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

View $100 flight on Sat, Oct 4, 2025Opens in a new window

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

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
Sat, Sep 27 - Sat, Oct 4
MDW
Chicago
YYC
Calgary
$251 Roundtrip, found 6 days ago
$251
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Sep 27 from Chicago to Calgary, returning Sat, Oct 4, priced at $251 found 6 days ago
Delta
Sat, Sep 6 - Sat, Sep 13
MDW
Chicago
YYC
Calgary
$261 Roundtrip, found 5 hours ago
$261
Roundtrip
found 5 hours ago
Select Delta flight, departing Sat, Sep 6 from Chicago to Calgary, returning Sat, Sep 13, priced at $261 found 5 hours ago
Delta
Sat, Aug 16 - Wed, Aug 20
MDW
Chicago
YYC
Calgary
$266 Roundtrip, found 3 days ago
$266
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Aug 16 from Chicago to Calgary, returning Wed, Aug 20, priced at $266 found 3 days ago
Delta
Sat, Aug 23 - Sat, Aug 30
MDW
Chicago
YYC
Calgary
$271 Roundtrip, found 9 hours ago
$271
Roundtrip
found 9 hours ago
Select Delta flight, departing Sat, Aug 23 from Chicago to Calgary, returning Sat, Aug 30, priced at $271 found 9 hours ago
Delta
Tue, Aug 19 - Sat, Aug 23
MDW
Chicago
YYC
Calgary
$273 Roundtrip, found 6 days ago
$273
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Aug 19 from Chicago to Calgary, returning Sat, Aug 23, priced at $273 found 6 days ago
Delta
Tue, Aug 19 - Sun, Aug 24
MDW
Chicago
YYC
Calgary
$273 Roundtrip, found 5 days ago
$273
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Aug 19 from Chicago to Calgary, returning Sun, Aug 24, priced at $273 found 5 days ago
Delta
Thu, Aug 21 - Tue, Aug 26
MDW
Chicago
YYC
Calgary
$274 Roundtrip, found 3 days ago
$274
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Aug 21 from Chicago to Calgary, returning Tue, Aug 26, priced at $274 found 3 days ago
Delta
Sat, Sep 27 - Sat, Oct 4
MDW
Chicago
YYC
Calgary
$279 Roundtrip, found 6 days ago
$279
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Sep 27 from Chicago to Calgary, returning Sat, Oct 4, priced at $279 found 6 days ago
Delta
Wed, Aug 20 - Sat, Aug 30
MDW
Chicago
YYC
Calgary
$288 Roundtrip, found 1 day ago
$288
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Aug 20 from Chicago to Calgary, returning Sat, Aug 30, priced at $288 found 1 day ago
WestJet
Thu, Aug 21 - Fri, Aug 22
MDW
Chicago
YYC
Calgary
$928 Roundtrip, found 1 day ago
$928
Roundtrip
found 1 day ago
Select WestJet flight, departing Thu, Aug 21 from Chicago to Calgary, returning Fri, Aug 22, priced at $928 found 1 day ago
Flights from Chicago (MDW) to Calgary (YYC)
Origin airport
Midway Intl.
Destination airport
Calgary Intl.
Airlines serving
Delta, WestJet
Roundtrip price
$251
Distance
1396 mi

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 September. 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.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Calgary Intl. Airport (YYC) cost?
Discover the latest flight deals from MDW to YYC by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to YYC?
The cheapest flights from MDW to YYC are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 MDW to YYC?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to YYC. Sort your results by "Price (lowest to highest)" to snap up a great deal.
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.

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*Available to One Key members.