'How To Get The Best Deal' Guides

Monday, April 6th 2020

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


Tagged Pages Archive | Illinois

2020
3
April
Calgary to Chicago, Illinois - $214 to $254 CAD roundtrip | non-stop flights (June 2020 to Feb 2021)

Chicago

United Airlines continues to occasionally show some very cheap non-stop flights from Calgary to Chicago.

There are now dates in warmer months available, such as June, July, and August.

Availability for travel

March, April, May, June, July, August, September, October, November, December 2020

January, February 2021

How to find and book this deal

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

Google Flights: Calgary to Chicago (non-stop flights)

Google Flights: Calgary to Chicago (non-stop flights)
^^ 3 day trips, more dates in July & August, about $25 more

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

- look for the dates that are $244 roundtrip or less.

2. Go to Flighthub

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

- Try the same dates you found on Google Flights. The price will be cheaper on Flighthub.

screenshot from Flighthub



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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 46,700 fellow passengers in Calgary, join us in the:
YYC Deals Facebook Group.
^^^ click the 'Join Group' button when you arrive.

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

Chicago

Read more



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

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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.

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