Cheap flights from Calgary to Chicago from $96
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Calgary to Chicago departing on 7/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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American Airlines flights from Calgary to Chicago O'Hare Intl Airport
Our best American Airlines deals on Calgary to Chicago O'Hare Intl Airport flight tickets
Air Canada flights from Calgary to Chicago O'Hare Intl Airport
Our best Air Canada deals on Calgary to Chicago O'Hare Intl Airport flight tickets
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How to get the cheapest flight ticket from Calgary to Chicago O'Hare Intl Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago O'Hare Intl Airport?
The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Calgary averaging around $184.
What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?
The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Sunday when prices can be found for as low as $171. This is often the case because there is less demand to fly during this day of the week. On the other hand, Tuesday is the most expensive day to depart from Calgary because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $436.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
Flying to Chicago O'Hare Intl Airport from Calgary in the morning is the least expensive time of day to depart. momondo users have found prices as low as $315 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $436. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Calgary to Chicago O'Hare Intl flight route?
Fly from Calgary to Chicago O'Hare Intl for the best Calgary - Chicago O'Hare Intl flight prices
How far in advance should I book a flight to Chicago O'Hare Intl Airport?
You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Calgary when booking 16 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $273 when searching 16 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Calgary for as low as $207 on momondo.
What cabin class options are available on Calgary to Chicago O'Hare Intl flights?
There are 4 cabin classes available to choose from on Calgary to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Calgary to Chicago O'Hare Intl?
WestJet, United Airlines, and Air Canada are the most popular carriers operating from Calgary to Chicago O'Hare Intl
What airlines fly to Chicago O'Hare Intl Airport?
WestJet, United Airlines and Air Canada are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Calgary according to our data. WestJet is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 4 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Calgary to Chicago O'Hare Intl Airport on average per day?
As of June 2025, there are 11 flights per day flying from Calgary to Chicago O'Hare Intl Airport. The most common time of day flights depart is 12:00PM, with 55% of flights taking off in the afternoon.
How many flights depart from Calgary to Chicago O'Hare Intl Airport on average per week?
As of June 2025, there are 83 flights per week flying from Calgary to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.
When to book flights from Calgary to Chicago O'Hare Intl Airport
Cheap Calgary to Chicago O'Hare Intl Airport (YYC to ORD) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Calgary to Chicago O'Hare Intl Airport
How far is Calgary to Chicago O'Hare Intl by plane?
The distance between Calgary and Chicago O'Hare Intl is about 1381.9 mi. Typically, this will take 3h 20m by plane in normal conditions.
When did momondo last update prices for flights from Calgary Airport to Chicago O'Hare Intl Airport?
Prices for flights from Calgary Airport to Chicago O'Hare Intl Airport are updated daily.
How many operators does momondo search for flights from Calgary Airport to Chicago O'Hare Intl Airport?
As of June 2025, there are 4 operators available to choose from for flights from Calgary Airport to Chicago O'Hare Intl Airport.
How old do you have to be to fly from Calgary Airport to Chicago O'Hare Intl Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Calgary Airport to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Calgary to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Calgary and Chicago O'Hare Intl Airport, the leading plane model is Boeing 737-700, making up 37.04% of the total bookings. Other popular models include Boeing 737 MAX 8 with 19.04%, Airbus A319 with 12.98%, and Boeing 737-800 Passenger/BBJ2 (winglets) with 9.75%.
What is the most popular airline from Calgary to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Calgary to Chicago O'Hare Intl Airport is WestJet (37% of total bookings). The next most popular airlines are United Airlines (25%), Air Canada (22%), and American Airlines (16%).
Best airlines flying from Calgary to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from Calgary to Chicago O'Hare Intl Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $109 | Free Cancellation | Rating 7.1 9,537 reviews | |||
| PriceFrom $139 | Free Cancellation | Rating 7.2 2,868 reviews | |||
| PriceFrom $205 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $239 | Free Cancellation | Rating 7.4 8,790 reviews |
United Airlines Flights From Calgary to Chicago O'Hare Intl Airport
United Airlines flight deals from Calgary to Chicago O'Hare Intl Airport start from $239 round-trip. Over the 10 United Airlines flights for this route in a normal week, average airfare is usually $473 round-trip - but some users have found much cheaper deals with momondo.
WestJet Flights From Calgary to Chicago O'Hare Intl Airport
Across 2,868 WestJet reviews on momondo, the average score is 7.2/10. WestJet flies from Calgary to Chicago O'Hare Intl Airport about 4 times each week, with ticket deals ranging from $139 to $195. Price data is based on momondo searches in the last 72 hours.
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Why should I use momondo to find a flight deal from Calgary to Chicago?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Calgary to Chicago for you.
Can I find flights from Calgary to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from Calgary on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Calgary to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Calgary.
I’m not ready to book a flight from Calgary to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Calgary are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.