Find Deals on Flights from Toronto Island to Chicago Midway (YTZ - 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 Island to Chicago Midway

(Round-trip)
Depart: Tue Sep 20 2016 Return: Wed Sep 28 2016 Trip spans 9 days
Depart: Thu Oct 13 2016 Return: Mon Oct 17 2016 Trip spans 5 days
Depart: Tue Dec 6 2016 Return: Tue Dec 13 2016 Trip spans 8 days
Depart: Thu Oct 27 2016 Return: Mon Oct 31 2016 Trip spans 5 days
Depart: Sat Dec 10 2016 Return: Tue Dec 13 2016 Trip spans 4 days
Depart: Wed Sep 28 2016 Return: Tue Oct 4 2016 Trip spans 7 days
Depart: Sat Oct 15 2016 Return: Sat Nov 5 2016 Trip spans 22 days
Depart: Sat Sep 24 2016 Return: Wed Sep 28 2016 Trip spans 5 days
Depart: Sun Sep 25 2016 Return: Wed Sep 28 2016 Trip spans 4 days
Depart: Tue Oct 4 2016 Return: Wed Oct 5 2016 Trip spans 2 days
Depart: Fri Oct 14 2016 Return: Wed Oct 19 2016 Trip spans 6 days
Depart: Sat Oct 22 2016 Return: Sat Oct 29 2016 Trip spans 8 days
Depart: Fri Dec 9 2016 Return: Tue Dec 13 2016 Trip spans 5 days
Depart: Sun Oct 23 2016 Return: Wed Oct 26 2016 Trip spans 4 days
Depart: Tue Sep 13 2016 Return: Thu Sep 15 2016 Trip spans 3 days
Depart: Thu Sep 22 2016 Return: Sat Sep 24 2016 Trip spans 3 days
Depart: Tue Nov 1 2016 Return: Thu Nov 10 2016 Trip spans 10 days
Depart: Fri Sep 23 2016 Return: Mon Sep 26 2016 Trip spans 4 days
Depart: Fri Sep 16 2016 Return: Sun Sep 18 2016 Trip spans 3 days
Depart: Thu Sep 29 2016 Return: Sat Oct 1 2016 Trip spans 3 days
Direct flights YTZ to MDW on Porter Airlines
Flight # Depart YTZ Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
383 6:45 am 7:35 am Sep 2 - Sep 2
383 7:00 am 7:50 am Aug 25 - Sep 1
383 8:10 am 9:00 am Sep 6 - Oct 28
385 9:00 am 9:50 am Aug 23 - Sep 2
385 9:40 am 10:30 am Aug 27 - Sep 3
387 9:55 am 10:45 am Sep 10 - Oct 29
387 10:00 am 10:45 am Sep 6 - Oct 25
387 10:05 am 10:55 am Sep 7 - Oct 28
387 10:50 am 11:40 am Sep 2 - Sep 2
387 10:55 am 11:45 am Aug 25 - Sep 1
387 11:00 am 11:50 am Aug 28 - Sep 4
387 11:00 am 11:50 am Sep 5 - Sep 11
387 11:00 am 11:50 am Sep 18 - Oct 2
389 12:05 pm 12:55 pm Sep 6 - Oct 29
389 12:30 pm 1:20 pm Aug 23 - Sep 2
389 12:45 pm 1:35 pm Sep 4 - Sep 5
389 12:50 pm 1:40 pm Sep 3 - Sep 3
389 1:15 pm 2:05 pm Sep 11 - Oct 23
391 1:30 pm 2:20 pm Sep 6 - Oct 28
393 3:05 pm 3:55 pm Sep 6 - Oct 28
391 3:20 pm 4:10 pm Aug 23 - Sep 3
391 3:35 pm 4:25 pm Sep 11 - Oct 23
391 3:40 pm 4:30 pm Sep 4 - Sep 5
395 4:50 pm 5:40 pm Sep 10 - Oct 29
393 5:50 pm 6:40 pm Sep 5 - Sep 5
393 5:50 pm 6:40 pm Aug 28 - Sep 4
393 5:55 pm 6:45 pm Aug 27 - Sep 3
393 5:55 pm 6:40 pm Aug 23 - Sep 1
393 5:55 pm 6:45 pm Sep 11 - Oct 2
395 5:55 pm 6:45 pm Sep 6 - Oct 28
393 6:00 pm 6:50 pm Sep 2 - Sep 2
395 8:05 pm 8:55 pm Aug 23 - Sep 2
395 8:10 pm 9:00 pm Sep 11 - Oct 2
395 8:15 pm 9:05 pm Sep 4 - Sep 5
397 8:30 pm 9:20 pm Sep 6 - 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
$186
Destination

Chicago
$186
Airlines Airline reviews

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

Overall
8.6
Boarding
8.5
Crew
8.8
Comfort
8.3
Food
8.3
Entertainment
6.7