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: Wed Mar 29 2017 Return: Sun Apr 2 2017 Trip spans 5 days
Major Airline
Major Airline
MDW
YUL
5h 05m
nonstop
YUL
MDW
7h 45m
nonstop
Depart: Thu Mar 23 2017 Return: Sun Mar 26 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
MDW
YUL
3h 40m
1 stop
YUL
MDW
4h 05m
1 stop
Depart: Fri Mar 24 2017 Return: Mon Mar 27 2017 Trip spans 4 days
United
United
ORD
YYZ
1h 30m
nonstop
YYZ
ORD
1h 43m
nonstop
Depart: Sat Apr 22 2017 Return: Mon Apr 24 2017 Trip spans 3 days
American Airlines
American Airlines
ORD
YYZ
1h 31m
nonstop
YYZ
ORD
1h 52m
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: Fri Mar 10 2017 Return: Tue Mar 14 2017 Trip spans 4 days
Delta
Delta
MDW
YYZ
3h 42m
1 stop
YYZ
MDW
5h 29m
1 stop
Depart: Wed May 3 2017 Return: Wed May 10 2017 Trip spans 8 days
WestJet
WestJet
ORD
YYC
3h 45m
nonstop
YYC
ORD
3h 22m
nonstop
Depart: Fri Mar 31 2017 Return: Sun Apr 2 2017 Trip spans 3 days
Major Airline
Major Airline
MDW
YUL
5h 35m
nonstop
YUL
MDW
6h 15m
nonstop
Depart: Wed Jun 14 2017 Return: Tue Jun 20 2017 Trip spans 7 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 40m
nonstop
YTZ
MDW
1h 45m
nonstop
Depart: Wed Apr 5 2017 Return: Sat Apr 8 2017 Trip spans 4 days
Major Airline
Major Airline
MDW
YUL
16h 30m
1 stop
YUL
MDW
5h 35m
1 stop
Depart: Thu Apr 13 2017 Return: Mon Apr 17 2017 Trip spans 5 days
United
United
ORD
YYZ
1h 33m
nonstop
YYZ
ORD
1h 51m
nonstop
Depart: Sat May 6 2017 Return: Wed May 10 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
MDW
YUL
4h 05m
1 stop
YUL
MDW
4h 35m
1 stop
Depart: Thu Apr 6 2017 Return: Sun Apr 9 2017 Trip spans 4 days
Major Airline
Major Airline
MDW
YUL
3h 45m
nonstop
YUL
MDW
6h 15m
nonstop
Depart: Sat Jul 22 2017 Return: Sat Jul 29 2017 Trip spans 8 days
Alaska Airlines
Alaska Airlines
ORD
YVR
6h 57m
1 stop
YVR
ORD
8h 17m
1 stop
Depart: Tue Mar 14 2017 Return: Wed Mar 15 2017 Trip spans 2 days
Delta
Delta
MDW
YYZ
4h 56m
1 stop
YYZ
MDW
4h 50m
1 stop
Depart: Thu Mar 9 2017 Return: Sun Mar 12 2017 Trip spans 4 days
American Airlines
American Airlines
ORD
YUL
2h 06m
nonstop
YUL
ORD
2h 47m
nonstop
Depart: Wed Apr 5 2017 Return: Sun Apr 16 2017 Trip spans 12 days
Delta
Delta
MDW
YYZ
3h 34m
1 stop
YYZ
MDW
5h 32m
1 stop
Depart: Wed Mar 8 2017 Return: Wed Mar 15 2017 Trip spans 7 days
Major Airline
Major Airline
MDW
YTZ
1h 37m
nonstop
YTZ
MDW
1h 50m
nonstop
Depart: Fri Mar 24 2017 Return: Mon Mar 27 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 37m
nonstop
YTZ
MDW
1h 50m
nonstop
Depart: Fri Jun 2 2017 Return: Sun Jun 4 2017 Trip spans 3 days
Air Canada
Air Canada
ORD
YTZ
5h 50m
1 stop
YTZ
ORD
5h 03m
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.

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 $241
only $205
Destination

Vancouver
$525
Calgary
$345
Montreal
$205
Toronto
only $241
only $218