Find Cheap Flights from Calgary to Chicago O'Hare International (YYC - ORD)

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Good to Know

Low Season:
October
Best time to beat the crowds
3%
expected price decrease
High Season:
February
Most popular time to fly
11%
expected price increase
Average price:
C$ 635
(avg. price over the last 2 weeks)
Good Deal:
C$ 471
or less (round trip)

When to Book Flights from Calgary to Chicago O'Hare International

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

When looking for a cheap flight, consider that 25% of our users selected a flight on this route for C$ 470 or less.
The cheapest flight from Calgary to Chicago O'Hare International was found, on average, 35 days before departure.
Book at least 2 weeks before departure in order to get a below-average price.
High season is considered to be January, February and March. The cheapest month to fly is October.
Morning departure is around 5% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Calgary to Chicago O'Hare International Flights

How long does a flight from Calgary to Chicago O'Hare International take?
An average nonstop flight takes 3h 22m, covering a distance of 2224 km.
How many flights are there between Calgary and Chicago O'Hare International?
There are 111 (nonstop) flights between Calgary and Chicago O'Hare International per week, averaging 16 per day.
Which airlines provide the cheapest flights from Calgary to Chicago O'Hare International?
In the past 3 days, the cheapest round-trip tickets were found on Multiple Airlines (C$ 347), Delta (C$ 390) and WestJet (C$ 587).
Do I need a passport to fly between Calgary and Chicago O'Hare International?
Yes.
Which airlines fly most frequently between Calgary and Chicago O'Hare International?
Air Canada (6 times daily), United (5 times daily), Aer Lingus (3 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly from Calgary to Chicago O'Hare International?
For Calgary to Chicago O'Hare International, Friday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Chicago O'Hare International back to Calgary, the best deals are generally found on Thursday, with Saturday being the most expensive.

Book cheap flights from Calgary to Chicago O'Hare International (round-trip)

Airports
Origin
Calgary
C$ 347
only
C$ 347
Destination
Chicago
C$ 347
only
C$ 347
Fri, 24 Nov
YYC
ORD
3h 30m
Thu, 30 Nov
ORD
YYC
8h 01m
C$ 347
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Wed, 14 Feb
YYC
ORD
9h 18m
Sat, 24 Feb
ORD
YYC
8h 48m
C$ 390
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13528 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
LAX
Excellent 9.3

Check in was easy through their app. Also very quick lines to drop off bags. Crew was very nice and respectful

Seat are a little bit too close together. But overall very comfortable

JFK
JAX
Good 7.6

Delta never used to be my first choice in airlines, but of my recent experience with them has been excellent. The people from the counter to the plane have been professional and courteous. This is why I will fly with them more frequently.

DTW
EWR
Excellent 8.0

Boarding was quick. Staff and crew were friendly. Everything went well despite the 30 min delay we had on the runway. They gave us snacks and we ended up still arriving on time.

MOB
ATL
Good 6.0

Felt like I was sitting in my neighbors lap!

LGA
CVG
Excellent 8.3

Plane was far too tight. Very uncomfortable for taller individuals.

Thu, 24 May
YYC
ORD
3h 22m
Mon, 28 May
ORD
YYC
3h 45m
C$ 587
Trip: 5 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 6 reviews
Overall
8.2
Boarding
8.3
Comfort
8.0
Crew
8.6
Entertainment
7.2
Food
7.3
YLW
YEG
Mediocre 3.3

Crew overworked but pleasant and doing their best. Self check in works well with assistance

Management decisions meant assigned crew arrived after our flight supposed to depart. Needed 1 more person to service passengers. We waited a long time after serving started to get served. We did not know that food could be preordered online and served soon after takeoff. No TV screens on back of chairs...had to rent device to see movies. Have app but not able to book and get points. Wrote to WJ for help but oo response

YVR
YYZ
Okay 5.3

The flights were on time and the staff were polite and nice.

Everything on a WestJet flight is extra and only the bare minimum is offered. There are no TVs in the seats and the seats themselves are small and jammed close together.

YVR
YLW
Okay 4.0

Timing flights were on time.

Baggage delay at vancuvour and as well as in calgary.

YLW
YVR
Excellent 10.0

Was on time and i was upgraded at no charge. The westjet staff is always friendly.

YYZ
POP
Good 6.0

The crew was very nice.

The plane was old so no entertainment, food was not good, could not sit in area waiting for flight, no chairs left and I was 5ere. Very early. Travelling is not great anymore, the crew try’s their best I know.

Sun, 3 Dec
YYC
ORD
3h 35m
Sat, 9 Dec
ORD
YYC
4h 10m
C$ 353
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Thu, 1 Feb
YYC
ORD
20h 21m
Sat, 3 Feb
ORD
YYC
10h 29m
C$ 362
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Fri, 27 Apr
YYC
ORD
22h 19m
Mon, 30 Apr
ORD
YYC
3h 45m
C$ 434
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Wed, 14 Mar
YYC
ORD
8h 55m
Mon, 2 Apr
ORD
YYC
5h 34m
C$ 526
Trip: 20 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13528 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CHA
ATL
Excellent 10.0

On time departure and arrival. The Airbus plane has enough legroom for tall persons.

LGA
CVG
Excellent 8.3

Plane was far too tight. Very uncomfortable for taller individuals.

JFK
LAX
Excellent 9.3

Check in was easy through their app. Also very quick lines to drop off bags. Crew was very nice and respectful

Seat are a little bit too close together. But overall very comfortable

ATL
BNA
Excellent 10.0

Compared to previous flight - this was so much better with upgrade to first class and extra space.

ATL
MCO
Excellent 10.0

Amazing experience thank you Delta

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*
Prices are per person, are for e–tickets and include all taxes & fees in CAD.

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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.