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 20 Jul 2017 Return: Tue 25 Jul 2017 Trip spans 6 days
C$260
Select
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 45m
nonstop
Depart: Sat 9 Dec 2017 Return: Tue 12 Dec 2017 Trip spans 4 days
C$260
Select
Major Airline
Major Airline
YYZ
ORD
1h 54m
nonstop
ORD
YYZ
1h 58m
nonstop
Depart: Wed 6 Sep 2017 Return: Sat 9 Sep 2017 Trip spans 4 days
C$262
Select
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Wed 25 Oct 2017 Return: Sat 28 Oct 2017 Trip spans 4 days
C$282
Select
Delta
Delta
YYZ
MDW
8h 22m
1 stop
MDW
YYZ
4h 42m
1 stop
Depart: Mon 16 Oct 2017 Return: Wed 18 Oct 2017 Trip spans 3 days
C$401
Select
WestJet
WestJet
YEG
ORD
6h 29m
1 stop
ORD
YEG
6h 03m
1 stop
Depart: Fri 11 Aug 2017 Return: Mon 21 Aug 2017 Trip spans 11 days
C$402
Select
American Airlines
American Airlines
YQB
ORD
7h 56m
2 stops
ORD
YQB
7h 08m
1 stop
Depart: Fri 4 Aug 2017 Return: Mon 7 Aug 2017 Trip spans 4 days
C$465
Select
United
United
YHZ
ORD
6h 39m
1 stop
ORD
YHZ
6h 27m
1 stop
Depart: Sat 5 Aug 2017 Return: Fri 11 Aug 2017 Trip spans 7 days
C$260
Select
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Thu 14 Sep 2017 Return: Tue 19 Sep 2017 Trip spans 6 days
C$262
Select
Major Airline
Major Airline
YYZ
ORD
1h 59m
nonstop
ORD
YYZ
1h 38m
nonstop
Depart: Sun 1 Oct 2017 Return: Thu 5 Oct 2017 Trip spans 5 days
C$263
Select
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Tue 19 Sep 2017 Return: Thu 21 Sep 2017 Trip spans 3 days
C$260
Select
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Thu 20 Jul 2017 Return: Sun 23 Jul 2017 Trip spans 4 days
C$263
Select
Major Airline
Major Airline
YYZ
ORD
1h 52m
nonstop
ORD
YYZ
1h 40m
nonstop
Depart: Wed 20 Sep 2017 Return: Fri 22 Sep 2017 Trip spans 3 days
C$295
Select
Delta
Delta
YYZ
MDW
5h 09m
1 stop
MDW
YYZ
3h 20m
1 stop
Depart: Thu 20 Jul 2017 Return: Mon 24 Jul 2017 Trip spans 5 days
C$274
Select
Air Canada
Air Canada
YYZ
ORD
1h 51m
nonstop
ORD
YYZ
1h 40m
nonstop
Depart: Sat 7 Oct 2017 Return: Fri 13 Oct 2017 Trip spans 7 days
C$260
Select
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Wed 18 Oct 2017 Return: Sat 21 Oct 2017 Trip spans 4 days
C$263
Select
Major Airline
Major Airline
YYZ
ORD
1h 55m
nonstop
ORD
YYZ
1h 36m
nonstop
Depart: Wed 23 Aug 2017 Return: Tue 19 Sep 2017 Trip spans 28 days
C$298
Select
Delta
Delta
YYZ
MDW
6h 15m
1 stop
MDW
YYZ
6h 54m
1 stop
Depart: Wed 22 Nov 2017 Return: Tue 28 Nov 2017 Trip spans 7 days
C$260
Select
Porter Airlines
Porter Airlines
YTZ
MDW
1h 50m
nonstop
MDW
YTZ
1h 37m
nonstop
Depart: Thu 19 Oct 2017 Return: Sun 22 Oct 2017 Trip spans 4 days
C$288
Select
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Tue 22 Aug 2017 Return: Sat 26 Aug 2017 Trip spans 5 days
C$267
Select
Major Airline
Major Airline
YYZ
ORD
1h 59m
nonstop
ORD
YYZ
1h 44m
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

Québec City
C$ 402
Edmonton
C$ 401
Halifax
C$ 465
Toronto
only C$ 260
only C$ 260
Destination

Chicago
only C$ 260
only C$ 260
Airlines Airline reviews

238 travellers who booked a flight from Toronto to Chicago rated their chosen airlines with an average of 7.4.

Overall
7.4
Boarding
7.5
Crew
8.0
Comfort
7.6
Food
6.4
Entertainment
6.6