$134 Cheap Flights from Calgary (YYC) to Chicago (MDW)

View $134 flight on Mon, May 5, 2025Opens in a new window

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

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Find available prices by choosing your travel dates.

Cheap Flights from Calgary to Chicago (YYC-MDW)

Prices were available within the past 7 days and start at $134 for one-way flights and $214 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, May 1 - Sat, May 3
YYC
Calgary
MDW
Chicago
$214 Roundtrip, found 6 days ago
$214
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, May 1 from Calgary to Chicago, returning Sat, May 3, priced at $214 found 6 days ago
Delta
Mon, May 5 - Tue, May 6
YYC
Calgary
MDW
Chicago
$215 Roundtrip, found 2 days ago
$215
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, May 5 from Calgary to Chicago, returning Tue, May 6, priced at $215 found 2 days ago
Delta
Thu, Jun 12 - Mon, Jun 16
YYC
Calgary
MDW
Chicago
$233 Roundtrip, found 2 days ago
$233
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Jun 12 from Calgary to Chicago, returning Mon, Jun 16, priced at $233 found 2 days ago
Delta
Mon, May 12 - Thu, May 15
YYC
Calgary
MDW
Chicago
$253 Roundtrip, found 3 days ago
$253
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, May 12 from Calgary to Chicago, returning Thu, May 15, priced at $253 found 3 days ago
Delta
Mon, May 5 - Tue, May 6
YYC
Calgary
MDW
Chicago
$271 Roundtrip, found 2 days ago
$271
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, May 5 from Calgary to Chicago, returning Tue, May 6, priced at $271 found 2 days ago
Delta
Fri, Apr 25 - Wed, May 7
YYC
Calgary
MDW
Chicago
$288 Roundtrip, found 1 day ago
$288
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Apr 25 from Calgary to Chicago, returning Wed, May 7, priced at $288 found 1 day ago
Delta
Thu, Jun 12 - Mon, Jun 16
YYC
Calgary
MDW
Chicago
$290 Roundtrip, found 2 days ago
$290
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Jun 12 from Calgary to Chicago, returning Mon, Jun 16, priced at $290 found 2 days ago
Delta
Sat, Jun 7 - Sun, Jun 8
YYC
Calgary
MDW
Chicago
$302 Roundtrip, found 2 days ago
$302
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Jun 7 from Calgary to Chicago, returning Sun, Jun 8, priced at $302 found 2 days ago
Delta
Tue, May 27 - Wed, May 28
YYC
Calgary
MDW
Chicago
$312 Roundtrip, found 6 days ago
$312
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, May 27 from Calgary to Chicago, returning Wed, May 28, priced at $312 found 6 days ago
WestJet
Wed, May 28 - Fri, May 30
YYC
Calgary
MDW
Chicago
$701 Roundtrip, found 2 days ago
$701
Roundtrip
found 2 days ago
Select WestJet flight, departing Wed, May 28 from Calgary to Chicago, returning Fri, May 30, priced at $701 found 2 days ago
Flights from Calgary (YYC) to Chicago (MDW)
Origin airport
Calgary Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, WestJet
Roundtrip price
$213
Distance
1396 mi

Calgary to Chicago Flights

The cheapest times to fly from Calgary to Chicago

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 Calgary to Chicago are during the month of May. You can find some of the cheapest flights from Calgary to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Calgary to Chicago

Sunday is one of the best days to book for cheap flights from Calgary to Chicago: 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 Calgary to Chicago

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 Calgary to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $134 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 Calgary to Chicago 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 Calgary to Chicago 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 Calgary Intl. Airport (YYC) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from YYC to MDW 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 YYC to MDW?
The cheapest flights from YYC to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from YYC to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from YYC to MDW. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Calgary Intl. Airport (YYC) to Midway Intl. Airport (MDW)?
Nonstop flights from Calgary Intl. Airport (YYC) to Midway Intl. Airport (MDW) aren’t available daily, so you’ll need to take a flight with a layover. Explore your options with Expedia’s filters. Enter your dates and pick either “1 Stop” or “2+ Stops.”
What day of the week has the most flights from YYC to MDW?
You’ll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Calgary Intl. Airport (YYC) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Calgary Intl. Airport (YYC) to Midway Intl. Airport (MDW) route, travel before 3 PM. Later departures have a 22% higher chance of cancellation.**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.
What airports do you fly into for Chicago from Calgary Intl. Airport (YYC)?
If you’re on a direct flight from Calgary Intl. Airport (YYC) to Chicago, O’Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Calgary Intl. Airport (YYC) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from YYC to MDW are generally more expensive. To secure the lowest rates, start looking for flights well ahead of time. That said, if you can play around with your travel dates, you may score a cheap fare right before your journey.
Is it cheaper to book a YYC to MDW flight and hotel package?
You’ll generally save money by booking a YYC to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it’s simple to manage it all in one place. After selecting your ideal accommodations and flights, consider other add-ons like car rentals, tours and activities.
Can I cancel or change the date of my flight from Calgary Intl. Airport (YYC) to Midway Intl. Airport (MDW)?
Generally, it’s possible to reschedule or cancel your YYC to MDW flight. However, for bookings 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 if any costs are involved. You’ll also find further details on our Customer Service portal.

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*Available to One Key members.