Tagged Pages Archive | Illinnois
2025
24
January
Calgary to Chicago, Illinois - $279 CAD roundtrip including taxes [Nonstop Flights, CBO]
24
January
WestJet has dropped the price of their flights from Calgary to Chicago, Illinois down to $279 CAD roundtrip including taxes, including a checked bag and a personal item.
The flights are nonstop both ways.
This is a CBO deal (Checked Bag Only). You cannot bring carry-on. However, in addition to your checked bag, you can still bring a personal item (something that fits under the seat in front of you).
If you have the WestJet World Elite credit card, which comes with free checked bags, you can book these flights for $184 CAD roundtrip.
To save money, sometimes couples or families will book one passenger with a checked bag, and the others without.
Availability for travel
May, June, September, October 2025
How to find and book this deal
1. Start with the following Google Flights search:
Google Flights: Calgary to Chicago
- Click on the departure date box to open up the calendar view.
- Browse for the cheapest dates by adjusting the trip length at the bottom.
- Look for the dates that are $248 roundtrip.
2. Go to Skyscanner
- Search for a flight from Calgary (YYC) to Chicago (ORD)
- Try the same dates you found on Google Flights.
- The price should drop to $184 roundtrip. WestJet charges $95 roundtrip for a checked bag.
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.
screenshot from Skyscanner
Sign up for YYC Deals Alerts from Calgary
Go to the Alerts Page to sign up for flight deal alerts by e-mail, Facebook, or Twitter.
Travellers from Calgary also often sign up for alerts from Edmonton and Vancouver.
Join us in the YYC Deals Facebook Group
For live discussion of this deal, or to get some amazing travel advice (about anywhere) from your 50,000 fellow passengers in Calgary, join us in the:
YYC 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.
2024
24
October
Calgary to Chicago, Illinois - $278 CAD roundtrip including taxes [Nonstop Flights]
24
October
2024
22
May
Calgary to Chicago, Illinois - $258 CAD roundtrip including taxes [Nonstop Flights]
22
May
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