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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Book cheap flights from Canada to Chicago

(Round-trip)
Depart: Wed Jun 14 2017 Return: Mon Jun 19 2017 Trip spans 6 days
Porter Airlines
Porter Airlines
YUL
MDW
6h 40m
1 stop
MDW
YUL
4h 05m
1 stop
Depart: Thu Aug 3 2017 Return: Sun Aug 6 2017 Trip spans 4 days
Major Airline
Major Airline
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 45m
nonstop
Depart: Tue Aug 15 2017 Return: Fri Aug 25 2017 Trip spans 11 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 34m
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: 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: Fri Jun 16 2017 Return: Sun Jun 18 2017 Trip spans 3 days
American Airlines
American Airlines
YOW
ORD
4h 47m
1 stop
ORD
YOW
7h 20m
1 stop
Depart: Wed Jun 14 2017 Return: Wed Jun 21 2017 Trip spans 8 days
WestJet
WestJet
YYC
ORD
3h 22m
nonstop
ORD
YYC
3h 45m
nonstop
Depart: Fri Oct 6 2017 Return: Sun Oct 8 2017 Trip spans 3 days
Alaska Airlines
Alaska Airlines
YVR
ORD
7h 12m
1 stop
ORD
YVR
9h 26m
1 stop
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: Fri Sep 22 2017 Return: Sun Sep 24 2017 Trip spans 3 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 31m
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: Fri Jul 7 2017 Return: Mon Jul 10 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Fri Jun 23 2017 Return: Sun Jun 25 2017 Trip spans 3 days
Major Airline
Major Airline
YUL
MDW
4h 55m
2 stops
MDW
YUL
3h 45m
2 stops
Depart: Sat Aug 12 2017 Return: Tue Aug 22 2017 Trip spans 11 days
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 34m
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: Fri Jul 28 2017 Return: Mon Jul 31 2017 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
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: 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: Fri Aug 4 2017 Return: Tue Aug 8 2017 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Tue Jun 27 2017 Return: Tue Jul 4 2017 Trip spans 8 days
United
United
YUL
ORD
2h 35m
nonstop
ORD
YUL
2h 09m
nonstop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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

Vancouver
$389
Calgary
$339
Ottawa
$329
Montreal
$197
Toronto
only $199
only $197
Destination

Chicago
only $199
only $197
Airlines Airline reviews

194 travelers who booked a flight from Montreal to Chicago rated their chosen airlines with an average of 6.8.

Overall
6.8
Boarding
6.8
Crew
7.5
Comfort
7.0
Food
5.4
Entertainment
6.1