Find Cheap 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
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: Wed Nov 1 2017 Return: Tue Nov 7 2017 Trip spans 7 days
Porter Airlines
Porter Airlines
YTZ
12:00a
MDW
1:50a
1h 50m
nonstop
MDW
12:00a
YTZ
1:37a
1h 37m
nonstop
Depart: Mon Feb 5 2018 Return: Sat Feb 10 2018 Trip spans 6 days
Delta
Delta
YYZ
12:00a
MDW
8:12a
8h 12m
1 stop
MDW
12:00a
YYZ
6:16a
6h 16m
1 stop
Depart: Sat Nov 4 2017 Return: Wed Nov 8 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
12:00a
MDW
1:50a
1h 50m
nonstop
MDW
12:00a
YTZ
1:35a
1h 35m
nonstop
Depart: Tue Oct 24 2017 Return: Mon Oct 30 2017 Trip spans 7 days
Porter Airlines
Porter Airlines
YTZ
12:00a
MDW
1:45a
1h 45m
nonstop
MDW
12:00a
YTZ
1:40a
1h 40m
nonstop
Depart: Wed Oct 11 2017 Return: Tue Nov 7 2017 Trip spans 28 days
Delta
Delta
YYZ
12:00a
MDW
5:17a
5h 17m
1 stop
MDW
12:00a
YYZ
7:39a
7h 39m
2 stops
Depart: Thu Oct 19 2017 Return: Mon Oct 23 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
12:00a
MDW
1:45a
1h 45m
nonstop
MDW
12:00a
YTZ
1:40a
1h 40m
nonstop
Depart: Tue Nov 7 2017 Return: Sat Nov 11 2017 Trip spans 5 days
Delta
Delta
YYZ
12:00a
MDW
7:20a
7h 20m
2 stops
MDW
12:00a
YYZ
7:13a
7h 13m
1 stop
Depart: Fri Dec 1 2017 Return: Mon Dec 4 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
12:00a
MDW
1:50a
1h 50m
nonstop
MDW
12:00a
YTZ
1:37a
1h 37m
nonstop
Depart: Sun Dec 10 2017 Return: Wed Dec 13 2017 Trip spans 4 days
Delta
Delta
YYZ
12:00a
MDW
5:09a
5h 09m
1 stop
MDW
12:00a
YYZ
3:06a
3h 06m
1 stop
Depart: Tue Oct 10 2017 Return: Sat Oct 14 2017 Trip spans 5 days
Delta
Delta
YYZ
12:00a
MDW
6:20a
6h 20m
1 stop
MDW
12:00a
YYZ
5:17a
5h 17m
1 stop
Depart: Fri Nov 3 2017 Return: Sun Nov 5 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
12:00a
MDW
1:50a
1h 50m
nonstop
MDW
12:00a
YTZ
1:37a
1h 37m
nonstop
Depart: Thu Nov 30 2017 Return: Sun Dec 3 2017 Trip spans 4 days
Delta
Delta
YYZ
12:00a
MDW
6:10a
6h 10m
1 stop
MDW
12:00a
YYZ
3:06a
3h 06m
1 stop
Depart: Sun Jan 7 2018 Return: Thu Jan 11 2018 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
12:00a
MDW
1:50a
1h 50m
nonstop
MDW
12:00a
YTZ
1:37a
1h 37m
nonstop
Depart: Fri Dec 8 2017 Return: Sun Dec 10 2017 Trip spans 3 days
Delta
Delta
YYZ
12:00a
MDW
3:50a
3h 50m
1 stop
MDW
12:00a
YYZ
3:06a
3h 06m
1 stop
Depart: Fri Nov 10 2017 Return: Mon Nov 13 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
12:00a
MDW
1:50a
1h 50m
nonstop
MDW
12:00a
YTZ
1:37a
1h 37m
nonstop
Depart: Thu Jan 18 2018 Return: Sun Jan 21 2018 Trip spans 4 days
Delta
Delta
YYZ
12:00a
MDW
3:27a
3h 27m
1 stop
MDW
12:00a
YYZ
6:54a
6h 54m
1 stop
Depart: Fri Oct 13 2017 Return: Sun Oct 15 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
