An airplane exhibit labeled "Concourse A" in an airport terminal.

CA $222 Cheap Flights from Calgary (YYC) to Chicago (MDW)

View CA $222 flight on Sat, Nov 21, 2026Opens in a new window

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

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our rewards
    Sign in

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

Prices were available within the past 7 days and start at CA $222 for one-way flights and CA $366 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Nov 21 - Sat, Dec 5
YYC
Calgary
MDW
Chicago
CA $366 Roundtrip, found 22 hours ago
CA $366
Roundtrip
found 22 hours ago
Select Delta flight, departing Sat, Nov 21 from Calgary to Chicago, returning Sat, Dec 5, priced at CA $366 found 22 hours ago
Delta
Tue, Nov 3 - Tue, Nov 17
YYC
Calgary
MDW
Chicago
CA $397 Roundtrip, found 13 hours ago
CA $397
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Nov 3 from Calgary to Chicago, returning Tue, Nov 17, priced at CA $397 found 13 hours ago
Delta
Tue, Oct 20 - Mon, Oct 26
YYC
Calgary
MDW
Chicago
CA $425 Roundtrip, found 6 days ago
CA $425
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Oct 20 from Calgary to Chicago, returning Mon, Oct 26, priced at CA $425 found 6 days ago
Delta
Tue, Nov 3 - Tue, Nov 17
YYC
Calgary
MDW
Chicago
CA $432 Roundtrip, found 13 hours ago
CA $432
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Nov 3 from Calgary to Chicago, returning Tue, Nov 17, priced at CA $432 found 13 hours ago
Delta
Tue, Sep 1 - Sat, Sep 5
YYC
Calgary
MDW
Chicago
CA $432 Roundtrip, found 23 hours ago
CA $432
Roundtrip
found 23 hours ago
Select Delta flight, departing Tue, Sep 1 from Calgary to Chicago, returning Sat, Sep 5, priced at CA $432 found 23 hours ago
Delta
Sat, Sep 5 - Sat, Sep 12
YYC
Calgary
MDW
Chicago
CA $435 Roundtrip, found 23 hours ago
CA $435
Roundtrip
found 23 hours ago
Select Delta flight, departing Sat, Sep 5 from Calgary to Chicago, returning Sat, Sep 12, priced at CA $435 found 23 hours ago
Delta
Sat, Nov 21 - Sat, Dec 5
YYC
Calgary
MDW
Chicago
CA $440 Roundtrip, found 22 hours ago
CA $440
Roundtrip
found 22 hours ago
Select Delta flight, departing Sat, Nov 21 from Calgary to Chicago, returning Sat, Dec 5, priced at CA $440 found 22 hours ago
Delta
Sat, Dec 5 - Tue, Dec 8
YYC
Calgary
MDW
Chicago
CA $443 Roundtrip, found 4 days ago
CA $443
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Dec 5 from Calgary to Chicago, returning Tue, Dec 8, priced at CA $443 found 4 days ago
Delta
Wed, Jan 6 - Thu, Jan 7
YYC
Calgary
MDW
Chicago
CA $446 Roundtrip, found 2 days ago
CA $446
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jan 6 from Calgary to Chicago, returning Thu, Jan 7, priced at CA $446 found 2 days ago
Delta
Sat, Nov 21 - Sat, Dec 5
YYC
Calgary
MDW
Chicago
CA $450 Roundtrip, found 22 hours ago
CA $450
Roundtrip
found 22 hours ago
Select Delta flight, departing Sat, Nov 21 from Calgary to Chicago, returning Sat, Dec 5, priced at CA $450 found 22 hours 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 $545
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $545

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

March is typically the cheapest month to fly

From CA $315 - CA $669 per traveller.

Frequently asked questions

How much does a flight from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from CA $222 and cheap return flights from CA $366 YYC to MDW with Expedia. One-way flights typically cost between CA$232 and CA$970, and return flights often range between CA$967 and CA$3026. 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 YYC to MDW ticket fares go up or down.
What is the cheapest month to fly from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest months to fly from YYC to MDW are typically during off-peak season 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 are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter YYC to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.)?
Porter Airlines is one of the cheapest airlines offering connecting return flights from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.), with tickets starting from around CA$1357 for flights that can be booked for departure within the next year. These flights typically include a layover in Pearson Intl. (YYZ). 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.
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 16 connecting flights per day from Calgary International Airport (YYC) to Chicago Midway International Airport (MDW). Some common connection points include Pearson International (YYZ), Minneapolis - St. Paul International (MSP), and Hartsfield-Jackson Atlanta International (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 around 12:20 AM. This service is offered by WestJet and Delta. This is a seasonal service, active only in October. An early departure like this can help you make the most of 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 International Airport (YYC) to Chicago Midway International Airport (MDW) on a Saturday, with around 16 flights available. This gives you a good selection of options if you're planning to travel on the weekend. Major airlines on this route include WestJet, Delta, and United.
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 Intl. (YYC) to Midway Intl. (MDW) are in the early morning, from 6am to 9am. Many major carriers, including Delta, WestJet and United, offer flights during this window. Many travellers prefer these times because it allows for an early start to their travel day, often leading to an earlier arrival at their destination.
How long does it take to fly from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are no nonstop flights from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.). For flights with one stop, you can expect the journey to take around 5 hours 30 minutes. This route covers a distance of approximately 2,248 kilometres. Keep in mind that these are average times, and your actual travel duration can vary depending on the specific routing, layover times, and even weather conditions.
Can you fly business or first class from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (MDW-Midway Intl.)?
You can fly business class or first class between YYC and MDW. First class cabins are available on Delta.
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, IL (MDW) from Calgary, AB (YYC)?
If you're planning to travel to Chicago from Calgary Intl. (YYC), you can fly directly into Midway Intl. (MDW). Some flights may connect through major hubs like Pearson Intl. (YYZ), Denver Intl. (DEN), or 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 $365
Distance
2234 km

Book with confidence

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 $366 rising to CA $707.  

Here are more money-saving tips: 

  • Fly in November 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

Explore a world of travel with Expedia

*Available to Expedia members.