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Tagged Pages Archive | Chicago
2025
29
April
Saskatoon to Chicago - $251 [CB] to $366 CAD roundtrip
29
April
WestJet has dropped the price of their flights from Saskatoon to Chicago, Illinois down to between $251 and $366 CAD roundtrip including taxes.
The flights have 1 stop in Calgary each way (Saskatoon does not have nonstop flights to Chicago).
I consider $251 roundtrip to be WestJet's clickbait (CB) price because it doesn't include checked luggage or carry-on. Not exactly a realistic way to travel. It's a price offered primarily to appear to be the cheapest in search engines and then upsell you.
$366 roundtrip is the more realistic price because at least it includes checked luggage.
But those with the WestJet World Elite credit card can take advantage of the clickbait price as it includes free checked luggage.
The airlines make a lot of their profits from credit cards these days, so they keep widening the gap between 'with luggage' and 'without luggage' prices to push people into getting their credit cards.
Availability for travel
May 2026
How to find and book this deal
1. Start with the following Google Flights search:
Google Flights: Saskatoon to Chicago
- Click on the departure date box to open up the calendar view.
- Explore for the cheapest dates by adjusting the trip length at the bottom.
- Look for the dates that are $325 roundtrip.
2. At this point, there are a few different ways you can book these flights...
For $252 roundtrip. This includes *only* a personal item (something that can fit under the seat in front of you).
- Those with the WestJet World Elite credit card can still bring free checked bags and may find this fare useful.
- To book this price go to Skyscanner or Kayak
- Try the same dates you found on Google Flights.
*OR*
For $367 roundtrip. This includes a personal item and a checked bag. But not carry-on.
- Once you have booked your flight above you will receive your WestJet reservation code (6 digits, alphanumeric).
At that point you can go to the WestJet Manage Trips page, log in, and look for the Baggage or Add Bags section.
Here you can add a checked bag for $115 roundtrip.
screenshot from Skyscanner
Can't find this deal anymore? Prices change as deals sell out. The key is to be among the first to know when an amazing deal is posted.
Click here for tips on how to never miss a deal again.
Sign up for YXE Deals Alerts from Saskatoon
Go to the Alerts Page to sign up for flight deal alerts by e-mail, Facebook, or Twitter.
Travellers from Saskatoon also often sign up for alerts from Calgary and Edmonton.
Live deal discussion & travel advice
For live discussion of this deal, or just to get some amazing travel advice (to anywhere) from your 8,000 fellow passengers in Saskatoon, join us in the
YXE Deals Facebook Group.
^^ click the 'Join Group' button when you arrive.
Hit Like if you like this deal! Click Share to show your friends on Facebook.
2013
11
July
Direct Flights from Saskatoon | the complete list
11
July
More and more travelers are getting fed up with the problems and headaches associated with connecting flights and stopovers. Below you will find a comprehensive list of everywhere you can fly to from Saskatoon on a direct flight, along with the best methods for finding direct flights.
Read more
2012
5
April
Saskatoon to Chicago - $318 roundtrip after taxes
5
April
The WestJet Blue Tag Thursday deals have been kind of ho-hum lately, but they dropped a *really* exciting one today! This is as cheap as I've ever seen to Chicago from Saskatoon. Ever.
Read more
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