'How To Get The Best Deal' Guides

Friday, April 4th 2025

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


Tagged Pages Archive | Yyc

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

Chicago

American Airlines has dropped the price of their flights from Calgary to Chicago, Illinois down to $204 CAD roundtrip including taxes.

The flights are non-stop each way.

This is a new record for the cheapest flights from Calgary to Chicago.

Great deals to Chicago are very rare.

Update 2/4 - United Airlines is still showing a few non-stop flights from Calgary to Chicago in October and November 2020 for $203 CAD roundtrip. Try the following dates on Flighthub ...

Nov 24, 25 to Nov 27, 28 -- new!


Availability for travel

mostly November and the first half of December 2019

January, February, March, April, early May, October, November 2020

How to find and book this deal

1. Go to Flighthub

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

Try one of the following date combinations:

Nov 16 to Nov 19
Nov 17, 18 to Nov 19, 24, 25, 26
Nov 19, 20 to Nov 24, 25, 26, 29, 30
Nov 21, 22 to Nov 25, 26, 29, 30

Nov 23, 24 to Nov 25, 26, 29, 30
Nov 25, 26 to Nov 29, 30, Dec 3, 4, 6
Nov 27 to Nov 29, 30, Dec 3, 4, 6

Dec 2, 3, 4 to Dec 4, 6, 10
Dec 5, 6, 7, 8 to Dec 10

[2020]

Jan 9, 10 to Jan 14

Apr 1, 2 to Apr 7

screenshot from Flighthub



Update 11/16 - Many dates have sold out by this point. Here is an update on dates that are still available....

1. Go to Flighthub

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

Try one of the following date combinations:

Nov 17, 18, 19, 20 to Nov 30
Nov 21, 22, 23 to Nov 30
Nov 24, 25, 26, 27 to Nov 30, Dec 2, 3, 4

Note: The Nov 30 and Dec 4 return dates currently have multiple seats available. The Dec 3 return date only has 1 seat available.

[2020]

Jan 9 to Jan 14 -- 1 seat

Sep 30 to Oct 2 -- 1 seat

Oct 7 to Oct 9 -- 1 seat

screenshot from Flighthub



Update 11/19 - By this point, only single seats appear to be available. Here is an update on dates that are still available, along with some new dates....

1. Go to Flighthub

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

Try one of the following date combinations:

Nov 20, 21, 22 to Nov 24, 25, 26, 27
Nov 23 to Nov 25, 26, 27, Dec 2, 4
Nov 24 to Nov 26, 27, Dec 2, 4
Nov 26, 27 to Dec 2, 4

screenshot from Flighthub



Update 11/27 - United Airlines is now showing non-stop flights from Calgary to Chicago for $255 CAD roundtrip in December 2019 and January, February, April, early May 2020

1. Try the following Google Flights search:

Google Flights: Calgary to Chicago (non-stop)

2. Click on the departure date box to open up the calendar view and browse for cheap date combinations

- look for the dates that are $256 CAD roundtrip.

- the April and early May dates are the most desirable, and likely to sell out first. Here is a list of the April / May dates currently available...

Apr 1 to Apr 7, 8, 9, 10
Apr 2, 3 to Apr 7, 8 10
Apr 7 to Apr 10, 15, 16
Apr 10 to Apr 15 -- over Easter, try Flighthub.

Apr 14 to Apr 16, 22, 29, 30
Apr 15, 17 to Apr 22
Apr 21 to Apr 28, 29, 30

Apr 22 to Apr 28, 29, 30
Apr 28, 29 to Apr 30, May 5

May 1 to May 5
May 5, 6 to May 12

screenshot from United Airlines



Update 12/16 - United Airlines is still showing non-stop flights from Calgary to Chicago for $244 CAD roundtrip in December 2019 and January, February 2020. There are currently dates over the Christmas holidays and New Year's Eve available.

1. Try the following Google Flights search:

Google Flights: Calgary to Chicago (non-stop)

- Click on the departure date box to open up the calendar view and browse for cheap date combinations

- Look for the dates that are $245 to $253 CAD roundtrip.

2. Go to Flighthub

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

- Use the same dates you found on Google Flights. The price will be cheaper on Flighthub.

screenshot from Flighthub



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.





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YYC Deals Facebook Group.
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2020
17
January
Calgary to Paris, France - $580 to $692 CAD roundtrip | August available

Paris, France

Read more



2019
26
December
Calgary to Toronto - $191 to $251 CAD roundtrip | non-stop flights

Toronto, Ontario

Read more



2019
14
December
Calgary to New York City - $281 CAD roundtrip including taxes | non-stop flights

New York City

Read more



2019
8
December
Calgary to Paris, France - $631 to $697 CAD roundtrip (or one-way for $149) | non-stop flights

Paris, France

Read more



2019
29
November
Calgary to Palm Springs, California - $259 to $287 CAD roundtrip including taxes | non-stop flights

Palm Springs, California

Read more



2019
28
November
Calgary to Tokyo or Osaka / Kyoto, Japan - $479 to $654 CAD roundtrip including taxes

Osaka Kyoto, Japan

Read more



2019
25
November
Calgary to Maui, Hawaii - $323 CAD roundtrip including taxes | non-stop flights

Maui, Hawaii

Read more



2019
10
November
Calgary to Houston, Texas - $244 CAD roundtrip | non-stop flights

NASA Space Center in Houston, Texas

Read more



2019
5
November
Calgary to Asuncion, Paraguay - $768 CAD roundtrip | August available

Asuncion, Paraguay

Read more



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