'How To Get The Best Deal' Guides

Tuesday, May 13th 2025

"I'm a travel junkie who's hooked on deals from YYC." - Chris Myden



2023
4
August
Calgary to Chicago - $264 to $284 CAD roundtrip including taxes [Nonstop Flights]

Chicago, Illinois

WestJet has dropped the price of their September flights from Calgary to Chicago down to $305 CAD roundtrip including taxes.

The flights are nonstop both ways.

UPDATE - United Airlines is still showing flights in October and early November for $272 CAD roundtrip.

Availability for travel

September, October, November 2023

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 and browse for cheap date combinations.

- Adjust the trip length at the bottom.

- Look for the dates that are $301-$312 roundtrip

2. Go to FlightHub or Skyscanner

- Try the same dates you found on Google Flights.

screenshot from FlightHub



screenshot from Kiwi



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.

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