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 15 Jun 2017 Return: Mon 19 Jun 2017 Trip spans 5 days
C$270
Select
Porter Airlines
Porter Airlines
YUL
MDW
4h 10m
1 stop
MDW
YUL
3h 50m
1 stop
Depart: Tue 31 Oct 2017 Return: Thu 2 Nov 2017 Trip spans 3 days
C$272
Select
Major Airline
Major Airline
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Thu 13 Jul 2017 Return: Sun 16 Jul 2017 Trip spans 4 days
C$281
Select
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 33m
nonstop
Depart: Fri 26 May 2017 Return: Mon 29 May 2017 Trip spans 4 days
C$308
Select
United
United
YYZ
ORD
1h 51m
nonstop
ORD
YYZ
1h 41m
nonstop
Depart: Sat 28 Oct 2017 Return: Tue 31 Oct 2017 Trip spans 4 days
C$313
Select
Delta
Delta
YYZ
MDW
7h 51m
1 stop
MDW
YYZ
3h 20m
1 stop
Depart: Fri 26 May 2017 Return: Sun 28 May 2017 Trip spans 3 days
C$319
Select
WestJet
WestJet
YYZ
ORD
1h 56m
nonstop
ORD
YYZ
5h 39m
1 stop
Depart: Sat 13 May 2017 Return: Thu 18 May 2017 Trip spans 6 days
C$424
Select
American Airlines
American Airlines
YUL
ORD
8h 10m
1 stop
ORD
YUL
6h 32m
1 stop
Depart: Tue 31 Oct 2017 Return: Thu 2 Nov 2017 Trip spans 3 days
C$272
Select
Major Airline
Major Airline
YYZ
ORD
1h 47m
nonstop
ORD
YYZ
1h 36m
nonstop
Depart: Fri 22 Sep 2017 Return: Mon 25 Sep 2017 Trip spans 4 days
C$545
Select
Alaska Airlines
Alaska Airlines
YVR
ORD
10h 47m
2 stops
ORD
YVR
6h 44m
1 stop
Depart: Wed 19 Jul 2017 Return: Wed 26 Jul 2017 Trip spans 8 days
C$278
Select
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Mon 12 Jun 2017 Return: Tue 13 Jun 2017 Trip spans 2 days
C$284
Select
Air Canada
Air Canada
YYZ
ORD
1h 51m
nonstop
ORD
YYZ
1h 33m
nonstop
Depart: Thu 15 Jun 2017 Return: Sun 18 Jun 2017 Trip spans 4 days
C$278
Select
Major Airline
Major Airline
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Mon 19 Jun 2017 Return: Wed 21 Jun 2017 Trip spans 3 days
C$280
Select
Porter Airlines
Porter Airlines
YUL
MDW
4h 40m
1 stop
MDW
YUL
4h 05m
1 stop
Depart: Wed 2 Aug 2017 Return: Mon 7 Aug 2017 Trip spans 6 days
C$284
Select
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 34m
nonstop
Depart: Fri 21 Jul 2017 Return: Wed 26 Jul 2017 Trip spans 6 days
C$280
Select
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Wed 7 Jun 2017 Return: Thu 8 Jun 2017 Trip spans 2 days
C$343
Select
WestJet
WestJet
YYZ
ORD
6h 53m
1 stop
ORD
YYZ
1h 37m
nonstop
Depart: Thu 7 Sep 2017 Return: Mon 11 Sep 2017 Trip spans 5 days
C$284
Select
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Fri 26 May 2017 Return: Sun 4 Jun 2017 Trip spans 10 days
C$295
Select
Major Airline
Major Airline
YYZ
ORD
5h 53m
1 stop
ORD
YYZ
5h 41m
1 stop
Depart: Wed 21 Jun 2017 Return: Mon 26 Jun 2017 Trip spans 6 days
C$366
Select
Delta
Delta
YXU
ORD
9h 04m
2 stops
ORD
YXU
11h 14m
2 stops
Depart: Thu 25 May 2017 Return: Mon 5 Jun 2017 Trip spans 12 days
C$283
Select
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 39m
nonstop
* Prices are per person, are for e–tickets and include all taxes & fees in CAD.

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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$ 545
London
C$ 366
Montreal
C$ 270
Toronto
only C$ 272
only C$ 272
Destination

Chicago
only C$ 272
only C$ 270
Airlines Airline reviews

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

Overall
6.9
Boarding
6.8
Crew
7.5
Comfort
7.0
Food
5.5
Entertainment
6.1