Find Cheap Flights from Canada to Chicago

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 Canada to Chicago

(Round-trip)
Depart: Wed Aug 23 2017 Return: Wed Aug 30 2017 Trip spans 8 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Fri Sep 8 2017 Return: Tue Sep 12 2017 Trip spans 5 days
Air Canada
Air Canada
YTZ
ORD
4h 38m
1 stop
ORD
YTZ
4h 15m
1 stop
Depart: Thu Aug 24 2017 Return: Mon Aug 28 2017 Trip spans 5 days
United
United
YUL
ORD
2h 40m
nonstop
ORD
YUL
2h 10m
nonstop
Depart: Wed Sep 13 2017 Return: Fri Sep 15 2017 Trip spans 3 days
Delta
Delta
YEG
ORD
8h 42m
1 stop
ORD
YEG
10h 13m
1 stop
Depart: Wed Nov 22 2017 Return: Sun Nov 26 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
YUL
ORD
2h 30m
nonstop
ORD
YUL
2h 00m
nonstop
Depart: Tue Oct 3 2017 Return: Tue Oct 10 2017 Trip spans 8 days
American Airlines
American Airlines
YOW
ORD
7h 23m
1 stop
ORD
YOW
14h 35m
1 stop
Depart: Thu Sep 14 2017 Return: Mon Sep 18 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 45m
nonstop
Depart: Sat Sep 30 2017 Return: Mon Oct 2 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Wed Oct 18 2017 Return: Mon Oct 23 2017 Trip spans 6 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Sat Aug 26 2017 Return: Tue Sep 12 2017 Trip spans 18 days
Air Canada
Air Canada
YTZ
ORD
4h 36m
1 stop
ORD
YTZ
4h 15m
1 stop
Depart: Fri Nov 10 2017 Return: Mon Nov 13 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Sun Sep 17 2017 Return: Wed Sep 20 2017 Trip spans 4 days
WestJet
WestJet
YHM
ORD
23h 49m
1 stop
ORD
YHM
16h 34m
1 stop
Depart: Fri Sep 1 2017 Return: Mon Sep 4 2017 Trip spans 4 days
United
United
YUL
ORD
2h 40m
nonstop
ORD
YUL
2h 10m
nonstop
Depart: Mon Oct 2 2017 Return: Thu Oct 5 2017 Trip spans 4 days
Delta
Delta
YEG
ORD
8h 25m
1 stop
ORD
YEG
10h 20m
1 stop
Depart: Fri Sep 1 2017 Return: Tue Sep 5 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
YUL
ORD
2h 35m
nonstop
ORD
YUL
2h 04m
nonstop
Depart: Thu Aug 31 2017 Return: Sun Sep 3 2017 Trip spans 4 days
Air Canada
Air Canada
YTZ
ORD
4h 31m
1 stop
ORD
YTZ
4h 40m
1 stop
Depart: Mon Oct 30 2017 Return: Mon Nov 6 2017 Trip spans 8 days
Delta
Delta
YUL
ORD
5h 42m
1 stop
ORD
YUL
6h 37m
1 stop
Depart: Fri Aug 25 2017 Return: Sun Aug 27 2017 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Thu Nov 23 2017 Return: Sun Nov 26 2017 Trip spans 4 days
Multiple Airlines
Multiple Airlines
YUL
ORD
2h 30m
nonstop
ORD
YUL
2h 00m
nonstop
Depart: Wed Sep 6 2017 Return: Mon Sep 11 2017 Trip spans 6 days
Air Canada
Air Canada
YUL
ORD
2h 23m
nonstop
ORD
YUL
2h 02m
nonstop
* 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

Edmonton
$282
Hamilton
$555
Ottawa
$300
Montreal
$282
Toronto
$206
Destination

Chicago
only $248
only $206
Airlines Airline reviews

97 travelers who booked a flight from Toronto to Chicago rated their chosen airlines with an average of 7.9.

Overall
8.2
Boarding
8.1
Crew
8.4
Comfort
8.0
Food
7.5
Entertainment
6.6