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
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: Sat Oct 15 2016 Return: Tue Oct 18 2016 Trip spans 4 days
Delta
Delta
YYZ
2:20a
MDW
6:19a
3h 59m
1 stop
MDW
1:55p
YYZ
7:29p
5h 34m
1 stop
Depart: Thu Oct 13 2016 Return: Sat Oct 15 2016 Trip spans 3 days
Major Airline
Major Airline
YYZ
10:15p
MDW
6:24a
8h 09m
2 stops
MDW
11:00p
YYZ
2:16a
3h 16m
2 stops
Depart: Tue Oct 18 2016 Return: Fri Oct 21 2016 Trip spans 4 days
Delta
Delta
YYZ
3:00a
MDW
8:41a
5h 41m
1 stop
MDW
5:18a
YYZ
9:56a
4h 38m
1 stop
Depart: Wed Oct 19 2016 Return: Fri Oct 21 2016 Trip spans 3 days
Delta
Delta
YYZ
2:15a
MDW
10:24a
8h 09m
1 stop
MDW
5:18a
YYZ
9:56a
4h 38m
1 stop
Depart: Thu Oct 20 2016 Return: Sat Oct 22 2016 Trip spans 3 days
Delta
Delta
YYZ
2:20a
MDW
5:43a
3h 23m
1 stop
MDW
12:40p
YYZ
4:32p
3h 52m
1 stop
Depart: Sat Oct 22 2016 Return: Tue Oct 25 2016 Trip spans 4 days
Delta
Delta
YYZ
2:20a
MDW
6:19a
3h 59m
1 stop
MDW
12:40p
YYZ
4:34p
3h 54m
1 stop
Depart: Mon Oct 24 2016 Return: Wed Oct 26 2016 Trip spans 3 days
Delta
Delta
YYZ
7:47a
MDW
12:58p
5h 11m
1 stop
MDW
2:30a
YYZ
8:00a
5h 30m
1 stop
Depart: Fri Oct 7 2016 Return: Sun Oct 9 2016 Trip spans 3 days
Major Airline
Major Airline
YYZ
3:47a
MDW
8:58a
5h 11m
1 stop
MDW
11:00p
YYZ
2:16a
3h 16m
1 stop
Depart: Tue Oct 25 2016 Return: Thu Oct 27 2016 Trip spans 3 days
Delta
Delta
YYZ
11:31a
MDW
2:57p
3h 26m
1 stop
MDW
2:30a
YYZ
8:00a
5h 30m
1 stop
Depart: Wed Oct 26 2016 Return: Fri Oct 28 2016 Trip spans 3 days
Delta
Delta
YYZ
2:20a
MDW
5:43a
3h 23m
1 stop
MDW
5:06a
YYZ
11:45a
6h 39m
1 stop
Depart: Sat Oct 29 2016 Return: Tue Nov 1 2016 Trip spans 4 days
Delta
Delta
YYZ
12:00p
MDW
7:52p
7h 52m
1 stop
MDW
5:06a
YYZ
11:45a
6h 39m
1 stop
Depart: Sun Oct 30 2016 Return: Tue Nov 1 2016 Trip spans 3 days
Delta
Delta
YYZ
5:50a
MDW
9:26a
3h 36m
1 stop
MDW
2:00a
YYZ
9:21a
7h 21m
1 stop
Depart: Mon Oct 31 2016 Return: Wed Nov 2 2016 Trip spans 3 days
Delta
Delta
YYZ
2:20a
MDW
5:43a
3h 23m
1 stop
MDW
3:00a
YYZ
6:16a
3h 16m
1 stop
Depart: Tue Nov 1 2016 Return: Wed Nov 23 2016 Trip spans 23 days
Delta
Delta
YYZ
1:25p
MDW
6:37p
5h 12m
1 stop
MDW
2:00a
YYZ
5:17a
3h 17m
1 stop
Depart: Sat Nov 12 2016 Return: Mon Nov 21 2016 Trip spans 10 days
Delta
Delta
YYZ
12:20p
MDW
5:54p
5h 34m
1 stop
MDW
6:08a
YYZ
3:29p
9h 21m
2 stops
Depart: Thu Nov 17 2016 Return: Sun Nov 20 2016 Trip spans 4 days
Delta
Delta
YYZ
2:00a
MDW
7:45a
5h 45m
1 stop
MDW
4:15a
YYZ
8:54a
4h 39m
1 stop
Depart: Sun Jan 8 2017 Return: Fri Jan 20 2017 Trip spans 13 days
Delta
Delta
YYZ
1:30a
MDW
6:42a
5h 12m
1 stop
MDW
7:35a
YYZ
10:45a
3h 10m
1 stop
Depart: Fri Mar 17 2017 Return: Fri Mar 31 2017 Trip spans 15 days
Delta
Delta
YYZ
2:30a
MDW
8:59a
6h 29m
1 stop
MDW
3:00a
YYZ
6:15a
3h 15m
1 stop
Depart: Wed Nov 2 2016 Return: Wed Nov 9 2016 Trip spans 8 days
Delta
Delta
YYZ
11:31a
MDW
5:56p
6h 25m
1 stop
MDW
4:14a
YYZ
8:54a
4h 40m
1 stop
Depart: Thu Nov 3 2016 Return: Tue Nov 8 2016 Trip spans 6 days
Delta
Delta
YYZ
2:20a
MDW
5:43a
3h 23m
1 stop
MDW
8:03a
YYZ
3:41p
7h 38m
2 stops
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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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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
$225
Destination

Chicago
$225
Airlines