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$ 620
(avg. price over the last 2 weeks)
Good Deal:
C$ 451
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

Looking for a cheap flight? 25% of our users found flights on this route for C$ 450 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 102% 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 35m, covering a distance of 2224 km.
How many flights are there between Calgary and Chicago O'Hare International?
There are 60 (nonstop) flights between Calgary and Chicago O'Hare International per week, averaging 8 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$ 351), Delta (C$ 360) and Air Canada (C$ 376).
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 (3 times daily), United (3 times daily), Aer Lingus (2 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, Wednesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago O'Hare International back to Calgary, the best deals are generally found on Thursday, with Tuesday being the most expensive.

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

Airports
Origin
Calgary
C$ 351
only
C$ 351
Destination
Chicago
C$ 351
only
C$ 351
Wed, 2 May
YYC
ORD
7h 33m
Thu, 3 May
ORD
YYC
3h 45m
C$ 351
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Fri, 2 Mar
YYC
ORD
8h 55m
Sun, 4 Mar
ORD
YYC
8h 48m
C$ 360
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
YVR
Mediocre 2.0

I was rerouted.

No one would reissue me a ticket for the next flight. Delta and West Jet kept saying the other company should do this, and in the end no one did and I had to purchase another ticket.

DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

CMH
DTW
Excellent 8.6

Easy to board.

Delayed due to weather.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

Tue, 6 Feb
YYC
ORD
7h 42m
Sat, 10 Feb
ORD
YYC
10h 29m
C$ 376
Trip: 5 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 6 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
BWI
YYZ
Mediocre 2.0

We arrived safely

YYZ
YVR
Good 6.0

The plane was unable to board on time ,the cabin was too cold. That was a hitch well managed but with a seat near the rear of the aircraft only food option was cup of soup rehydrated with hot water or snacks. May be better food provision could be implemented.

YYT
YYZ
Excellent 9.0

When I got sick, staff were friendly, helpful and soothing until the arrival of the ambulance. They made me feel much better during a very stressful situation.

YYZ
FRA
Good 6.0

I liked the movie selection, the service, and food/drinks.

With a 20 minute layover, I barely made the flight and my checked bags/luggage did not make it. This had a horrible influence on my trip and I am heavily disappointed in Air Canada.

YYC
ORD
Excellent 8.3

Overall it was good. The crew was very friendly. The plane was small and it was a short flight, so everything else was average as expected for a short flight.

Fri, 6 Apr
YYC
ORD
8h 54m
Wed, 11 Apr
ORD
YYC
9h 45m
C$ 381
Trip: 6 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 6 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
BWI
YYZ
Mediocre 2.0

We arrived safely

LHR
YOW
Excellent 10.0

Air Canada is fantastic. Will never use air india.

I liked everything about AirCanada and nothing about Airindia.

YYZ
POS
Mediocre 2.0

Did not get to go

YYZ
LGA
Mediocre 2.0

flight was cancelled. poor communication.

SYD
YVR
Good 7.6

The crew was friendly & nice. The flight went pretty smooth. I thought movie choices were good. There was a good mix of newer movies & older classics.

Food was disappointing even for a plane food. Not very tasty. Airlines should switch to using compostable cups & silverware. Each flight uses so many plastic cups! I hope they get recycled but it’d be better to go an extra step & switch to compostable cups & silver to reduce the waste.

Wed, 7 Feb
YYC
ORD
5h 49m
Sat, 10 Feb
ORD
YYC
10h 29m
C$ 399
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Wed, 7 Mar
YYC
ORD
7h 35m
Sun, 11 Mar
ORD
YYC
7h 33m
C$ 439
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
YVR
Mediocre 2.0

I was rerouted.

No one would reissue me a ticket for the next flight. Delta and West Jet kept saying the other company should do this, and in the end no one did and I had to purchase another ticket.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

YUL
MSP
Good 6.0

We got on the plane and it went to where it was supposed to go.

MSP
DSM
Good 6.0

The plane went where it was supposed to go.

Sat, 14 Apr
YYC
ORD
3h 35m
Sun, 15 Apr
ORD
YYC
9h 46m
C$ 405
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Fri, 13 Jul
YYC
ORD
8h 25m
Fri, 27 Jul
ORD
YYC
6h 53m
C$ 670
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
PHL
MSP
Mediocre 2.0

The flight itself was fine.

The flight was delayed and it set off a slew of connection problems.

MSP
DSM
Good 6.0

The plane went where it was supposed to go.

ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

SFO
LAX
Good 7.6

Everyone was really nice and responsive.

Seats are a little older. Not as comfortable as other flights. But not bad.

Sun, 14 Jan
YYC
ORD
8h 58m
Tue, 16 Jan
ORD
YYC
11h 02m
C$ 825
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
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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.

Calgary to Chicago O'Hare International Flight Information

Flights Arrive in Chicago O'Hare International
Flights Depart from Calgary
Flight Price C$ 351
Distance 2224 km
Airlines Delta, Air Canada