CA $214 Cheap Flights from Calgary (YYC) to Chicago (MDW)

View CA $214 flight on Thu, May 28, 2026Opens in a new window

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

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Cheap flights from Calgary (YYC) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $214 for one-way flights and CA $314 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Oct 31 - Sat, Nov 14
YYC
Calgary
MDW
Chicago
CA $314 Roundtrip, found 11 hours ago
CA $314
Roundtrip
found 11 hours ago
Select Delta flight, departing Sat, Oct 31 from Calgary to Chicago, returning Sat, Nov 14, priced at CA $314 found 11 hours ago
Delta
Wed, May 20 - Fri, Aug 21
YYC
Calgary
MDW
Chicago
CA $326 Roundtrip, found 3 days ago
CA $326
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, May 20 from Calgary to Chicago, returning Fri, Aug 21, priced at CA $326 found 3 days ago
Delta
Tue, May 19 - Tue, May 26
YYC
Calgary
MDW
Chicago
CA $331 Roundtrip, found 6 days ago
CA $331
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, May 19 from Calgary to Chicago, returning Tue, May 26, priced at CA $331 found 6 days ago
Delta
Wed, Aug 12 - Fri, Aug 14
YYC
Calgary
MDW
Chicago
CA $338 Roundtrip, found 5 days ago
CA $338
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Aug 12 from Calgary to Chicago, returning Fri, Aug 14, priced at CA $338 found 5 days ago
Delta
Sat, Oct 31 - Wed, Nov 18
YYC
Calgary
MDW
Chicago
CA $354 Roundtrip, found 11 hours ago
CA $354
Roundtrip
found 11 hours ago
Select Delta flight, departing Sat, Oct 31 from Calgary to Chicago, returning Wed, Nov 18, priced at CA $354 found 11 hours ago
Delta
Thu, May 21 - Wed, May 27
YYC
Calgary
MDW
Chicago
CA $362 Roundtrip, found 1 day ago
CA $362
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, May 21 from Calgary to Chicago, returning Wed, May 27, priced at CA $362 found 1 day ago
Delta
Wed, Aug 12 - Fri, Aug 14
YYC
Calgary
MDW
Chicago
CA $363 Roundtrip, found 5 days ago
CA $363
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Aug 12 from Calgary to Chicago, returning Fri, Aug 14, priced at CA $363 found 5 days ago
Delta
Sun, May 10 - Sat, May 16
YYC
Calgary
MDW
Chicago
CA $368 Roundtrip, found 6 days ago
CA $368
Roundtrip
found 6 days ago
Select Delta flight, departing Sun, May 10 from Calgary to Chicago, returning Sat, May 16, priced at CA $368 found 6 days ago
Delta
Wed, May 20 - Wed, May 27
YYC
Calgary
MDW
Chicago
CA $378 Roundtrip, found 2 days ago
CA $378
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, May 20 from Calgary to Chicago, returning Wed, May 27, priced at CA $378 found 2 days ago
WestJet
Sun, May 31 - Wed, Jun 3
YYC
Calgary
MDW
Chicago
CA $1,176 Roundtrip, found 5 days ago
CA $1,176
Roundtrip
found 5 days ago
Select WestJet flight, departing Sun, May 31 from Calgary to Chicago, returning Wed, Jun 3, priced at CA $1,176 found 5 days ago

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 centre is 23 minutes. Flights from CA $544
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $544

Frequently asked questions

How much does a flight from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
One-way flights typically cost between $483 and $1,807 and return flights often range between $483 and $1,807. 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 Anaa (AAA) to Toronto, ON (YYZ-Pearson Intl.) ticket fares go up or down.
How do I find cheap flights from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway 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 Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway 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.
How many flights per day from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are approximately 15 connecting flights per day from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.). Some common connection points include Pearson Intl. (YYZ), Minneapolis - St. Paul Intl. (MSP), and Hartsfield-Jackson Atlanta Intl. (ATL).
What is the earliest flight from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Calgary International Airport (YYC) to Midway International Airport (MDW) typically departs at approximately 12:20 AM local time. This service is operated by WestJet and Delta. This is a seasonal service active in October. An early departure like this can help maximize your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.)?
You'll typically find the most flights from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.) on a Wednesday, with around 22 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include WestJet, Delta Air Lines, and United Airlines. Wednesday offers notably more flight options compared to other days.
What are the most popular departure times for flights from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Calgary International Airport (YYC) to Midway International Airport (MDW) are in the early morning, from 6am to 9am. About 57% of passengers prefer this time. Many major carriers, including Delta and WestJet, offer flights during this window. This timing works well because it allows you to get an early start on your travel day.
How long does it take to fly from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.)?
Flights from YYC to MDW with one stop typically take around 5 hours 30 minutes, covering approximately 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 Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.)?
Select the "Business class" and "First class" filters when looking for YYC to MDW flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway 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 Chicago from Calgary Intl. (YYC)?
When traveling from Calgary Intl. (YYC) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like Vancouver Intl. (YVR), Edmonton Intl. (YEG), Seattle - Tacoma Intl. (SEA) before reaching Chicago. 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 Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway 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 Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package 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 Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway 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
Calgary Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, WestJet
Roundtrip price
CA $314
Distance
2234 km

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Calgary to Chicago Flights

The easy way to book your flights from Calgary to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Calgary whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Midway Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Calgary to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Calgary Intl., YYC to Midway Intl., MDW 

Sort your search results by price to find great deals on your flight from Calgary to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Calgary currently is just CA $314 rising to CA $1,176.  

Here are more money-saving tips: 

  • Fly in October when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Calgary 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Calgary to Chicago Flights

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