12:00a
MDW
1:45a
1h 45m
nonstop
MDW
12:00a
YTZ
1:40a
1h 40m
nonstop
Depart: Wed Dec 13 2017 Return: Sun Dec 17 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
12:00a
MDW
1:50a
1h 50m
nonstop
MDW
12:00a
YTZ
1:37a
1h 37m
nonstop
Depart: Thu Mar 29 2018 Return: Tue Apr 3 2018 Trip spans 6 days
Delta
Delta
YYZ
12:00a
MDW
3:27a
3h 27m
1 stop
MDW
12:00a
YYZ
7:24a
7h 24m
1 stop
Depart: Wed Feb 21 2018 Return: Sat Feb 24 2018 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
12:00a
MDW
1:50a
1h 50m
nonstop
MDW
12:00a
YTZ
1:37a
1h 37m
nonstop
Direct flights YTO to MDW on Porter Airlines
Flight # Depart YTZ Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
385 8:25 am 9:10 am Oct 16 - Oct 31
385 8:25 am 9:10 am Oct 7 - Oct 13
385 8:25 am 9:10 am Sep 11 - Oct 6
387 9:40 am 10:25 am Oct 10 - Oct 31
387 9:40 am 10:25 am Sep 9 - Oct 3
387 9:50 am 10:35 am Sep 18 - Oct 6
387 9:50 am 10:35 am Oct 9 - Oct 30
387 10:30 am 11:15 am Oct 7 - Oct 7
389 11:50 am 12:35 pm Sep 14 - Oct 6
389 11:50 am 12:35 pm Oct 15 - Oct 27
389 11:50 am 12:35 pm Oct 7 - Oct 13
389 12:05 pm 12:50 pm Sep 23 - Sep 30
389 12:05 pm 12:50 pm Oct 14 - Oct 28
389 12:30 pm 1:15 pm Sep 12 - Oct 4
389 12:30 pm 1:15 pm Oct 11 - Oct 31
391 1:35 pm 2:20 pm Oct 10 - Oct 16
391 1:35 pm 2:20 pm Oct 19 - Oct 30
391 1:35 pm 2:20 pm Sep 14 - Oct 6
391 1:40 pm 2:25 pm Oct 9 - Oct 15
391 1:40 pm 2:25 pm Sep 24 - Oct 8
391 1:40 pm 2:25 pm Oct 22 - Oct 29
391 1:45 pm 2:30 pm Oct 7 - Oct 7
395 3:15 pm 4:00 pm Oct 14 - Oct 28
395 3:15 pm 4:00 pm Sep 16 - Sep 30
393 3:30 pm 4:15 pm Oct 10 - Oct 31
393 3:30 pm 4:15 pm Sep 12 - Oct 4
393 3:50 pm 4:35 pm Sep 14 - Oct 27
393 3:55 pm 4:40 pm Sep 17 - Oct 8
393 3:55 pm 4:40 pm Oct 22 - Oct 29
393 3:55 pm 4:40 pm Oct 9 - Oct 15
393 4:30 pm 5:15 pm Oct 7 - Oct 7
395 5:59 pm 6:44 pm Oct 10 - Oct 16
395 5:59 pm 6:44 pm Sep 18 - Oct 2
395 5:59 pm 6:44 pm Oct 23 - Oct 30
395 6:00 pm 6:45 pm Oct 11 - Oct 31
395 6:00 pm 6:45 pm Sep 12 - Oct 4
395 6:10 pm 6:55 pm Sep 14 - Oct 27
395 6:15 pm 7:00 pm Oct 9 - Oct 15
395 6:15 pm 7:00 pm Sep 17 - Oct 8
395 6:15 pm 7:00 pm Oct 22 - Oct 29
397 7:55 pm 8:40 pm Oct 9 - Oct 15
397 7:55 pm 8:40 pm Sep 17 - Oct 1
397 7:55 pm 8:40 pm Oct 22 - Oct 29
397 8:00 pm 8:45 pm Oct 8 - Oct 8
397 8:20 pm 9:05 pm Oct 10 - Oct 31
397 8:20 pm 9:05 pm Sep 12 - Oct 5
397 8:30 pm 9:15 pm Sep 15 - Oct 27
* 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 $234
only $195
Destination

Chicago
$195
Airlines Airline reviews

91 travelers who booked a flight from Toronto to Chicago rated their chosen airlines with an average of 8.3.

Overall
8.5
Boarding
8.4
Crew
8.7
Comfort
8.4
Food
8.2
Entertainment
7.0