Find Deals on Flights from Toronto to Chicago Midway (YTO - 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 to Chicago Midway

(Round-trip)
Depart: Sat Nov 12 2016 Return: Mon Nov 14 2016 Trip spans 3 days
Major Airline
Major Airline
YTZ
2:05a
MDW
4:00a
1h 55m
nonstop
MDW
8:55p
YTZ
10:30p
1h 35m
nonstop
Depart: Tue Oct 18 2016 Return: Sat Oct 22 2016 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
9:30a
MDW
11:20a
1h 50m
nonstop
MDW
7:25a
YTZ
9:00a
1h 35m
nonstop
Depart: Tue Nov 15 2016 Return: Wed Nov 16 2016 Trip spans 2 days
Delta
Delta
YYZ
10:35a
MDW
2:00p
3h 25m
1 stop
MDW
2:00a
YYZ
5:17a
3h 17m
1 stop
Depart: Mon Oct 24 2016 Return: Wed Oct 26 2016 Trip spans 3 days
Major Airline
Major Airline
YTZ
4:05a
MDW
5:55a
1h 50m
1 stop
MDW
11:25a
YTZ
1:00p
1h 35m
1 stop
Depart: Thu Oct 20 2016 Return: Tue Oct 25 2016 Trip spans 6 days
Porter Airlines
Porter Airlines
YTZ
11:05a
MDW
12:55p
1h 50m
nonstop
MDW
12:35p
YTZ
2:10p
1h 35m
nonstop
Depart: Thu Oct 27 2016 Return: Sun Oct 30 2016 Trip spans 4 days
Major Airline
Major Airline
YTZ
7:05a
MDW
8:55a
1h 50m
nonstop
MDW
2:00a
YTZ
3:35a
1h 35m
nonstop
Depart: Wed Nov 16 2016 Return: Fri Nov 18 2016 Trip spans 3 days
Delta
Delta
YYZ
4:50a
MDW
8:28a
3h 38m
1 stop
MDW
4:14a
YYZ
8:54a
4h 40m
1 stop
Depart: Sun Oct 23 2016 Return: Fri Oct 28 2016 Trip spans 6 days
Porter Airlines
Porter Airlines
YTZ
7:00a
MDW
8:50a
1h 50m
nonstop
MDW
9:35a
YTZ
11:10a
1h 35m
nonstop
Depart: Fri Oct 21 2016 Return: Fri Oct 28 2016 Trip spans 8 days
Major Airline
Major Airline
YTZ
12:10a
MDW
2:00a
1h 50m
nonstop
MDW
1:40a
YTZ
3:10a
1h 30m
nonstop
Depart: Thu Nov 24 2016 Return: Wed Nov 30 2016 Trip spans 7 days
Delta
Delta
YYZ
1:21a
MDW
4:52a
3h 31m
1 stop
MDW
2:00a
YYZ
5:15a
3h 15m
1 stop
Depart: Thu Nov 3 2016 Return: Sun Nov 6 2016 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
4:20p
MDW
6:15p
1h 55m
nonstop
MDW
7:30a
YTZ
9:05a
1h 35m
nonstop
Depart: Sat Oct 22 2016 Return: Sun Oct 30 2016 Trip spans 9 days
Major Airline
Major Airline
YTZ
1:55a
MDW
3:45a
1h 50m
1 stop
MDW
6:50a
YTZ
8:30a
1h 40m
1 stop
Depart: Sat Jan 7 2017 Return: Wed Jan 11 2017 Trip spans 5 days
Delta
Delta
YYZ
1:30a
MDW
6:50a
5h 20m
1 stop
MDW
7:15a
YYZ
2:35p
7h 20m
1 stop
Depart: Fri Nov 18 2016 Return: Sun Nov 20 2016 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
10:30a
MDW
12:25p
1h 55m
nonstop
MDW
5:00a
YTZ
6:35a
1h 35m
nonstop
Depart: Wed Oct 26 2016 Return: Sun Oct 30 2016 Trip spans 5 days
Major Airline
Major Airline
YTZ
12:10a
MDW
2:00a
1h 50m
1 stop
MDW
11:00p
YTZ
12:35a
1h 35m
1 stop
Depart: Thu Feb 23 2017 Return: Mon Feb 27 2017 Trip spans 5 days
Delta
Delta
YYZ
1:05a
MDW
5:01a
3h 56m
1 stop
MDW
1:15p
YYZ
6:07p
4h 52m
1 stop
