$100 Cheap Flights from Chicago (MDW) to Calgary (YYC)

View $100 flight on Thu, Dec 11, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Calgary International Airport (YYC)

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Cheap Flights from Chicago to Calgary (MDW-YYC)

Prices were available within the past 7 days and start at $100 for one-way flights and $251 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Dec 11 - Tue, Dec 16
MDW
Chicago
YYC
Calgary
$251 Roundtrip, just found
$251
Roundtrip
just found
Select Delta flight, departing Thu, Dec 11 from Chicago to Calgary, returning Tue, Dec 16, priced at $251 just found
Delta
Thu, Jan 22 - Tue, Jan 27
MDW
Chicago
YYC
Calgary
$260 Roundtrip, found 12 hours ago
$260
Roundtrip
found 12 hours ago
Select Delta flight, departing Thu, Jan 22 from Chicago to Calgary, returning Tue, Jan 27, priced at $260 found 12 hours ago
Delta
Wed, Jan 7 - Mon, Jan 12
MDW
Chicago
YYC
Calgary
$265 Roundtrip, found 3 days ago
$265
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jan 7 from Chicago to Calgary, returning Mon, Jan 12, priced at $265 found 3 days ago
Delta
Sat, Nov 29 - Wed, Dec 3
MDW
Chicago
YYC
Calgary
$271 Roundtrip, found 3 days ago
$271
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Nov 29 from Chicago to Calgary, returning Wed, Dec 3, priced at $271 found 3 days ago
Delta
Wed, Jan 7 - Mon, Jan 12
MDW
Chicago
YYC
Calgary
$275 Roundtrip, found 3 days ago
$275
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jan 7 from Chicago to Calgary, returning Mon, Jan 12, priced at $275 found 3 days ago
Delta
Sat, Dec 6 - Thu, Dec 25
MDW
Chicago
YYC
Calgary
$290 Roundtrip, found 1 day ago
$290
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Dec 6 from Chicago to Calgary, returning Thu, Dec 25, priced at $290 found 1 day ago
Delta
Sun, Nov 9 - Thu, Nov 13
MDW
Chicago
YYC
Calgary
$293 Roundtrip, found 13 hours ago
$293
Roundtrip
found 13 hours ago
Select Delta flight, departing Sun, Nov 9 from Chicago to Calgary, returning Thu, Nov 13, priced at $293 found 13 hours ago
Delta
Fri, Nov 14 - Mon, Nov 17
MDW
Chicago
YYC
Calgary
$294 Roundtrip, found 4 days ago
$294
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Nov 14 from Chicago to Calgary, returning Mon, Nov 17, priced at $294 found 4 days ago
Delta
Sun, Dec 21 - Thu, Jan 8
MDW
Chicago
YYC
Calgary
$300 Roundtrip, found 5 hours ago
$300
Roundtrip
found 5 hours ago
Select Delta flight, departing Sun, Dec 21 from Chicago to Calgary, returning Thu, Jan 8, priced at $300 found 5 hours ago
WestJet
Tue, Oct 28 - Wed, Oct 29
MDW
Chicago
YYC
Calgary
$939 Roundtrip, found 6 days ago
$939
Roundtrip
found 6 days ago
Select WestJet flight, departing Tue, Oct 28 from Chicago to Calgary, returning Wed, Oct 29, priced at $939 found 6 days ago

Alternative airports near Calgary

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Calgary Intl. YYC. Cheapest and Closest option available. Average driving time to city center is 15 minutes. Flights from $306
YYC
Calgary Intl.
CheapestClosest
Average driving time to city center15 min
Flights from $306

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Calgary Intl. Airport (YYC) cost?
Snag a cheap one-way flight from $100 or cheap return flight from $251 from Midway Intl. Airport (MDW) to Calgary Intl. Airport (YYC) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Calgary Intl. Airport (YYC)?
The cheapest month to fly from MDW to YYC is December, when there's less demand. Off-peak months are typically when airlines offer better prices between these airports.
Which airlines fly direct from Midway Intl. Airport (MDW) to Calgary Intl. Airport (YYC)?
You can't take a direct flight from Chicago, IL (MDW-Midway Intl.) to Calgary Intl. Airport (YYC). However, you can easily journey to Calgary without any layovers by departing from O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Calgary Intl. Airport (YYC)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest MDW to YYC flight.
How many flights per day from Midway Intl. Airport (MDW) to Calgary Intl. Airport (YYC)?
You'll need to hop on a flight with a layover if you're traveling from Midway Intl. Airport (MDW) to Calgary Intl. Airport (YYC). Direct flights don't operate daily on this route. However, simply filter your search to include one or more stops to discover an option that works for you.
What day of the week has the most flights from MDW to YYC?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Calgary Intl. Airport (YYC)?
To arrive at Calgary Intl. Airport (YYC) without delays, pick a flight that leaves from Midway Intl. Airport (MDW) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Calgary Intl. Airport (YYC) last-minute?
Holding off until just before your trip to book a flight from MDW to YYC generally means paying more. Although you may find some last-minute offers, they aren't always guaranteed. Keep your travel plans flexible to boost your chances of landing a bargain.
Is it cheaper to book a MDW to YYC flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to YYC flight and hotel package with Expedia could lead to significant savings. Better yet, having everything in one easy place takes the hassle out of travel planning. Just secure your flights and select from our extensive range of hotels, then tailor your trip with extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Calgary Intl. Airport (YYC)?
You can usually cancel or reschedule your MDW to YYC flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Calgary Intl.
Airlines serving
Delta, WestJet
Roundtrip price
$250
Distance
1396 mi

Book with confidence

Chicago to Calgary Flights

The cheapest times to fly from Chicago to Calgary

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Calgary are during the month of December. You can find some of the cheapest flights from Chicago to Calgary with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Calgary

Sunday is one of the best days to book for cheap flights from Chicago to Calgary: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Calgary

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Calgary in 2025. You can also book with separate airlines for your outbound and return journeys, from $100 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Calgary flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Calgary airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Calgary Flights

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*Available to One Key members.