CHI

Find cheap WestJet flights to Chicago from C$ 135

1 adult
1 adult, Economy, 0 bags

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Flight Deals

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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip WestJet flight deals to Chicago

Wed, 20 May - Tue, 26 May
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
C$ 252WestJet
Mon, 4 May - Fri, 8 May
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
C$ 276WestJet
Mon, 4 May - Fri, 8 May
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
C$ 278WestJet
Thu, 7 May - Mon, 11 May
WestJet Logo
7:30 a.m. - 4:40 p.m.
YVR
-
ORD
7h 10m
1 stop
WestJet Logo
5:30 p.m. - 10:35 p.m.
ORD
-
YVR
7h 05m
1 stop
C$ 279WestJet
Thu, 21 May - Tue, 26 May
WestJet Logo
6:00 a.m. - 4:40 p.m.
YVR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 10:35 p.m.
ORD
-
YVR
7h 05m
1 stop
C$ 280WestJet
Fri, 3 Apr - Mon, 6 Apr
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$ 282WestJet
Fri, 22 May - Tue, 26 May
WestJet Logo
6:00 a.m. - 4:40 p.m.
YVR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 10:35 p.m.
ORD
-
YVR
7h 05m
1 stop
C$ 282WestJet
Fri, 3 Apr - Fri, 17 Apr
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$ 283WestJet
Thu, 28 May - Mon, 1 Jun
WestJet Logo
6:00 a.m. - 4:40 p.m.
YVR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 10:35 p.m.
ORD
-
YVR
7h 05m
1 stop
C$ 283WestJet
Fri, 10 Apr - Mon, 13 Apr
WestJet Logo
6:00 a.m. - 1:35 p.m.
YEG
-
ORD
6h 35m
1 stop
WestJet Logo
2:20 p.m. - 9:16 p.m.
ORD
-
YEG
7h 56m
1 stop
C$ 283WestJet
Useful Info

Good to know

Low seasonJanuary
Cheapest flightC$ 135
Average price round-tripC$ 810
Good deal round-tripC$ 688
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Calgary to Chicago
(avg. price over the last 2 weeks)
or less

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

  • Is WestJet cheaper than other airlines flying to Chicago?

    With an average return price of C$ 810, WestJet is cheaper than Air Canada when it comes to flights to Chicago. However, the cheapest airline flying to Chicago is American Airlines, with an average return price of C$ 668.

  • Which other airlines fly to Chicago?

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

  • How much is a flight to Chicago with WestJet?

    On average, WestJet flights to Chicago cost C$ 810 for a round-trip.

  • 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.

Top tips for your flights to Chicago with WestJet

  • The cheapest flight to Chicago with WestJet found on KAYAK in the last 2 weeks departed from Calgary and cost C$ 255.
  • If you’re intending to fly with WestJet, book your flight to Chicago at least 1 week before departure to ensure a below-average price.
  • High season for flights to Chicago with WestJet is May and prices are highest at this time. The cheapest month to fly is January.

WestJet customer reviews

7.2
Good3,265 verified ratings
7.9Crew
6.1Entertainment
6.2Food
7.4Boarding
7.0Comfort
Traveler rating:
Sort by:
D
10.0 Wonderful
Excellent
M
2.0 Poor
No kiosk to help pre boarding unlike other airlines, still lost the luggage despite its own crew/TSA or security tagging it, poor handling of lost luggage and possibly compensation is likely poor too.
M
2.0 Poor
No pre boarding kiosk to check in, baggage claim detected luggage didn’t leave the airport, poorly managed recovery of lost luggage, and blame lost tag from conveyor to TSA/security, very poor from TSA/security check to delivery, crucial if compensation will go thru and will likely wait for months unlike United,
J
10.0 Wonderful
Can't complain
I
2.0 Poor
Waited at airport from 10 am till 4 pm and no flight due to fog. Ugh.
A
10.0 Wonderful
As someone who never flies WestJet unless there is no other viable option I have to give this crew credit where credit is due. Extremely well done everyone.
M
6.0 Okay
Everything was great until we had to get our bags. The bags came out in several different batches over 90 minutes after we landed maybe more we got our bags. So much for the old West Jet where they promised bags in 20 minutes. I Next time I will pack lighter and go with a carry-on.
A
8.0 Very good
Flight left on time. The crew was very friendly. I had to buy a proper meal. Small cookie and a drink just doesn’t cut it for a 4.5 hours flight.
A
10.0 Wonderful
Good
L
8.0 Very good
Flight was good, crew was excellent. No complaints at all
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.
Air Canada flights to Chicago
United Airlines flights to Chicago
American Airlines flights to Chicago
Porter Airlines flights to Chicago