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

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
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 Midway

(Round-trip)
Depart: Mon May 8 2017 Return: Tue May 16 2017 Trip spans 9 days
Delta
Delta
YYC
8:35p
MDW
7:23a
10h 48m
2 stops
MDW
9:00a
YYC
5:56p
8h 56m
2 stops
Depart: Mon May 1 2017 Return: Thu May 11 2017 Trip spans 11 days
Delta
Delta
YYC
10:30a
MDW
5:10p
6h 40m
1 stop
MDW
5:10a
YYC
10:28a
5h 18m
1 stop
Depart: Thu Mar 30 2017 Return: Tue Apr 4 2017 Trip spans 6 days
Delta
Delta
YYC
10:30a
MDW
5:11p
6h 41m
1 stop
MDW
2:25a
YYC
10:21a
7h 56m
1 stop
Depart: Sat May 6 2017 Return: Sat May 13 2017 Trip spans 8 days
Delta
Delta
YYC
10:30a
MDW
5:07p
6h 37m
1 stop
MDW
2:30a
YYC
10:31a
8h 01m
1 stop
Depart: Fri Apr 7 2017 Return: Sat Apr 15 2017 Trip spans 9 days
Delta
Delta
YYC
10:30a
MDW
5:11p
6h 41m
1 stop
MDW
2:25a
YYC
10:36a
8h 11m
1 stop
Depart: Wed Mar 29 2017 Return: Sat Apr 1 2017 Trip spans 4 days
Delta
Delta
YYC
10:30a
MDW
5:11p
6h 41m
1 stop
MDW
11:10a
YYC
7:20p
8h 10m
1 stop
Depart: Sun Apr 30 2017 Return: Thu May 11 2017 Trip spans 12 days
Delta
Delta
YYC
10:30a
MDW
5:11p
6h 41m
1 stop
MDW
5:10a
YYC
10:28a
5h 18m
1 stop
Depart: Fri Apr 28 2017 Return: Tue May 2 2017 Trip spans 5 days
Delta
Delta
YYC
10:30a
MDW
5:11p
6h 41m
1 stop
MDW
2:30a
YYC
10:28a
7h 58m
1 stop
Depart: Mon Jun 5 2017 Return: Mon Jun 19 2017 Trip spans 15 days
Delta
Delta
YYC
10:30a
MDW
5:10p
6h 40m
1 stop
MDW
11:24a
YYC
6:27p
7h 03m
1 stop
Depart: Wed Aug 30 2017 Return: Sun Sep 3 2017 Trip spans 5 days
Delta
Delta
YYC
11:30a
MDW
5:15p
5h 45m
1 stop
MDW
5:04a
YYC
10:32a
5h 28m
1 stop
Depart: Sat Apr 1 2017 Return: Wed Apr 5 2017 Trip spans 5 days
Delta
Delta
YYC
10:30a
MDW
5:07p
6h 37m
1 stop
MDW
2:25a
YYC
10:21a
7h 56m
1 stop
Depart: Tue Mar 28 2017 Return: Sat Apr 1 2017 Trip spans 5 days
Delta
Delta
YYC
2:00a
MDW
1:10p
11h 10m
2 stops
MDW
11:10a
YYC
7:20p
8h 10m
1 stop
Depart: Sat Sep 9 2017 Return: Sat Sep 16 2017 Trip spans 8 days
Delta
Delta
YYC
4:15a
MDW
11:44a
7h 29m
1 stop
MDW
11:24a
YYC
6:25p
7h 01m
1 stop
Depart: Wed Jul 19 2017 Return: Mon Jul 24 2017 Trip spans 6 days
Delta
Delta
YYC
11:30a
MDW
5:15p
5h 45m
1 stop
MDW
11:24a
YYC
6:27p
7h 03m
1 stop
Depart: Fri Apr 14 2017 Return: Mon Apr 17 2017 Trip spans 4 days
Delta
Delta
YYC
10:30a
MDW
5:11p
6h 41m
1 stop
MDW
1:27p
YYC
7:24p
5h 57m
1 stop
Depart: Tue Jun 20 2017 Return: Sun Jun 25 2017 Trip spans 6 days
Delta
Delta
YYC
11:30a
MDW
5:15p
5h 45m
1 stop
MDW
11:24a
YYC
6:27p
7h 03m
1 stop
Depart: Sat Mar 25 2017 Return: Sun Mar 26 2017 Trip spans 2 days
Delta
Delta
YYC
10:30a
MDW
5:07p
6h 37m
1 stop
MDW
2:30a
YYC
10:33a
8h 03m
1 stop
Depart: Thu Apr 20 2017 Return: Sun Apr 23 2017 Trip spans 4 days
Delta
Delta
YYC
10:30a
MDW
5:11p
6h 41m
1 stop
MDW
11:10a
YYC
7:24p
8h 14m
1 stop
Depart: Thu Apr 27 2017 Return: Sun Apr 30 2017 Trip spans 4 days
Delta
Delta
YYC
10:30a
MDW
5:11p
6h 41m
1 stop
MDW
5:10a
YYC
10:21a
5h 11m
1 stop
Depart: Sun Apr 2 2017 Return: Wed Apr 5 2017 Trip spans 4 days
Delta
Delta
YYC
4:25a
MDW
9:35a
5h 10m
1 stop
MDW
2:25a
YYC
10:21a
7h 56m
1 stop
* 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.

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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
$366
Destination

Chicago
$366
Airlines