'How To Get The Best Deal' Guides

Thursday, July 3rd 2025

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


Tagged Pages Archive | Yyc

2025
20
May
Calgary to Chicago, Illinois - $254 CAD roundtrip including taxes [Nonstop Flights]

Chicago

United Airlines has dropped the price of their flights from Calgary to Chicago, Illinois down to $254 CAD roundtrip including taxes.

The flights are nonstop both ways.

Don't be fooled by the WestJet flights, which are a few dollars cheaper, but missing something rather important: the option to bring clothes with you.

UPDATE: Dates are available with American Airlines for $254 to $279 roundtrip, with carry-on included. Dates in September, October.

Availability for travel

December 2024

February, March, April, May, June, August, September, October, November 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.

- Explore for the cheapest dates by adjusting the trip length at the bottom.

- Look for the dates that are $278 roundtrip

2. Go to Kayak or Skyscanner

3. Search for a flight from Calgary (YYC) to Chicago (ORD)

- Try the same dates you found on Google Flights.



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 Kayak



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
13
May
Calgary to New York City - $334 CAD roundtrip including taxes [Nonstop Flights]

New York City

Read more



2025
12
May
Calgary to Sydney, Nova Scotia (or vice versa) - $461 CAD roundtrip including taxes [Nonstop Flights, CBO]

Sydney, Nova Scotia

Read more



2025
30
April
Calgary to Tokyo, Japan in Business Class - $2491 CAD roundtrip including taxes [Nonstop Flights]

Tokyo, Japan

Read more



2025
28
April
Calgary to Cancun, Mexico - $424 CAD roundtrip including taxes [Nonstop Flights, CBO]

Cancun, Mexico

Read more



2025
5
April
Calgary to Nashville, Tennessee - $260 CAD roundtrip including taxes [Nonstop Flights, CBO]

Nashville, Tenneseee

Read more



2025
5
April
Calgary to Auckland, New Zealand - $893 to $945 CAD roundtrip including taxes

Auckland, New Zealand

Read more



2025
4
April
Calgary to Mumbai or Bengaluru, India - $891 to $980 CAD roundtrip including taxes

Mumbai, India

Read more



2025
26
March
Calgary to Mexico City - $479 CAD roundtrip including taxes [Nonstop Flights, CBO]

Mexico City

Read more



2025
14
March
Calgary to Paris, France - $487 to $539 CAD roundtrip including taxes [Nonstop Flights]

Paris, France

Read more



« Previous Page     Next Page »










Join The YYC Deals Facebook Group
    What happens when over 70,000 people     from Calgary...

    * crowdsource the best deals from YYC?

    * offer up their unbiased travel advice?

    Join the group and find out!


(click 'Join Group' when you arrive)