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

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Fri 11/24
Fri 12/1
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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
12%
expected price increase
Average Price:
$469
(avg. price over the last 2 weeks)
Good Deal:
$347
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 $347 or less.
The cheapest flight from Calgary to Chicago O'Hare International was found 35 days before departure, on average.
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 57% 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 1382 miles.
How many flights are there between Calgary and Chicago O'Hare International?
There are 121 (nonstop) flights between Calgary and Chicago O'Hare International per week, averaging 19 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 Air Canada ($268), Delta ($277) and WestJet ($467).
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 (6 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 Calgary to Chicago O'Hare International?
For Calgary to Chicago O'Hare International, Thursday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago O'Hare International back to Calgary, the best deals are generally found on Saturday, with Tuesday being the most expensive.

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

Airports
Origin
Calgary
$268
only
$268
Destination
Chicago
$268
only
$268
Thu, Nov 30
YYC
ORD
8h 15m
Mon, Dec 4
ORD
YYC
7h 56m
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
ORD
YYZ
Mediocre 2.0

Nothing

Flight delay led us to miss our connecting flight. Air Canada then lost our luggage for 6 days on our honeymoon!

LHR
YVR
Okay 5.6

They have good entertainment system and library

The plane delayed for almost 90m due to a mechanical issue. Of course, we missed our connection in Vancouver. Upon arriving in Vancouver, there was no help at all or guidance. Customer support desk was manned by one agent even in the presence of long queues.

BOS
YYZ
Excellent 9.3

T

The waiting area at the Boston airport is poor. It is very small, rundown and with limited access to refreshments. It's ok but certainly not a selling point.

HND
YYZ
Okay 4.4

Lowest fare

Online checkin failed, airport kiosk couldn't handle how names are written on Japanese passports (it's English) and had to wait 2 hours on the line to check in because they were down to 1 agent toward the end. Made it to the gate just as boarding started. Very limited entertainment options for modern day airlines. Uncomfortable seating.

YYC
ORD
Okay 5.3

Run by united but more efficient than a recent Air Canada flight.

3 hour flight and had to pay extra for entertainment. Only two biscuits given for food. Cramped seats for anyone 6ft tall.

Thu, Dec 7
YYC
ORD
6h 29m
Fri, Dec 15
ORD
YYC
10h 38m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

LAX
HNL
Okay 5.0

The gentleman at the gate was super helpful and helped us check our bags at the gate.

Zero leg room. Zero arm room. The entertainment system did not function. No food for such a long flight unless you pay more then the food is actually worth.

Thu, May 17
YYC
ORD
3h 22m
Mon, May 21
ORD
YYC
3h 45m
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
YYC
YWG
Excellent 10.0

Friendly staff 8

YEG
YMM
Good 7.6

Overall flight and connections were good. Board process was smooth and flight departed and arrived on time. Watch for baggage delays when arriving in Fort McMurray as they can sometimes be excessive. No entertainment provided on the smaller planes but most people have some form of entertainment with them.

YYZ
YYC
Mediocre 2.6

I had a very rude and mean flight attendant. I was yelled at and wasn’t offered any beverages or food afterwards. I was ending a phone call with the rcmp and without rudely hanging up on him due to my truck being stolen and being out of the country for 11 days. I was yelled at from 6 rows away in a very arrogant rude tone for the whole plane to hear. I was embarrassed and uncomfortable for the rest of the flight as well as being in a bad mood. Not being offered any beverages or food afterwards also made for a long flight. Was not impressed in the slightest as I fly with west jet every week and have never had such a rude flight attendant.

YSB
YYZ
Good 6.4

The crew was friendly and funny.

The Westjet staff at the Sudbury airport was not exactly friendly. My flight was departing at 6am, and they ask to be there 45 mins before which would have been at 5:15am, I got there at 5:20am and the gate was closed. At 5:25am an employee came to check me in but still advised me to be 45 mins in advance next time. I was only 5 mins late and they weren't even at the gate on my arrival. The security at the airport was rude.

