Find Cheap Flights from Canada to Chicago

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 Canada to Chicago

(Round-trip)
Depart: Sat Oct 14 2017 Return: Tue Oct 17 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 45m
nonstop
Depart: Wed Oct 11 2017 Return: Mon Oct 16 2017 Trip spans 6 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Sat Oct 14 2017 Return: Wed Oct 18 2017 Trip spans 5 days
American Airlines
American Airlines
YYZ
ORD
1h 51m
nonstop
ORD
YYZ
5h 30m
1 stop
Depart: Fri Nov 10 2017 Return: Tue Nov 14 2017 Trip spans 5 days
Delta
Delta
YVR
ORD
6h 06m
1 stop
ORD
YVR
9h 05m
1 stop
Depart: Sat Nov 4 2017 Return: Wed Nov 8 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Thu Oct 12 2017 Return: Tue Oct 17 2017 Trip spans 6 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Sat Oct 28 2017 Return: Tue Oct 31 2017 Trip spans 4 days
American Airlines
American Airlines
YYZ
ORD
1h 51m
nonstop
ORD
YYZ
11h 33m
1 stop
Depart: Thu Oct 12 2017 Return: Tue Oct 17 2017 Trip spans 6 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Fri Oct 13 2017 Return: Tue Oct 17 2017 Trip spans 5 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Tue Nov 28 2017 Return: Mon Dec 4 2017 Trip spans 7 days
Delta
Delta
YVR
ORD
8h 20m
1 stop
ORD
YVR
8h 45m
1 stop
Depart: Sat Dec 16 2017 Return: Sun Dec 31 2017 Trip spans 16 days
American Airlines
American Airlines
YYZ
ORD
1h 54m
nonstop
ORD
YYZ
1h 36m
nonstop
Depart: Tue Oct 24 2017 Return: Mon Oct 30 2017 Trip spans 7 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Tue Oct 24 2017 Return: Mon Oct 30 2017 Trip spans 7 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Wed Nov 29 2017 Return: Sun Dec 3 2017 Trip spans 5 days
Delta
Delta
YVR
ORD
8h 20m
1 stop
ORD
YVR
6h 01m
1 stop
Depart: Tue Dec 19 2017 Return: Sun Dec 31 2017 Trip spans 13 days
American Airlines
American Airlines
YYZ
ORD
1h 54m
nonstop
ORD
YYZ
1h 36m
nonstop
Depart: Wed Oct 11 2017 Return: Mon Oct 16 2017 Trip spans 6 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 45m
nonstop
Depart: Sat Feb 3 2018 Return: Sat Feb 10 2018 Trip spans 8 days
Delta
Delta
YVR
ORD
7h 55m
1 stop
ORD
YVR
8h 53m
2 stops
Depart: Thu Oct 12 2017 Return: Mon Oct 16 2017 Trip spans 5 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Thu Jan 18 2018 Return: Sun Jan 21 2018 Trip spans 4 days
American Airlines
American Airlines
YYZ
ORD
1h 54m
nonstop
ORD
YYZ
1h 36m
nonstop
Depart: Fri Oct 13 2017 Return: Tue Oct 17 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
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

Vancouver
$228
Toronto
only $205
only $195
Destination

Chicago
only $205
only $195
Airlines Airline reviews

276 travelers who booked a flight from Toronto to Chicago rated their chosen airlines with an average of 7.4.

Overall
7.4
Boarding
7.3
Crew
8.0
Comfort
7.5
Food
6.5
Entertainment
6.6