grab a cheap last-minute fare.
Is it cheaper to book a YYZ to DPA flight and hotel package?
You'll typically save money by securing a YYZ to DPA flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one place. After choosing your ideal flights and accommodations, consider adding extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Pearson Intl. Airport (YYZ) to Dupage Airport (DPA)?
Typically, you're able to reschedule or cancel your YYZ to DPA flight. However, additional fees may apply, especially if you made your booking over 24 hours ago. Check your itinerary for the airline's rules and fees on flight changes, or if you'd like further details, go to our Customer Service portal.

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*Available to One Key members.