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
17 Sep.
YYC
1:30 a.m.
Calgary airport
12h 39m
2 Stops
3:09 p.m.
ORD
Chicago O'Hare Intl airport
Delta
25 Sep.
ORD
7:30 a.m.
Chicago O'Hare Intl airport
12h 08m
2 Stops
6:38 p.m.
YYC
Calgary airport
371 CAD
Delta
Delta
22 Oct.
YYC
5:29 a.m.
Calgary airport
6h 47m
1 Stop
1:16 p.m.
ORD
Chicago O'Hare Intl airport
Delta
01 Nov.
ORD
1:20 a.m.
Chicago O'Hare Intl airport
12h 37m
2 Stops
12:57 p.m.
YYC
Calgary airport
377 CAD
United Airlines
United Airlines
22 Sep.
YYC
12:15 a.m.
Calgary airport
3h 25m
4:40 a.m.
ORD
Chicago O'Hare Intl airport
United Airlines
26 Sep.
ORD
12:20 a.m.
Chicago O'Hare Intl airport
7h 15m
1 Stop
6:35 a.m.
YYC
Calgary airport
383 CAD
Aer Lingus
Aer Lingus
28 Aug.
YYC
12:15 a.m.
Calgary airport
3h 26m
4:41 a.m.
ORD
Chicago O'Hare Intl airport
Aer Lingus
03 Sep.
ORD
2:45 p.m.
Chicago O'Hare Intl airport
3h 52m
5:37 p.m.
YYC
Calgary airport
492 CAD
United Airlines
United Airlines
22 Sep.
YYC
12:15 a.m.
Calgary airport
3h 25m
4:40 a.m.
ORD
Chicago O'Hare Intl airport
United Airlines
26 Sep.
ORD
12:20 a.m.
Chicago O'Hare Intl airport
7h 15m
1 Stop
6:35 a.m.
YYC
Calgary airport
383 CAD
American Airlines
American Airlines
15 Aug.
YYC
10:39 a.m.
Calgary airport
3h 34m
3:13 p.m.
ORD
Chicago O'Hare Intl airport
American Airlines
22 Aug.
ORD
12:37 a.m.
Chicago O'Hare Intl airport
7h 57m
1 Stop
7:34 a.m.
YYC
Calgary airport
558 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 ?
April
The cheapest time of year to fly to Chicago from Calgary is April. The most expensive is August.
WHAT IS THE CHEAPEST DAY TO FLY ?
Wednesday
The cheapest day of the week is typically Wednesday. The most expensive is typically Sunday
WHEN IS THE CHEAPEST TIME TO FLY ?
in the evening
Calgary to Chicago flights are approximately 145% more expensive at noon than in the evening
WHAT IS THE CHEAPEST AIRLINE THAT FLIES ?
Frontier
Frontier, Alaska Airlines, and Air Canada are the most popular carriers operating from Calgary to Chicago
WHAT IS THE CHEAPEST ROUTE?
Calgary - Chicago O'Hare Intl
Fly from Calgary to Chicago O'Hare Intl for the best Calgary - Chicago flight prices
WHEN IS THE CHEAPEST TIME TO BOOK A FLIGHT ?
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 22m The fastest flight from Calgary to Chicago takes 3h 22m.
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