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Find cheap WestJet flights to Chicago from C$ 166

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Cheap WestJet Flight Deals to Chicago

 
Here are some of the best deals found on KAYAK recently from WestJet to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip WestJet flight deals to Chicago

KAYAK's recommended round-trip WestJet deals departing in the coming months to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
WestJet Logo
1:25 p.m. - 9:20 p.m.YYZ-ORD
8h 55m1 stop
WestJet Logo
11:05 a.m. - 11:55 p.m.ORD-YYZ
11h 50m1 stop
C$ 183WestJet
Find Deal
Fri, 30 May - Sat, 31 May
WestJet Logo
12:15 p.m. - 4:44 p.m.YYC-ORD
3h 29mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 264WestJet
Find Deal
Tue, 10 Jun - Tue, 24 Jun
WestJet Logo
12:15 p.m. - 4:44 p.m.YYC-ORD
3h 29mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 270WestJet
Find Deal
Tue, 10 Jun - Tue, 24 Jun
WestJet Logo
7:00 a.m. - 4:44 p.m.YVR-ORD
7h 44m1 stop
WestJet Logo
5:30 p.m. - 10:35 p.m.ORD-YVR
7h 05m1 stop
C$ 298WestJet
Find Deal
Wed, 4 Jun - Tue, 10 Jun
WestJet Logo
12:15 p.m. - 4:44 p.m.YYC-ORD
3h 29mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 299WestJet
Find Deal
Wed, 21 May - Sun, 25 May
WestJet Logo
12:15 p.m. - 4:43 p.m.YYC-ORD
3h 28mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 300WestJet
Find Deal
Fri, 3 Oct - Mon, 6 Oct
WestJet Logo
7:00 a.m. - 4:44 p.m.YVR-ORD
7h 44m1 stop
WestJet Logo
5:30 p.m. - 10:35 p.m.ORD-YVR
7h 05m1 stop
C$ 307WestJet
Find Deal
Fri, 23 May - Sun, 25 May
WestJet Logo
7:00 a.m. - 4:44 p.m.YVR-ORD
7h 44m1 stop
WestJet Logo
5:30 p.m. - 12:10 a.m.ORD-YVR
8h 40m1 stop
C$ 327WestJet
Find Deal
Wed, 11 Jun - Tue, 24 Jun
WestJet Logo
12:15 p.m. - 4:43 p.m.YYC-ORD
3h 28mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 339WestJet
Find Deal
Fri, 12 Sep - Sun, 14 Sep
WestJet Logo
7:00 a.m. - 4:44 p.m.YVR-ORD
7h 44m1 stop
WestJet Logo
5:30 p.m. - 10:35 p.m.ORD-YVR
7h 05m1 stop
C$ 341WestJet
Find Deal
Mon, 9 Jun - Tue, 24 Jun
Useful Info

Good to know

Low seasonJanuary
High seasonAugust
Cheapest flightC$ 166
Average price round-tripC$ 492
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Calgary to Chicago
(price for this month)

When to book flights with WestJet to Chicago

Average price per month
Flight prices as travel date approaches

FAQs for flying to Chicago with WestJet

  • Which other airlines fly to Chicago?

    Along with WestJet, you can also fly to Chicago with United Airlines, United Airlines, Air Canada, Air Canada and Porter Airlines.

  • Which airport do WestJet flights to Chicago fly into?

    WestJet flights to Chicago will fly into either Chicago O'Hare Airport, Chicago Midway Airport and Chicago Greater Rockford.

WestJet customer reviews

7.2
GoodBased on 2,826 verified guest reviews
7.4Boarding
7.9Crew
6.2Food
6.1Entertainment
7.1Comfort
Pros +
Cons -
Show reviews that mention
Traveler rating:
Sort by:
M
10.0 Wonderful
Again, outstanding friendly staff! Really helpful throughout our experience.
M
10.0 Wonderful
The staff were the friendliest I have encountered in years. Absolutely great!
M
10.0 Wonderful
Outstanding, once again.
A
8.0 Very good
On time. Everything ok.
E
8.0 Very good
My husband required a wheelchair to get to the airplane and the service he received was exemplary. Thank you.
M
8.0 Very good
No I flight internet. Thus no entertainment.
M
10.0 Wonderful
Internet on both flights was sketchy. Thus in flight entertainment was non- existent on MN - Balrimote leg.
T
8.0 Very good
..
R
10.0 Wonderful
crew was great, wifi was very poor could not even load a youtube video
J
8.0 Very good
WestJet was able to re-book us to the next available flight at no charge when air traffic controller staffing shortage delayed our inbound flight
Read more about WestJet

Everything you need to know for your flight to Chicago

Other airlines flying to Chicago

Flights from the other most popular airlines that fly to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
American Airlines flights to Chicago
Air Canada flights to Chicago
United Airlines flights to Chicago
Porter Airlines flights to Chicago

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