$122 Cheap Flights from Chicago (MDW) to Calgary (YYC)

View $122 flight on Fri, May 8, 2026Opens 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 $122 for one-way flights and $274 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, May 8 - Sun, May 10
MDW
Chicago
YYC
Calgary
$274 Roundtrip, found 1 day ago
$274
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, May 8 from Chicago to Calgary, returning Sun, May 10, priced at $274 found 1 day ago
Delta
Mon, Apr 27 - Sun, May 10
MDW
Chicago
YYC
Calgary
$289 Roundtrip, found 2 days ago
$289
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Apr 27 from Chicago to Calgary, returning Sun, May 10, priced at $289 found 2 days ago
Delta
Fri, May 8 - Sat, May 16
MDW
Chicago
YYC
Calgary
$289 Roundtrip, found 5 days ago
$289
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, May 8 from Chicago to Calgary, returning Sat, May 16, priced at $289 found 5 days ago
Delta
Fri, May 8 - Sun, May 10
MDW
Chicago
YYC
Calgary
$300 Roundtrip, found 1 day ago
$300
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, May 8 from Chicago to Calgary, returning Sun, May 10, priced at $300 found 1 day ago
Delta
Thu, Aug 27 - Mon, Aug 31
MDW
Chicago
YYC
Calgary
$306 Roundtrip, found 6 hours ago
$306
Roundtrip
found 6 hours ago
Select Delta flight, departing Thu, Aug 27 from Chicago to Calgary, returning Mon, Aug 31, priced at $306 found 6 hours ago
Delta
Mon, Jun 1 - Fri, Jun 5
MDW
Chicago
YYC
Calgary
$306 Roundtrip, found 2 hours ago
$306
Roundtrip
found 2 hours ago
Select Delta flight, departing Mon, Jun 1 from Chicago to Calgary, returning Fri, Jun 5, priced at $306 found 2 hours ago
Delta
Mon, Apr 27 - Sun, May 10
MDW
Chicago
YYC
Calgary
$315 Roundtrip, found 2 days ago
$315
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Apr 27 from Chicago to Calgary, returning Sun, May 10, priced at $315 found 2 days ago
Delta
Fri, May 8 - Sat, May 16
MDW
Chicago
YYC
Calgary
$321 Roundtrip, found 5 days ago
$321
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, May 8 from Chicago to Calgary, returning Sat, May 16, priced at $321 found 5 days ago
Delta
Thu, Aug 27 - Mon, Aug 31
MDW
Chicago
YYC
Calgary
$325 Roundtrip, found 6 hours ago
$325
Roundtrip
found 6 hours ago
Select Delta flight, departing Thu, Aug 27 from Chicago to Calgary, returning Mon, Aug 31, priced at $325 found 6 hours ago
WestJet
Mon, Jun 22 - Tue, Jun 23
MDW
Chicago
YYC
Calgary
$1,102 Roundtrip, found 5 hours ago
$1,102
Roundtrip
found 5 hours ago
Select WestJet flight, departing Mon, Jun 22 from Chicago to Calgary, returning Tue, Jun 23, priced at $1,102 found 5 hours 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 $989
YYC
Calgary Intl.
CheapestClosest
Average driving time to city center15 min
Flights from $989

Frequently asked questions

How much does a flight from Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.) cost?
You can find cheap one-way flights from $122 and cheap return flights from $274 Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.) with Expedia. One-way flights usually range from $99 to $1413. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.)?
The cheapest month to fly from MDW to YYC is May when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.)?
Enter MDW to YYC and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.)?
WestJet is one of the cheapest airlines offering connecting flights from Midway Intl. (MDW) to Calgary Intl. (YYC) with a layover in Minneapolis - St. Paul Intl. starting from around $593. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.)?
To find a cheap flight from Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.)?
The earliest flight from Chicago Midway International Airport (MDW) to Calgary International Airport (YYC) typically departs at around 6:00 AM, operated by Delta and Alaska Airlines. This is a seasonal service active in September, allowing you to start your day early and maximize your time in Calgary. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.)?
The most popular departure times for flights from Chicago Midway International Airport (MDW) to Calgary International Airport (YYC) are in the late morning, from 9am to noon. About 49% of passengers prefer this time window. Many major carriers, including Delta, United, and WestJet, offer flights during this window. This timing works well because it allows you to start your day in Chicago and arrive in Calgary with plenty of time to explore.
How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.)?
Flying from MDW to YYC with a connection usually takes about 8 hours, traveling roughly 1,397 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.)?
First class seats are offered on the MDW to YYC route with Delta Air Lines.
How do I earn miles on a Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Calgary from Midway Intl. (MDW)?
If you're planning to travel to Calgary from Midway Intl. (MDW), you can fly into Calgary Intl. (YYC) Some flights may connect through major hubs like Minneapolis - St. Paul Intl. (MSP), Hartsfield-Jackson Atlanta Intl. (ATL), Detroit Metropolitan Wayne County (DTW) before reaching Calgary. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.) flight and hotel package?
Securing a Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.) Calgary Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.)?
If you booked your Chicago, IL (MDW-Midway Intl.) to Calgary, AB (YYC-Calgary Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Midway Intl.
Destination airport
Calgary Intl.
Airlines serving
Delta, WestJet
Roundtrip price
$273
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 May. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $122 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

*Flight schedules are subject to change.

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*Available to One Key members.