Find Deals on Flights from Canada to Chicago Midway

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 Canada to Chicago Midway

(Round-trip)
Depart: Fri May 12 2017 Return: Sun May 14 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
YUL
MDW
6h 15m
1 stop
MDW
YUL
6h 10m
1 stop
Depart: Thu Mar 16 2017 Return: Mon Mar 20 2017 Trip spans 5 days
Major Airline
Major Airline
YUL
MDW
4h 45m
nonstop
MDW
YUL
3h 45m
nonstop
Depart: Mon Mar 27 2017 Return: Mon Apr 3 2017 Trip spans 8 days
Delta
Delta
YYZ
MDW
7h 37m
1 stop
MDW
YYZ
7h 06m
1 stop
Depart: Fri Mar 24 2017 Return: Sun Mar 26 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
YUL
MDW
4h 45m
1 stop
MDW
YUL
3h 40m
1 stop
Depart: Sat Mar 25 2017 Return: Mon Mar 27 2017 Trip spans 3 days
Major Airline
Major Airline
YUL
MDW
3h 45m
nonstop
MDW
YUL
3h 45m
nonstop
Depart: Thu Mar 30 2017 Return: Sat Apr 8 2017 Trip spans 10 days
Porter Airlines
Porter Airlines
YUL
MDW
4h 15m
1 stop
MDW
YUL
4h 25m
1 stop
Depart: Fri May 12 2017 Return: Mon May 15 2017 Trip spans 4 days
Major Airline
Major Airline
YUL
MDW
4h 55m
nonstop
MDW
YUL
3h 40m
nonstop
Depart: Sun Apr 2 2017 Return: Tue Apr 4 2017 Trip spans 3 days
Delta
Delta
YYZ
MDW
5h 32m
1 stop
MDW
YYZ
4h 37m
1 stop
Depart: Fri Apr 7 2017 Return: Sun Apr 9 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
YUL
MDW
3h 40m
1 stop
MDW
YUL
6h 00m
1 stop
Depart: Fri Apr 21 2017 Return: Sun Apr 23 2017 Trip spans 3 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Mon Apr 3 2017 Return: Thu Apr 6 2017 Trip spans 4 days
Delta
Delta
YYZ
MDW
5h 23m
1 stop
MDW
YYZ
3h 34m
1 stop
Depart: Thu Apr 20 2017 Return: Sun Apr 23 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YUL
MDW
5h 25m
1 stop
MDW
YUL
4h 30m
1 stop
Depart: Thu Aug 3 2017 Return: Mon Aug 7 2017 Trip spans 5 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Thu Apr 20 2017 Return: Mon Apr 24 2017 Trip spans 5 days
Delta
Delta
YYZ
MDW
5h 32m
1 stop
MDW
YYZ
7h 06m
1 stop
Depart: Mon May 1 2017 Return: Tue May 2 2017 Trip spans 2 days
Porter Airlines
Porter Airlines
YUL
MDW
4h 40m
1 stop
MDW
YUL
5h 05m
1 stop
Depart: Thu May 4 2017 Return: Tue May 9 2017 Trip spans 6 days
Delta
Delta
YYZ
MDW
5h 01m
1 stop
MDW
YYZ
6h 43m
1 stop
Depart: Fri Jun 16 2017 Return: Tue Jun 20 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YUL
MDW
5h 30m
1 stop
MDW
YUL
4h 55m
1 stop
Depart: Thu Jun 1 2017 Return: Tue Jul 4 2017 Trip spans 34 days
Delta
Delta
YYZ
MDW
6h 26m
1 stop
MDW
YYZ
6h 59m
1 stop
Depart: Sat Aug 19 2017 Return: Sun Aug 20 2017 Trip spans 2 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Fri May 5 2017 Return: Mon May 8 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YUL
MDW
6h 15m
1 stop
MDW
YUL
3h 40m
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,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Montreal
$188
Toronto
only $228
only $205
Destination

Chicago
$188