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Calgary Deals Blog
Tagged Pages Archive | Chicago
2019
15
November
Calgary to Chicago, Illinois - $204 CAD roundtrip | non-stop flights (new record!)
15
November
American Airlines has dropped the price of their flights from Calgary to Chicago, Illinois down to $204 CAD roundtrip including taxes.
The flights are non-stop each way.
This is a new record for the cheapest flights from Calgary to Chicago.
Great deals to Chicago are very rare.
Update @ 9 AM MST - The April 2020 dates have sold out.
Update 11/16 - Many dates have sold out by this point. Scroll down to the bottom of the blog post for an update on dates that are still available.
Availability for travel
mostly November and the first half of December 2019
and a few in 2020
How to find and book this deal
1. Go to Flighthub
2. Search for a flight from Calgary (YYC) to Chicago (ORD)
Try one of the following date combinations:
Nov 16 to Nov 19
Nov 17, 18 to Nov 19, 24, 25, 26
Nov 19, 20 to Nov 24, 25, 26, 29, 30
Nov 21, 22 to Nov 25, 26, 29, 30
Nov 23, 24 to Nov 25, 26, 29, 30
Nov 25, 26 to Nov 29, 30, Dec 3, 4, 6
Nov 27 to Nov 29, 30, Dec 3, 4, 6
Dec 2, 3, 4 to Dec 4, 6, 10
Dec 5, 6, 7, 8 to Dec 10
[2020]
Jan 9, 10 to Jan 14
Apr 1, 2 to Apr 7
screenshot from Flighthub
Update 11/16 - Many dates have sold out by this point. Here is an update on dates that are still available....
1. Go to Flighthub
2. Search for a flight from Calgary (YYC) to Chicago (ORD)
Try one of the following date combinations:
Nov 17, 18, 19, 20 to Nov 30
Nov 21, 22, 23 to Nov 30
Nov 24, 25, 26, 27 to Nov 30, Dec 3, 4
Note: The Nov 30 and Dec 4 return dates currently have multiple seats available. The Dec 3 return date only has 1 seat available.
[2020]
Jan 9 to Jan 14 -- 1 seat
Sep 30 to Oct 2 -- 1 seat
Oct 7 to Oct 9 -- 1 seat
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 43,700 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.
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.
Read more
2011
28
June
The 'United or AA has dropped their last minute flights to Chicago' thread
28
June
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
2011
19
May
Last minute May long weekend idea? There's a flight to Chicago for $334 after tax.
19
May
If anyone's looking for a last minute May long weekend idea, there's a flight on American Airlines to Chicago for $334 roundtrip after tax.
Read more
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