Find Deals on Flights from Calgary to Chicago (YYC - CHI)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
Students
under 26
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Calgary to Chicago

(Round-trip)
Depart: Wed Apr 19 2017 Return: Tue Apr 25 2017 Trip spans 7 days
Delta
Delta
YYC
ORD
6h 22m
1 stop
ORD
YYC
10h 40m
2 stops
Depart: Wed May 3 2017 Return: Sat May 6 2017 Trip spans 4 days
WestJet
WestJet
YYC
ORD
3h 22m
nonstop
ORD
YYC
3h 48m
nonstop
Depart: Wed Mar 8 2017 Return: Sun Mar 12 2017 Trip spans 5 days
Major Airline
Major Airline
YYC
ORD
8h 53m
2 stops
ORD
YYC
27h 52m
2 stops
Depart: Tue Feb 7 2017 Return: Tue Feb 14 2017 Trip spans 8 days
Delta
Delta
YYC
MDW
6h 29m
1 stop
MDW
YYC
11h 47m
2 stops
Depart: Wed Jun 14 2017 Return: Wed Jun 28 2017 Trip spans 15 days
WestJet
WestJet
YYC
ORD
3h 22m
nonstop
ORD
YYC
3h 48m
nonstop
Depart: Tue Feb 14 2017 Return: Tue Feb 21 2017 Trip spans 8 days
Delta
Delta
YYC
ORD
12h 48m
2 stops
ORD
YYC
12h 17m
2 stops
Depart: Thu Jan 26 2017 Return: Tue Jan 31 2017 Trip spans 6 days
Delta
Delta
YYC
ORD
10h 16m
1 stop
ORD
YYC
10h 30m
2 stops
Depart: Thu Feb 2 2017 Return: Sun Feb 5 2017 Trip spans 4 days
Delta
Delta
YYC
ORD
10h 10m
2 stops
ORD
YYC
10h 14m
1 stop
Depart: Thu Feb 2 2017 Return: Sun Feb 5 2017 Trip spans 4 days
Delta
Delta
YYC
MDW
13h 00m
2 stops
MDW
YYC
10h 59m
2 stops
Depart: Sat May 13 2017 Return: Wed May 17 2017 Trip spans 5 days
Delta
Delta
YYC
ORD
3h 22m
nonstop
ORD
YYC
3h 48m
nonstop
Depart: Wed Apr 19 2017 Return: Tue Apr 25 2017 Trip spans 7 days
Delta
Delta
YYC
MDW
9h 58m
2 stops
MDW
YYC
11h 58m
2 stops
Depart: Mon Jan 23 2017 Return: Fri Jan 27 2017 Trip spans 5 days
Delta
Delta
YYC
MDW
10h 34m
2 stops
MDW
YYC
11h 32m
2 stops
Depart: Tue May 9 2017 Return: Sat May 13 2017 Trip spans 5 days
Delta
Delta
YYC
MDW
9h 55m
2 stops
MDW
YYC
8h 09m
1 stop
Depart: Sat May 13 2017 Return: Wed May 17 2017 Trip spans 5 days
Delta
Delta
YYC
MDW
5h 38m
1 stop
MDW
YYC
12h 43m
2 stops
Depart: Wed Mar 8 2017 Return: Sun Mar 12 2017 Trip spans 5 days
Delta
Delta
YYC
MDW
6h 23m
1 stop
MDW
YYC
8h 03m
1 stop
Depart: Wed Mar 22 2017 Return: Mon Mar 27 2017 Trip spans 6 days
Delta
Delta
YYC
MDW
12h 21m
2 stops
MDW
YYC
11h 01m
2 stops
Depart: Wed Mar 22 2017 Return: Sun Mar 26 2017 Trip spans 5 days
Delta
Delta
YYC
ORD
12h 21m
2 stops
ORD
YYC
13h 07m
2 stops
Depart: Tue Jul 4 2017 Return: Thu Jul 27 2017 Trip spans 24 days
Delta
Delta
YYC
ORD
9h 03m
1 stop
ORD
YYC
7h 48m
1 stop
Depart: Wed Jun 7 2017 Return: Fri Jun 16 2017 Trip spans 10 days
Delta
Delta
YYC
MDW
10h 03m
2 stops
MDW
YYC
14h 15m
2 stops
Depart: Sat Apr 1 2017 Return: Sat Apr 15 2017 Trip spans 15 days
Delta
Delta
YYC
MDW
5h 41m
1 stop
MDW
YYC
5h 29m
1 stop
Direct flights YYC to CHI on United
Flight # Depart YYC Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
5496 7:40 am 12:15 pm Feb 2 - Feb 14
5496 7:40 am 12:15 pm Feb 1 - Feb 15
5496 7:43 am 12:18 pm Jan 13 - Jan 30
5496 7:43 am 12:18 pm Jan 12 - Jan 31
5496 8:10 am 12:45 pm Feb 16 - Mar 8
614 8:10 am 12:40 pm Feb 19 - Feb 26
5877 12:22 pm 4:50 pm Feb 18 - Feb 25
842 12:35 pm 4:55 pm Jan 12 - Feb 14
842 12:35 pm 4:55 pm Jan 13 - Feb 3
842 12:35 pm 4:55 pm Feb 6 - Feb 15
1460 12:36 pm 4:56 pm Feb 16 - Mar 1
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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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,
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Airports
Origin

Calgary
$254
Destination

Chicago
only $254
only $263