Find Deals on 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: Sat Apr 22 2017 Return: Wed Apr 26 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YUL
MDW
6h 30m
1 stop
MDW
YUL
4h 05m
1 stop
Depart: Sat Apr 29 2017 Return: Mon May 1 2017 Trip spans 3 days
Air Canada
Air Canada
YYZ
ORD
1h 43m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Sun May 21 2017 Return: Tue May 23 2017 Trip spans 3 days
United
United
YYZ
ORD
2h 00m
nonstop
ORD
YYZ
1h 32m
nonstop
Depart: Thu Aug 3 2017 Return: Mon Aug 7 2017 Trip spans 5 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Tue Jul 11 2017 Return: Tue Jul 25 2017 Trip spans 15 days
WestJet
WestJet
YYZ
ORD
6h 14m
1 stop
ORD
YYZ
1h 36m
nonstop
Depart: Tue Apr 25 2017 Return: Tue May 2 2017 Trip spans 8 days
Delta
Delta
YYZ
MDW
8h 18m
1 stop
MDW
YYZ
4h 39m
1 stop
Depart: Mon Jun 19 2017 Return: Wed Jun 28 2017 Trip spans 10 days
Porter Airlines
Porter Airlines
YUL
MDW
3h 40m
1 stop
MDW
YUL
6h 15m
1 stop
Depart: Fri Jun 30 2017 Return: Tue Jul 4 2017 Trip spans 5 days
United
United
YYZ
ORD
1h 51m
nonstop
ORD
YYZ
1h 29m
nonstop
Depart: Thu Jul 13 2017 Return: Sun Jul 16 2017 Trip spans 4 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 34m
nonstop
Depart: Tue Aug 22 2017 Return: Mon Aug 28 2017 Trip spans 7 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Thu Sep 14 2017 Return: Wed Sep 20 2017 Trip spans 7 days
WestJet
WestJet
YYZ
ORD
6h 14m
1 stop
ORD
YYZ
1h 36m
nonstop
Depart: Tue May 2 2017 Return: Fri May 12 2017 Trip spans 11 days
Porter Airlines
Porter Airlines
YUL
MDW
4h 40m
1 stop
MDW
YUL
4h 40m
1 stop
Depart: Wed Sep 20 2017 Return: Tue Sep 26 2017 Trip spans 7 days
Delta
Delta
YYZ
MDW
7h 52m
1 stop
MDW
YYZ
5h 04m
1 stop
Depart: Sun Apr 23 2017 Return: Tue Apr 25 2017 Trip spans 3 days
Major Airline
Major Airline
YUL
ORD
4h 40m
1 stop
ORD
YUL
4h 13m
1 stop
Depart: Sun Jun 11 2017 Return: Sat Jun 17 2017 Trip spans 7 days
Porter Airlines
Porter Airlines
YUL
MDW
3h 50m
1 stop
MDW
YUL
6h 35m
1 stop
Depart: Thu Aug 17 2017 Return: Sun Aug 20 2017 Trip spans 4 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 34m
nonstop
Depart: Thu Apr 20 2017 Return: Sun Apr 23 2017 Trip spans 4 days
WestJet
WestJet
YYZ
ORD
5h 51m
1 stop
ORD
YYZ
6h 00m
1 stop
Depart: Fri Apr 21 2017 Return: Sun Apr 23 2017 Trip spans 3 days
Major Airline
Major Airline
YYZ
ORD
1h 50m
nonstop
ORD
YYZ
1h 34m
nonstop
Depart: Thu May 4 2017 Return: Tue May 9 2017 Trip spans 6 days
Delta
Delta
YYZ
MDW
7h 11m
1 stop
MDW
YYZ
7h 02m
1 stop
Depart: Fri Sep 22 2017 Return: Mon Sep 25 2017 Trip spans 4 days
WestJet
WestJet
YYZ
ORD
6h 14m
1 stop
ORD
YYZ
5h 39m
1 stop
* 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.

We compile tonnes of data for you
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

Montreal
$190
Toronto
only $202
only $202
Destination

Chicago
only $202
only $190
Airlines Airline reviews

182 travelers who booked a flight from Montreal to Chicago rated their chosen airlines with an average of 6.9.

Overall
6.9
Boarding
6.9
Crew
7.5
Comfort
7.0
Food
5.5
Entertainment
6.1