Find Deals on 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
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 Canada to Chicago

(Round-trip)
Depart: Fri Feb 10 2017 Return: Sun Feb 12 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Wed Feb 8 2017 Return: Sat Feb 11 2017 Trip spans 4 days
Major Airline
Major Airline
YYZ
ORD
2h 02m
nonstop
ORD
YYZ
1h 34m
nonstop
Depart: Thu Apr 6 2017 Return: Sun Apr 9 2017 Trip spans 4 days
Air Canada
Air Canada
YYZ
ORD
1h 43m
nonstop
ORD
YYZ
1h 40m
nonstop
Depart: Sat Mar 4 2017 Return: Fri Mar 31 2017 Trip spans 27 days
American Airlines
American Airlines
YUL
ORD
2h 47m
nonstop
ORD
YUL
2h 06m
nonstop
Depart: Fri May 26 2017 Return: Mon May 29 2017 Trip spans 4 days
United
United
YUL
ORD
2h 20m
nonstop
ORD
YUL
2h 10m
nonstop
Depart: Tue Feb 21 2017 Return: Tue Mar 7 2017 Trip spans 15 days
Delta
Delta
YXU
ORD
8h 48m
2 stops
ORD
YXU
10h 15m
2 stops
Depart: Wed Jun 21 2017 Return: Fri Jun 23 2017 Trip spans 3 days
WestJet
WestJet
YEG
ORD
5h 27m
1 stop
ORD
YEG
6h 12m
1 stop
Depart: Mon Apr 10 2017 Return: Sun Apr 16 2017 Trip spans 7 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Thu Mar 2 2017 Return: Sun Mar 5 2017 Trip spans 4 days
Major Airline
Major Airline
YYZ
ORD
1h 52m
nonstop
ORD
YYZ
1h 35m
nonstop
Depart: Wed Mar 22 2017 Return: Sun Mar 26 2017 Trip spans 5 days
Air Canada
Air Canada
YYZ
ORD
1h 57m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Fri Mar 17 2017 Return: Tue Mar 21 2017 Trip spans 5 days
Major Airline
Major Airline
YTZ
MDW
1h 50m
1 stop
MDW
YTZ
1h 35m
1 stop
Depart: Thu May 18 2017 Return: Mon May 22 2017 Trip spans 5 days
Alaska Airlines
Alaska Airlines
YVR
ORD
7h 36m
1 stop
ORD
YVR
6h 57m
1 stop
Depart: Fri Feb 10 2017 Return: Mon Feb 13 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Fri Feb 10 2017 Return: Tue Mar 14 2017 Trip spans 32 days
Delta
Delta
YYZ
MDW
5h 22m
1 stop
MDW
YYZ
4h 57m
1 stop
Depart: Tue Apr 4 2017 Return: Tue Apr 25 2017 Trip spans 22 days
Major Airline
Major Airline
YYZ
ORD
1h 50m
nonstop
ORD
YYZ
1h 34m
nonstop
Depart: Tue Mar 14 2017 Return: Sat Mar 18 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Tue Feb 14 2017 Return: Tue Feb 28 2017 Trip spans 15 days
Delta
Delta
YYZ
MDW
5h 22m
1 stop
MDW
YYZ
9h 57m
2 stops
Depart: Tue Jan 31 2017 Return: Wed Feb 1 2017 Trip spans 2 days
American Airlines
American Airlines
YUL
ORD
11h 17m
1 stop
ORD
YUL
2h 09m
nonstop
Depart: Fri May 5 2017 Return: Sun May 7 2017 Trip spans 3 days
Major Airline
Major Airline
YYZ
ORD
1h 54m
nonstop
ORD
YYZ
1h 36m
nonstop
Depart: Sun Apr 2 2017 Return: Thu Apr 6 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 34m
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
$443
Edmonton
$308
London
$226
Montreal
$224
Toronto
only $200
only $196
Destination

Chicago
only $200
only $196
Airlines Airline reviews

231 travelers who booked a flight from Toronto to Chicago rated their chosen airlines with an average of 7.3.

Overall
7.4
Boarding
7.3
Crew
7.9
Comfort
7.4
Food
6.3
Entertainment
6.4