CA $230 Cheap Flights from Calgary (YYC) to Chicago (MDW)

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Cheap flights from Calgary (YYC) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $230 for one-way flights and CA $402 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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Flight from Calgary to Chicago (YYC - MDW) route information
Origin airport
Calgary Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, WestJet
Roundtrip price
CA $401
Distance
2234 km

Calgary to Chicago Flights

The easy way to book your flights from Calgary to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Calgary whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Midway Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Calgary to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Calgary Intl., YYC to Midway Intl., MDW 

Sort your search results by price to find great deals on your flight from Calgary to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Calgary currently is just CA $402 rising to CA $508.  

Here are more money-saving tips: 

  • Fly in April when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Calgary 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Frequently asked questions

How much is a flight from YYC Calgary International Airport to Chicago Airport?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip journey from YYC Calgary International Airport to Midway Intl. Airport (MDW) was CA $402. Cheap fares don’t stick around for long, so book yours today. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from YYC Calgary International Airport to Midway Airport?
We understand that life can throw the odd curveball, so we’ve made it as easy as possible for you to cancel your trip online. Just head to the Customer Service Portal and follow the instructions.
How do I find cheap flights from YYC Calgary International Airport to Midway Intl. Airport (MDW) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for YYC Calgary International Airport to Midway Intl. Airport (MDW) flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from YYC Calgary International Airport to Midway Intl. Airport (MDW)?
The flying distance between YYC (YYC) and Midway Airport (MDW) is 2,300 kilometers. Listen to some music or get stuck into a book and the trip will whiz by.
Which airlines fly direct from YYC to Midway Airport?
If you want to travel straight from YYC Calgary International Airport to Midway Intl. Airport (MDW), you’ll have to book a flight with one or more stops. Unfortunately, there aren’t any airlines that fly directly between these airports.
Are YYC Calgary International Airport to Midway Intl. Airport (MDW) flight tickets cheaper when they're purchased at the last minute?
Last-minute bookings from YYC to Midway Intl. Airport (MDW) can be hit-or-miss. You might be lucky and score a bargain, but you could also miss out entirely! If you’d prefer to start planning early on, Expedia compares flight deals up to a year in advance. Just bear in mind that not all airlines list their prices that far in advance. Our suggestion? Check back often as prices are updated frequently.
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