'How To Get The Best Deal' Guides

Wednesday, December 11th 2019

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



2019
2
December
Calgary to Chicago, Illinois - $204 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 @ 9 AM MST - The April 2020 dates have sold out.

Update 11/16 - Many dates have sold out by this point. Scroll down to the bottom of the blog post for an update on dates that are still available.

Update 11/19 - By this point, only single seats seem to be available. Scroll down to the bottom of the blog post for another update on dates that are still available.

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. Scroll down to the bottom of this blog post for the update.

Availability for travel

mostly November and the first half of December 2019

and a few in 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



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.





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 43,700 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.









People That Liked This Page Also Liked:

tags for this post You may also want to check out pages that were tagged with:

Be The First To Know About The Next Amazing Deal!

Head to the YYC Deals Alerts Page where you can choose to be notified by e-mail, Facebook, Twitter, or RSS Feed the moment an amazing travel deal from Calgary is found.

Setting up alerts allows you to be one of the first to see a new deal, before it sells out.
And don't worry, alerts are only sent when it's truly an amazing deal.

Like Our Site? Follow Us!

Subscribe to Our Feed!

Comments from Facebookers

Comments from Everyone Else

10 Responses to "Calgary to Chicago, Illinois - $204 CAD roundtrip | non-stop flights (new record!)"


    Has Laurie been here?
       Laurie on November 15th, 2019

    Booked this great deal. Been awhile since I've taken advantage of the deals. Thanks,

    Has Chi been here?
       Chi on November 15th, 2019

    Booked, but tried to book for my sister right after mine and it was all gone for next weekend :( Such a great deal!!

    Has Admit been here?
       Admit on November 15th, 2019

    Booked for April; $219. Great deal.

    Has Chris Myden been here?
       Chris Myden on November 15th, 2019

    Have fun in Chicago! Great city to visit. I would go back just for the true deep dish pizza :)

    Has Diana been here?
       Diana on November 15th, 2019

    Booked the flight Nov 27 to Nov 30 for my husband and I. Great deal! Thank you.

    Has Kathy been here?
       Kathy on November 15th, 2019

    Was able to book for April but by the time we figured out a bunch of moving parts regarding family etc. the flight had jumped from $300 to $397 (within like an hour) but it is still a great deal. We have family near Chicago and last time we flew there I think we paid almost $2K.

    Has Chris Myden been here?
       Chris Myden on November 15th, 2019

    Chicago never goes on sale any more. Looking back through the history, the last time there was a great deal from YYC to Chicago was 2014 ! ($279 CAD roundtrip with Westjet, which was a new record at the time).

    Has Jodi been here?
       Jodi on November 15th, 2019

    Next weekend is now up to $357. Missed booking the deal.

    Has Rosa been here?
       Rosa on November 15th, 2019

    Flights have gone up but some dates are still available for $300

    Has Arie been here?
       Arie on November 15th, 2019

    My wife scored two tickets this morning for $204.17 each, for the end of this month. Chicago here we come! Thanks Chris!

Leave a Reply











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

    * crowdsource the best travel deals from YYC?

    * offer up their unbiased travel advice?

    Join the group and find out!


(click the 'Join Group' button, when you arrive)