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: Thu Jan 19 2017 Return: Fri Jan 20 2017 Trip spans 2 days
Major Airline
Major Airline
YTZ
10:05a
MDW
11:55a
1h 50m
nonstop
MDW
11:00p
YTZ
12:37a
1h 37m
nonstop
Depart: Wed Jan 18 2017 Return: Sun Jan 22 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
3:05p
MDW
4:55p
1h 50m
nonstop
MDW
12:15p
YTZ
1:52p
1h 37m
nonstop
Depart: Mon Jan 9 2017 Return: Wed Jan 11 2017 Trip spans 3 days
Delta
Delta
YYZ
8:30a
MDW
2:05p
5h 35m
1 stop
MDW
9:08a
YYZ
1:59p
4h 51m
1 stop
Depart: Sun Feb 5 2017 Return: Fri Feb 10 2017 Trip spans 6 days
Major Airline
Major Airline
YTZ
10:50p
MDW
12:40a
1h 50m
nonstop
MDW
9:30a
YTZ
11:07a
1h 37m
nonstop
Depart: Tue Jan 24 2017 Return: Thu Feb 2 2017 Trip spans 10 days
Porter Airlines
Porter Airlines
YTZ
8:35a
MDW
10:25a
1h 50m
nonstop
MDW
2:30p
YTZ
4:07p
1h 37m
nonstop
Depart: Sun Mar 12 2017 Return: Fri Mar 24 2017 Trip spans 13 days
Major Airline
Major Airline
YTZ
4:40a
MDW
6:30a
1h 50m
1 stop
MDW
11:30a
YTZ
1:07p
1h 37m
1 stop
Depart: Fri Feb 3 2017 Return: Sun Feb 5 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
8:35a
MDW
10:25a
1h 50m
nonstop
MDW
2:35p
YTZ
4:12p
1h 37m
nonstop
Depart: Sun Jan 15 2017 Return: Tue Jan 17 2017 Trip spans 3 days
Delta
Delta
YYZ
1:15a
MDW
9:31a
8h 16m
1 stop
MDW
7:20a
YYZ
1:59p
6h 39m
1 stop
Depart: Fri Jan 13 2017 Return: Wed Jan 18 2017 Trip spans 6 days
Major Airline
Major Airline
YTZ
10:05a
MDW
11:55a
1h 50m
nonstop
MDW
12:20a
YTZ
1:55a
1h 35m
nonstop
Depart: Thu Mar 9 2017 Return: Mon Mar 13 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
8:35a
MDW
10:25a
1h 50m
nonstop
MDW
6:20a
YTZ
7:55a
1h 35m
nonstop
Depart: Wed Jan 25 2017 Return: Wed Feb 8 2017 Trip spans 15 days
Major Airline
Major Airline
YTZ
7:55a
MDW
9:45a
1h 50m
nonstop
MDW
5:05a
YTZ
6:42a
1h 37m
nonstop
Depart: Mon Mar 13 2017 Return: Fri Mar 24 2017 Trip spans 12 days
Porter Airlines
Porter Airlines
YTZ
1:55p
MDW
3:45p
1h 50m
nonstop
MDW
6:20a
YTZ
7:55a
1h 35m
nonstop
Depart: Fri Jun 9 2017 Return: Sun Jun 11 2017 Trip spans 3 days
Major Airline
Major Airline
YTZ
12:00p
MDW
1:45p
1h 45m
1 stop
MDW
3:50a
YTZ
5:30a
1h 40m
1 stop
Depart: Thu Apr 6 2017 Return: Sun Apr 9 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
1:55p
MDW
3:45p
1h 50m
nonstop
MDW
3:35p
YTZ
5:12p
1h 37m
nonstop
Depart: Mon Jan 16 2017 Return: Wed Jan 18 2017 Trip spans 3 days
Major Airline
Major Airline
YTZ
7:55a
MDW
9:45a
1h 50m
nonstop
MDW
12:20a
YTZ
1:55a
1h 35m
nonstop
Depart: Wed Apr 12 2017 Return: Mon Apr 17 2017 Trip spans 6 days
Porter Airlines
Porter Airlines
YTZ
1:55p
MDW
3:40p
1h 45m
nonstop
MDW
9:35a
YTZ
11:15a
1h 40m
nonstop
Depart: Mon Jan 23 2017 Return: Thu Jan 26 2017 Trip spans 4 days
Major Airline
Major Airline
YTZ
12:55a
MDW
2:45a
1h 50m
1 stop
MDW
9:30a
YTZ
11:07a
1h 37m
1 stop
Depart: Tue May 9 2017 Return: Tue May 16 2017 Trip spans 8 days
Porter Airlines
Porter Airlines
YTZ
6:25a
MDW
8:10a
1h 45m
nonstop
MDW
9:30a
YTZ
11:10a
1h 40m
nonstop
Depart: Fri Jun 2 2017 Return: Fri Jul 7 2017 Trip spans 36 days
Major Airline
Major Airline
YTZ
5:40a
MDW
7:25a
1h 45m
nonstop
MDW
4:05a
YTZ
5:45a
1h 40m
nonstop
Depart: Sun Jun 11 2017 Return: Mon Jun 12 2017 Trip spans 2 days
Porter Airlines
Porter Airlines
YTZ
9:40a
MDW
11:25a
1h 45m
nonstop
MDW
7:50a
YTZ
9:29a
1h 39m
nonstop
Direct flights YTO to MDW on Porter Airlines
Flight # Depart YTZ Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
385 8:50 am 9:40 am Jan 4 - Feb 17
383 9:50 am 10:45 am Dec 25 - Jan 3
383 9:50 am 10:45 am Dec 17 - Dec 24
387 10:55 am 11:45 am Jan 5 - Feb 17
389 11:20 am 12:10 pm Jan 7 - Feb 11
387 11:55 am 12:50 pm Dec 18 - Dec 18
389 12:00 pm 12:50 pm Jan 8 - Feb 19
391 1:00 pm 1:55 pm Jan 2 - Jan 3
393 1:25 pm 2:15 pm Jan 4 - Jan 19
391 1:55 pm 2:50 pm Dec 17 - Dec 17
391 2:25 pm 3:15 pm Jan 14 - Feb 11
393 2:35 pm 3:30 pm Dec 25 - Jan 1
391 2:55 pm 3:45 pm Jan 7 - Jan 7
393 3:10 pm 4:05 pm Dec 18 - Dec 24
393 3:10 pm 4:05 pm Dec 26 - Jan 3
393 3:40 pm 4:30 pm Jan 8 - Feb 12
395 4:30 pm 5:20 pm Dec 25 - Dec 25
395 5:30 pm 6:25 pm Jan 1 - Jan 1
395 5:55 pm 6:45 pm Jan 9 - Feb 17
395 6:10 pm 7:00 pm Jan 4 - Jan 6
397 8:05 pm 8:55 pm Jan 6 - Feb 17
397 8:29 pm 9:20 pm Jan 8 - Feb 12
397 8:29 pm 9:24 pm Dec 19 - Jan 3
397 8:45 pm 9:40 pm Dec 18 - Dec 18
* 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.

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Airports
Origin

Toronto
only $229
only $198
Destination

Chicago
$198
Airlines Airline reviews

55 travelers who booked a flight from Toronto to Chicago rated their chosen airlines with an average of 8.5.

Overall
8.6
Boarding
8.7
Crew
8.8
Comfort
8.5
Food
8.6
Entertainment
7.0