WestJet
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Calgary International Airport
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United States
O'Hare International Airport
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Scan through all non-stop flights from Calgary to Chicago. The full flight schedule below gives an overview of all non-stop flights from YYC to ORD, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Known for its continental climate, Chicago features hot, humid summers with temperatures above 30°C (86°F) and cold, snowy winters that often drop below 0°C (32°F). This striking seasonal contrast offers travelers a variety of activities, from summer hiking to winter sports, ensuring year-round appeal.
The best time to visit Chicago is from March to November, covering spring, summer, and fall. While summer can be hot, it also sees slightly more rainfall than other seasons.
In total there are 3 airlines operating nonstop flights from Calgary YYC to Chicago ORD. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their YYC ORD flight schedule.
Flights from YYC to ORD are operated 14 times a week, with an average of 2 flights per day. Departure times vary between 06:15 - 14:14. The earliest flight departs at 06:15, the last flight departs at 14:14. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
You can fly in Economy, Premium Economy and Business Class. First Class is not available on this route (at least not as a non-stop flight).
The fastest direct flight from Calgary to Chicago takes 3 hours and 30 minutes. The flight distance between Calgary and Chicago is 1,381 miles (or 2,223 km).
There are 2 airports in Chicago: O'Hare International Airport (ORD) and Midway International Airport (MDW).
There are 14 flights per week flying from Calgary to Chicago (as of April 2026).
3 hours and 30 minutes is the average flight time from Calgary to Chicago.
The distance from Calgary to Chicago is 1,381 miles (2,223 kilometers).
American Airlines, United Airlines and WestJet are flying nonstop from Calgary to Chicago.
Oneworld and Star Alliance are flying nonstop from Calgary to Chicago.
You can fly non-stop in Economy, Premium Economy and Business Class.
Aircraft types that fly from Calgary to Chicago:
The earliest flight departs at 06:15 from Calgary and arrives at 10:45 at Chicago.
The latest flight departs at 14:14 from Calgary and arrives at 18:59 at Chicago.
1,381 miles (2,223 km) · 3h 30m
09:00
13:35
WestJet
WS 1610
WestJet
Boeing 737 MAX 8
Y
W
J
F
09:00
13:35
WestJet
WS 1610
WestJet
Boeing 737-700 (winglets)
Y
W
J
F
09:00
13:35
WestJet
WS 1610
WestJet
Boeing 737-700 (winglets)
Y
W
J
F
09:00
13:35
WestJet
WS 1610
WestJet
Boeing 737-800 (winglets)
Y
W
J
F
09:00
13:35
WestJet
WS 1610
WestJet
Boeing 737-700 (winglets)
Y
W
J
F
09:00
13:35
WestJet
WS 1610
WestJet
Boeing 737 MAX 8
Y
W
J
F
12:00
16:40
WestJet
WS 1610
WestJet
Boeing 737-800 (winglets)
Y
W
J
F
12:00
16:40
WestJet
WS 1610
WestJet
Boeing 737 MAX 8
Y
W
J
F
12:00
16:40
WestJet
WS 1610
WestJet
Boeing 737-800 Sky Interior
Y
W
J
F
12:34
17:01
United Airlines
Star Alliance
UA 1655
United Airlines
Boeing 737-700
Y
W
J
F
12:34
17:03
United Airlines
Star Alliance
UA 1655
United Airlines
Airbus A320-100/200
Y
W
J
F
12:34
17:01
United Airlines
Star Alliance
UA 1655
United Airlines
Boeing 737-700
Y
W
J
F
13:30
18:10
American Airlines
Oneworld
AA 4161
American Airlines
Embraer 175
Y
W
J
F
13:40
18:15
American Airlines
Oneworld
AA 4161
American Airlines
Embraer 175
Y
W
J
F
13:40
18:15
American Airlines
Oneworld
AA 4161
American Airlines
Embraer 175
Y
W
J
F
13:40
18:15
American Airlines
Oneworld
AA 4161
American Airlines
Embraer 175
Y
W
J
F
13:40
18:15
American Airlines
Oneworld
AA 4161
American Airlines
Embraer 175
Y
W
J
F
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