Find Cheap Flights to Chicago

Depart
Return
1 adult
Adults
18+
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 to Chicago

(Round-trip)
Depart: Fri 21 Apr 2017 Return: Sat 29 Apr 2017 Trip spans 9 days
C$265
Select
Major Airline
Major Airline
YUL
MDW
4h 10m
nonstop
MDW
YUL
4h 05m
nonstop
Depart: Wed 3 May 2017 Return: Sat 6 May 2017 Trip spans 4 days
C$265
Select
Porter Airlines
Porter Airlines
YUL
MDW
6h 40m
1 stop
MDW
YUL
4h 05m
1 stop
Depart: Sun 16 Apr 2017 Return: Wed 19 Apr 2017 Trip spans 4 days
C$269
Select
Air Canada
Air Canada
YYZ
ORD
1h 43m
nonstop
ORD
YYZ
1h 30m
nonstop
Depart: Sat 20 May 2017 Return: Wed 24 May 2017 Trip spans 5 days
C$295
Select
WestJet
WestJet
YYZ
ORD
6h 14m
1 stop
ORD
YYZ
5h 39m
1 stop
Depart: Sun 30 Apr 2017 Return: Wed 3 May 2017 Trip spans 4 days
C$297
Select
Delta
Delta
YXU
ORD
8h 26m
2 stops
ORD
YXU
11h 04m
2 stops
Depart: Tue 25 Apr 2017 Return: Wed 26 Apr 2017 Trip spans 2 days
C$319
Select
American Airlines
American Airlines
YUL
ORD
2h 36m
nonstop
ORD
YUL
2h 07m
nonstop
Depart: Thu 18 May 2017 Return: Tue 23 May 2017 Trip spans 6 days
C$381
Select
United
United
YUL
ORD
2h 23m
nonstop
ORD
YUL
2h 01m
nonstop
Depart: Sat 3 Jun 2017 Return: Tue 6 Jun 2017 Trip spans 4 days
C$265
Select
Porter Airlines
Porter Airlines
YUL
MDW
6h 00m
1 stop
MDW
YUL
6h 05m
1 stop
Depart: Tue 18 Apr 2017 Return: Mon 24 Apr 2017 Trip spans 7 days
C$269
Select
Air Canada
Air Canada
YYZ
ORD
1h 43m
nonstop
ORD
YYZ
1h 40m
nonstop
Depart: Mon 14 Aug 2017 Return: Tue 15 Aug 2017 Trip spans 2 days
C$269
Select
Major Airline
Major Airline
YYZ
ORD
1h 53m
nonstop
ORD
YYZ
1h 58m
nonstop
Depart: Mon 17 Apr 2017 Return: Thu 20 Apr 2017 Trip spans 4 days
C$268
Select
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Thu 3 Aug 2017 Return: Mon 7 Aug 2017 Trip spans 5 days
C$269
Select
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 34m
nonstop
Depart: Tue 18 Apr 2017 Return: Mon 24 Apr 2017 Trip spans 7 days
C$300
Select
Delta
Delta
YYZ
MDW
5h 25m
1 stop
MDW
YYZ
7h 06m
1 stop
Depart: Thu 8 Jun 2017 Return: Tue 13 Jun 2017 Trip spans 6 days
C$288
Select
Major Airline
Major Airline
YUL
ORD
6h 34m
1 stop
ORD
YUL
5h 56m
1 stop
Depart: Tue 18 Apr 2017 Return: Mon 24 Apr 2017 Trip spans 7 days
C$268
Select
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Thu 7 Sep 2017 Return: Mon 11 Sep 2017 Trip spans 5 days
C$269
Select
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Sat 22 Apr 2017 Return: Mon 24 Apr 2017 Trip spans 3 days
C$300
Select
Delta
Delta
YYZ
MDW
9h 53m
2 stops
MDW
YYZ
4h 49m
1 stop
Depart: Thu 24 Aug 2017 Return: Sun 27 Aug 2017 Trip spans 4 days
C$295
Select
Major Airline
Major Airline
YTZ
MDW
1h 45m
1 stop
MDW
YTZ
1h 40m
1 stop
Depart: Mon 1 May 2017 Return: Tue 2 May 2017 Trip spans 2 days
C$268
Select
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Thu 20 Jul 2017 Return: Mon 24 Jul 2017 Trip spans 5 days
C$271
Select
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 34m
nonstop
* Prices are per person, are for e–tickets and include all taxes & fees in CAD.

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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.

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Airports
Origin

London
C$ 297
Montreal
C$ 265
Toronto
only C$ 269
only C$ 268
Destination

Chicago
only C$ 269
only C$ 265
Airlines Airline reviews

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

Overall
7.0
Boarding
6.9
Crew
7.6
Comfort
7.1
Food
5.5
Entertainment
6.2