Cheap flights from Calgary to Chicago from $109
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 4/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Deals available from 900+ travel sites.
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted 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
American Airlines flights from Calgary to Chicago
Our best American Airlines deals on Calgary to Chicago flight tickets
WestJet flights from Calgary to Chicago
Our best WestJet deals on Calgary to Chicago flight tickets
See travel insights to Chicago from
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 typical price of a round-trip flight between Calgary and Chicago?
What is the cheapest month to fly to Chicago?
The month of February is, on average, the cheapest month to fly to Chicago from Calgary, with most prices found around $198. If you’re not able to fly to Chicago in February, then May is your next best option. Flight prices from Calgary to Chicago during May average around $199.
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 Sunday when prices can be found for as low as $274. This is often the case because there is less demand to fly during this day of the week. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Calgary to Chicago for around $404.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Calgary to Chicago during this time can be as low as $215. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $356.
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 25 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $323 when searching 25 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 $211 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.
What is the cheapest airline that flies from Calgary to Chicago?
Air Canada, WestJet, and American Airlines are the most popular carriers operating from Calgary to Chicago
What 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 32% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 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?
5 flights are operational daily from Calgary to Chicago as of March 2025. The most popular departure time for this route is 12:00PM, with 95% of flights per day taking off in the afternoon.
How many flights depart from Calgary to Chicago on average per week?
37 flights are operational weekly from Calgary to Chicago as of March 2025. The most popular departure day for this route is Mon, with 22% 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 1397.6 mi away from Calgary. In terms of flight time, this usually takes a little over 3h 25m.
When did momondo last update prices for flights from Calgary Airport to Chicago?
Prices for flights from Calgary Airport to Chicago were last updated today.
How many operators does momondo search for flights from Calgary Airport to Chicago?
As of March 2025, there are 4 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 a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to 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?
momondo data reveals that the most frequently booked plane model on the route from Calgary to Chicago is Boeing 737-700, representing 28.70% of all bookings. The subsequent popular models are Airbus A319 at 17.95%, Boeing 737-800 at 14.31%, and Boeing 737-700 Passenger/BBJ1 (winglets) at 8.64%.
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 31% of the total bookings. Other popular airlines include Air Canada with 25%, United Airlines with 23%, and American Airlines with 13%.
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 $139 | Free Cancellation | Rating 7.2 2,776 reviews | |||
| PriceFrom $154 | Free Cancellation | Rating 7.0 8,870 reviews | |||
| PriceFrom $219 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $239 | Free Cancellation | Rating 7.4 8,631 reviews |
United Airlines Flights From Calgary to Chicago
United Airlines operates around 6 flights from Calgary to Chicago every week. The average price of these flights found in the last 72 hours has been $490, but momondo users have found United Airlines deals from Calgary to Chicago from as low as $239 round-trip. United Airlines has been scored 7.4/10 in 8,631 reviews.
WestJet Flights From Calgary to Chicago
Another popular option for Calgary to Chicago flights is WestJet (7.2/10, 2,776 ratings). WestJet flies from Calgary to Chicago around 2 times per week, with deals starting from $139 round-trip and rising to an average price of around $219.
Traveling 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?
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. momondo allows you to filter the results for Calgary to Chicago flights to just show those with flexible booking policies.
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?
If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Calgary and alert you when they change.