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Calgary Deals Blog
Tagged Pages Archive | Chicago
2020
6
April
Calgary to Chicago, Illinois - $214 to $254 CAD roundtrip | non-stop flights (June 2020 to Feb 2021)
6
April
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
Google Flights: Calgary to Chicago
^^ 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
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 46,700 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.
2020
11
February
Calgary to Chicago, Illinois - $199 CAD roundtrip | non-stop flights (single seats)
11
February
2020
5
February
Calgary to Chicago, Illinois - $204 to $227 CAD roundtrip | non-stop flights (new record!)
5
February
2018
10
July
3-in-1 trip: Calgary to Chicago, Puerto Rico, *and* New York City - $452 including taxes
10
July
2018
10
May
2-in-1 trip: Calgary to Chicago and Mazatlan, Mexico - $346 CAD roundtrip including taxes
10
May
2014
12
March
Crazy day! Cheap flights to Maui, San Francisco, Chicago, New York
12
March
2013
29
May
Calgary to Chicago | $330 roundtrip after taxes
29
May
2013
20
March
Calgary to New York City | $354 roundtrip after taxes
20
March
2012
5
April
Calgary to Chicago - $291 roundtrip after taxes!
5
April
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
12
September
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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