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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights to Chicago

(Round-trip)
Depart: Fri 8 Sep 2017 Return: Mon 11 Sep 2017 Trip spans 4 days
C$257
Select
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 50m
nonstop
Depart: Thu 14 Sep 2017 Return: Mon 18 Sep 2017 Trip spans 5 days
C$275
Select
Multiple Airlines
Multiple Airlines
YYZ
ORD
1h 51m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Tue 19 Sep 2017 Return: Sun 24 Sep 2017 Trip spans 6 days
C$284
Select
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Wed 20 Sep 2017 Return: Mon 25 Sep 2017 Trip spans 6 days
C$298
Select
Delta
Delta
YYZ
MDW
6h 25m
1 stop
MDW
YYZ
7h 34m
1 stop
Depart: Sun 17 Sep 2017 Return: Mon 18 Sep 2017 Trip spans 2 days
C$318
Select
American Airlines
American Airlines
YOW
ORD
4h 49m
1 stop
ORD
YOW
7h 06m
2 stops
Depart: Thu 28 Sep 2017 Return: Mon 2 Oct 2017 Trip spans 5 days
C$491
Select
United
United
YVR
ORD
4h 05m
nonstop
ORD
YVR
10h 15m
1 stop
Depart: Thu 14 Sep 2017 Return: Mon 18 Sep 2017 Trip spans 5 days
C$259
Select
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Tue 5 Sep 2017 Return: Sun 10 Sep 2017 Trip spans 6 days
C$523
Select
WestJet
WestJet
YEG
ORD
19h 18m
1 stop
ORD
YEG
6h 03m
1 stop
Depart: Mon 11 Sep 2017 Return: Mon 18 Sep 2017 Trip spans 8 days
C$278
Select
Multiple Airlines
Multiple Airlines
YYZ
ORD
1h 54m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Fri 8 Sep 2017 Return: Mon 11 Sep 2017 Trip spans 4 days
C$307
Select
Air Canada
Air Canada
YTZ
ORD
4h 33m
1 stop
ORD
YTZ
4h 15m
1 stop
Depart: Thu 14 Sep 2017 Return: Sun 17 Sep 2017 Trip spans 4 days
C$299
Select
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 40m
nonstop
Depart: Thu 14 Sep 2017 Return: Sun 17 Sep 2017 Trip spans 4 days
C$316
Select
Air Canada
Air Canada
YYZ
ORD
1h 44m
nonstop
ORD
YYZ
1h 31m
nonstop
Depart: Tue 19 Sep 2017 Return: Sun 24 Sep 2017 Trip spans 6 days
C$309
Select
Porter Airlines
Porter Airlines
YTZ
MDW
1h 45m
nonstop
MDW
YTZ
1h 45m
nonstop
Depart: Tue 3 Oct 2017 Return: Tue 10 Oct 2017 Trip spans 8 days
C$387
Select
Delta
Delta
YEG
MDW
5h 27m
1 stop
MDW
YEG
7h 25m
1 stop
Depart: Tue 26 Sep 2017 Return: Fri 29 Sep 2017 Trip spans 4 days
C$329
Select
Air Canada
Air Canada
YHM
ORD
6h 08m
1 stop
ORD
YHM
4h 53m
1 stop
Depart: Sat 9 Sep 2017 Return: Wed 13 Sep 2017 Trip spans 5 days
C$371
Select
Multiple Airlines
Multiple Airlines
YUL
ORD
2h 40m
nonstop
ORD
YUL
2h 02m
nonstop
Depart: Sat 9 Sep 2017 Return: Wed 13 Sep 2017 Trip spans 5 days
C$323
Select
Porter Airlines
Porter Airlines
YUL
MDW
3h 25m
1 stop
MDW
YUL
3h 40m
1 stop
Depart: Wed 30 Aug 2017 Return: Sun 3 Sep 2017 Trip spans 5 days
C$432
Select
American Airlines
American Airlines
YYZ
ORD
1h 53m
nonstop
ORD
YYZ
6h 00m
1 stop
Depart: Tue 12 Sep 2017 Return: Tue 19 Sep 2017 Trip spans 8 days
C$393
Select
Delta
Delta
YYJ
ORD
6h 13m
1 stop
ORD
YYJ
13h 14m
2 stops
Depart: Sat 16 Sep 2017 Return: Mon 18 Sep 2017 Trip spans 3 days
C$394
Select
Multiple Airlines
Multiple Airlines
YUL
ORD
6h 18m
1 stop
ORD
YUL
2h 02m
nonstop
* Prices are per person, are for e–tickets and include all taxes & fees in CAD.

We attempt to get accurate prices, however, prices are not guaranteed.

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.

We compile tonnes of data for you
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,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Vancouver
C$ 491
Edmonton
C$ 387
Victoria
C$ 393
Hamilton
C$ 329
Ottawa
C$ 318
Montreal
C$ 323
Toronto
only C$ 275
only C$ 257
Destination

Chicago
only C$ 275
only C$ 257
Airlines Airline reviews

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

Overall
7.5
Boarding
7.4
Crew
7.9
Comfort
7.5
Food
6.4
Entertainment
6.6