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Find and compare WestJet flights to Chicago

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Recent WestJet flights to Chicago found by users

Cheap WestJet Flight Deals to Chicago

Enter your travel dates to find the best prices.
WestJet Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
WestJet Logo
2:20 p.m. - 5:15 p.m.ORD-YYC
3h 55mdirect
C$ 241WestJet
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Fri, 5 Dec - Fri, 12 Dec
WestJet Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
WestJet Logo
2:20 p.m. - 5:15 p.m.ORD-YYC
3h 55mdirect
C$ 245WestJet
Find Deal
Fri, 5 Dec - Fri, 12 Dec
WestJet Logo
12:13 p.m. - 4:59 p.m.YYZ-ORD
5h 46m1 stop
WestJet Logo
6:02 p.m. - 8:58 a.m.ORD-YYZ
13h 56m1 stop
C$ 371WestJet
Find Deal
Tue, 16 Dec - Sat, 3 Jan
WestJet Logo
12:09 p.m. - 5:22 p.m.YYZ-ORD
6h 13m1 stop
WestJet Logo
6:50 a.m. - 11:20 a.m.ORD-YYZ
3h 30m1 stop
C$ 377WestJet
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Tue, 30 Dec - Wed, 7 Jan
WestJet Logo
6:30 a.m. - 1:10 p.m.YYZ-MDW
7h 40m1 stop
WestJet Logo
10:49 a.m. - 5:02 p.m.MDW-YYZ
5h 13m1 stop
C$ 377WestJet
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Tue, 9 Dec - Tue, 16 Dec
WestJet Logo
6:30 p.m. - 10:22 a.m.YYZ-ORD
16h 52m2 stops
WestJet Logo
8:55 a.m. - 2:48 p.m.ORD-YYZ
4h 53m1 stop
C$ 378WestJet
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Fri, 5 Dec - Sun, 7 Dec
WestJet Logo
6:30 a.m. - 10:33 a.m.YYZ-ORD
5h 03m1 stop
WestJet Logo
7:20 a.m. - 9:53 p.m.ORD-YYZ
13h 33m2 stops
C$ 380WestJet
Find Deal
Sat, 13 Dec - Sun, 14 Dec
WestJet Logo
7:45 p.m. - 1:35 p.m.YVR-ORD
15h 50m1 stop
WestJet Logo
2:20 p.m. - 12:15 a.m.ORD-YVR
11h 55m1 stop
C$ 380WestJet
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Thu, 4 Dec - Fri, 12 Dec
WestJet Logo
6:00 a.m. - 9:34 p.m.YYZ-ORD
16h 34m1 stop
WestJet Logo
6:02 p.m. - 8:58 a.m.ORD-YYZ
13h 56m1 stop
C$ 384WestJet
Find Deal
Wed, 31 Dec - Fri, 2 Jan
WestJet Logo
3:38 p.m. - 8:35 p.m.YYZ-ORD
5h 57m1 stop
WestJet Logo
6:45 a.m. - 2:48 p.m.ORD-YYZ
7h 03m1 stop
C$ 385WestJet
Find Deal
Mon, 15 Dec - Fri, 19 Dec

WestJet flights to Chicago at a glance

Fastest flight time

3h 28m

Direct flights

Mon, Tue, Sat and Sun

Airports in Chicago

1 airport
The fastest flight from Canada to Chicago takes 3h 28m
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Direct flights go from Canada to Chicago on Monday, Tuesday, Saturday and Sunday. There are no airlines offering direct flights.
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There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
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Insights on WestJet flights to Chicago

Data designed to help you find the right flight

What is the cheapest day to depart on your Economy Class flight to Chicago?

The cheapest day to depart from Canada to Chicago is on a Saturday when prices can be found for as low as C$ 147. Be sure to avoid booking your departure on a Tuesday as prices are generally higher than usual. According to our data, the average Economy Class ticket price to Chicago on a Tuesday is C$ 298.

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Canada when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 289 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Canada for as low as C$ 216 on momondo.

Can stopping save me money on Canada to Chicago flights?

You could potentially save up to 61% on your flight if you consider stops on a Canada to Chicago flight.

Frequently asked questions about flights to Chicago with WestJet

Is WestJet generally cheaper than other airlines for flights to Chicago?

Lots of factors influence the price of a flight, whether that's with WestJet or other airlines, so it is best to search and compare before booking. The airline flying to Chicago with the cheapest average round-trip price tends to be Porter Airlines.

Which other airlines fly to Chicago?

Aside from WestJet, Porter Airlines and United Airlines also fly to Chicago.

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