'How To Get The Best Deal' Guides

Tuesday, May 30th 2023

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

Calgary to Chicago - $293 to $305 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 now showing a couple of nonstop flights from Calgary to Chicago for $293 CAD roundtrip in October.

Availability for travel

September, October 2023

How to find and book this deal

1. Go to Kiwi or Skyscanner

- Try one of the following date combinations:

Sep 7 to Sep 12, 14, 17, 19, 21, 26, 28
Sep 10 to Sep 12, 14, 17, 19, 21, 26, 28
Sep 12 to Sep 14, 17, 19, 21, 26, 28

Sep 14 to Sep 17, 19, 21, 26, 28, Oct 3, 5
Sep 19 to Sep 21, 26, 28, Oct 3, 5
Sep 26 to Sep 28, Oct 3, 5

Oct 3 to Oct 8 -- $293 w/ United
Oct 4 to Oct 8 -- $293 w/ United

[Sold Out Dates]

Sep 2 to Sep 7, 12, 14
Sep 17 to Sep 19, 21, 26, 28
Sep 28 to Oct 1, 3, 5, 8 -- Thu to Sun

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.

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