$158 Cheap United flights Toronto (YYZ) to Chicago (ORD)

You’ll discover affordable return United Airlines flights from $182 from YYZ to ORD by sorting your results from “Price (lowest to highest)” on Expedia. Or look for options from $158 for a one-way trip.**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.

January is one of the cheapest months to get away to Chicago with United Airlines. You could also find excellent prices on one-way and return tickets in February.

Look for United Airlines flights from YYZ to ORD about one month before you want to leave. The most affordable time to book 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. Regardless of itinerary or 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 17% on average 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.

United Airlines offers direct flights from Pearson Intl. Airport (YYZ) to O’Hare Intl. Airport (ORD), with 41 weekly departures. Simply choose the “Nonstop” and “Airline” filters while searching on Expedia to show all direct United Airlines flights to ORD.

Take off from Pearson Intl. Airport (YYZ) for O’Hare Intl. Airport (ORD) on a direct United Airlines flight, and you’ll be in the sky for around 2h 12m.

Tuesday has the most United Airlines flights from Pearson Intl. Airport (YYZ) to O’Hare Intl. Airport (ORD). With 6 daily departures, this is the best day of the week to find something that will suit your schedule.

Taking off from YYZ at 6:52AM UTC-5, the first United Airlines flight to ORD lands at 8:05AM UTC-6. Traveling early means you’re less likely to experience delays.* Not a morning person? The last United Airlines flight from YYZ to ORD departs at 9:00PM UTC-5 and touches down at 10:13PM 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.

O’Hare Intl. Airport (ORD) is the primary Chicago gateway for United Airlines flights from Pearson Intl. Airport (YYZ).

A rewarding loyalty program and the ability to rack up points through United Mileage Plus are the start of the reasons to leave from YYZ to ORD with United Airlines. Plus, when you sign up to our One Key™ program, you can receive OneKeyCash™* on top of any airline loyalty program earnings. It’s yours to use wherever your next trip takes you.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

You’ll likely board an Embraer 170 or an Embraer 175 when flying United Airlines from Pearson Intl. Airport (YYZ) to O’Hare Intl. Airport (ORD). However, keep in mind that a different aircraft could be assigned to your route due to operational demands.

It’s usually possible to cancel or reschedule your flight, although there may be additional fees if you booked over 24 hours ago. Want to keep your options open? Make use of our “No cancel fee” or “Changes included” filter to find flights that won’t charge you extra if you need to revise your plans. To modify your booking, go to “Trips,” select your flight and click on “Manage Booking” for more information.