$108 Cheap American Airlines flights Toronto (YYZ) to Chicago (ORD)

Finding cheap one-way American Airlines flights from YYZ to ORD from $108 on Expedia couldn’t be easier — just filter by “Price (lowest to highest).” Or check out our budget-friendly return fares from $166 for your next exciting vacation.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Browse for return or one-way flights to Chicago in January or February. You could find cheaper fares with American Airlines during these off-season months.

Start your search for American Airlines flights from YYZ to ORD about one month before you want to go. The most affordable time to reserve an international flight is usually 18 to 29 days ahead of your departure date when you can save 17% versus booking four to five months in advance. No matter your itinerary and fare class, the best day of the week to book international airfare is usually Sunday. Friday is often the most expensive. Passengers who book on a Sunday can save an average of 17% compared to those who book on a Friday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC’s global airline sales database.

Jet off on one of American Airlines’s 27 direct weekly flights from Pearson Intl. Airport (YYZ) to O’Hare Intl. Airport (ORD). To see your choices, enter your origin, destination and dates and hit search. Next, apply the “Nonstop” and “Airline” filters.

From takeoff to touchdown, a direct American Airlines flight from Pearson Intl. Airport (YYZ) to O’Hare Intl. Airport (ORD) takes around 2h 4m.

Wednesday has the most American Airlines flights from Pearson Intl. Airport (YYZ) to O’Hare Intl. Airport (ORD). With 4 daily departures, this is a great day to book something that will work for your schedule.

Jetting off from YYZ at 6:15AM UTC-5, the earliest American Airlines flight to ORD lands at 7:30AM UTC-6. Flying early means you’re less likely to experience delays.* Not an early riser? The last American Airlines flight from YYZ to ORD departs at 6:20PM UTC-5 and touches down at 7:20PM UTC-6.*Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.

American Airlines flights from Pearson Intl. Airport (YYZ) to Chicago come in to O’Hare Intl. Airport (ORD). This is the main gateway here.

American Airlines generally operates Embraer 170 planes for flights from Pearson Intl. Airport (YYZ) to O’Hare Intl. Airport (ORD). Bear in mind that aircraft type can differ depending on operational needs, so the plane you catch might be different on the day.

Depending on the ticket type you purchased, a fee typically applies if you modify or cancel your flight more than 24 hours after it’s been confirmed. To find plane tickets with more flexibility, select our “No cancel fee” or “Changes included” filter while searching for flights. For more information on changing or canceling your reservation, head to “Trips,” select your flight and tick “Manage Booking.”