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: Tue Aug 22 2017 Return: Wed Aug 23 2017 Trip spans 2 days
Porter Airlines
Porter Airlines
YTZ
1:55p
MDW
3:40p
1h 45m
nonstop
MDW
12:50p
YTZ
2:35p
1h 45m
nonstop
Depart: Sat Sep 9 2017 Return: Tue Sep 12 2017 Trip spans 4 days
Delta
Delta
YYZ
11:30a
MDW
7:14p
7h 44m
1 stop
MDW
2:15p
YYZ
7:17p
5h 02m
1 stop
Depart: Mon Aug 28 2017 Return: Wed Aug 30 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
8:15a
MDW
10:00a
1h 45m
nonstop
MDW
8:05a
YTZ
9:45a
1h 40m
nonstop
Depart: Thu Sep 28 2017 Return: Sat Sep 30 2017 Trip spans 3 days
Delta
Delta
YYZ
2:30a
MDW
8:55a
6h 25m
1 stop
MDW
2:25a
YYZ
7:15a
4h 50m
1 stop
Depart: Tue Aug 29 2017 Return: Wed Aug 30 2017 Trip spans 2 days
Porter Airlines
Porter Airlines
YTZ
6:40a
MDW
8:25a
1h 45m
nonstop
MDW
8:05a
YTZ
9:45a
1h 40m
nonstop
Depart: Tue Oct 3 2017 Return: Wed Oct 11 2017 Trip spans 9 days
Delta
Delta
YYZ
7:55a
MDW
2:47p
6h 52m
1 stop
MDW
2:30a
YYZ
7:03a
4h 33m
1 stop
Depart: Wed Aug 30 2017 Return: Mon Sep 11 2017 Trip spans 13 days
Porter Airlines
Porter Airlines
YTZ
1:55p
MDW
3:40p
1h 45m
nonstop
MDW
3:25p
YTZ
5:05p
1h 40m
nonstop
Depart: Mon Oct 30 2017 Return: Wed Nov 8 2017 Trip spans 10 days
Delta
Delta
YYZ
2:15a
MDW
10:07a
7h 52m
1 stop
MDW
2:00a
YYZ
5:20a
3h 20m
1 stop
Depart: Sat Sep 2 2017 Return: Tue Sep 5 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
2:00p
MDW
3:45p
1h 45m
nonstop
MDW
1:25p
YTZ
3:10p
1h 45m
nonstop
Depart: Tue Oct 31 2017 Return: Sat Nov 4 2017 Trip spans 5 days
Delta
Delta
YYZ
2:15a
MDW
5:50a
3h 35m
1 stop
MDW
2:30a
YYZ
7:12a
4h 42m
1 stop
Depart: Mon Sep 4 2017 Return: Mon Sep 18 2017 Trip spans 15 days
Porter Airlines
Porter Airlines
YTZ
6:00a
MDW
7:45a
1h 45m
nonstop
MDW
7:15a
YTZ
8:55a
1h 40m
nonstop
Depart: Wed Nov 1 2017 Return: Sat Nov 4 2017 Trip spans 4 days
Delta
Delta
YYZ
2:30a
MDW
7:32a
5h 02m
1 stop
MDW
2:30a
YYZ
7:12a
4h 42m
1 stop
Depart: Tue Sep 5 2017 Return: Mon Sep 18 2017 Trip spans 14 days
Porter Airlines
Porter Airlines
YTZ
3:55p
MDW
5:40p
1h 45m
nonstop
MDW
9:15a
YTZ
10:55a
1h 40m
nonstop
Depart: Sun Nov 5 2017 Return: Tue Nov 7 2017 Trip spans 3 days
Delta
Delta
YYZ
1:15a
MDW
4:50a
3h 35m
1 stop
MDW
1:15p
YYZ
6:34p
5h 19m
1 stop
Depart: Wed Sep 6 2017 Return: Mon Sep 18 2017 Trip spans 13 days
Porter Airlines
Porter Airlines
YTZ
8:00a
MDW
9:45a
1h 45m
nonstop
MDW
1:00p
YTZ
2:40p
1h 40m
nonstop
Depart: Tue Nov 7 2017 Return: Thu Nov 9 2017 Trip spans 3 days
Delta
Delta
YYZ
1:15a
MDW
9:07a
7h 52m
1 stop
MDW
2:00a
YYZ
5:20a
3h 20m
1 stop
Depart: Thu Sep 7 2017 Return: Mon Sep 18 2017 Trip spans 12 days
Porter Airlines
Porter Airlines
YTZ
3:55p
MDW
5:40p
1h 45m
nonstop
MDW
9:15a
YTZ
10:55a
1h 40m
nonstop
Depart: Sun Sep 3 2017 Return: Wed Sep 6 2017 Trip spans 4 days
