Cheap flights from Calgary to Chicago from $167
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 12/8. 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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Fly from
Fly to
Route
Depart
Return
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 12/11
9:07 am-4:49 pm
1 stop7h 42m
Chicago O'Hare Intl
Sun 12/13
6:00 am-10:37 pm
1 stop16h 37m
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Thu 10/22
1:51 pm-6:36 pm
Nonstop3h 45m
Chicago O'Hare Intl
Wed 10/28
10:00 am-12:51 pm
Nonstop3h 51m
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 11/20
1:37 pm-4:10 pm
Nonstop2h 33m
Chicago O'Hare Intl
Fri 11/27
8:40 am-1:35 pm
Nonstop4h 55m
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Wed 12/2
1:20 am-8:08 am
1 stop6h 48m
Chicago O'Hare Intl
Sun 12/13
4:30 pm-1:06 am
1 stop8h 36m
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Mon 11/2
1:45 am-10:07 am
1 stop8h 22m
Chicago O'Hare Intl
Sat 11/7
3:40 pm-1:50 am
1 stop10h 10m
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 10/23
1:51 pm-6:36 pm
Nonstop3h 45m
Chicago O'Hare Intl
Thu 10/29
10:00 am-12:51 pm
Nonstop3h 51m
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Fri 11/20
3:06 pm-10:59 pm
1 stop7h 53m
Chicago O'Hare Intl
Fri 11/27
8:40 am-1:35 pm
Nonstop4h 55m
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Thu 12/3
7:00 am-10:59 pm
1 stop15h 59m
Chicago O'Hare Intl
Sat 12/12
10:55 am-11:53 pm
1 stop12h 58m
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Sat 11/21
8:45 am-3:41 pm
1 stop6h 56m
Chicago O'Hare Intl
Sun 11/22
6:23 am-2:15 pm
1 stop7h 52m
CalgaryChicago
YYC Calgary - ORD Chicago O'Hare Intl
YYCORD
Calgary
Thu 10/29
7:45 am-4:40 pm
1 stop7h 55m
Chicago O'Hare Intl
Sun 11/1
12:30 pm-10:40 pm
1 stop10h 10m
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?
Prices are currently typical for flights on this route.
Typical prices usually range from $213 to $357.The lowest price recently found on this route was $294.
What is the cheapest month to fly to Chicago?
The month of May is, on average, the cheapest month to fly to Chicago from Calgary, with most prices found around $260. If you’re not able to fly to Chicago in May, then January is your next best option. Flight prices from Calgary to Chicago during January average around $262.
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 $409. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Calgary to Chicago for around $613.
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 morning. Flights from Calgary to Chicago during this time can be as low as $383. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $734.
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 from Calgary 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 $326 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 $224 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?
No. A direct flight is the cheapest option for a flight between Calgary to Chicago.
How have Calgary to Chicago flight prices changed over time?
As of October 2026, prices for Calgary to Chicago flights are approximately 14% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Calgary to Chicago?
United Airlines and Delta are the most popular carriers operating from Calgary to Chicago
What airlines fly to Chicago?
United Airlines, WestJet and American Airlines are the top three most popular airlines that fly to Chicago from Calgary according to our data. United Airlines is the first choice among our users, with 36% of people opting to fly with this airline when traveling 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?
9 flights are operational daily from Calgary to Chicago as of October 2026. The most popular departure time for this route is 12:00PM, with 100% of flights per day taking off in the afternoon.
How many flights depart from Calgary to Chicago on average per week?
63 flights are operational weekly from Calgary to Chicago as of October 2026. The most popular departure day for this route is Thu, with 17% 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
Frequently asked questions about flying 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 2h 20m.
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 October 2026, 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 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 737-800, representing 49.82% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 12.82%, Boeing 737-700 Passenger/BBJ1 (winglets) at 10.12%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 10.05%.
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 58% of the total bookings. Other popular airlines include American Airlines with 22% and United Airlines with 20%.
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 $135 | Free Cancellation | Rating 7.4 10,350 reviews | |||
| PriceFrom $149 | Free Cancellation | Rating 7.1 11,758 reviews | |||
| PriceFrom $163 | Free Cancellation | Rating 7.2 3,449 reviews | |||
| PriceFrom $195 | Free Cancellation | Rating 7.0 12,150 reviews | |||
| PriceFrom $253 | Free Cancellation | Rating 7.8 8,653 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 $318, but momondo users have found Delta deals from Calgary to Chicago from as low as $253 round-trip. Delta has been scored 7.8/10 in 8,653 reviews.
United Airlines Flights From Calgary to Chicago
Another popular option for Calgary to Chicago flights is United Airlines (7.4/10, 10,350 ratings). United Airlines flies from Calgary to Chicago around 7 times per week, with deals starting from $135 round-trip and rising to an average price of around $341.
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.