$119 Cheap United flights Calgary (YYC) to Chicago (ORD)

You can discover cheap return United Airlines flights from $181 from YYC to ORD by filtering your results from "Price (lowest to highest)" on Expedia. Or search for deals from $119 for a one-way journey.**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.

To discover affordable flights from YYC to ORD with United Airlines, begin your search about one month before your intended departure. You can save 17% when you book your international tickets 18 to 29 days ahead instead of booking four to five months in advance. Another good tip? Booking on Sunday can lead to average savings of 17% compared to Friday (the most expensive day).**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.

The earliest United Airlines flight from YYC to ORD takes off at 12:41PM UTC-7, arriving at 5:15PM UTC-6. If you want to head off later in the day, the last United Airlines flight leaves YYC at 12:41PM UTC-7 and touches down at ORD at 5:15PM UTC-6. Flying earlier is generally a smart option as morning flights are less likely to experience cancellations.**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.

Depart from YYC to ORD with United Airlines and enjoy a range of perks including a rewarding loyalty program. When booking through Expedia as a United Mileage Plus and One Key™ member, you may also earn OneKeyCash™* to spend on select future travel purchases.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.