Find Deals on Flights from Chicago 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
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 to Canada

(Round-trip)
Depart: Tue Apr 18 2017 Return: Fri Apr 21 2017 Trip spans 4 days
Major Airline
Major Airline
MDW
YUL
4h 25m
nonstop
YUL
MDW
4h 30m
nonstop
Depart: Thu Apr 20 2017 Return: Sun Apr 23 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
MDW
YUL
4h 10m
1 stop
YUL
MDW
6h 00m
1 stop
Depart: Fri Apr 21 2017 Return: Sun Apr 23 2017 Trip spans 3 days
Air Canada
Air Canada
ORD
YYZ
1h 31m
nonstop
YYZ
ORD
1h 45m
nonstop
Depart: Fri Jun 30 2017 Return: Mon Jul 3 2017 Trip spans 4 days
United
United
ORD
YYZ
1h 32m
nonstop
YYZ
ORD
1h 52m
nonstop
Depart: Sat Apr 15 2017 Return: Wed Apr 19 2017 Trip spans 5 days
Delta
Delta
MDW
YYZ
4h 53m
1 stop
YYZ
MDW
5h 32m
1 stop
Depart: Thu Apr 13 2017 Return: Sun Apr 16 2017 Trip spans 4 days
American Airlines
American Airlines
ORD
YUL
2h 09m
nonstop
YUL
ORD
2h 40m
nonstop
Depart: Fri Apr 28 2017 Return: Mon May 1 2017 Trip spans 4 days
Major Airline
Major Airline
MDW
YUL
5h 20m
1 stop
YUL
MDW
5h 40m
1 stop
Depart: Fri Jun 9 2017 Return: Sun Jun 11 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 40m
nonstop
YTZ
MDW
1h 45m
nonstop
Depart: Tue Sep 12 2017 Return: Tue Sep 26 2017 Trip spans 15 days
Alaska Airlines
Alaska Airlines
ORD
YYJ
8h 24m
1 stop
YYJ
ORD
6h 17m
1 stop
Depart: Tue May 9 2017 Return: Sat May 13 2017 Trip spans 5 days
Major Airline
Major Airline
MDW
YUL
5h 25m
nonstop
YUL
MDW
6h 30m
nonstop
Depart: Sat Jul 22 2017 Return: Wed Aug 2 2017 Trip spans 12 days
Air Canada
Air Canada
ORD
YYZ
1h 34m
nonstop
YYZ
ORD
1h 44m
nonstop
Depart: Thu May 4 2017 Return: Sun May 7 2017 Trip spans 4 days
WestJet
WestJet
ORD
YLW
6h 10m
1 stop
YLW
ORD
6h 47m
1 stop
Depart: Thu Jun 15 2017 Return: Sun Jun 18 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 40m
nonstop
YTZ
MDW
1h 45m
nonstop
Depart: Wed May 31 2017 Return: Sat Jun 3 2017 Trip spans 4 days
Major Airline
Major Airline
MDW
YUL
4h 40m
nonstop
YUL
MDW
6h 30m
nonstop
Depart: Wed May 3 2017 Return: Mon May 8 2017 Trip spans 6 days
Delta
Delta
MDW
YYZ
4h 41m
1 stop
YYZ
MDW
3h 31m
1 stop
Depart: Thu Jun 1 2017 Return: Mon Jun 5 2017 Trip spans 5 days
Major Airline
Major Airline
MDW
YUL
4h 05m
nonstop
YUL
MDW
5h 40m
nonstop
Depart: Thu Apr 20 2017 Return: Sun Apr 23 2017 Trip spans 4 days
Air Canada
Air Canada
ORD
YUL
2h 00m
nonstop
YUL
ORD
2h 23m
nonstop
Depart: Thu May 4 2017 Return: Sun May 7 2017 Trip spans 4 days
Delta
Delta
MDW
YYZ
4h 41m
1 stop
YYZ
MDW
5h 48m
1 stop
Depart: Thu Jul 20 2017 Return: Sun Jul 23 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 40m
nonstop
YTZ
MDW
1h 45m
nonstop
Depart: Fri Apr 21 2017 Return: Mon Apr 24 2017 Trip spans 4 days
Major Airline
Major Airline
MDW
YTZ
1h 40m
nonstop
YTZ
MDW
1h 45m
nonstop
* 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.

We compile tonnes of data for you
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
only $226
only $203
Destination

Victoria
$430
Montreal
$203
Toronto
only $226
only $213
Kelowna
$467