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: Fri Sep 15 2017 Return: Tue Sep 19 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Sat Nov 25 2017 Return: Wed Nov 29 2017 Trip spans 5 days
Delta
Delta
YYZ
MDW
7h 16m
1 stop
MDW
YYZ
5h 57m
1 stop
Depart: Sun Sep 17 2017 Return: Fri Sep 22 2017 Trip spans 6 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Mon Feb 5 2018 Return: Fri Feb 9 2018 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 34m
nonstop
Depart: Thu Jan 25 2018 Return: Fri Jan 26 2018 Trip spans 2 days
Delta
Delta
YYZ
MDW
5h 55m
1 stop
MDW
YYZ
3h 32m
1 stop
Depart: Tue Nov 7 2017 Return: Fri Nov 10 2017 Trip spans 4 days
Delta
Delta
YYZ
MDW
5h 24m
1 stop
MDW
YYZ
4h 29m
1 stop
Depart: Sat Oct 7 2017 Return: Wed Oct 11 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 45m
nonstop
Depart: Tue Sep 12 2017 Return: Thu Sep 14 2017 Trip spans 3 days
Delta
Delta
YYZ
MDW
6h 25m
1 stop
MDW
YYZ
4h 50m
1 stop
Depart: Thu Oct 12 2017 Return: Mon Oct 16 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Tue Oct 10 2017 Return: Sat Oct 14 2017 Trip spans 5 days
Delta
Delta
YYZ
MDW
6h 20m
1 stop
MDW
YYZ
7h 12m
1 stop
Depart: Fri Nov 24 2017 Return: Mon Nov 27 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Mon Dec 4 2017 Return: Fri Dec 8 2017 Trip spans 5 days
Delta
Delta
YYZ
MDW
3h 23m
1 stop
MDW
YYZ
3h 15m
1 stop
Depart: Thu Jan 25 2018 Return: Fri Jan 26 2018 Trip spans 2 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 34m
nonstop
Depart: Sat Nov 25 2017 Return: Wed Nov 29 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Mon Dec 11 2017 Return: Fri Dec 15 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Wed Dec 13 2017 Return: Sun Dec 17 2017 Trip spans 5 days
Delta
Delta
YYZ
MDW
3h 50m
1 stop
MDW
YYZ
7h 59m
2 stops
Depart: Thu Sep 28 2017 Return: Sun Oct 1 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Wed Nov 22 2017 Return: Sun Nov 26 2017 Trip spans 5 days
Delta
Delta
YYZ
MDW
3h 23m
1 stop
MDW
YYZ
3h 09m
1 stop
Depart: Thu Sep 14 2017 Return: Sun Sep 17 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Tue Dec 19 2017 Return: Fri Dec 22 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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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.

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Airports
Origin

Toronto
only $229
only $203
Destination

Chicago
$203
Airlines Airline reviews

86 travelers who booked a flight from Toronto to Chicago rated their chosen airlines with an average of 8.3.

Overall
8.6
Boarding
8.5
Crew
8.7
Comfort
8.5
Food
8.2
Entertainment
7.1