Find Deals on Flights from Canada to Chicago Midway

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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Book cheap flights from Canada to Chicago Midway

(Round-trip)
Depart: Fri Jan 13 2017 Return: Sun Jan 15 2017 Trip spans 3 days
Major Airline
Major Airline
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Fri Dec 30 2016 Return: Wed Jan 11 2017 Trip spans 13 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 55m
nonstop
MDW
YTZ
1h 35m
nonstop
Depart: Sat Apr 8 2017 Return: Tue Apr 11 2017 Trip spans 4 days
Delta
Delta
YYZ
MDW
3h 58m
1 stop
MDW
YYZ
6h 40m
1 stop
Depart: Mon Jan 9 2017 Return: Wed Jan 11 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Thu Feb 9 2017 Return: Sun Feb 12 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Thu Jan 19 2017 Return: Sun Jan 22 2017 Trip spans 4 days
Delta
Delta
YYZ
MDW
6h 30m
1 stop
MDW
YYZ
5h 09m
1 stop
Depart: Tue Apr 18 2017 Return: Tue Apr 25 2017 Trip spans 8 days
Major Airline
Major Airline
YUL
MDW
5h 45m
1 stop
MDW
YUL
4h 05m
1 stop
Depart: Wed Feb 15 2017 Return: Wed Mar 15 2017 Trip spans 28 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Wed Mar 8 2017 Return: Thu Mar 16 2017 Trip spans 8 days
Major Airline
Major Airline
YUL
MDW
3h 40m
nonstop
MDW
YUL
4h 15m
nonstop
Depart: Fri Jan 6 2017 Return: Tue Jan 17 2017 Trip spans 12 days
Delta
Delta
YYZ
MDW
7h 23m
1 stop
MDW
YYZ
7h 04m
1 stop
Depart: Thu Feb 16 2017 Return: Sun Feb 19 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Sun Feb 26 2017 Return: Thu Mar 2 2017 Trip spans 5 days
Major Airline
Major Airline
YUL
MDW
4h 05m
2 stops
MDW
YUL
5h 20m
2 stops
Depart: Wed Feb 15 2017 Return: Wed Mar 15 2017 Trip spans 28 days
Delta
Delta
YYZ
MDW
6h 30m
1 stop
MDW
YYZ
4h 47m
1 stop
Depart: Fri Feb 24 2017 Return: Mon Feb 27 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 34m
nonstop
Depart: Fri Feb 17 2017 Return: Sat Feb 25 2017 Trip spans 9 days
Delta
Delta
YYZ
MDW
3h 56m
1 stop
MDW
YYZ
3h 56m
1 stop
Depart: Tue Dec 27 2016 Return: Fri Dec 30 2016 Trip spans 4 days
Major Airline
Major Airline
YTZ
MDW
1h 55m
nonstop
MDW
YTZ
1h 35m
nonstop
Depart: Fri Mar 3 2017 Return: Sun Mar 5 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Wed Mar 15 2017 Return: Wed Mar 22 2017 Trip spans 8 days
Delta
Delta
YYZ
MDW
7h 14m
1 stop
MDW
YYZ
7h 15m
2 stops
Depart: Wed Mar 15 2017 Return: Wed Mar 22 2017 Trip spans 8 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Sun Dec 25 2016 Return: Mon Jan 2 2017 Trip spans 9 days
Major Airline
Major Airline
YUL
MDW
23h 50m
nonstop
MDW
YUL
4h 05m
nonstop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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

Montreal
$227
Toronto
only $225
only $197
Destination

Chicago
$197
Airlines Airline reviews

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

Overall
8.6
Boarding
8.7
Crew
8.8
Comfort
8.5
Food
8.6
Entertainment
7.0