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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Book cheap flights from Canada to Chicago Midway

(Round-trip)
Depart: Wed Jun 14 2017 Return: Mon Jun 19 2017 Trip spans 6 days
Porter Airlines
Porter Airlines
YUL
MDW
6h 40m
1 stop
MDW
YUL
4h 05m
1 stop
Depart: Thu Aug 3 2017 Return: Sun Aug 6 2017 Trip spans 4 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 45m
nonstop
Depart: Sun Oct 29 2017 Return: Sat Dec 2 2017 Trip spans 35 days
Delta
Delta
YYZ
MDW
5h 20m
1 stop
MDW
YYZ
5h 13m
1 stop
Depart: Mon Nov 20 2017 Return: Thu Nov 23 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Fri Jun 23 2017 Return: Sun Jun 25 2017 Trip spans 3 days
Major Airline
Major Airline
YUL
MDW
4h 55m
2 stops
MDW
YUL
3h 45m
2 stops
Depart: Fri Jul 7 2017 Return: Mon Jul 10 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Fri Jun 23 2017 Return: Tue Jun 27 2017 Trip spans 5 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
2 stops
MDW
YTZ
1h 40m
2 stops
Depart: Wed Jun 14 2017 Return: Tue Jun 27 2017 Trip spans 14 days
Delta
Delta
YYZ
MDW
5h 09m
1 stop
MDW
YYZ
5h 21m
1 stop
Depart: Fri Jul 28 2017 Return: Mon Jul 31 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Sat Aug 12 2017 Return: Tue Aug 22 2017 Trip spans 11 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Wed Sep 27 2017 Return: Sat Sep 30 2017 Trip spans 4 days
Delta
Delta
YYZ
MDW
8h 22m
1 stop
MDW
YYZ
5h 13m
1 stop
Depart: Thu Aug 31 2017 Return: Mon Sep 4 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 45m
nonstop
Depart: Thu Aug 31 2017 Return: Mon Sep 4 2017 Trip spans 5 days
Major Airline
Major Airline
YUL
MDW
5h 05m
nonstop
MDW
YUL
3h 55m
nonstop
Depart: Fri Sep 1 2017 Return: Tue Sep 5 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Fri Sep 8 2017 Return: Mon Sep 11 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Sat Aug 19 2017 Return: Tue Aug 22 2017 Trip spans 4 days
Delta
Delta
YYZ
MDW
6h 08m
1 stop
MDW
YYZ
5h 11m
1 stop
Depart: Tue May 30 2017 Return: Fri Jun 23 2017 Trip spans 25 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
2 stops
MDW
YTZ
1h 40m
2 stops
Depart: Wed Jun 14 2017 Return: Tue Jun 27 2017 Trip spans 14 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Sat Jun 17 2017 Return: Sat Jun 24 2017 Trip spans 8 days
Delta
Delta
YYZ
MDW
4h 10m
1 stop
MDW
YYZ
5h 15m
1 stop
Depart: Wed Jul 5 2017 Return: Mon Jul 10 2017 Trip spans 6 days
Major Airline
Major Airline
YOW
MDW
3h 15m
nonstop
MDW
YOW
13h 56m
nonstop
* 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

Ottawa
$279
Montreal
$197
Toronto
only $221
only $197
Destination

Chicago
$197