
Book Cheap American Airlines flight from Calgary (YYC) to Chicago (ORD) from CA $410
Find The Best Day to Book a Cheap American Airlines Flights From Calgary to Chicago
Cheapest American Airlines Flights from Calgary (YYC) to Chicago (ORD)
The cheapest flights to O'Hare Intl. found within the past 7 days were CA $589 round trip and CA $410 one way. Prices and availability subject to change. Additional terms may apply.
ORD From YYC Economy Coach Packages on Similar Airlines



Frequently asked questions
Grab a great American Airlines flight from YYC to ORD
To find a great deal on American Airlines flights with Travelocity, simply enter your origin and destination airports, pick your travel dates, and hit search. From here, you can sort by price, flight duration, and arrival/departure time. You can also filter to find nonstop flights.
Flying American Airlines Calgary to Chicago gives you fights to choose from. With that direct flight time of , you’ll be touching down before you know it.
Find cheap flights with American Airlines between Calgary and Chicago
American Airlines has a range of great fares on stacks of flights, and to find the most affordable for you, there are a few tricks you can try. Booking in advance, for example, is a great way to grab a fantastic deal. Also, choose the cheapest month, if you can. One-way flights from Calgary to Chicago with American Airlines are September.
The more flexible you are, the more affordable flights you’re likely to find. Consider one-way flights and connecting flights, as well as standard roundtrip and direct options. Even if you’re flying today, cheap last-minute flights are easy to find by entering your travel dates and hitting search.
Reasons to book your American Airlines flights with Travelocity
Travelocity makes it easy to book a seat, anywhere in the world. The vast inventory, fast search, and advanced filters put some of the best deals on the planet in one place. Whether you’re traveling on business, with friends, family, or on your own, take your pick from some fantastic options. And with free cancellation and pay later options, you can travel more and worry less.
Airport code | Country | Airport name | Number of flights |
|---|---|---|---|
| DFW | USA | Dallas-Fort Worth Intl. | 599 |
| CLT | USA | Charlotte-Douglas Intl. | 536 |
| ORD | USA | O'Hare Intl. | 317 |
| PHL | USA | Philadelphia Intl. | 247 |
| MIA | USA | Miami Intl. | 193 |
| DCA | USA | Ronald Reagan Washington National | 152 |
| PHX | USA | Sky Harbor Intl. | 141 |
| LAX | USA | Los Angeles Intl. | 81 |
| LGA | USA | LaGuardia | 72 |
| BOS | USA | Logan Intl. | 57 |
Travelers ❤️ these 🏨 after their flight to Chicago

Hilton Chicago O'Hare Airport
We were very happy with our stay to include the cleanliness, breakfast and the room overall.
Reviewed on Apr 11, 2026

Hyatt Regency O'Hare Chicago
We opted out of having breakfast due to it costing 25 dollars per person. Room was okay, terrible pillows. Staff very nice.
Reviewed on Apr 10, 2026

Holiday Inn Chicago O'Hare – Rosemont by IHG
Accommodation was wonderful. Parking is safe and easy
Reviewed on Apr 11, 2026
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