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
Air Canada
Air Canada
20 Aug.
YYC
6:20 p.m.
Calgary airport
7h 53m
1 Stop
3:13 a.m.
+1
ORD
Chicago O'Hare Intl airport
Air Canada
22 Aug.
ORD
1:00 a.m.
Chicago O'Hare Intl airport
8h 49m
1 Stop
8:49 a.m.
YYC
Calgary airport
411 CAD
United Airlines
United Airlines
15 Sep.
YYC
12:15 a.m.
Calgary airport
3h 25m
4:40 a.m.
ORD
Chicago O'Hare Intl airport
United Airlines
30 Sep.
ORD
5:05 a.m.
Chicago O'Hare Intl airport
3h 40m
7:45 a.m.
YYC
Calgary airport
411 CAD
United Airlines
United Airlines
19 Sep.
YYC
6:47 a.m.
Calgary airport
3h 19m
11:06 a.m.
ORD
Chicago O'Hare Intl airport
United Airlines
30 Sep.
ORD
5:05 a.m.
Chicago O'Hare Intl airport
3h 40m
7:45 a.m.
YYC
Calgary airport
411 CAD
United Airlines
United Airlines
19 Sep.
YYC
6:47 a.m.
Calgary airport
3h 19m
11:06 a.m.
ORD
Chicago O'Hare Intl airport
United Airlines
30 Sep.
ORD
5:05 a.m.
Chicago O'Hare Intl airport
3h 40m
7:45 a.m.
YYC
Calgary airport
411 CAD
United Airlines
United Airlines
15 Sep.
YYC
12:15 a.m.
Calgary airport
3h 25m
4:40 a.m.
ORD
Chicago O'Hare Intl airport
United Airlines
30 Sep.
ORD
5:05 a.m.
Chicago O'Hare Intl airport
3h 40m
7:45 a.m.
YYC
Calgary airport
411 CAD
Aer Lingus
Aer Lingus
20 Jun.
YYC
12:19 a.m.
Calgary airport
3h 24m
4:43 a.m.
ORD
Chicago O'Hare Intl airport
Aer Lingus
21 Jun.
ORD
2:45 p.m.
Chicago O'Hare Intl airport
3h 46m
5:31 p.m.
YYC
Calgary airport
520 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
CHEAPEST MONTH TO FLY
April
The cheapest time of year to fly to Chicago from Calgary is April. The most expensive is July.
CHEAPEST DAY TO FLY
Wednesday
The cheapest day of the week is typically Wednesday. The most expensive is typically Sunday
CHEAPEST TIME TO FLY
in the Evening
Calgary to Chicago flights are approximately 33% more expensive at Noon than in the Evening
CHEAPEST AIRLINE
Frontier
Frontier, Alaska Airlines, and Air Canada are the most popular carriers operating from Calgary to Chicago
CHEAPEST ROUTE
Calgary - Chicago O'Hare Intl
Fly from Calgary to Chicago O'Hare Intl for the best Calgary - Chicago flight prices
CHEAPEST TIME TO BOOK
56 days before
The cheapest time to buy a flight from Calgary to Chicago is approximately 56 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 24m
The fastest flight from Calgary to Chicago takes 3h 24m.
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)

Flights from Calgary to:

Flights to Chicago from:

  • Calgary
  • Alberta
  • Canada
  • North America