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: Thu Jun 22 2017 Return: Sun Jun 25 2017 Trip spans 4 days
Major Airline
Major Airline
YTZ
11:55a
MDW
1:40p
1h 45m
nonstop
MDW
11:30p
YTZ
1:10a
1h 40m
nonstop
Depart: Mon Nov 20 2017 Return: Thu Nov 23 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
10:50a
MDW
12:40p
1h 50m
nonstop
MDW
6:50a
YTZ
8:27a
1h 37m
nonstop
Depart: Sun Oct 29 2017 Return: Sat Dec 2 2017 Trip spans 35 days
Delta
Delta
YYZ
1:55p
MDW
7:15p
5h 20m
1 stop
MDW
12:10p
YYZ
5:23p
5h 13m
1 stop
Depart: Wed Jun 14 2017 Return: Tue Jun 27 2017 Trip spans 14 days
Porter Airlines
Porter Airlines
YTZ
6:25a
MDW
8:10a
1h 45m
nonstop
MDW
3:25p
YTZ
5:05p
1h 40m
nonstop
Depart: Fri Jun 30 2017 Return: Tue Jul 4 2017 Trip spans 5 days
Major Airline
Major Airline
YTZ
12:25a
MDW
2:10a
1h 45m
1 stop
MDW
1:50a
YTZ
3:30a
1h 40m
1 stop
Depart: Wed Jun 21 2017 Return: Thu Jun 22 2017 Trip spans 2 days
Porter Airlines
Porter Airlines
YTZ
11:55a
MDW
1:40p
1h 45m
nonstop
MDW
3:25p
YTZ
5:05p
1h 40m
nonstop
Depart: Tue Aug 1 2017 Return: Thu Aug 3 2017 Trip spans 3 days
Major Airline
Major Airline
YTZ
9:55a
MDW
11:40a
1h 45m
3 stops
MDW
1:50a
YTZ
3:29a
1h 39m
3 stops
Depart: Thu Jun 29 2017 Return: Wed Jul 5 2017 Trip spans 7 days
Porter Airlines
Porter Airlines
YTZ
4:15p
MDW
6:00p
1h 45m
nonstop
MDW
3:25p
YTZ
5:05p
1h 40m
nonstop
Depart: Wed Sep 27 2017 Return: Sat Sep 30 2017 Trip spans 4 days
Major Airline
Major Airline
YTZ
2:25a
MDW
4:10a
1h 45m
nonstop
MDW
5:45a
YTZ
7:25a
1h 40m
nonstop
Depart: Sat Jul 1 2017 Return: Tue Jul 4 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
10:50a
MDW
12:35p
1h 45m
nonstop
MDW
8:05a
YTZ
9:45a
1h 40m
nonstop
Depart: Sat Jul 22 2017 Return: Sat Aug 12 2017 Trip spans 22 days
Major Airline
Major Airline
YTZ
6:25a
MDW
8:10a
1h 45m
1 stop
MDW
7:50a
YTZ
9:30a
1h 40m
1 stop
Depart: Thu Jul 6 2017 Return: Mon Jul 31 2017 Trip spans 26 days
Porter Airlines
Porter Airlines
YTZ
10:00a
MDW
11:45a
1h 45m
nonstop
MDW
1:00p
YTZ
2:45p
1h 45m
nonstop
Depart: Wed Jun 28 2017 Return: Wed Jul 12 2017 Trip spans 15 days
Major Airline
Major Airline
YTZ
9:55a
MDW
11:40a
1h 45m
nonstop
MDW
5:40a
YTZ
7:25a
1h 45m
nonstop
Depart: Sat Jul 8 2017 Return: Mon Jul 10 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
10:25a
MDW
12:10p
1h 45m
nonstop
MDW
3:25p
YTZ
5:05p
1h 40m
nonstop
Depart: Tue Jul 11 2017 Return: Thu Jul 13 2017 Trip spans 3 days
Major Airline
Major Airline
YTZ
6:55a
MDW
8:40a
