Cheap flights from Calgary to Chicago from C$ 141
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 17/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names, great deals
Big names, great deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Early arrival? Instantly customize your resultsTrusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Calgary to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last-minute flights
Cheap direct flights
WestJet flights from Calgary to Chicago O'Hare Intl Airport
Our best WestJet 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
See travel insights to Chicago from
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?
In general, May is the cheapest month to fly from Calgary to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 269. The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Calgary averaging around C$ 283.
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 Thursday when prices can be found for as low as C$ 660. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Calgary to Chicago O'Hare Intl Airport for around C$ 1,000.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
In the evening is the cheapest time of day to fly from Calgary to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 486. Flying to Chicago O'Hare Intl Airport in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 1,491 on average. Flights to Chicago O'Hare Intl Airport from Calgary at noon are generally more expensive because this time of day is more convenient for travellers’ schedules.
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 25 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around C$ 415 when searching 25 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 C$ 279 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?
Air Canada, WestJet, and American Airlines are the most popular carriers operating from Calgary to Chicago O'Hare Intl
Which airlines fly to Chicago O'Hare Intl Airport?
WestJet, Air Canada and United Airlines 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 48% of people opting to fly with this airline when travelling to Chicago O'Hare Intl Airport. Keep in mind that there are 5 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?
4 flights are operational daily from Calgary to Chicago O'Hare Intl Airport as of April 2025. The most popular departure time for this route is 12:00p.m., with 95% of flights per day taking off in the afternoon.
How many flights depart from Calgary to Chicago O'Hare Intl Airport on average per week?
30 flights are operational weekly from Calgary to Chicago O'Hare Intl Airport as of April 2025. The most popular departure day for this route is Tue, with 20% of flights per week 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?
There are 2223.9 km between Calgary and Chicago O'Hare Intl. 3h 25m is a normal flight duration for this route.
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 were last updated today.
How many operators does momondo search for flights from Calgary Airport to Chicago O'Hare Intl Airport?
As of April 2025, there are 5 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?
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 O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The travel and health documents required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Calgary to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Calgary to Chicago O'Hare Intl Airport is Boeing 737-700 (38.95% of total bookings). The next most popular plane models are Airbus A319 (17.43%), Boeing 737-800 (9.71%), and Boeing 737 MAX 8 (8.88%).
What is the most popular airline from Calgary to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Calgary and Chicago O'Hare Intl Airport, the leading airline is WestJet, making up 46% of the total bookings. Other popular airlines include Air Canada with 26%, United Airlines with 19%, and Delta with 5%.
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 C$ 154 | Free Cancellation | Rating 7.0 9,242 reviews | |||
| PriceFrom C$ 170 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom C$ 178 | Free Cancellation | Rating 7.2 2,823 reviews | |||
| PriceFrom C$ 200 | Free Cancellation | Rating 8.0 7,936 reviews | |||
| PriceFrom C$ 253 | Free Cancellation | Rating 7.4 8,696 reviews |
United Airlines Flights From Calgary to Chicago O'Hare Intl Airport
Across 1 United Airlines flight from Calgary to Chicago O'Hare Intl Airport this week, the average price was C$ 424, with the best United Airlines deals starting from C$ 183 round-trip. 8,696 users have rated United Airlines on momondo, with an average score of 7.4/10.
American Airlines Flights From Calgary to Chicago O'Hare Intl Airport
The best American Airlines deal for Calgary to Chicago O'Hare Intl Airport flight tickets found on momondo in the last 72 hours was C$ 123, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at C$ 263 round-trip. American Airlines operates 7 flights out of Calgary into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 10,000 American Airlines reviews by users on momondo have scored the airline at 7.2/10.
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 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?
Yes momondo offers price alerts on flights to Chicago from Calgary. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.