Cheap flights from Calgary to Chicago

Round-trip
Economy
Calgary (YYC)
Chicago (CHI)
Fri. 3/7
Fri. 10/7
Any month
Compare vs. momondo |

Flight information for Calgary to Chicago
(YYC to CHI)

Find info about flight duration, direct flights, and airports for your flight from Calgary to Chicago
Best price found 505 C$ The best flight deal from Calgary to Chicago found on momondo in the last 72 hours is 505 C$
Fastest flight time 3h 19m The fastest flight from Calgary to Chicago takes 3h 19m.
Direct flights None There are no direct flights from Calgary to Chicago. Popular non-direct routes for this connection are Calgary - Chicago Midway and Calgary - Chicago O'Hare Intl.
Airports in Chicago 3 airports There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

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 August.
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 17% 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 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 to Chicago?
60 days before
The cheapest time to buy a flight from Calgary to Chicago is approximately 60 days before departure
60
Days before departure
0

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
Cheapest
Best
Quickest
Multiple Airlines
8 Oct.
YYC
Calgary
3h 19m
ORD
Chicago O'Hare Intl
12 Oct.
ORD
Chicago O'Hare Intl
6h 57m
1 stop
YYC
Calgary
Delta
9 Oct.
YYC
Calgary
9h 24m
1 stop
ORD
Chicago O'Hare Intl
12 Oct.
ORD
Chicago O'Hare Intl
8h 09m
1 stop
YYC
Calgary
Multiple Airlines
18 Sep.
YYC
Calgary
3h 19m
ORD
Chicago O'Hare Intl
21 Sep.
ORD
Chicago O'Hare Intl
6h 56m
1 stop
YYC
Calgary

Find the cheapest one-way flights from Calgary to Chicago

If you're looking for one-way flights from Calgary to Chicago, view some of our deals below provided by Delta
Cheapest
Best
Quickest
Delta
18 Jul.
YYC
Calgary
6h 05m
1 stop
ORD
Chicago O'Hare Intl
Delta
5 Jul.
YYC
Calgary
9h 13m
2 stops
ORD
Chicago O'Hare Intl
Multiple Airlines
12 Jul.
YYC
Calgary
11h 00m
2 stops
MDW
Chicago Midway

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
Edmonton to Chicago Flights
Fastest flight time
10h 07m
Cheapest price
348 C$
Grande Prairie to Chicago Flights
Fastest flight time
12h 25m
Cheapest price
532 C$
Calgary to Decatur, Illinois Flights
Fastest flight time
11h 31m
Cheapest price
714 C$
Fort McMurray to Chicago Flights
Fastest flight time
14h 25m
Cheapest price
2,649 C$
View more

Flights from Calgary to:

Flights to Chicago from:

  • Round-trip
  • One-way
  • Multi-city
  • Economy
  • Premium Economy
  • Business
  • First
  • Multiple
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First