$132 Cheap Flights from Calgary (YYC) to Chicago (MDW)

View $132 flight on Thu, Jan 29, 2026Opens in a new window

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

Cheap Flights from Calgary to Chicago (YYC-MDW)

Prices were available within the past 7 days and start at $132 for one-way flights and $213 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Jan 9 - Tue, Jan 20
YYC
Calgary
MDW
Chicago
$213 Roundtrip, found 2 days ago
$213
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Jan 9 from Calgary to Chicago, returning Tue, Jan 20, priced at $213 found 2 days ago
Delta
Tue, Nov 25 - Tue, Dec 2
YYC
Calgary
MDW
Chicago
$214 Roundtrip, found 2 days ago
$214
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Nov 25 from Calgary to Chicago, returning Tue, Dec 2, priced at $214 found 2 days ago
Delta
Sat, Jan 17 - Tue, Jan 20
YYC
Calgary
MDW
Chicago
$214 Roundtrip, found 3 days ago
$214
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Jan 17 from Calgary to Chicago, returning Tue, Jan 20, priced at $214 found 3 days ago
Delta
Tue, Nov 25 - Mon, Dec 1
YYC
Calgary
MDW
Chicago
$224 Roundtrip, found 3 days ago
$224
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Nov 25 from Calgary to Chicago, returning Mon, Dec 1, priced at $224 found 3 days ago
Delta
Tue, Dec 30 - Wed, Jan 14
YYC
Calgary
MDW
Chicago
$233 Roundtrip, found 20 hours ago
$233
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Dec 30 from Calgary to Chicago, returning Wed, Jan 14, priced at $233 found 20 hours ago
Delta
Tue, Dec 30 - Tue, Jan 13
YYC
Calgary
MDW
Chicago
$234 Roundtrip, found 2 days ago
$234
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Dec 30 from Calgary to Chicago, returning Tue, Jan 13, priced at $234 found 2 days ago
Delta
Mon, Nov 24 - Tue, Dec 2
YYC
Calgary
MDW
Chicago
$236 Roundtrip, just found
$236
Roundtrip
just found
Select Delta flight, departing Mon, Nov 24 from Calgary to Chicago, returning Tue, Dec 2, priced at $236 just found
Delta
Tue, Nov 25 - Sat, Nov 29
YYC
Calgary
MDW
Chicago
$237 Roundtrip, found 2 days ago
$237
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Nov 25 from Calgary to Chicago, returning Sat, Nov 29, priced at $237 found 2 days ago
Delta
Thu, Jan 29 - Mon, Feb 2
YYC
Calgary
MDW
Chicago
$248 Roundtrip, just found
$248
Roundtrip
just found
Select Delta flight, departing Thu, Jan 29 from Calgary to Chicago, returning Mon, Feb 2, priced at $248 just found
Delta
Thu, Jan 1 - Wed, Jan 14
YYC
Calgary
MDW
Chicago
$250 Roundtrip, found 20 hours ago
$250
Roundtrip
found 20 hours ago
Select Delta flight, departing Thu, Jan 1 from Calgary to Chicago, returning Wed, Jan 14, priced at $250 found 20 hours ago

Find the cheapest month to fly from Calgary (YYC) to Chicago (MDW)

January is typically the cheapest month to fly

From $214 - $652 per traveler.

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $236
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $236

Frequently asked questions

How much does a flight from Calgary Intl. Airport (YYC) to Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight from $132 or cheap return flight from $213 from Calgary Intl. Airport (YYC) to Midway Intl. Airport (MDW) 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 Calgary Intl. Airport (YYC) to Midway Intl. Airport (MDW)?
January is the most affordable month to fly from YYC to MDW. Traveling during an off-peak travel window is often the key to finding better deals on flights.
What is the cheapest airline that flies from Calgary Intl. Airport (YYC) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest YYC to MDW flight.
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.

Travel information

Origin airport
Calgary Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, WestJet
Roundtrip price
$212
Distance
1396 mi

Book with confidence

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 January. 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 $132 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.

 

Calgary to Chicago Flights

Explore a world of travel with Expedia

*Available to One Key members.