Tagged Pages Archive | North America
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.
2025
20
January
Calgary to Boston - $317 CAD roundtrip including taxes [Nonstop Flights, CBO]
20
January
2025
15
January
Calgary to Puerto Vallarta or Cancun, Mexico - $376 CAD roundtrip including taxes [Nonstop Flights]
15
January
2024
12
December
Calgary to San Diego, California - $284 CAD roundtrip including taxes
12
December
2024
5
December
Calgary to Yellowknife, Northwest Territories (or vice-versa) - $198 to $222 CAD roundtrip including taxes [Nonstop Flights]
5
December
2024
24
October
Calgary to Chicago, Illinois - $278 CAD roundtrip including taxes [Nonstop Flights]
24
October
2024
9
October
Calgary to Hawaii for under $369 CAD roundtrip including taxes
9
October
2024
28
August
Calgary to Denver, Colorado - $174 to $219 CAD roundtrip including taxes [Nonstop Flights, Summer]
28
August
2024
27
August
Calgary to Moncton, New Brunswick - $290 CAD roundtrip including taxes [Nonstop Flights, CBO]
27
August
2024
19
August
Calgary to Philadelphia, Charlotte, or Dallas - $245 to $253 CAD roundtrip including taxes
19
August
Sites