Find Cheap Flights from Calgary to Chicago (YYC - CHI)

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Fri 12/15
Fri 12/22
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Good to Know

Low Season:
October
Best time to beat the crowds
2%
expected price decrease
High Season:
July
Most popular time to fly
9%
expected price increase
Average Price:
$458
(avg. price over the last 2 weeks)
Good Deal:
$340
or less (round trip)

When to Book Flights from Calgary to Chicago

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 $340 or less.
The cheapest flight from Calgary to Chicago was found 34 days before departure, on average.
Book at least 1 week before departure in order to get a below-average price.
High season is considered to be June, July and August. The cheapest month to fly is October.
Morning departure is around 4% 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 Flights

How long does a flight from Calgary to Chicago take?
An average nonstop flight takes 3h 30m, covering a distance of 1397 miles.
How many flights are there between Calgary and Chicago?
There are 119 (nonstop) flights between Calgary and Chicago per week, averaging 19 per day.
Which airlines provide the cheapest flights from Calgary to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Air Canada ($258), Delta ($276) and Multiple Airlines ($285).
Do I need a passport to fly between Calgary and Chicago?
Yes.
Which airlines fly most frequently between Calgary and Chicago?
United (6 times daily), Air Canada (5 times daily), Aer Lingus (4 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Calgary to Chicago?
For Calgary to Chicago, Thursday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago back to Calgary, the best deals are generally found on Thursday, with Friday being the most expensive.

Book cheap flights from Calgary to Chicago (round-trip)

Airports
Origin
Calgary
$258
only
$258
Destination
Chicago
$258
only
$258
$297
only
$297
Thu, Jan 11
YYC
ORD
8h 55m
Sun, Jan 14
ORD
YYC
9h 34m
Trip: 4 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 6 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YYZ
YEG
Excellent 10.0

Food was great

Nothing

MSP
YYZ
Excellent 8.6

Crew and flight were great

Not great food, but that's ok.

MCO
YYZ
Good 6.0

Flight back was OK but flight to Orlando was not. Travelling with s 94 yr old man in a wheelchair. Everything at Pearson is not conduscent to travel with a handicapped person. Poor layout, poor assistance, non caring people, long distances,, and final straw was air canada started boarding without calling for handicapped first. We had to stop them and then fight our way up the aisle with people all in the way. Terrible, just lousey. 3 and a half hours before flight we arrived and didn't even have a chance to get some lunch before flight. I give Toronto and air Canada the worst possible rating of any airport or airline I've ever dealt with. John O"Hearn

NRT
YVR
Excellent 10.0

Nothing to complain

YYZ
MCO
Excellent 10.0

The exact timing going and coming

After returning back and the airplane taxing on the ground it takes one hour to go out of the airport gate to my riding although I have no luggage

Fri, Jan 12
YYC
ORD
6h 18m
Tue, Jan 16
ORD
YYC
8h 54m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ZAG
CDG
Good 6.0

Old plane, bad food & old crew

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

MSP
YXE
Excellent 9.3

I was traveling for medical reasons and the Delta crew took great care of me, made sure I was at my connecting gate on time, and even put me in a better seat on the plane. Not sure if that was a coincidental upgrade, or intentional, but it was perfect.

Wed, Jan 24
YYC
ORD
3h 30m
Thu, Feb 1
ORD
YYC
9h 34m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Feb 22
YYC
ORD
8h 42m
Mon, Feb 26
ORD
YYC
10h 29m
Trip: 5 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 6 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YVR
LAX
Excellent 8.0

I had an episode of anxiety over very minor turbulence which I sometimes get and both ladies who happened to be on duty were very reassuring and sympathetic to me. I had my 6 year old daughter also on the plane who is not anxious at all, so I was able to speak to one of the staff in French so as not to transfer my anxiety to my daughter who doesn't understand French. This was great. Over half way through the flight they gave me some earphones and suggested I watch a movie. This helped so much.

YYC
YYZ
Excellent 10.0

Flight cancelled due to weather, the workers made it seamless.

Had to tack on extra expenses for food while waiting for the next flight. Should have gotten some type of vouchers to cover meals at the very least during cancellations. That would be next level.

NRT
YVR
Excellent 10.0

Nothing to complain

YYZ
ORD
Excellent 8.0

Meh

Meh

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.

Tue, Jan 16
YYC
ORD
6h 18m
Fri, Jan 19
ORD
YYC
7h 18m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
GSO
ATL
Excellent 10.0

Plane nice and comfortable

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

Sat, Jan 27
YYC
ORD
3h 30m
Wed, Jan 31
ORD
YYC
9h 34m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Jan 26
YYC
ORD
7h 17m
Mon, Jan 29
ORD
YYC
11h 05m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

Tue, Jan 23
YYC
ORD
3h 30m
Wed, Jan 31
ORD
YYC
7h 01m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Feb 21
YYC
ORD
6h 09m
Mon, Feb 26
ORD
YYC
7h 18m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

GSO
ATL
Excellent 10.0

Plane nice and comfortable

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

Wed, Jan 24
YYC
ORD
3h 30m
Mon, Jan 29
ORD
YYC
7h 56m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Feb 22
YYC
ORD
7h 10m
Mon, Feb 26
ORD
YYC
7h 18m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

MSP
YXE
Excellent 9.3

I was traveling for medical reasons and the Delta crew took great care of me, made sure I was at my connecting gate on time, and even put me in a better seat on the plane. Not sure if that was a coincidental upgrade, or intentional, but it was perfect.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

Sat, Jan 27
YYC
ORD
3h 30m
Thu, Feb 1
ORD
YYC
7h 01m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Apr 18
YYC
ORD
8h 50m
Sat, Apr 21
ORD
YYC
5h 39m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
GSO
ATL
Excellent 10.0

Plane nice and comfortable

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

Tue, Jan 23
YYC
ORD
3h 30m
Tue, Jan 30
ORD
YYC
5h 46m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Jan 26
YYC
ORD
5h 47m
Thu, Feb 1
ORD
YYC
9h 34m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Feb 10
YYC
ORD
7h 48m
Tue, Feb 20
ORD
YYC
7h 18m
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

Mon, Jan 22
YYC
ORD
6h 52m
Sun, Jan 28
ORD
YYC
6h 42m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Jan 5
YYC
ORD
7h 17m
Sun, Jan 14
ORD
YYC
7h 18m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

MSP
YXE
Excellent 9.3

I was traveling for medical reasons and the Delta crew took great care of me, made sure I was at my connecting gate on time, and even put me in a better seat on the plane. Not sure if that was a coincidental upgrade, or intentional, but it was perfect.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

Fri, Jan 26
YYC
ORD
7h 05m
Sat, Jan 27
ORD
YYC
6h 42m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Jan 8
YYC
MDW
6h 33m
Sat, Jan 13
MDW
YYC
5h 43m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

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*
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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.