'How To Get The Best Deal' Guides

Tuesday, February 18th 2020

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

Tagged Pages Archive | Ord

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

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