'How To Get The Best Deal' Guides

Sunday, February 23rd 2020

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

Tagged Pages Archive | American Airlines

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.

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