CA $184 Cheap Flights from Calgary (YYC) to Chicago (ORD)

View CA $184 flight on Thu, May 28, 2026Opens in a new window

Popular airlines from Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD)

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

Prices were available within the past 7 days and start at CA $184 for one-way flights and CA $298 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Sat, May 23 - Wed, May 27
YYC
Calgary
ORD
Chicago
CA $298 Roundtrip, just found
CA $298
Roundtrip
just found
Select WestJet flight, departing Sat, May 23 from Calgary to Chicago, returning Wed, May 27, priced at CA $298 just found
WestJet
Tue, May 19 - Sat, May 23
YYC
Calgary
ORD
Chicago
CA $299 Roundtrip, found 2 hours ago
CA $299
Roundtrip
found 2 hours ago
Select WestJet flight, departing Tue, May 19 from Calgary to Chicago, returning Sat, May 23, priced at CA $299 found 2 hours ago
Air Canada
Sat, May 9 - Sat, May 9
YYC
Calgary
ORD
Chicago
CA $312 Roundtrip, found 1 day ago
CA $312
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, May 9 from Calgary to Chicago, returning Sat, May 9, priced at CA $312 found 1 day ago
Delta
Sat, May 23 - Wed, May 27
YYC
Calgary
ORD
Chicago
CA $315 Roundtrip, just found
CA $315
Roundtrip
just found
Select Delta flight, departing Sat, May 23 from Calgary to Chicago, returning Wed, May 27, priced at CA $315 just found
United
Sun, May 24 - Mon, May 25
YYC
Calgary
ORD
Chicago
CA $317 Roundtrip, found 1 day ago
CA $317
Roundtrip
found 1 day ago
Select United flight, departing Sun, May 24 from Calgary to Chicago, returning Mon, May 25, priced at CA $317 found 1 day ago
American Airlines
Sat, May 23 - Wed, May 27
YYC
Calgary
ORD
Chicago
CA $321 Roundtrip, just found
CA $321
Roundtrip
just found
Select American Airlines flight, departing Sat, May 23 from Calgary to Chicago, returning Wed, May 27, priced at CA $321 just found
WestJet
Mon, May 11 - Sat, May 16
YYC
Calgary
ORD
Chicago
CA $324 Roundtrip, found 5 hours ago
CA $324
Roundtrip
found 5 hours ago
Select WestJet flight, departing Mon, May 11 from Calgary to Chicago, returning Sat, May 16, priced at CA $324 found 5 hours ago
WestJet
Thu, May 28 - Sun, May 31
YYC
Calgary
ORD
Chicago
CA $326 Roundtrip, just found
CA $326
Roundtrip
just found
Select WestJet flight, departing Thu, May 28 from Calgary to Chicago, returning Sun, May 31, priced at CA $326 just found
Delta
Sun, May 24 - Thu, Jun 4
YYC
Calgary
ORD
Chicago
CA $326 Roundtrip, found 4 days ago
CA $326
Roundtrip
found 4 days ago
Select Delta flight, departing Sun, May 24 from Calgary to Chicago, returning Thu, Jun 4, priced at CA $326 found 4 days ago
American Airlines
Sat, May 23 - Wed, May 27
YYC
Calgary
ORD
Chicago
CA $328 Roundtrip, just found
CA $328
Roundtrip
just found
Select American Airlines flight, departing Sat, May 23 from Calgary to Chicago, returning Wed, May 27, priced at CA $328 just found

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city centre is 16 minutes. Flights from CA $954
MDW
Midway Intl.
Closest
Average driving time to city centre16 min
Flights from CA $954

Frequently asked questions

How much does a flight from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
One-way flights typically cost between $442 and $2,392 and return flights often range between $980 and $4,000. 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.
Which airlines fly direct from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Enter YYC to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare 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 airline to fly with from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl.) will differ from traveler to traveler. If you like to fly early, WS offers early morning flights. If price is the most important factor, AA typically offers the lowest fares. AC offers the most daily flights from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl.), which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare 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 (ORD-O'Hare Intl.)?
There are approximately 5 nonstop flights per day from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl.). For even more choice, look at flights that include layovers, as there are around 72 connecting flights per day. Some common connection points include Pearson Intl. (YYZ), Seattle - Tacoma Intl. (SEA), and Vancouver Intl. (YVR).
What is the earliest flight from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Calgary International Airport (YYC) to O'Hare International Airport (ORD) typically departs at approximately 12:05 AM local time, operated by Air Canada. This is a seasonal service active in April. 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 (ORD-O'Hare Intl.)?
You'll typically find the most flights from Calgary Intl. (YYC) to O'Hare Intl. (ORD) on a Thursday, with around 45 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include Air Canada, WestJet, and United Airlines. Flight schedules are notably busier on Thursdays compared to other days of the week, offering you more choices.
What are the most popular departure times for flights from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl.) are in the early morning, from 6am to 9am. About 32% of passengers prefer this time. Many major carriers, including United Airlines, Air Canada and Delta, offer flights during this window. This timing works well because it allows you to get an early start on your travel day and arrive in Chicago with plenty of time for your activities.
How long does it take to fly from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A nonstop flight from YYC to ORD typically takes around 3 hours 30 minutes, covering approximately 1,382 miles. Connecting flights on this route usually add 4 hours 50 minutes to your travel time. 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 (ORD-O'Hare Intl.)?
Select the "Business class" and "First class" filters when looking for YYC to ORD flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How much is a business class flight from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A direct, round-trip business class ticket from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically costs between 3,614 CAD - 5,862 CAD. A non-stop, one-way business class flight is usually around 1,150 CAD - 1,572 CAD. You may also be able to find a cheaper business class journey between Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Anaa (AAA) (AAA) to Toronto, ON (YYZ-Pearson Intl.) (YYZ) if you opt for a connecting flight.
How do I earn miles on a Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare 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 Midway Intl. (MDW) and O'Hare Intl. (ORD). Some flights may connect through major hubs like Pearson Intl. (YYZ), Edmonton Intl. (YEG), Salt Lake City Intl. (SLC) 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 (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare 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 (ORD-O'Hare Intl.) flight and hotel package?
Securing a Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare 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 (ORD-O'Hare Intl.)?
If you booked your Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare 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
O'Hare Intl.
Airlines serving
Air Canada, Alaska Airlines, American Airlines, Delta, Porter Airlines, United, WestJet
Roundtrip price
CA $297
Distance
2211 km
Average flight time
4 hours 34 mins

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 O'Hare 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 O'Hare Intl., ORD 

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 $298 rising to CA $328.  

Here are more money-saving tips: 

  • Fly in May 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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