Cheap flights from Calgary to Chicago from C$ 128
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 11/10. 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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WestJet flights from Calgary to Chicago
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United Airlines flights from Calgary to Chicago
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How to get the cheapest flight ticket from Calgary to Chicago
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?
The month of February is another great option to travel to Chicago, with average flight prices from Calgary averaging around C$ 273.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 666. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,005. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.
What is the cheapest time of day to depart on your flight to Chicago?
In the afternoon is the cheapest time of day to fly from Calgary to Chicago when you can find flight prices for as low as C$ 361. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,431 per ticket.
What is the cheapest Calgary to Chicago flight route?
Fly from Calgary to Chicago O'Hare Intl for the best Calgary - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Calgary when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 375 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Calgary for as low as C$ 283 on momondo.
What cabin class options are available on Calgary to Chicago flights?
There are 4 cabin classes available to choose from on Calgary to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Calgary to Chicago flights?
You could potentially save up to 2% on your flight if you consider stops on a Calgary to Chicago flight.
How have Calgary to Chicago flight prices changed over time?
As of July 2025, prices for Calgary to Chicago flights are approximately 10% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Calgary to Chicago?
WestJet, American Airlines, and United Airlines are the most popular carriers operating from Calgary to Chicago
Which airlines fly to Chicago?
WestJet, Air Canada and United Airlines are the top three most popular airlines that fly to Chicago from Calgary according to our data. WestJet is the first choice among our users, with 45% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Calgary to Chicago on average per day?
As of July 2025, there are 11 flights per day flying from Calgary to Chicago. The most common time of day flights depart is 12:00p.m., with 58% of flights taking off in the afternoon.
How many flights depart from Calgary to Chicago on average per week?
79 flights are operational weekly from Calgary to Chicago as of July 2025. The most popular departure day for this route is Tue, with 19% of flights per week taking off on this day.
When to book flights from Calgary to Chicago
Cheap Calgary to Chicago (YYC to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Calgary to Chicago
How far is Calgary to Chicago by plane?
Chicago is 2249.2 km away from Calgary. Flights usually cover this in 3h 20m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Calgary Airport to Chicago?
Prices for flights from Calgary Airport to Chicago are updated daily.
How many operators does momondo search for flights from Calgary Airport to Chicago?
As of July 2025, there are 5 operators available to choose from for flights from Calgary Airport to Chicago.
How old do you have to be to fly from Calgary Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Calgary Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Calgary to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Calgary to Chicago is Boeing 737-700 (37.34% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (17.64%), Airbus A319 (11.07%), and Boeing 737-800 Passenger/BBJ2 (winglets) (9.80%).
What is the most popular airline from Calgary to Chicago?
Based on momondo bookings for flights between Calgary and Chicago, the leading airline is WestJet, making up 44% of the total bookings. Other popular airlines include Air Canada with 26%, United Airlines with 15%, and American Airlines with 10%.
Best airlines flying from Calgary to Chicago
Compare and see reviews for airlines that fly from Calgary to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom C$ 148 | Free Cancellation | Rating 7.1 9,683 reviews | |||
| PriceFrom C$ 169 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom C$ 175 | Free Cancellation | Rating 7.2 2,920 reviews | |||
| PriceFrom C$ 184 | Free Cancellation | Rating 8.0 7,958 reviews | |||
| PriceFrom C$ 249 | Free Cancellation | Rating 7.4 8,844 reviews |
Delta Flights From Calgary to Chicago
Delta operates around 3 flights from Calgary to Chicago every week. The average price of these flights found in the last 72 hours has been C$ 268, but momondo users have found Delta deals from Calgary to Chicago from as low as C$ 135 round-trip. Delta has been scored 8.0/10 in 7,962 reviews.
United Airlines Flights From Calgary to Chicago
The best United Airlines deal for Calgary to Chicago flight tickets found on momondo in the last 72 hours was C$ 183, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at C$ 401 round-trip. United Airlines operates 10 flights out of Calgary into Chicago in an average week, so prices vary by time and availability. 8,844 United Airlines reviews by users on momondo have scored the airline at 7.4/10.
Travelling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Calgary to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Calgary to Chicago. momondo saves you time and could save you money on your trip.
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 for Calgary to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
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.