1h 45m
nonstop
MDW
5:40a
YTZ
7:25a
1h 45m
nonstop
Depart: Sun Jul 9 2017 Return: Fri Jul 28 2017 Trip spans 20 days
Porter Airlines
Porter Airlines
YTZ
9:30a
MDW
11:15a
1h 45m
nonstop
MDW
9:40a
YTZ
11:20a
1h 40m
nonstop
Depart: Tue Jul 18 2017 Return: Fri Jul 21 2017 Trip spans 4 days
Major Airline
Major Airline
YTZ
6:55a
MDW
8:40a
1h 45m
nonstop
MDW
7:00a
YTZ
8:45a
1h 45m
nonstop
Depart: Wed Aug 9 2017 Return: Wed Aug 23 2017 Trip spans 15 days
Porter Airlines
Porter Airlines
YTZ
1:55p
MDW
3:40p
1h 45m
nonstop
MDW
9:40a
YTZ
11:20a
1h 40m
nonstop
Depart: Tue Aug 22 2017 Return: Fri Aug 25 2017 Trip spans 4 days
Major Airline
Major Airline
YTZ
2:40a
MDW
4:25a
1h 45m
3 stops
MDW
11:25a
YTZ
1:05p
1h 40m
3 stops
Depart: Thu Aug 10 2017 Return: Tue Aug 15 2017 Trip spans 6 days
Porter Airlines
Porter Airlines
YTZ
8:15a
MDW
10:00a
1h 45m
nonstop
MDW
8:05a
YTZ
9:45a
1h 40m
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 Jul 1 - Jul 7
385 8:25 am 9:10 am May 29 - Jun 30
387 9:50 am 10:35 am May 27 - Jun 24
387 10:05 am 10:50 am Jul 3 - Jul 9
387 10:25 am 11:10 am May 30 - Jun 25
387 10:40 am 11:25 am Jun 26 - Jul 1
389 12:00 pm 12:45 pm May 24 - Jun 23
389 12:05 pm 12:50 pm Jun 4 - Jun 25
389 12:10 pm 12:55 pm Jun 5 - Jun 19
389 12:10 pm 12:55 pm Jul 2 - Jul 9
389 12:15 pm 1:00 pm Jun 26 - Jun 30
391 12:15 pm 1:00 pm May 27 - Jun 24
391 1:10 pm 1:55 pm Jul 1 - Jul 1
391 1:30 pm 2:15 pm Jul 3 - Jul 9
391 1:35 pm 2:20 pm Jun 26 - Jun 30
391 1:40 pm 2:25 pm Jul 2 - Jul 2
391 1:40 pm 2:25 pm Jun 1 - Jun 25
395 2:45 pm 3:30 pm May 27 - Jun 24
393 2:50 pm 3:35 pm Jul 1 - Jul 1
393 2:55 pm 3:40 pm Jun 27 - Jun 28
393 3:25 pm 4:10 pm Jun 26 - Jun 30
393 3:55 pm 4:40 pm Jul 2 - Jul 9
393 3:55 pm 4:40 pm Jun 6 - Jun 25
393 3:55 pm 4:40 pm May 28 - Jun 5
395 5:55 pm 6:40 pm May 23 - Jun 30
395 6:15 pm 7:00 pm Jul 1 - Jul 3
395 6:15 pm 7:00 pm Jun 4 - Jun 25
397 7:55 pm 8:40 pm May 23 - Jun 22
397 8:00 pm 8:45 pm May 26 - Jun 23
397 8:10 pm 8:55 pm Jun 4 - Jun 25
397 8:15 pm 9:00 pm Jun 26 - Sep 4
* 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.

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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,
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Airports
Origin

Toronto
only $221
only $198
Destination

Chicago
$198
Airlines Airline reviews

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

Overall
8.6
Boarding
8.8
Crew
8.8
Comfort
8.4
Food
8.3
Entertainment
6.9