Find Deals on Flights from Toronto Pearson Intl to Chicago Midway (YYZ - MDW)

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 Toronto Pearson Intl to Chicago Midway

(Round-trip)
Depart: Fri Jan 6 2017 Return: Tue Jan 10 2017 Trip spans 5 days
Delta
Delta
YYZ
7:57a
MDW
12:47p
4h 50m
1 stop
MDW
1:45a
YYZ
5:25a
3h 40m
1 stop
Depart: Sat Jan 7 2017 Return: Tue Jan 10 2017 Trip spans 4 days
Delta
Delta
YYZ
8:00a
MDW
12:09p
4h 09m
1 stop
MDW
1:45a
YYZ
5:25a
3h 40m
1 stop
Depart: Mon Jan 9 2017 Return: Wed Jan 11 2017 Trip spans 3 days
Delta
Delta
YYZ
8:30a
MDW
12:11p
3h 41m
1 stop
MDW
1:45a
YYZ
5:25a
3h 40m
1 stop
Depart: Tue Jan 10 2017 Return: Thu Jan 12 2017 Trip spans 3 days
Delta
Delta
YYZ
12:49p
MDW
6:46p
5h 57m
1 stop
MDW
7:20a
YYZ
12:45p
5h 25m
1 stop
Depart: Thu Jan 19 2017 Return: Sun Jan 22 2017 Trip spans 4 days
Delta
Delta
YYZ
1:15a
MDW
7:45a
6h 30m
1 stop
MDW
10:40a
YYZ
5:44p
7h 04m
1 stop
Depart: Fri Feb 24 2017 Return: Mon Feb 27 2017 Trip spans 4 days
Delta
Delta
YYZ
1:10a
MDW
9:27a
8h 17m
1 stop
MDW
11:30a
YYZ
3:26p
3h 56m
1 stop
Depart: Wed Jan 11 2017 Return: Thu Jan 12 2017 Trip spans 2 days
Delta
Delta
YYZ
1:15a
MDW
7:45a
6h 30m
1 stop
MDW
7:20a
YYZ
12:45p
5h 25m
1 stop
Depart: Thu Jan 12 2017 Return: Fri Jan 13 2017 Trip spans 2 days
Delta
Delta
YYZ
1:15a
MDW
7:45a
6h 30m
1 stop
MDW
9:08a
YYZ
1:59p
4h 51m
1 stop
Depart: Fri Jan 13 2017 Return: Mon Jan 16 2017 Trip spans 4 days
Delta
Delta
YYZ
1:00a
MDW
7:59a
6h 59m
2 stops
MDW
7:20a
YYZ
11:00a
3h 40m
1 stop
Depart: Tue Jan 17 2017 Return: Sat Jan 21 2017 Trip spans 5 days
Delta
Delta
YYZ
12:49p
MDW
6:46p
5h 57m
1 stop
MDW
12:11p
YYZ
5:31p
5h 20m
1 stop
Depart: Fri Jan 20 2017 Return: Sun Jan 22 2017 Trip spans 3 days
Delta
Delta
YYZ
1:15a
MDW
9:33a
8h 18m
1 stop
MDW
7:20a
YYZ
1:59p
6h 39m
1 stop
Depart: Thu Jan 26 2017 Return: Sun Jan 29 2017 Trip spans 4 days
Delta
Delta
YYZ
6:49a
MDW
12:11p
5h 22m
1 stop
MDW
7:20a
YYZ
1:59p
6h 39m
1 stop
Depart: Fri Jan 27 2017 Return: Sun Jan 29 2017 Trip spans 3 days
Delta
Delta
YYZ
1:30a
MDW
7:57a
6h 27m
1 stop
MDW
1:40p
YYZ
4:57p
3h 17m
1 stop
Depart: Wed Feb 15 2017 Return: Wed Mar 15 2017 Trip spans 28 days
Delta
Delta
YYZ
1:15a
MDW
7:45a
6h 30m
1 stop
MDW
2:25a
YYZ
7:12a
4h 47m
1 stop
Depart: Fri Feb 17 2017 Return: Sat Feb 25 2017 Trip spans 9 days
Delta
Delta
YYZ
1:05a
MDW
5:01a
3h 56m
1 stop
MDW
11:30a
YYZ
3:26p
3h 56m
1 stop
Depart: Sat Feb 18 2017 Return: Sat Feb 25 2017 Trip spans 8 days
Delta
Delta
YYZ
1:30a
MDW
6:50a
5h 20m
1 stop
MDW
11:30a
YYZ
3:26p
3h 56m
1 stop
Depart: Wed Mar 15 2017 Return: Wed Mar 22 2017 Trip spans 8 days
Delta
Delta
YYZ
8:50a
MDW
4:04p
7h 14m
1 stop
MDW
3:00a
YYZ
10:15a
7h 15m
2 stops
Depart: Thu Feb 9 2017 Return: Tue Feb 14 2017 Trip spans 6 days
Delta
Delta
YYZ
1:15a
MDW
7:45a
6h 30m
1 stop
MDW
1:20a
YYZ
6:28a
5h 08m
1 stop
Depart: Fri Mar 3 2017 Return: Sun Mar 5 2017 Trip spans 3 days
Delta
Delta
YYZ
1:10a
MDW
9:27a
8h 17m
1 stop
MDW
11:30a
YYZ
3:26p
3h 56m
1 stop
Depart: Fri Apr 28 2017 Return: Mon May 1 2017 Trip spans 4 days
Delta
Delta
YYZ
2:10a
MDW
5:50a
3h 40m
1 stop
MDW
11:05a
YYZ
5:48p
6h 43m
1 stop
* 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
$231
Destination

Chicago
$231
Airlines