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
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 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: Wed Jan 18 2017 Return: Thu Jan 19 2017 Trip spans 2 days
Major Airline
Major Airline
ORD
YYZ
1h 35m
nonstop
YYZ
ORD
2h 02m
nonstop
Depart: Wed Jan 11 2017 Return: Thu Jan 19 2017 Trip spans 9 days
Delta
Delta
MDW
YYZ
4h 50m
1 stop
YYZ
MDW
6h 30m
1 stop
Depart: Thu Jan 12 2017 Return: Sun Jan 15 2017 Trip spans 4 days
American Airlines
American Airlines
ORD
YUL
2h 09m
nonstop
YUL
ORD
2h 47m
nonstop
Depart: Sun Jan 15 2017 Return: Mon Jan 16 2017 Trip spans 2 days
Air Canada
Air Canada
ORD
YOW
4h 51m
1 stop
YOW
ORD
4h 50m
1 stop
Depart: Thu May 18 2017 Return: Mon May 22 2017 Trip spans 5 days
WestJet
WestJet
ORD
YEG
6h 12m
1 stop
YEG
ORD
6h 27m
1 stop
Depart: Wed Jan 11 2017 Return: Wed Jan 18 2017 Trip spans 8 days
Alaska Airlines
Alaska Airlines
ORD
YVR
8h 05m
1 stop
YVR
ORD
8h 49m
1 stop
Depart: Tue Jun 20 2017 Return: Fri Jun 30 2017 Trip spans 11 days
United
United
ORD
YHZ
5h 19m
1 stop
YHZ
ORD
6h 37m
1 stop
Depart: Mon Jan 23 2017 Return: Mon Jan 30 2017 Trip spans 8 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 34m
nonstop
YTZ
MDW
1h 50m
nonstop
Depart: Thu Apr 20 2017 Return: Mon Apr 24 2017 Trip spans 5 days
Major Airline
Major Airline
MDW
YTZ
1h 39m
nonstop
YTZ
MDW
1h 45m
nonstop
Depart: Thu Jan 26 2017 Return: Fri Jan 27 2017 Trip spans 2 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 35m
nonstop
YTZ
MDW
1h 50m
nonstop
Depart: Thu Jun 15 2017 Return: Tue Jun 20 2017 Trip spans 6 days
Major Airline
Major Airline
ORD
YYZ
1h 44m
nonstop
YYZ
ORD
1h 47m
nonstop
Depart: Fri Jan 13 2017 Return: Mon Jan 16 2017 Trip spans 4 days
Delta
Delta
MDW
YYZ
4h 51m
1 stop
YYZ
MDW
6h 14m
1 stop
Depart: Sun Jan 29 2017 Return: Fri Feb 3 2017 Trip spans 6 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 37m
nonstop
YTZ
MDW
1h 50m
nonstop
Depart: Fri Dec 30 2016 Return: Tue Jan 3 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
YYZ
1h 35m
nonstop
YYZ
ORD
1h 55m
nonstop
Depart: Tue Jan 31 2017 Return: Thu Feb 2 2017 Trip spans 3 days
Delta
Delta
MDW
YYZ
4h 50m
1 stop
YYZ
MDW
6h 30m
1 stop
Depart: Fri Feb 10 2017 Return: Sun Feb 12 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
MDW
YTZ
1h 35m
nonstop
YTZ
MDW
1h 50m
nonstop
Depart: Wed May 24 2017 Return: Mon May 29 2017 Trip spans 6 days
Major Airline
Major Airline
MDW
YTZ
1h 40m
nonstop
YTZ
MDW
1h 45m
nonstop
Depart: Sun May 7 2017 Return: Fri May 12 2017 Trip spans 6 days
American Airlines
American Airlines
ORD
YUL
4h 45m
1 stop
YUL
ORD
7h 31m
1 stop
Depart: Tue Mar 14 2017 Return: Tue Mar 21 2017 Trip spans 8 days
Air Canada
Air Canada
ORD
YEG
8h 17m
1 stop
YEG
ORD
8h 40m
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 $218
only $218
Destination

Vancouver
$375
Edmonton
$315
Ottawa
$282
Montreal
$264
Halifax
$418
Toronto
only $218
only $218