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

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Frequently asked questions

Is it cheaper to buy a plane ticket from YYZ to DuPage Airport last minute?
When it's time to book your flights, it's always better to be prepared. While you may be able to score a deal on a Pearson Intl. Airport (YYZ) to DPA flight at the last minute, tickets usually don't get cheaper as the departure date nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to lock in a domestic flight is between 28 – 35 days in advance. For international journeys it's three to four months.
What airports do you fly into for Chicago from Toronto?
With Dupage Airport (DPA), O'Hare Intl. Airport (ORD) and Lewis University Airport (LOT) to select from, journeying from Toronto to Chicago is a snap. The city's key hub, Dupage Airport (DPA), is roughly 48 kilometers west of the downtown area. Along with the price of tickets, consider things like bus or train options from the airport and the distance to your hotel when choosing where to fly into. Get your Chicago vacation off on the right foot by discovering Wrigley Field and Millennium Park.
Can I change the date of my flight from Toronto Pearson Airport to Dupage Airport (DPA)?
Quickly make changes to your Toronto Pearson Airport to DuPage Airport flight by logging in to the Expedia Trips portal. But before you begin, read through the rules in your itinerary to find out what you're able to do and what charges may apply. Some carriers charge a change fee per person, on top of any difference in prices. But if you booked in the last 24 hours, you may be able to cancel for free and arrange new flights. You can also check out our Customer Service portal for more useful advice and to chat with our Virtual Agent.

Travel information

Travel information

Origin airport
Pearson Intl.
Destination airport
Dupage
Distance
727 km

Book with confidence

Book with confidence

Toronto to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Toronto to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Toronto to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is now!

Toronto to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia