'How To Get The Best Deal' Guides

Friday, July 19th 2024

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

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


American Airlines continues to occasionally show some extremely cheap non-stop flights from Calgary to Chicago.

In this case, they have dropped them down to $149 USD roundtrip, which works out to $199 CAD roundtrip.

But it also appears that most dates have single seats only. Meaning, if you search for 1 passenger, the cheap price will show up. If you search for 2 or more, it will not. I haven't tried every date combination though.

At the same time, Air Canada has dropped the price of their 1-stop flights from Calgary to Chicago down to $214 CAD roundtrip with availability in every month of 2020. But with these flights, it takes 7-9 hours to get to Chicago, versus 4 hours with a non-stop flight.

I've posted an update below with instructions on how to find the 1-stop flights.

Availability for travel

October, November 2020

How to find and book this deal

1. Go to Kayak ($USD currency version)

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

- Try one of the following date combinations:

Oct 21, 22 to Oct 24, 25
Oct 26 to Nov 4
Oct 29, 31 to Nov 4

Nov 1 to Nov 7
Nov 24 to Nov 27

NOTE: This is the $USD currency version of Kayak

The price should show up as $149 USD which will work out to $199 CAD roundtrip including taxes when booked with a Canadian credit card, including the typical 2.5% foreign exchange fee.

If you use a credit card that does not charge foreign exchange fees, it will be even cheaper.

Air Canada has also dropped the price of their 1-stop flights from Calgary to Chicago down to $214 CAD roundtrip with availability in every month of 2020

1. Try a Google Flights search like this one...

Google Flights: Calgary to Chicago

- click on the departure date box and browse for cheap date combinations

- look for the dates that are around $236 roundtrip.

- if you try to book these through Google Flights you may notice that the price jumps up. Instead, what you want to do is...

2. Go to Flighthub

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

- Try the same dates you found on Google Flights

- After your Flighthub search completes you may want to click on the '1-stop only' filter on the left hand side.

screenshot from Kayak ($USD currency version)

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.

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

No Responses to "Calgary to Chicago, Illinois - $199 CAD roundtrip | non-stop flights (single seats)"

Comments are automatically closed 30 days after the post is made.

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

    * crowdsource the best deals from YYC?

    * offer up their unbiased travel advice?

    Join the group and find out!

(click 'Join Group' when you arrive)