Delta
Delta
YYZ
1:58p
MDW
7:16p
5h 18m
1 stop
MDW
2:25a
YYZ
7:15a
4h 50m
1 stop
Depart: Fri Sep 8 2017 Return: Tue Sep 12 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
1:55p
MDW
3:40p
1h 45m
nonstop
MDW
10:00a
YTZ
11:40a
1h 40m
nonstop
Depart: Fri Sep 15 2017 Return: Mon Sep 18 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
11:50a
MDW
1:35p
1h 45m
nonstop
MDW
1:00p
YTZ
2:45p
1h 45m
nonstop
Direct flights YTO to MDW on Porter Airlines
Flight # Depart YTZ Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
381 7:00 am 7:45 am Aug 17 - Aug 21
385 8:00 am 8:45 am Sep 1 - Sep 1
385 8:25 am 9:10 am Aug 14 - Aug 31
385 8:25 am 9:10 am Aug 5 - Aug 11
385 8:25 am 9:10 am Jul 26 - Aug 4
385 8:25 am 9:10 am Sep 2 - Sep 8
387 9:55 am 10:40 am Aug 12 - Aug 26
387 10:05 am 10:50 am Aug 20 - Aug 27
387 10:05 am 10:50 am Aug 7 - Aug 13
387 10:40 am 11:25 am Aug 14 - Sep 1
387 10:40 am 11:25 am Sep 2 - Sep 2
387 10:40 am 11:25 am Aug 5 - Aug 11
387 10:40 am 11:25 am Jul 26 - Aug 4
389 11:50 am 12:35 pm Aug 12 - Aug 26
389 12:00 pm 12:45 pm Sep 1 - Sep 8
389 12:10 pm 12:55 pm Aug 7 - Aug 13
389 12:10 pm 12:55 pm Jul 30 - Aug 6
389 12:10 pm 12:55 pm Aug 20 - Aug 27
389 12:15 pm 1:00 pm Jul 26 - Aug 4
389 12:15 pm 1:00 pm Aug 8 - Aug 31
391 12:50 pm 1:35 pm Sep 2 - Sep 2
391 1:00 pm 1:45 pm Sep 1 - Sep 4
391 1:10 pm 1:55 pm Aug 5 - Aug 5
391 1:30 pm 2:15 pm Aug 20 - Aug 27
391 1:30 pm 2:15 pm Aug 7 - Aug 13
391 1:35 pm 2:20 pm Jul 28 - Aug 4
391 1:35 pm 2:20 pm Aug 8 - Aug 11
391 1:35 pm 2:20 pm Aug 18 - Aug 25
391 1:40 pm 2:25 pm Aug 6 - Aug 6
391 2:00 pm 2:45 pm Jul 27 - Aug 3
391 2:00 pm 2:45 pm Aug 10 - Aug 31
391 2:25 pm 3:10 pm Aug 12 - Aug 26
393 2:55 pm 3:40 pm Jul 26 - Aug 2
393 2:55 pm 3:40 pm Aug 9 - Aug 30
393 3:25 pm 4:10 pm Aug 8 - Aug 14
393 3:25 pm 4:10 pm Aug 17 - Sep 1
393 3:25 pm 4:10 pm Jul 27 - Aug 4
393 3:30 pm 4:15 pm Aug 5 - Aug 5
393 3:45 pm 4:30 pm Sep 2 - Sep 2
393 3:50 pm 4:35 pm Aug 20 - Sep 3
393 3:50 pm 4:35 pm Jul 30 - Aug 6
393 3:50 pm 4:35 pm Aug 7 - Aug 13
395 4:30 pm 5:15 pm Aug 12 - Aug 26
395 5:55 pm 6:40 pm Jul 26 - Aug 4
395 5:55 pm 6:40 pm Aug 14 - Sep 1
395 5:55 pm 6:40 pm Aug 5 - Aug 11
395 6:00 pm 6:45 pm Sep 2 - Sep 2
395 6:15 pm 7:00 pm Aug 7 - Aug 13
395 6:15 pm 7:00 pm Aug 20 - Sep 3
395 6:15 pm 7:00 pm Jul 30 - Aug 6
397 8:15 pm 9:00 pm Aug 20 - Sep 3
397 8:15 pm 9:00 pm Aug 7 - Aug 13
397 8:15 pm 9:00 pm Jul 30 - Aug 6
397 8:20 pm 9:05 pm Jul 26 - Aug 4
397 8:20 pm 9:05 pm Aug 8 - Sep 1
* 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 $206
Destination

Chicago
$206
Airlines Airline reviews

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

Overall
8.7
Boarding
8.6
Crew
8.8
Comfort
8.5
Food
8.4
Entertainment
7.1