Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 321,000 hotels worldwide and 400 airlines worldwide.

Secure incredible value with Expedia's Price Guarantee.

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Find cheap flights from Calgary (YYC) to Chicago (ORD)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Chicago

C$346.19

Find cheap flights from Calgary (YYC) to Chicago (ORD)

Question : Looking for the quickest flight from YYC to ORD?
Answer : If you're able to take the fastest direct flight (which is offered by United Airlines), you will be able to leave YYC at 12:35 PM MST and get to ORD at 4:55 PM CST (three hours and 20 minutes). Remember, there is a one-hour time change.

Question : Would you be willing to change your travel days if it saved you money?
Answer : Friday is your cheapest day to fly in the month of January. Flexibility is paramount when booking travel plans in order to keep travel costs down.

Question : How does Calgary to Chicago stack up against the rest of the world in overall promptness?
Answer : Using the combined on-time percentage and average delay breakdown, Calgary to Chicago currently has a 3 out of a possible 5 star rating. A 3-star rating means you should feel slightly worried about getting to Chicago on time.

Question : Which airline can you expect delays with on this route?
Answer : NetJets Aviation is late on 100% of flights from Calgary International Airport (YYC) to O'Hare International Airport (ORD) at the moment. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.

Question : Is the price you found a good deal?
Answer : Prices for this trip tend to fluctuate much more than other flights from Canada. They can vary anywhere from $262 to $2,371. Remember, you can save by booking further in advance.

Question : How often are flights late from Calgary International Airport (YYC) to O'Hare International Airport (ORD)?
Answer : Passengers are currently getting to their destination on schedule 80% of the time, which ranks in the 65th percentile worldwide. When there is a delay, it averages about half an hour.

Question : How many departure times are there on a given day?
Answer : Each day is different, but on average, you can expect to see five available departure times. You won't have as many options on this route as most other routes departing Canada.

Calgary to Chicago Flights

Ready for an adventure? Thought so! Prepare to see the sights when you book your trip from Calgary to Chicago with Expedia.ca. Whether you’re visiting for business or pleasure, we know how important it is to bring home travel stories. Maybe your tales will include the best dinner of your life, or the weirdest street art you saw in the city, or the concert that turned you into a fan of a new band. Whatever it is, your new favourite anecdote is right around the corner. Book your trip from YYC to ORD and begin your journey!

Getting a cheap deal on your trip sets the tone for the perfect holiday. And with Expedia.ca, you know you can travel from Calgary to Chicago on the cheap, with enough money left over for a stellar time in the city. That could mean more tours with the kids, more concerts with the spouse, more dessert amongst co-workers, or even front row seats to a sports game if you’re travelling solo. It’s your holiday! Make it great.

Travelling shouldn’t cost an arm and a leg before you even get to relax on the plane’s armrests. Count on Expedia.ca to get you the best discounts on flights from YYC to ORD. And remember this: You can also save big when you bundle. Add a hotel or car rental deal to your flight and witness those savings add up. Hey, more money for more souvenirs, right? Right! Pack your bags and we’ll see you on the route.

Combine your Chicago flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from with Expedia Canada. Use us as your top travel destination and have the confidence that you’re getting a bargain!