Find Cheap Flights from Toronto to Chicago (YTO - CHI)

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

(Round-trip)
Depart: Mon Nov 20 2017 Return: Thu Nov 23 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Thu Nov 16 2017 Return: Tue Nov 21 2017 Trip spans 6 days
Major Airline
Major Airline
YYZ
ORD
1h 42m
nonstop
ORD
YYZ
1h 32m
nonstop
Depart: Thu Jun 15 2017 Return: Sun Jun 18 2017 Trip spans 4 days
United
United
YYZ
ORD
1h 51m
nonstop
ORD
YYZ
1h 33m
nonstop
Depart: Tue Aug 8 2017 Return: Wed Aug 16 2017 Trip spans 9 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 34m
nonstop
Depart: Sun Oct 29 2017 Return: Sat Dec 2 2017 Trip spans 35 days
Delta
Delta
YYZ
MDW
5h 20m
1 stop
MDW
YYZ
5h 13m
1 stop
Depart: Sat Aug 12 2017 Return: Tue Aug 22 2017 Trip spans 11 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Thu Jun 22 2017 Return: Sun Jun 25 2017 Trip spans 4 days
United
United
YYZ
ORD
1h 51m
nonstop
ORD
YYZ
1h 33m
nonstop
Depart: Fri Jun 23 2017 Return: Tue Jun 27 2017 Trip spans 5 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
2 stops
MDW
YTZ
1h 40m
2 stops
Depart: Thu Jul 6 2017 Return: Sun Jul 9 2017 Trip spans 4 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 33m
nonstop
Depart: Wed Jun 14 2017 Return: Tue Jun 27 2017 Trip spans 14 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Fri Oct 6 2017 Return: Sun Oct 8 2017 Trip spans 3 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Wed Jun 14 2017 Return: Tue Jun 27 2017 Trip spans 14 days
Delta
Delta
YYZ
MDW
5h 09m
1 stop
MDW
YYZ
5h 21m
1 stop
Depart: Sat Jul 1 2017 Return: Tue Jul 4 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Tue Aug 15 2017 Return: Sun Aug 20 2017 Trip spans 6 days
Major Airline
Major Airline
YYZ
ORD
1h 54m
nonstop
ORD
YYZ
1h 38m
nonstop
Depart: Tue Jun 27 2017 Return: Thu Jul 6 2017 Trip spans 10 days
Air Canada
Air Canada
YTZ
ORD
4h 36m
1 stop
ORD
YTZ
4h 50m
1 stop
Depart: Sat Jul 8 2017 Return: Mon Jul 10 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Thu Sep 14 2017 Return: Sat Sep 16 2017 Trip spans 3 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Wed Sep 27 2017 Return: Sat Sep 30 2017 Trip spans 4 days
Delta
Delta
YYZ
MDW
8h 22m
1 stop
MDW
YYZ
5h 13m
1 stop
Depart: Mon Aug 7 2017 Return: Tue Aug 22 2017 Trip spans 16 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Thu Jul 20 2017 Return: Sat Jul 22 2017 Trip spans 3 days
Air Canada
Air Canada
YTZ
ORD
7h 31m
1 stop
ORD
YTZ
6h 40m
1 stop
Direct flights YTO to CHI on American Airlines
Flight # Depart YYZ Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
2937 8:16 am 9:10 am Jun 2 - Aug 21
2937 8:16 am 9:12 am May 20 - Jun 1
3137 11:45 am 12:39 pm May 20 - Jun 1
3094 11:47 am 12:39 pm Jun 3 - Jun 10
3094 11:47 am 12:39 pm Jun 17 - Aug 19
3137 11:47 am 12:39 pm Jun 2 - Jun 15
3137 11:47 am 12:39 pm Jun 16 - Aug 21
3497 3:14 pm 4:07 pm Jun 16 - Aug 21
3497 3:14 pm 4:07 pm Jun 2 - Jun 15
3516 3:14 pm 4:06 pm May 20 - Jun 1
3511 6:15 pm 7:09 pm Jun 1 - Jun 1
3827 6:20 pm 7:12 pm Jun 3 - Aug 19
3623 6:21 pm 7:14 pm Jun 6 - Jun 6
3623 6:21 pm 7:14 pm Jun 7 - Aug 16
3623 6:21 pm 7:14 pm Jun 2 - Aug 21
3348 7:55 pm 8:47 pm May 21 - Jun 2
3348 7:55 pm 8:47 pm Jun 4 - Aug 20
3348 7:55 pm 8:47 pm Jun 5 - Aug 21
* 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 $199
only $197
Destination

Chicago
only $199
only $197
Airlines Airline reviews

258 travelers who booked a flight from Toronto to Chicago rated their chosen airlines with an average of 7.2.

Overall
7.3
Boarding
7.3
Crew
7.8
Comfort
7.3
Food
6.2
Entertainment
6.3