Find Cheap 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: Wed Jun 14 2017 Return: Thu Jun 15 2017 Trip spans 2 days
Porter Airlines
Porter Airlines
YUL
MDW
5h 40m
1 stop
MDW
YUL
6h 05m
1 stop
Depart: Fri May 12 2017 Return: Mon May 15 2017 Trip spans 4 days
Major Airline
Major Airline
YUL
MDW
4h 10m
nonstop
MDW
YUL
11h 30m
nonstop
Depart: Sun May 28 2017 Return: Wed May 31 2017 Trip spans 4 days
Delta
Delta
YYZ
MDW
5h 48m
1 stop
MDW
YYZ
4h 41m
1 stop
Depart: Tue Jul 25 2017 Return: Mon Jul 31 2017 Trip spans 7 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Fri Jun 16 2017 Return: Sun Jun 18 2017 Trip spans 3 days
Major Airline
Major Airline
YUL
MDW
3h 45m
nonstop
MDW
YUL
6h 24m
nonstop
Depart: Thu Jun 1 2017 Return: Tue Jun 6 2017 Trip spans 6 days
Porter Airlines
Porter Airlines
YUL
MDW
5h 45m
1 stop
MDW
YUL
5h 55m
1 stop
Depart: Thu Jun 22 2017 Return: Mon Jun 26 2017 Trip spans 5 days
Major Airline
Major Airline
YUL
MDW
6h 15m
nonstop
MDW
YUL
26h 15m
nonstop
Depart: Thu Jul 13 2017 Return: Mon Jul 17 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Sun Jun 11 2017 Return: Wed Jun 14 2017 Trip spans 4 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Sun May 14 2017 Return: Wed May 17 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Wed Oct 25 2017 Return: Mon Oct 30 2017 Trip spans 6 days
Delta
Delta
YYZ
MDW
3h 35m
1 stop
MDW
YYZ
5h 04m
1 stop
Depart: Wed Aug 2 2017 Return: Sun Aug 6 2017 Trip spans 5 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Sat May 20 2017 Return: Wed Jun 7 2017 Trip spans 19 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Tue Sep 12 2017 Return: Thu Sep 14 2017 Trip spans 3 days
Delta
Delta
YYZ
MDW
5h 40m
1 stop
MDW
YYZ
3h 20m
1 stop
Depart: Fri Jun 2 2017 Return: Tue Jun 6 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 39m
nonstop
Depart: Sat Sep 23 2017 Return: Mon Sep 25 2017 Trip spans 3 days
Delta
Delta
YYZ
MDW
4h 03m
1 stop
MDW
YYZ
5h 13m
1 stop
Depart: Fri Oct 6 2017 Return: Sun Oct 8 2017 Trip spans 3 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Wed Aug 2 2017 Return: Mon Aug 7 2017 Trip spans 6 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Wed Aug 30 2017 Return: Sun Sep 3 2017 Trip spans 5 days
Major Airline
Major Airline
YUL
MDW
4h 00m
nonstop
MDW
YUL
3h 50m
nonstop
Depart: Sun Jun 4 2017 Return: Sat Jun 10 2017 Trip spans 7 days
Delta
Delta
YYZ
MDW
4h 39m
1 stop
MDW
YYZ
4h 48m
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

Montreal
$190
Toronto
only $224
only $197
Destination

Chicago
$190