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
12%
expected price increase
Average Price:
$440
(avg. price over the last 2 weeks)
Good Deal:
$349
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 $348 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 28% 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 1382 miles.
How many flights are there between Calgary and Chicago O'Hare International?
There are 143 (nonstop) flights between Calgary and Chicago O'Hare International per week, averaging 20 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 Delta ($284), Multiple Airlines ($305) and Air Canada ($400).
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?
United (9 times daily), Air Canada (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 Wednesday is the most expensive. Flying from Chicago O'Hare International back to Calgary, the best deals are generally found on Monday, with Saturday being the most expensive.

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

Airports
Origin
Calgary
$284
only
$284
Destination
Chicago
$284
only
$284
Thu, Mar 1
YYC
ORD
7h 24m
Mon, Mar 5
ORD
YYC
7h 37m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

JFK
CDG
Excellent 10.0

The food and the service

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

Sun, Apr 29
YYC
ORD
22h 19m
Tue, May 8
ORD
YYC
19h 55m
Trip: 10 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jun 6
YYC
ORD
3h 35m
Mon, Jun 11
ORD
YYC
3h 44m
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
6.5
YUL
ORD
Excellent 9.6

Friendliness of staff My familly got to follow my flight very closely.

Delays and harsh trubulance (altough i know that wasn’t air Canada’s fault for the weather) The changing of gates and the changing of boarding time without being updated on the application. The changing of the gate was changed moments before the boarding

LGA
YYZ
Okay 5.0

Stewardess seems very annoyed with flight. There was turbulence so the passengers needed to stay seated - a gentleman next to me asked for a glass of water since there was no refreshment service - the stewardess was very short with him. It’s not the passengers fault. I was surprised - usually the staff is a lot more professional than that.

LAX
YYZ
Excellent 8.0

Plane delayed 1 hour and a half. No compensation.

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.

ATL
YYZ
Okay 5.0

I arrived safely

I didn't appreciate losing my luggage as I came to Canada for a wedding and I didn't have access to my things. The flight was direct so I don't understand why my luggage was lost.

Fri, Mar 2
YYC
ORD
8h 41m
Mon, Mar 5
ORD
YYC
7h 37m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

Thu, Mar 1
YYC
ORD
17h 47m
Sun, Mar 4
ORD
YYC
6h 47m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Apr 25
YYC
ORD
9h 16m
Sat, Apr 28
ORD
YYC
8h 03m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

SLC
YYZ
Excellent 9.6

Z

Wed, Mar 7
YYC
ORD
8h 57m
Mon, Mar 12
ORD
YYC
9h 08m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Mar 1
YYC
ORD
7h 24m
Mon, Mar 5
ORD
YYC
5h 52m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
CDG
Excellent 10.0

The food and the service

SLC
YYZ
Excellent 9.6

Z

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

Sat, Apr 14
YYC
ORD
7h 42m
Wed, Apr 18
ORD
YYC
5h 20m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Apr 10
YYC
ORD
9h 16m
Thu, Apr 12
ORD
YYC
7h 03m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
CDG
Excellent 10.0

The food and the service

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

Tue, Apr 17
YYC
ORD
8h 34m
Sun, Apr 22
ORD
YYC
6h 58m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Apr 11
YYC
ORD
9h 09m
Thu, Apr 19
ORD
YYC
7h 03m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

Mon, Apr 16
YYC
ORD
9h 16m
Thu, Apr 19
ORD
YYC
7h 03m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SLC
YYZ
Excellent 9.6

Z

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

JFK
CDG
Excellent 10.0

The food and the service

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

Mon, Apr 30
YYC
ORD
22h 19m
Mon, May 7
ORD
YYC
19h 55m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Apr 17
YYC
ORD
9h 16m
Thu, Apr 19
ORD
YYC
6h 58m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

Sun, Apr 29
YYC
ORD
22h 19m
Mon, May 7
ORD
YYC
19h 55m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Thu, May 10
YYC
ORD
22h 19m
Mon, May 14
ORD
YYC
19h 55m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Apr 12
YYC
ORD
9h 16m
Thu, Apr 19
ORD
YYC
7h 03m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

Sat, Apr 14
YYC
ORD
7h 42m
Thu, Apr 19
ORD
YYC
5h 33m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Apr 13
YYC
ORD
9h 16m
Thu, Apr 19
ORD
YYC
6h 58m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

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Calgary to Chicago O'Hare International Flight Information

Avg. Flight Duration 3h 39m
Flights Arrive in Chicago O'Hare International
Flights Depart from Calgary
Flight Price $284
Distance 1382 miles
Airlines Delta, Air Canada
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

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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.