Tagged Pages Archive | Chicago
2025
20
May
Calgary to Chicago, Illinois - $254 CAD roundtrip including taxes [Nonstop Flights]
20
May
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
24
January
Calgary to Chicago, Illinois - $279 CAD roundtrip including taxes [Nonstop Flights, CBO]
24
January
2024
22
May
Calgary to Chicago, Illinois - $258 CAD roundtrip including taxes [Nonstop Flights]
22
May
2023
4
August
Calgary to Chicago - $264 to $284 CAD roundtrip including taxes [Nonstop Flights]
4
August
2023
14
July
Calgary to Austin, Detroit, Chicago, or Washington DC - $249 to $288 CAD roundtrip including taxes [New Record]
14
July
2020
6
April
Calgary to Chicago, Illinois - $214 to $254 CAD roundtrip | non-stop flights (June 2020 to Feb 2021)
6
April
2020
11
February
Calgary to Chicago, Illinois - $199 CAD roundtrip | non-stop flights (single seats)
11
February
2020
5
February
Calgary to Chicago, Illinois - $204 to $227 CAD roundtrip | non-stop flights (new record!)
5
February
2018
10
July
3-in-1 trip: Calgary to Chicago, Puerto Rico, *and* New York City - $452 including taxes
10
July
2018
10
May
2-in-1 trip: Calgary to Chicago and Mazatlan, Mexico - $346 CAD roundtrip including taxes
10
May
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