Find Deals on Flights from Chicago Midway to Canada

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 Chicago Midway to Canada

(Round-trip)
Depart: Sun Jan 15 2017 Return: Fri Jan 20 2017 Trip spans 6 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 37m
nonstop
YTZ
MDW
1h 50m
nonstop
Depart: Thu Jun 29 2017 Return: Sun Jul 9 2017 Trip spans 11 days
Major Airline
Major Airline
MDW
YTZ
1h 40m
nonstop
YTZ
MDW
1h 45m
nonstop
Depart: Fri Jan 13 2017 Return: Sun Jan 15 2017 Trip spans 3 days
Delta
Delta
MDW
YYZ
6h 39m
1 stop
YYZ
MDW
8h 16m
1 stop
Depart: Wed Dec 28 2016 Return: Mon Jan 9 2017 Trip spans 13 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 35m
nonstop
YTZ
MDW
1h 50m
nonstop
Depart: Wed Feb 1 2017 Return: Sun Feb 5 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 37m
nonstop
YTZ
MDW
1h 50m
nonstop
Depart: Tue Jan 17 2017 Return: Thu Jan 19 2017 Trip spans 3 days
Major Airline
Major Airline
MDW
YUL
5h 05m
nonstop
YUL
MDW
3h 40m
nonstop
Depart: Sun Dec 25 2016 Return: Fri Dec 30 2016 Trip spans 6 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 35m
nonstop
YTZ
MDW
1h 55m
nonstop
Depart: Fri Jan 13 2017 Return: Mon Jan 16 2017 Trip spans 4 days
Delta
Delta
MDW
YYZ
5h 03m
1 stop
YYZ
MDW
6h 14m
1 stop
Depart: Wed Feb 15 2017 Return: Tue Feb 21 2017 Trip spans 7 days
Major Airline
Major Airline
MDW
YUL
3h 40m
nonstop
YUL
MDW
5h 55m
nonstop
Depart: Tue Jan 24 2017 Return: Thu Jan 26 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 37m
nonstop
YTZ
MDW
1h 50m
nonstop
Depart: Wed Jan 18 2017 Return: Sun Jan 22 2017 Trip spans 5 days
Delta
Delta
MDW
YYZ
7h 06m
1 stop
YYZ
MDW
5h 48m
1 stop
Depart: Tue Feb 7 2017 Return: Tue Feb 14 2017 Trip spans 8 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 37m
nonstop
YTZ
MDW
1h 50m
nonstop
Depart: Mon Feb 13 2017 Return: Thu Feb 16 2017 Trip spans 4 days
Delta
Delta
MDW
YYZ
4h 51m
1 stop
YYZ
MDW
6h 27m
1 stop
Depart: Mon Apr 17 2017 Return: Wed Apr 19 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 40m
nonstop
YTZ
MDW
1h 45m
nonstop
Depart: Thu Feb 23 2017 Return: Fri Mar 3 2017 Trip spans 9 days
Delta
Delta
MDW
YYZ
4h 57m
1 stop
YYZ
MDW
5h 14m
1 stop
Depart: Sat Mar 11 2017 Return: Thu Mar 16 2017 Trip spans 5 days
Major Airline
Major Airline
MDW
YHZ
6h 10m
1 stop
YHZ
MDW
10h 40m
1 stop
Depart: Fri Feb 24 2017 Return: Thu Mar 2 2017 Trip spans 7 days
Delta
Delta
MDW
YYZ
4h 57m
1 stop
YYZ
MDW
8h 17m
1 stop
Depart: Mon Mar 20 2017 Return: Thu Apr 6 2017 Trip spans 18 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 37m
nonstop
YTZ
MDW
1h 50m
nonstop
Depart: Tue Apr 4 2017 Return: Tue Apr 18 2017 Trip spans 15 days
Major Airline
Major Airline
MDW
YHZ
8h 05m
2 stops
YHZ
MDW
10h 00m
2 stops
Depart: Mon Mar 13 2017 Return: Fri Mar 17 2017 Trip spans 5 days
Delta
Delta
MDW
YYZ
6h 44m
1 stop
YYZ
MDW
8h 02m
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

Chicago
$212
Destination

Montreal
$246
Halifax
$314
Toronto
only $246
only $212