'How To Get The Best Deal' Guides

Saturday, December 21st 2024

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


Tagged Pages Archive | Chicago

2024
24
October
Calgary to Chicago, Illinois - $278 CAD roundtrip including taxes [Nonstop Flights]

Chicago

United Airlines has dropped the price of their February, March, and April 2025 flights from Calgary to Chicago, Illinois down to $278 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: A few April dates are available again for $284 roundtrip.

Availability for travel

December 2024

February, March, April 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.

[April Dates]

Apr 8 to Apr 16, 17, 19
Apr 9 to Apr 16, 17, 19
Apr 12 to Apr 16, 17, 19
Apr 14 to Apr 16, 17, 19
Apr 15 to Apr 17, 19
Apr 16 to Apr 19


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



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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.



2024
22
May
Calgary to Chicago, Illinois - $258 CAD roundtrip including taxes [Nonstop Flights]

Chicago

Read more



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

Chicago, Illinois

Read more



2023
14
July
Calgary to Austin, Detroit, Chicago, or Washington DC - $249 to $288 CAD roundtrip including taxes [New Record]

Washington, D.C.

Read more



2020
6
April
Calgary to Chicago, Illinois - $214 to $254 CAD roundtrip | non-stop flights (June 2020 to Feb 2021)

Chicago

Read more



2020
11
February
Calgary to Chicago, Illinois - $199 CAD roundtrip | non-stop flights (single seats)

Chicago

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2020
5
February
Calgary to Chicago, Illinois - $204 to $227 CAD roundtrip | non-stop flights (new record!)

Chicago

Read more



2018
10
July
3-in-1 trip: Calgary to Chicago, Puerto Rico, *and* New York City - $452 including taxes

Chicago, Puerto Rico, and New York City

Read more



2018
10
May
2-in-1 trip: Calgary to Chicago and Mazatlan, Mexico - $346 CAD roundtrip including taxes

Chicago and Mazatlan, Mexico

Read more



2014
12
March
Crazy day! Cheap flights to Maui, San Francisco, Chicago, New York

Maui, Hawaii

Read more



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