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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Book cheap flights from Canada to Chicago

(Round-trip)
Depart: Wed Jul 12 2017 Return: Wed Jul 19 2017 Trip spans 8 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Fri Dec 15 2017 Return: Sun Dec 31 2017 Trip spans 17 days
Major Airline
Major Airline
YTZ
MDW
1h 50m
3 stops
MDW
YTZ
1h 37m
3 stops
Depart: Wed Jul 12 2017 Return: Wed Jul 19 2017 Trip spans 8 days
Air Canada
Air Canada
YTZ
ORD
4h 31m
1 stop
ORD
YTZ
4h 40m
1 stop
Depart: Fri Sep 1 2017 Return: Tue Sep 5 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
YUL
ORD
2h 40m
nonstop
ORD
YUL
2h 04m
nonstop
Depart: Sat Sep 2 2017 Return: Sun Sep 3 2017 Trip spans 2 days
American Airlines
American Airlines
YQB
ORD
7h 07m
1 stop
ORD
YQB
6h 50m
1 stop
Depart: Wed Oct 11 2017 Return: Wed Oct 25 2017 Trip spans 15 days
WestJet
WestJet
YEG
ORD
6h 29m
1 stop
ORD
YEG
6h 03m
1 stop
Depart: Fri Aug 11 2017 Return: Wed Aug 23 2017 Trip spans 13 days
Delta
Delta
YEG
MDW
5h 43m
1 stop
MDW
YEG
12h 12m
2 stops
Depart: Sat Jul 15 2017 Return: Fri Jul 21 2017 Trip spans 7 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Mon Aug 21 2017 Return: Thu Aug 24 2017 Trip spans 4 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
3 stops
MDW
YTZ
1h 40m
3 stops
Depart: Sat Aug 5 2017 Return: Tue Aug 8 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 45m
nonstop
Depart: Sun Nov 5 2017 Return: Tue Nov 7 2017 Trip spans 3 days
Major Airline
Major Airline
YTZ
MDW
1h 50m
2 stops
MDW
YTZ
1h 34m
2 stops
Depart: Sun Aug 20 2017 Return: Wed Aug 23 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 45m
nonstop
Depart: Tue Aug 22 2017 Return: Sat Aug 26 2017 Trip spans 5 days
Air Canada
Air Canada
YTZ
ORD
4h 31m
1 stop
ORD
YTZ
4h 40m
1 stop
Depart: Fri Sep 1 2017 Return: Fri Oct 13 2017 Trip spans 43 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 39m
nonstop
Depart: Thu Jul 13 2017 Return: Sun Jul 16 2017 Trip spans 4 days
Multiple Airlines
Multiple Airlines
YUL
ORD
2h 35m
nonstop
ORD
YUL
2h 04m
nonstop
Depart: Thu Sep 7 2017 Return: Fri Sep 15 2017 Trip spans 9 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Fri Jul 14 2017 Return: Sat Jul 15 2017 Trip spans 2 days
Air Canada
Air Canada
YUL
ORD
2h 21m
nonstop
ORD
YUL
2h 04m
nonstop
Depart: Wed Sep 13 2017 Return: Wed Sep 27 2017 Trip spans 15 days
Major Airline
Major Airline
YUL
MDW
4h 10m
1 stop
MDW
YUL
6h 05m
1 stop
Depart: Sat Aug 26 2017 Return: Sat Sep 2 2017 Trip spans 8 days
American Airlines
American Airlines
YQB
ORD
13h 38m
2 stops
ORD
YQB
4h 35m
1 stop
Depart: Sun Oct 1 2017 Return: Thu Oct 5 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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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.

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Airports
Origin

Québec City
$307
Edmonton
$311
Montreal
$255
Toronto
$198
Destination

Chicago
only $259
only $198
Airlines Airline reviews

71 travelers who booked a flight from Toronto to Chicago rated their chosen airlines with an average of 8.5.

Overall
8.7
Boarding
8.8
Crew
8.9
Comfort
8.5
Food
8.4
Entertainment
7.2