Find Deals on 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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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Toronto to Chicago

(Round-trip)
Depart: Sat Oct 15 2016 Return: Sat Oct 29 2016 Trip spans 15 days
Major Airline
Major Airline
YYZ
ORD
1h 49m
nonstop
ORD
YYZ
1h 33m
nonstop
Depart: Sat Oct 22 2016 Return: Sat Nov 5 2016 Trip spans 15 days
Delta
Delta
YYZ
MDW
3h 59m
1 stop
MDW
YYZ
3h 52m
1 stop
Depart: Sat Oct 29 2016 Return: Mon Oct 31 2016 Trip spans 3 days
Air Canada
Air Canada
YYZ
ORD
1h 40m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Sat Dec 3 2016 Return: Sun Dec 4 2016 Trip spans 2 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 55m
nonstop
MDW
YTZ
1h 35m
nonstop
Depart: Sat Oct 22 2016 Return: Mon Oct 24 2016 Trip spans 3 days
Major Airline
Major Airline
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 35m
nonstop
Depart: Tue Oct 25 2016 Return: Tue Nov 8 2016 Trip spans 15 days
Delta
Delta
YYZ
MDW
5h 48m
1 stop
MDW
YYZ
5h 49m
1 stop
Depart: Tue Dec 6 2016 Return: Fri Dec 9 2016 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 55m
nonstop
MDW
YTZ
1h 35m
nonstop
Depart: Wed Oct 26 2016 Return: Sun Oct 30 2016 Trip spans 5 days
Major Airline
Major Airline
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 35m
nonstop
Depart: Wed Nov 2 2016 Return: Sat Nov 5 2016 Trip spans 4 days
Delta
Delta
YYZ
MDW
7h 22m
1 stop
MDW
YYZ
6h 46m
1 stop
Depart: Thu Oct 27 2016 Return: Sun Oct 30 2016 Trip spans 4 days
Major Airline
Major Airline
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 35m
nonstop
Depart: Wed Nov 23 2016 Return: Sun Nov 27 2016 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 55m
nonstop
MDW
YTZ
1h 35m
nonstop
Depart: Mon Dec 5 2016 Return: Sat Dec 10 2016 Trip spans 6 days
Delta
Delta
YYZ
MDW
5h 29m
1 stop
MDW
YYZ
3h 05m
1 stop
Depart: Fri Oct 28 2016 Return: Sat Oct 29 2016 Trip spans 2 days
Major Airline
Major Airline
YYZ
ORD
1h 46m
nonstop
ORD
YYZ
1h 33m
nonstop
Depart: Fri Oct 28 2016 Return: Sun Oct 30 2016 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 35m
nonstop
Depart: Mon Dec 5 2016 Return: Sat Dec 10 2016 Trip spans 6 days
Delta
Delta
YYZ
ORD
5h 55m
1 stop
ORD
YYZ
6h 40m
1 stop
Depart: Sat Oct 29 2016 Return: Mon Oct 31 2016 Trip spans 3 days
Major Airline
Major Airline
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 35m
nonstop
Depart: Fri Mar 31 2017 Return: Sun Apr 2 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Tue Nov 1 2016 Return: Wed Nov 2 2016 Trip spans 2 days
Major Airline
Major Airline
YTZ
MDW
1h 55m
1 stop
MDW
YTZ
1h 35m
1 stop
Depart: Thu Nov 3 2016 Return: Mon Nov 7 2016 Trip spans 5 days
Delta
Delta
YYZ
MDW
6h 29m
1 stop
MDW
YYZ
8h 44m
2 stops
Depart: Thu Oct 20 2016 Return: Fri Oct 21 2016 Trip spans 2 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 30m
nonstop
Direct flights YTO to CHI on American Airlines
Flight # Depart YYZ Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
3634 7:59 am 9:01 am Nov 6 - Nov 24
3634 7:59 am 8:47 am Oct 31 - Nov 3
3634 7:59 am 9:01 am Nov 4 - Nov 5
3634 8:10 am 9:02 am Oct 30 - Oct 30
3634 8:15 am 9:07 am Oct 6 - Oct 29
3534 10:16 am 11:15 am Nov 6 - Nov 21
3534 10:16 am 11:15 am Nov 4 - Nov 5
3534 10:19 am 11:10 am Oct 30 - Nov 3
3534 10:19 am 11:10 am Oct 6 - Oct 29
3194 11:45 am 12:35 pm Sep 27 - Oct 28
3194 11:45 am 12:35 pm Oct 29 - Nov 3
3194 11:45 am 12:35 pm Nov 1 - Nov 1
3814 11:45 am 12:35 pm Nov 5 - Nov 5
3814 11:45 am 12:35 pm Nov 6 - Nov 23
3814 11:45 am 12:35 pm Nov 4 - Nov 4
3516 3:15 pm 4:10 pm Nov 4 - Nov 5
3516 3:15 pm 4:10 pm Nov 6 - Nov 20
3516 3:15 pm 4:05 pm Oct 6 - Nov 3
3216 6:15 pm 7:07 pm Nov 5 - Nov 5
3216 6:15 pm 7:07 pm Nov 4 - Nov 4
3288 6:15 pm 7:07 pm Nov 6 - Nov 27
3754 6:15 pm 7:04 pm Oct 6 - Oct 13
3754 6:15 pm 7:04 pm Oct 19 - Nov 2
3754 6:15 pm 7:04 pm Oct 18 - Nov 3
3754 6:15 pm 7:04 pm Oct 7 - Oct 17
3348 7:48 pm 8:34 pm Oct 6 - Oct 6
3348 7:48 pm 8:34 pm Oct 7 - Oct 30
3348 7:48 pm 8:34 pm Nov 1 - Nov 3
3348 7:48 pm 8:43 pm Nov 4 - Nov 4
3348 7:48 pm 8:43 pm Nov 6 - Nov 23
* 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,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Toronto
only $177
only $180
Destination

Chicago
only $177
only $180
Airlines Airline reviews

163 travelers who booked a flight from Toronto to Chicago rated their chosen airlines with an average of 7.3.

Overall
7.4
Boarding
7.4
Crew
7.9
Comfort
7.5
Food
6.5
Entertainment
6.7