'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 | Chicago

2020
11
February
Calgary to Chicago, Illinois - $199 CAD roundtrip | non-stop flights (single seats)

Chicago

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

Chicago

Read more



2018
10
July
3-in-1 trip: Calgary to Chicago, Puerto Rico, *and* New York City - $452 including taxes

Chicago, Puerto Rico, and New York City

Read more



2018
10
May
2-in-1 trip: Calgary to Chicago and Mazatlan, Mexico - $346 CAD roundtrip including taxes

Chicago and Mazatlan, Mexico

Read more



2014
12
March
Crazy day! Cheap flights to Maui, San Francisco, Chicago, New York

Maui, Hawaii

Read more



2013
29
May
Calgary to Chicago | $330 roundtrip after taxes

Chicago

Read more



2013
20
March
Calgary to New York City | $354 roundtrip after taxes

New York City

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2012
5
April
Calgary to Chicago - $291 roundtrip after taxes!

The WestJet Blue Tag Thursday deals have been kind of ho-hum lately, but they dropped a *really* exciting one today! I believe this is as cheap as I've ever seen to Chicago from Calgary. Ever.

Read more



2011
12
September
Kalispell to Chicago - $200 roundtrip after taxes - any date

While I do watch for interesting fares out of Montana, the truth is that it's pretty rare to see one that's worth the drive. Allegiant Air has cheap flights to Vegas, but on the major airlines, prices from Montana aren't usually significantly better to warrant the 5 hour drive from Calgary. We're not like Toronto where we can hop across the border to Buffalo. Flying out of the U.S. for us is a significant investment of time.

Read more



2011
28
June
The 'United or AA has dropped their last minute flights to Chicago' thread

American Airlines just dropped another one of those cheap flights to Chicago. Try July 2 to 4 on AA.com - $335 roundtrip after tax, direct each way.

Read more



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