Depart: Sat Nov 19 2016 Return: Mon Nov 28 2016 Trip spans 10 days
Porter Airlines
Porter Airlines
YTZ
7:05a
MDW
9:00a
1h 55m
nonstop
MDW
2:00a
YTZ
3:35a
1h 35m
nonstop
Depart: Wed Nov 2 2016 Return: Mon Nov 7 2016 Trip spans 6 days
Major Airline
Major Airline
YTZ
7:30a
MDW
9:25a
1h 55m
nonstop
MDW
1:50a
YTZ
3:25a
1h 35m
nonstop
Depart: Mon Nov 21 2016 Return: Fri Nov 25 2016 Trip spans 5 days
Delta
Delta
YYZ
8:51a
MDW
3:10p
6h 19m
1 stop
MDW
4:15a
YYZ
7:26a
3h 11m
1 stop
Depart: Tue Nov 22 2016 Return: Mon Nov 28 2016 Trip spans 7 days
Porter Airlines
Porter Airlines
YTZ
10:30a
MDW
12:25p
1h 55m
nonstop
MDW
2:40p
YTZ
4:15p
1h 35m
nonstop
Direct flights YTO to MDW on Porter Airlines
Flight # Depart YTZ Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
383 7:30 am 8:20 am Oct 8 - Oct 8
383 8:10 am 9:00 am Sep 29 - Oct 28
383 8:10 am 9:05 am Nov 7 - Nov 15
383 8:10 am 9:05 am Oct 31 - Nov 4
387 9:50 am 10:45 am Nov 5 - Nov 5
387 9:55 am 10:45 am Oct 1 - Oct 29
387 10:00 am 10:50 am Nov 1 - Nov 1
387 10:00 am 10:45 am Oct 11 - Oct 11
387 10:05 am 10:55 am Sep 29 - Oct 28
387 10:15 am 11:10 am Oct 31 - Nov 4
387 10:15 am 11:10 am Nov 7 - Nov 14
387 10:50 am 11:40 am Oct 9 - Oct 9
387 10:55 am 11:45 am Oct 12 - Oct 26
387 10:55 am 11:50 am Nov 6 - Dec 11
387 10:55 am 11:50 am Oct 30 - Oct 30
387 11:00 am 11:50 am Oct 16 - Oct 23
389 12:05 pm 12:55 pm Oct 11 - Oct 17
389 12:05 pm 12:55 pm Oct 20 - Oct 29
389 12:05 pm 1:00 pm Nov 5 - Nov 5
389 12:05 pm 12:55 pm Sep 29 - Oct 10
389 12:30 pm 1:25 pm Oct 31 - Nov 4
389 12:30 pm 1:25 pm Nov 7 - Nov 24
389 1:15 pm 2:10 pm Nov 6 - Dec 11
389 1:15 pm 2:10 pm Oct 30 - Oct 30
389 1:15 pm 2:05 pm Oct 2 - Oct 23
391 1:30 pm 2:20 pm Sep 29 - Oct 28
393 3:05 pm 3:55 pm Sep 29 - Oct 28
393 3:30 pm 4:25 pm Nov 7 - Nov 23
393 3:30 pm 4:25 pm Oct 31 - Nov 4
391 3:35 pm 4:30 pm Nov 6 - Dec 11
391 3:35 pm 4:30 pm Oct 30 - Oct 30
391 3:35 pm 4:25 pm Oct 2 - Oct 23
395 4:50 pm 5:40 pm Oct 1 - Oct 29
395 4:50 pm 5:45 pm Nov 5 - Nov 5
393 5:55 pm 6:45 pm Oct 16 - Oct 23
395 5:55 pm 6:45 pm Sep 29 - Oct 28
395 5:55 pm 6:50 pm Oct 31 - Nov 4
395 5:55 pm 6:50 pm Nov 7 - Nov 15
393 6:00 pm 6:55 pm Nov 6 - Dec 11
393 6:00 pm 6:55 pm Oct 30 - Oct 30
393 6:05 pm 6:55 pm Oct 9 - Oct 9
395 8:10 pm 9:00 pm Oct 16 - Oct 23
395 8:15 pm 9:10 pm Nov 6 - Dec 11
395 8:15 pm 9:10 pm Oct 30 - Oct 30
397 8:20 pm 9:15 pm Oct 31 - Nov 4
397 8:20 pm 9:15 pm Nov 7 - Nov 15
397 8:30 pm 9:20 pm Sep 29 - Oct 28
* 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
only $224
only $183
Destination

Chicago
$183
Airlines Airline reviews

47 travelers who booked a flight from Toronto to Chicago rated their chosen airlines with an average of 8.4.

Overall
8.6
Boarding
8.6
Crew
8.9
Comfort
8.5
Food
8.5
Entertainment
7.0