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: Thu 16 Mar 2017 Return: Mon 20 Mar 2017 Trip spans 5 days
C$254
Select
Major Airline
Major Airline
YUL
MDW
4h 45m
nonstop
MDW
YUL
3h 45m
nonstop
Depart: Thu 23 Mar 2017 Return: Sat 25 Mar 2017 Trip spans 3 days
C$254
Select
Porter Airlines
Porter Airlines
YUL
MDW
3h 40m
1 stop
MDW
YUL
4h 25m
1 stop
Depart: Mon 15 May 2017 Return: Fri 19 May 2017 Trip spans 5 days
C$273
Select
Air Canada
Air Canada
YYZ
ORD
1h 43m
nonstop
ORD
YYZ
1h 41m
nonstop
Depart: Thu 10 Aug 2017 Return: Sat 2 Sep 2017 Trip spans 24 days
C$294
Select
United
United
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 34m
nonstop
Depart: Wed 15 Mar 2017 Return: Thu 23 Mar 2017 Trip spans 9 days
C$301
Select
Delta
Delta
YYZ
MDW
3h 43m
1 stop
MDW
YYZ
4h 42m
1 stop
Depart: Fri 17 Mar 2017 Return: Sun 19 Mar 2017 Trip spans 3 days
C$315
Select
American Airlines
American Airlines
YUL
ORD
2h 47m
nonstop
ORD
YUL
12h 23m
1 stop
Depart: Wed 3 May 2017 Return: Fri 5 May 2017 Trip spans 3 days
C$374
Select
WestJet
WestJet
YXE
ORD
5h 49m
1 stop
ORD
YXE
6h 16m
1 stop
Depart: Wed 3 May 2017 Return: Mon 8 May 2017 Trip spans 6 days
C$481
Select
Alaska Airlines
Alaska Airlines
YVR
ORD
11h 34m
2 stops
ORD
YVR
9h 41m
1 stop
Depart: Fri 24 Mar 2017 Return: Sun 26 Mar 2017 Trip spans 3 days
C$254
Select
Porter Airlines
Porter Airlines
YUL
MDW
5h 25m
1 stop
MDW
YUL
5h 05m
1 stop
Depart: Sat 8 Apr 2017 Return: Mon 10 Apr 2017 Trip spans 3 days
C$254
Select
Major Airline
Major Airline
YUL
MDW
5h 35m
nonstop
MDW
YUL
3h 40m
nonstop
Depart: Thu 10 Aug 2017 Return: Mon 14 Aug 2017 Trip spans 5 days
C$273
Select
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 34m
nonstop
Depart: Thu 30 Mar 2017 Return: Sat 8 Apr 2017 Trip spans 10 days
C$254
Select
Porter Airlines
Porter Airlines
YUL
MDW
4h 15m
1 stop
MDW
YUL
4h 25m
1 stop
Depart: Sat 13 May 2017 Return: Wed 17 May 2017 Trip spans 5 days
C$254
Select
Major Airline
Major Airline
YUL
ORD
6h 08m
1 stop
ORD
YUL
5h 56m
1 stop
Depart: Fri 18 Aug 2017 Return: Mon 21 Aug 2017 Trip spans 4 days
C$273
Select
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 34m
nonstop
Depart: Thu 23 Mar 2017 Return: Mon 3 Apr 2017 Trip spans 12 days
C$301
Select
Delta
Delta
YYZ
MDW
7h 52m
1 stop
MDW
YYZ
7h 06m
1 stop
Depart: Wed 5 Apr 2017 Return: Sun 9 Apr 2017 Trip spans 5 days
C$254
Select
Porter Airlines
Porter Airlines
YUL
MDW
6h 00m
1 stop
MDW
YUL
5h 05m
1 stop
Depart: Fri 31 Mar 2017 Return: Sun 2 Apr 2017 Trip spans 3 days
C$315
Select
American Airlines
American Airlines
YUL
ORD
2h 47m
nonstop
ORD
YUL
12h 23m
1 stop
Depart: Tue 28 Mar 2017 Return: Thu 30 Mar 2017 Trip spans 3 days
C$269
Select
Major Airline
Major Airline
YYZ
ORD
1h 54m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Mon 3 Apr 2017 Return: Thu 6 Apr 2017 Trip spans 4 days
C$301
Select
Delta
Delta
YYZ
MDW
5h 23m
1 stop
MDW
YYZ
3h 34m
1 stop
Depart: Fri 31 Mar 2017 Return: Mon 3 Apr 2017 Trip spans 4 days
C$275
Select
Air Canada
Air Canada
YYZ
ORD
1h 57m
nonstop
ORD
YYZ
1h 30m
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

Vancouver
C$ 481
Saskatoon
C$ 374
Montreal
C$ 254
Toronto
C$ 269
Destination

Chicago
only C$ 254
only C$ 254
Airlines Airline reviews

178 travellers 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
6.2