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 Jan 5 2018 Return: Wed Jan 10 2018 Trip spans 6 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Tue Jan 9 2018 Return: Fri Jan 12 2018 Trip spans 4 days
Delta
Delta
YYZ
MDW
6h 14m
1 stop
MDW
YYZ
3h 25m
1 stop
Depart: Tue Jan 9 2018 Return: Thu Jan 11 2018 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Thu Jan 11 2018 Return: Mon Jan 15 2018 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 40m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Thu Jan 11 2018 Return: Thu Jan 25 2018 Trip spans 15 days
Delta
Delta
YYZ
MDW
6h 14m
1 stop
MDW
YYZ
4h 50m
1 stop
Depart: Fri Jan 12 2018 Return: Sun Jan 14 2018 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 40m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Sat Jan 13 2018 Return: Thu Jan 25 2018 Trip spans 13 days
Delta
Delta
YYZ
MDW
4h 32m
1 stop
MDW
YYZ
4h 50m
1 stop
Depart: Mon Jan 15 2018 Return: Thu Jan 18 2018 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Tue Jan 16 2018 Return: Sun Jan 28 2018 Trip spans 13 days
Delta
Delta
YYZ
MDW
7h 23m
1 stop
MDW
YYZ
6h 30m
2 stops
Depart: Tue Jan 16 2018 Return: Sun Jan 28 2018 Trip spans 13 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Tue Jan 23 2018 Return: Thu Jan 25 2018 Trip spans 3 days
Delta
Delta
YYZ
MDW
6h 13m
1 stop
MDW
YYZ
4h 50m
1 stop
Depart: Thu Jan 18 2018 Return: Sun Jan 21 2018 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 40m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Fri Jan 26 2018 Return: Sun Jan 28 2018 Trip spans 3 days
Delta
Delta
YYZ
MDW
6h 14m
1 stop
MDW
YYZ
6h 30m
2 stops
Depart: Sat Jan 20 2018 Return: Mon Jan 22 2018 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Fri Jan 26 2018 Return: Sun Jan 28 2018 Trip spans 3 days
Delta
Delta
YYZ
MDW
6h 14m
1 stop
MDW
YYZ
6h 30m
2 stops
Depart: Mon Jan 22 2018 Return: Mon Jan 29 2018 Trip spans 8 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Sun Jan 28 2018 Return: Wed Jan 31 2018 Trip spans 4 days
Delta
Delta
YYZ
MDW
8h 53m
2 stops
MDW
YYZ
7h 44m
1 stop
Depart: Tue Jan 23 2018 Return: Thu Jan 25 2018 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Tue Feb 6 2018 Return: Wed Feb 14 2018 Trip spans 9 days
Delta
Delta
YYZ
MDW
7h 00m
1 stop
MDW
YYZ
4h 50m
1 stop
Depart: Wed Jan 24 2018 Return: Mon Jan 29 2018 Trip spans 6 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.

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.

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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.

If you have more questions or if you have a bad price to report to us,
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Airports
Origin

Toronto
only $205
only $183
Destination

Chicago
$183