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Cheap YYC to ORD Flights

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

Calgary to Chicago route information

Origin Airport Calgary Intl.
Destination Airport O'Hare Intl.
Airlines Serving Air Canada, Alaska Airlines, American Airlines, Delta, Frontier Airlines, United, WestJet
Flight Price $240
Distance 1,381 mi



Cheap YYC to ORD Flights

  • What is the cheapest day to fly to Chicago?

    Tickets are currently $276, which is 33% less than the average price for this route. As of Aug 26th, the cheapest day to fly from Calgary to Chicago is Sep 6th.
  • How long is the flight from YYC to ORD?

    United Airlines can get you there in three hours and 20 minutes. So, if you were to leave Calgary at 12:35 PM MDT, you would get to Chicago at 4:55 PM CDT. Just enough time for you to catch up on your television shows before your flight touches down (don't forget, there is a one-hour time change).
  • How long do most people visit Chicago?

    Of course, you're not most people, but if you were, you'd stay around five days.
  • What is the cheapest airline flying from Calgary to Chicago?

    Air Canada is offering the best deal at $276. Better look fast because prices range all the way up to $805 over the next three months.
  • What is the cheapest day to fly?

    The cheapest day to fly from Calgary to Chicago is on Friday. So, if you are trying to save a little money on your next flight look for flights on that day.
  • Can I change the date of my flight?

    Yes, you can adjust your departure date. If you would like to save a little money in doing so, the cheapest day to fly in September is Friday. Having flexibility in your travel plans means you can save more, so be sure to plan ahead when possible.
  • How long does it take to fly from Calgary to Chicago?

    United Airlines currently holds the shortest travel time with three hours and 20 minutes. For example, you would arrive in Chicago at 4:55 PM CDT if you left Calgary at 12:35 PM MDT. Remember, there is a one-hour time difference.

Calgary to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Calgary to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at, we’ll pair you up with YYC to ORD flights that won’t make your bank account wince. Ready to temporarily leave behind Calgary for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to ORD with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Package Disclaimer

*Savings amount equal to 100% when flight + hotel are booked together. Prices based on searches conducted by fellow shoppers within the past 24 hours. There is no guarantee that these prices will be in effect at the time of your search. Vacation package savings are based on comparison to prices on of the same components booked separately. Savings vary based on origin/destination, length of trip, stay dates and travel partners, and aren't available on all packages.