Find Cheap 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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Toronto Pearson Intl to Chicago Midway

(Round-trip)
Depart: Wed Sep 6 2017 Return: Sat Sep 9 2017 Trip spans 4 days
Delta
Delta
YYZ
2:30a
MDW
8:55a
6h 25m
1 stop
MDW
2:25a
YYZ
7:15a
4h 50m
1 stop
Depart: Sat Sep 9 2017 Return: Tue Sep 12 2017 Trip spans 4 days
Delta
Delta
YYZ
11:30a
MDW
7:14p
7h 44m
1 stop
MDW
2:15p
YYZ
7:17p
5h 02m
1 stop
Depart: Thu Sep 28 2017 Return: Sat Sep 30 2017 Trip spans 3 days
Delta
Delta
YYZ
2:30a
MDW
8:55a
6h 25m
1 stop
MDW
2:25a
YYZ
7:15a
4h 50m
1 stop
Depart: Tue Aug 29 2017 Return: Wed Sep 6 2017 Trip spans 9 days
Delta
Delta
YYZ
1:58p
MDW
7:16p
5h 18m
1 stop
MDW
2:25a
YYZ
7:15a
4h 50m
1 stop
Depart: Thu Aug 31 2017 Return: Wed Sep 6 2017 Trip spans 7 days
Delta
Delta
YYZ
2:30a
MDW
7:22a
4h 52m
1 stop
MDW
2:25a
YYZ
7:15a
4h 50m
1 stop
Depart: Sat Sep 2 2017 Return: Wed Sep 6 2017 Trip spans 5 days
Delta
Delta
YYZ
11:30a
MDW
7:14p
7h 44m
1 stop
MDW
2:25a
YYZ
7:15a
4h 50m
1 stop
Depart: Sun Sep 3 2017 Return: Wed Sep 6 2017 Trip spans 4 days
Delta
Delta
YYZ
1:58p
MDW
7:16p
5h 18m
1 stop
MDW
2:25a
YYZ
7:15a
4h 50m
1 stop
Depart: Tue Oct 3 2017 Return: Sat Oct 7 2017 Trip spans 5 days
Delta
Delta
YYZ
1:55p
MDW
7:15p
5h 20m
1 stop
MDW
2:30a
YYZ
7:12a
4h 42m
1 stop
Depart: Wed Oct 4 2017 Return: Sun Oct 8 2017 Trip spans 5 days
Delta
Delta
YYZ
2:30a
MDW
8:40a
6h 10m
1 stop
MDW
3:00a
YYZ
6:05a
3h 05m
1 stop
Depart: Wed Aug 30 2017 Return: Wed Sep 6 2017 Trip spans 8 days
Delta
Delta
YYZ
5:30a
MDW
1:15p
7h 45m
2 stops
MDW
2:25a
YYZ
7:15a
4h 50m
1 stop
Depart: Tue Sep 5 2017 Return: Sat Sep 9 2017 Trip spans 5 days
Delta
Delta
YYZ
2:30a
MDW
8:55a
6h 25m
1 stop
MDW
2:25a
YYZ
7:15a
4h 50m
1 stop
Depart: Thu Oct 26 2017 Return: Sat Oct 28 2017 Trip spans 3 days
Delta
Delta
YYZ
2:30a
MDW
8:40a
6h 10m
1 stop
MDW
1:10p
YYZ
6:23p
5h 13m
1 stop
Depart: Wed Aug 23 2017 Return: Wed Aug 30 2017 Trip spans 8 days
Delta
Delta
YYZ
5:30a
MDW
2:23p
8h 53m
2 stops
MDW
2:25a
YYZ
7:15a
4h 50m
1 stop
Depart: Thu Nov 16 2017 Return: Sat Nov 25 2017 Trip spans 10 days
Delta
Delta
YYZ
1:30a
MDW
6:32a
5h 02m
1 stop
MDW
11:30a
YYZ
3:40p
4h 10m
1 stop
Depart: Tue Nov 21 2017 Return: Sat Nov 25 2017 Trip spans 5 days
Delta
Delta
YYZ
10:10a
MDW
5:03p
6h 53m
1 stop
MDW
12:10p
YYZ
5:23p
5h 13m
1 stop
Depart: Thu Nov 2 2017 Return: Mon Nov 6 2017 Trip spans 5 days
Delta
Delta
YYZ
2:30a
MDW
8:40a
6h 10m
1 stop
MDW
11:15a
YYZ
6:34p
7h 19m
1 stop
Depart: Wed Jan 3 2018 Return: Wed Jan 10 2018 Trip spans 8 days
Delta
Delta
YYZ
1:15a
MDW
4:42a
3h 27m
1 stop
MDW
8:40a
YYZ
3:34p
6h 54m
1 stop
Depart: Wed Jan 17 2018 Return: Sat Jan 20 2018 Trip spans 4 days
Delta
Delta
YYZ
12:05p
MDW
6:08p
6h 03m
1 stop
MDW
12:10p
YYZ
5:30p
5h 20m
1 stop
Depart: Thu Sep 7 2017 Return: Sat Sep 9 2017 Trip spans 3 days
Delta
Delta
YYZ
2:30a
MDW
7:22a
4h 52m
1 stop
MDW
2:25a
YYZ
7:15a
4h 50m
1 stop
Depart: Tue Sep 12 2017 Return: Sat Sep 16 2017 Trip spans 5 days
Delta
Delta
YYZ
7:45a
MDW
1:15p
5h 30m
1 stop
MDW
2:25a
YYZ
7:15a
4h 50m
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.

We compile tonnes of data for you
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,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Toronto
$221
Destination

Chicago
$221
Airlines