Cheap flights from Calgary to Chicago

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Calgary to Chicago flight comparison made easy

Below you can see the best fares for your route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Calgary to Chicago by changing tabs
Quickest
Cheapest
Delta
Delta
25 Nov.
YYC
1:10 a.m.
Calgary airport
7h 50m
1 Stop
10:00 a.m.
ORD
Chicago O'Hare Intl airport
Delta
30 Nov.
ORD
3:10 a.m.
Chicago O'Hare Intl airport
6h 45m
1 Stop
8:55 a.m.
YYC
Calgary airport
386 CAD
Delta
Delta
26 Nov.
YYC
8:50 a.m.
Calgary airport
5h 34m
1 Stop
3:24 p.m.
MDW
Chicago Midway airport
Delta
01 Dec.
MDW
12:15 a.m.
Chicago Midway airport
5h 54m
1 Stop
5:09 a.m.
YYC
Calgary airport
386 CAD
Delta
Delta
27 Nov.
YYC
1:10 a.m.
Calgary airport
7h 50m
1 Stop
10:00 a.m.
ORD
Chicago O'Hare Intl airport
Delta
07 Dec.
ORD
12:30 a.m.
Chicago O'Hare Intl airport
7h 55m
1 Stop
7:25 a.m.
YYC
Calgary airport
386 CAD
United Airlines
United Airlines
01 May
YYC
9:15 a.m.
Calgary airport
3h 25m
1:40 p.m.
ORD
Chicago O'Hare Intl airport
United Airlines
03 May
ORD
4:50 a.m.
Chicago O'Hare Intl airport
3h 55m
7:45 a.m.
YYC
Calgary airport
471 CAD
Major Airline
Major Airline
23 Nov.
YYC
5:15 a.m.
Calgary airport
3h 36m
9:51 a.m.
ORD
Chicago O'Hare Intl airport
Major Airline
01 Dec.
ORD
1:45 p.m.
Chicago O'Hare Intl airport
4h 00m
4:45 p.m.
YYC
Calgary airport
407 CAD
United Airlines
United Airlines
28 Nov.
YYC
1:30 a.m.
Calgary airport
3h 26m
5:56 a.m.
ORD
Chicago O'Hare Intl airport
United Airlines
29 Nov.
ORD
6:55 a.m.
Chicago O'Hare Intl airport
5h 57m
1 Stop
11:52 a.m.
YYC
Calgary airport
425 CAD

How to get the cheapest flight 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 for your trip
What is the cheapest month to fly to Chicago?
September
The cheapest time of year to fly to Chicago from Calgary is September. The most expensive is December.
What is the cheapest day to fly to Chicago?
Tuesday
The cheapest day of the week is typically Tuesday. The most expensive is typically Sunday
When is the cheapest time to fly to Chicago?
in the evening
Calgary to Chicago flights are approximately 21% more expensive in the morning than in the evening
What is the cheapest airline that flies to Chicago?
Frontier
Frontier, Alaska Airlines, and Finnair are the most popular carriers operating from Calgary to Chicago
What is the cheapest route?
Calgary - Chicago Midway
Fly from Calgary to Chicago Midway for the best Calgary - Chicago flight prices
When is the cheapest time to book a flight to Chicago?
57 days before
The cheapest time to buy a flight from Calgary to Chicago is approximately 57 days before departure
60
Days before departure
0

Flight information for Calgary to Chicago

Find info about flight duration, direct flights, and airports for your flight from Calgary to Chicago
Fastest flight time 3h 26m The fastest flight from Calgary to Chicago takes 3h 26m.
Direct flights Every day Direct flights go from Calgary to Chicago every day.
Airports in Chicago 3 airports There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

Alternative routes for Calgary to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Calgary to Indianapolis
Fastest flight time
5h 29m
Cheapest price
366 CAD

Flights from Calgary to:

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