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: Wed Jul 5 2017 Return: Wed Jul 12 2017 Trip spans 8 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Wed Jul 5 2017 Return: Wed Jul 12 2017 Trip spans 8 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 34m
nonstop
Depart: Fri Jun 2 2017 Return: Fri Jun 9 2017 Trip spans 8 days
Major Airline
Major Airline
YYZ
ORD
1h 52m
nonstop
ORD
YYZ
1h 45m
nonstop
Depart: Fri Jun 23 2017 Return: Mon Jun 26 2017 Trip spans 4 days
WestJet
WestJet
YYZ
ORD
6h 53m
1 stop
ORD
YYZ
5h 39m
1 stop
Depart: Tue Sep 12 2017 Return: Tue Sep 19 2017 Trip spans 8 days
Delta
Delta
YYZ
MDW
6h 00m
1 stop
MDW
YYZ
5h 17m
1 stop
Depart: Sat Jul 8 2017 Return: Tue Jul 11 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Tue Jun 13 2017 Return: Thu Jul 6 2017 Trip spans 24 days
Air Canada
Air Canada
YYZ
ORD
1h 43m
nonstop
ORD
YYZ
1h 33m
nonstop
Depart: Sun Jul 16 2017 Return: Mon Jul 17 2017 Trip spans 2 days
Major Airline
Major Airline
YYZ
ORD
1h 52m
nonstop
ORD
YYZ
1h 45m
nonstop
Depart: Fri Jul 21 2017 Return: Wed Jul 26 2017 Trip spans 6 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 34m
nonstop
Depart: Sat Apr 29 2017 Return: Wed May 17 2017 Trip spans 19 days
American Airlines
American Airlines
YYZ
ORD
1h 51m
nonstop
ORD
YYZ
1h 33m
nonstop
Depart: Wed May 17 2017 Return: Thu May 18 2017 Trip spans 2 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Wed Sep 13 2017 Return: Wed Sep 20 2017 Trip spans 8 days
Major Airline
Major Airline
YYZ
ORD
1h 54m
nonstop
ORD
YYZ
1h 48m
nonstop
Depart: Sat Sep 23 2017 Return: Sat Oct 14 2017 Trip spans 22 days
Delta
Delta
YYZ
MDW
4h 03m
1 stop
MDW
YYZ
5h 13m
1 stop
Depart: Fri May 26 2017 Return: Mon May 29 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Fri Jun 16 2017 Return: Mon Jun 19 2017 Trip spans 4 days
Air Canada
Air Canada
YYZ
ORD
1h 43m
nonstop
ORD
YYZ
1h 34m
nonstop
Depart: Thu Aug 17 2017 Return: Sun Aug 20 2017 Trip spans 4 days
WestJet
WestJet
YYZ
ORD
6h 14m
1 stop
ORD
YYZ
5h 43m
1 stop
Depart: Fri Jun 2 2017 Return: Wed Jun 7 2017 Trip spans 6 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Sat Aug 19 2017 Return: Tue Aug 22 2017 Trip spans 4 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 34m
nonstop
Depart: Fri Jun 16 2017 Return: Mon Jun 19 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Thu Oct 26 2017 Return: Sun Oct 29 2017 Trip spans 4 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 33m
nonstop
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 9:12 am May 5 - Jun 1
2937 8:16 am 9:10 am Jun 2 - Aug 21
2937 8:16 am 9:10 am Apr 22 - May 4
3137 11:45 am 12:37 pm Apr 23 - May 4
3137 11:45 am 12:39 pm May 5 - Jun 1
3137 11:47 am 12:39 pm Jun 2 - Jun 15
3516 3:10 pm 4:00 pm Apr 23 - May 4
3497 3:14 pm 4:07 pm Jun 2 - Jun 15
3516 3:14 pm 4:06 pm May 5 - Jun 1
2971 6:15 pm 7:09 pm May 5 - May 5
2971 6:15 pm 7:09 pm May 7 - May 7
3216 6:15 pm 7:07 pm Apr 28 - May 4
3511 6:15 pm 7:09 pm Jun 1 - Jun 1
3511 6:15 pm 7:09 pm May 8 - May 29
3511 6:15 pm 7:08 pm May 6 - May 27
3511 6:15 pm 7:09 pm May 9 - May 31
3623 6:21 pm 7:14 pm Jun 2 - Aug 21
3348 7:50 pm 8:40 pm May 4 - May 4
3348 7:50 pm 8:40 pm Apr 25 - May 3
3348 7:55 pm 8:47 pm May 5 - Jun 2
* 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 $197
only $196
Destination

Chicago
only $197
only $196
Airlines Airline reviews

228 travelers who booked a flight from Toronto to Chicago rated their chosen airlines with an average of 7.4.

Overall
7.4
Boarding
7.4
Crew
7.9
Comfort
7.5
Food
6.3
Entertainment
6.5