'How To Get The Best Deal' Guides

Monday, July 28th 2025

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


Tagged Pages Archive | Flight Deals

2025
3
July
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 $254 to $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
26
June
Calgary to Sydney, Australia - $863 CAD roundtrip including taxes

Sydney, Australia

Read more



2025
14
June
Calgary to Boston - $276 CAD roundtrip including taxes [Nonstop Flights, CBO]

Boston

Read more



2025
8
June
Calgary to Brisbane or Melbourne, Australia - $1043 CAD roundtrip including taxes

Brisbane, Australia

Read more



2025
6
June
Calgary to Amsterdam, Netherlands - $657 to $672 CAD roundtrip including taxes

Amsterdam, Netherlands

Read more



2025
4
June
Calgary to Palm Springs, California - $278 CAD roundtrip including taxes [Nonstop Flights, CBO]

Palm Springs, California

Read more



2025
30
May
Calgary to Punta Cana, Dominican Republic - $430 CAD roundtrip including taxes [Nonstop Flights, CBO]

Punta Cana, Dominican Republic

Read more



2025
29
May
Calgary to Washington, D.C. - $270 CAD roundtrip including taxes [Nonstop Flights, CBO]

Washington, D.C.

Read more



2025
26
May
Calgary to Edinburgh, Scotland - $574 to $674 CAD roundtrip including taxes | Nonstop Flights

Edinburgh, Scotland

Read more



2025
24
May
Calgary to Kuala Lumpur, Malaysia - $812 to $912 CAD roundtrip including taxes

Kuala Lumpur, Malaysia

Read more



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