'How To Get The Best Deal' Guides

Monday, November 18th 2019

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


Tagged Pages Archive | Ord

2019
15
November
Calgary to Chicago, Illinois - $204 CAD roundtrip | non-stop flights (new record!)

Chicago

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

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



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

Read more



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



2011
19
May
Last minute May long weekend idea? There's a flight to Chicago for $334 after tax.

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



2011
20
April
Another cheap last minuter to Chicago - $341 roundtrip after tax

UPDATE @ 8:05 AM - This AA price has now sold out, but interestingly enough, Delta has matched it, but into Chicago's other airport (MDW).

Read more



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