BZE
YYZ
Okay 5.0

Good snacks $

Title says it.

Thu, Dec 7
YYC
ORD
7h 42m
Mon, Dec 11
ORD
YYC
9h 34m
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
MCO
YYZ
Excellent 10.0

Flight actually left Orlando early once all passengers were on board

BOS
YYZ
Excellent 9.3

T

The waiting area at the Boston airport is poor. It is very small, rundown and with limited access to refreshments. It's ok but certainly not a selling point.

YYZ
BOG
Excellent 8.0

The Air Canada app to have access to the entertainment on board did not work.

DEN
YYZ
Good 6.6

Good boarding.Easy check in.

Food! Not appealing. Did not eat more than a few bites.

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.

Thu, Nov 30
YYC
ORD
6h 29m
Mon, Dec 4
ORD
YYC
10h 38m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
HPN
Good 7.3

It was on time

It was crowded and cramped.

LAX
HNL
Okay 5.0

The gentleman at the gate was super helpful and helped us check our bags at the gate.

Zero leg room. Zero arm room. The entertainment system did not function. No food for such a long flight unless you pay more then the food is actually worth.

OMA
ATL
Good 7.6

My comfort zone seat

SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

MIA
ATL
Excellent 8.3

They gave me extra pretzels and 2 cans of soda

The seats were awful.. Miniscule

Wed, Mar 14
YYC
ORD
7h 35m
Tue, Mar 20
ORD
YYC
6h 53m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
HNL
Okay 5.0

The gentleman at the gate was super helpful and helped us check our bags at the gate.

Zero leg room. Zero arm room. The entertainment system did not function. No food for such a long flight unless you pay more then the food is actually worth.

PTY
ATL
Excellent 9.6

Crew was kind, entertainment and food were good

Seats are really tight

AMS
YYZ
Excellent 8.3

The flight attendant named Steven went so far beyond the call. He was attentive, he fixed our video system when no one else could and when he learned we were celebrating an anniversary he brought us a present. He was awesome!

JFK
CUN
Excellent 9.0

Entertainment and crew were great- comfortable seats, got to watch a couple of movies with headphones provided by Delta; forgot mine so I assumed I would be miserable thru the whole 4 hour flight. so glad I was wrong! Would definitely take another flight with Delta... looking into the frequent flyer program as we speak

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

Sat, Dec 16
YYC
ORD
6h 18m
Tue, Dec 19
ORD
YYC
6h 07m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
PTY
ATL
Excellent 9.6

Crew was kind, entertainment and food were good

Seats are really tight

SAV
ATL
Good 7.0

The flight was on schedule

It was crowded and cramped.

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

OMA
ATL
Good 7.6

My comfort zone seat

AMS
YYZ
Excellent 8.3

The flight attendant named Steven went so far beyond the call. He was attentive, he fixed our video system when no one else could and when he learned we were celebrating an anniversary he brought us a present. He was awesome!

Mon, Mar 26
YYC
ORD
7h 35m
Sat, Mar 31
ORD
YYC
8h 48m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 13693 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
PBI
ATL
Good 6.0

On time; safe flight

Service from boarding to landing was impersonal. No headphones etc. Etc.

LAX
HNL
Okay 5.0

The gentleman at the gate was super helpful and helped us check our bags at the gate.

Zero leg room. Zero arm room. The entertainment system did not function. No food for such a long flight unless you pay more then the food is actually worth.

SEA
SJC
Okay 5.6

No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok.

The pilot did a nice job of flying in and banking so we could see the view..

PHL
JFK
Excellent 9.0

We were probably in the air for 30 mins; great short flight. Plane wasn’t filled so had plenty of space.

AMS
YYZ
Excellent 8.3

The flight attendant named Steven went so far beyond the call. He was attentive, he fixed our video system when no one else could and when he learned we were celebrating an anniversary he brought us a present. He was awesome!

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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.