Find Cheap 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
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: Sun Aug 27 2017 Return: Mon Aug 28 2017 Trip spans 2 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 45m
nonstop
Depart: Sat Jul 22 2017 Return: Mon Jul 31 2017 Trip spans 10 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 45m
nonstop
Depart: Tue Sep 12 2017 Return: Tue Sep 19 2017 Trip spans 8 days
Delta
Delta
YYZ
MDW
5h 09m
1 stop
MDW
YYZ
7h 59m
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: Fri Sep 1 2017 Return: Tue Sep 5 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Wed Sep 20 2017 Return: Fri Sep 22 2017 Trip spans 3 days
Delta
Delta
YYZ
MDW
6h 10m
1 stop
MDW
YYZ
3h 20m
1 stop
Depart: Thu Sep 14 2017 Return: Mon Sep 18 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 39m
nonstop
Depart: Wed Oct 25 2017 Return: Tue Oct 31 2017 Trip spans 7 days
Delta
Delta
YYZ
MDW
6h 10m
1 stop
MDW
YYZ
3h 35m
1 stop
Depart: Fri Jul 21 2017 Return: Sun Jul 23 2017 Trip spans 3 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 45m
nonstop
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
Depart: Fri Dec 1 2017 Return: Sun Dec 3 2017 Trip spans 3 days
Delta
Delta
YYZ
MDW
6h 10m
1 stop
MDW
YYZ
3h 20m
1 stop
Depart: Fri Oct 20 2017 Return: Fri Oct 27 2017 Trip spans 8 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Tue Nov 7 2017 Return: Sat Nov 11 2017 Trip spans 5 days
Delta
Delta
YYZ
MDW
5h 24m
1 stop
MDW
YYZ
5h 13m
1 stop
Depart: Sat Jul 15 2017 Return: Tue Jul 18 2017 Trip spans 4 days
Major Airline
Major Airline
YUL
MDW
3h 40m
nonstop
MDW
YUL
6h 25m
nonstop
Depart: Wed Nov 1 2017 Return: Thu Nov 2 2017 Trip spans 2 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Thu Jul 20 2017 Return: Mon Jul 24 2017 Trip spans 5 days
Major Airline
Major Airline
YUL
MDW
3h 40m
nonstop
MDW
YUL
6h 50m
nonstop
Depart: Mon Dec 18 2017 Return: Mon Dec 25 2017 Trip spans 8 days
Delta
Delta
YYZ
MDW
6h 10m
1 stop
MDW
YYZ
4h 51m
1 stop
Depart: Mon Nov 20 2017 Return: Thu Nov 23 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Fri Jul 21 2017 Return: Sat Aug 5 2017 Trip spans 16 days
Major Airline
Major Airline
YUL
MDW
6h 35m
nonstop
MDW
YUL
6h 05m
nonstop
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 40m
nonstop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Montreal
$275
Toronto
only $223
only $195
Destination

Chicago
$195
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