$107 Cheap American Airlines flights Calgary (YYC) to Chicago (ORD)

Scoring cheap one-way American Airlines flights from YYC to ORD from $107 on Expedia couldn’t be simpler — just filter by “Price (lowest to highest).” Alternatively, check out our budget-friendly return fares from $157 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.

Search for one-way or return flights to Chicago in January or February. You could find an affordable fare with American Airlines during these off-season months.

Start your search for American Airlines flights from YYC to ORD about one month before you want to leave. The cheapest 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 to book international airfare is usually Sunday. Friday is often the most expensive. Passengers booking 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.

Use the “Nonstop” filter when browsing for direct American Airlines flights from YYC to ORD. It’s also a good way to compare other carriers offering the same nonstop trip.

Browse American Airlines’s earliest flights from YYC to ORD by checking the “Early Morning” and “Morning” filters. Not only will you get to where you’re going sooner, early departures also experience 20% fewer 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.

Board an American Airlines flight from Calgary Intl. Airport (YYC) to Chicago, and you’ll likely arrive at O’Hare Intl. Airport (ORD). This is the airline’s main hub here.

Changes are often free within 24 hours of booking, but your airline may add a charge after that time. For further information about modifying your reservation, check out your “Trips,” select your flight and click on “Manage Booking.” If you want the freedom to change your itinerary without extra charges, tick the “Changes included” or “No cancel fee” filter when planning your next adventure.